Virtual Assistants

What to Look for When Hiring: Essential Qualities in Virtual Assistants

People at a table working on laptops.Have you ever wondered what to look for when hiring virtually

Outsource School founders Nathan and Connor have, and their search is how the company was born. Now, they help business owners understand the fundamentals of virtual hiring.

In this post, we’re sharing with you the essentials of what to look for when hiring. This way, you can zero in on the best for your next virtual team member.

Communication is Key

Strong communication is one of the most important skills for any virtual hire to have. This is how you can bridge the physical distance in today’s increasingly remote work environment. Without face-to-face interaction, you need clear and concise communication for successful teamwork.

Trust and Rapport

First off, strong communication fosters trust and rapport within virtual teams. Moreover, virtual hires need to articulate ideas effectively, present information, and ask clarifying questions. This is because they communicate mostly through non-voice means, which can be tricky. 


We find that strong communication minimizes misunderstandings and delays, leading to a more productive work environment. This is because teams can identify and address issues collaboratively, which also leads to better problem-solving outcomes.

Virtual hires who can communicate well with clients also build trust with the company. Furthermore, teams that focus on communicating effectively can ensure clear project expectations and delivery. That’s the recipe for happy clients.

Positive Team Spirit

Open and honest communication also fosters a positive team spirit and minimizes potential conflicts. Communication skills plus a great attitude makes for teams that pay close attention and understand the nuances of what’s being said. When in doubt, they ask clarifying questions instead of guessing or just not caring. 

Assessing Communication Skills in Potential Hires

During the application stage, make sure you review cover letters and resumes before scheduling interviews. Analyze how well each candidate presents themselves in writing. Look for clear, concise language, proper grammar, and effective articulation of skills and experience. 

Keep a List

Throughout the interview process, keep a list in front of you of what to look for when hiring. This will guide you and help you track candidates’ answers. Develop a set of standardized communication-focused questions to ensure a fair and consistent evaluation process across all candidates.

These questions should prompt the candidates to describe past situations where they used communication skills effectively. Then, encourage the candidates to elaborate on their responses. This allows you to assess their thought process, articulation skills, and ability to provide clear explanations. 

Communication Cues

Pay close attention to how candidates express themselves. Observe their verbal and nonverbal cues like eye contact, body language, and tone of voice. If you want to get a deeper look, ask candidates to give a short presentation during the interview. This can be simulations of real-world scenarios relevant to the position.

You can use that to evaluate the candidates’ ability to structure information, present ideas clearly, and handle questions from a panel. This also helps you to assess technical communication skills relevant to the job. To assess written communication, give candidates short writing assignments relevant to the job role. 

People enjoying talking and working together at a table.

Examples of Essential Communication Skills 


Verbal communication skills are always part of what to look for when hiring for any position. Even with non-voice positions, you will still be talking to these people.

However, especially for client-facing voice roles, aim for candidates with clear and concise delivery. They should be easy to understand, avoiding jargon or overly complex language. Look for a confident and professional tone, too, which inspires trust. 

The best candidates will pay close attention to what others are saying, acknowledging and responding thoughtfully to questions and concerns. They can also adjust their communication based on the audience and situation.

Give special notice to candidates who ask thoughtful questions to clarify information, demonstrate curiosity, and engage in productive discussions.


In terms of written communication, look for strong grammar and punctuation as well as reading ease. The best candidates can convey complex information in a clear and concise manner. They can also adapt their writing style depending on the recipient. A bonus is a strong vocabulary and ability to use words precisely.

Be sure you don’t overlook nonverbal communication skills. Pre-select candidates who make appropriate eye contact to show attentiveness and engagement. Their body language should be positive and open, too. Look for facial expressions congruent with verbal communication. Check that candidates exhibit proper video conferencing etiquette, too, such as muting their microphone when not speaking and dressing professionally.

Additional Skills

The special few will have additional skills.

First, they will show the ability to approach disagreements respectfully and work collaboratively to find solutions.

Second, they will be able to effectively lead meetings. This means keeping discussions focused, ensuring everyone has a chance to participate, and summarizing key points all throughout.

For some positions, the ability to deliver clear and engaging presentations to a larger audience might be important. 

Technical Proficiency and Adaptability

Assessing a candidate’s adaptability to new technologies and troubleshooting skills is crucial for remote and in-person positions alike.

Behavioral Questions

During the interview, ask behavioral interview questions that prompt candidates to describe situations where they had to learn a new technology or troubleshoot an issue. 

Technical Assessments

Consider incorporating technical assessments tailored to the role. This could involve providing simulated software interfaces or common technical challenges faced in the position. Then, evaluate the candidate’s ability to navigate or troubleshoot them.

Live challenges can assess candidates’ ability to adapt to solving new problems and using unfamiliar frameworks. Evaluate their thought process, efficiency, and approach.

Soft Skills

In terms of hiring soft skills, look for indicators that candidates are adaptable. For example, they should show a genuine interest in learning new things and have the ability to explain technical concepts clearly. They should have the capacity to find solutions using available resources and show determination to overcome challenges.

Note that for entry-level positions, a willingness to learn might be more important than extensive technical knowledge. Also, while technical skills are important, don’t categorically overlook less skilled candidates. They might actually align better with your company values, which is important.

In line with this, note that certifications are not always a guarantee of competence. Use them only as indicators of a baseline level of knowledge, and possibly a commitment to professional development.

Four men laughing while freelancing together

Emotional Intelligence and Soft Skills

In the world of virtual teams, physical distance can create barriers to communication and collaboration. This makes emotional intelligence (EQ) more crucial for success.

Emotional Undercurrents

Virtual team members rely more on interpreting verbal cues, tone of voice, and written communication style to understand emotional undercurrents. Strong EQ equips them to decode these signals and respond appropriately. EQ also fosters trust and rapport despite physical distance.

Virtual team members with high EQ can create a sense of connection through active listening, empathy, and positive communication. This leads to a more cohesive and collaborative team environment.

Clarity and Empathy

Of equal importance is how EQ fosters clear, concise, and considerate communication. This reduces misunderstandings and communication breakdowns that can be common in virtual settings.

Moreover, virtual teams with high EQ can navigate disagreements constructively, approaching conflict with empathy and finding solutions that address everyone’s concerns.

In addition, EQ helps virtual team members manage their own emotions and be sensitive to the emotions of others. This can reduce stress levels and prevent burnout, which can be more prevalent in isolated work environments.


Leaders with high EQ can motivate and inspire virtual team members, even from afar. They set a clear vision and communicate goals effectively. They also recognize and appreciate individual contributions and create a positive virtual work environment.

Leaders with strong soft skills can empower their teams and create a sense of ownership over projects. This helps them delegate tasks more effectively and encourage teams to deliver results independently.

Essential EQ Skills for Virtual Teams

Understanding one’s own emotions and how they impact others is crucial for effective communication and self-management. The ability to put oneself in another’s shoes and understand their perspective is essential for building trust and rapport in a virtual setting.

Strong social skills allow virtual team members to build relationships, collaborate effectively, and navigate complex social situations that might arise online. EQ fosters the ability to build and maintain positive working relationships with virtual colleagues and clients, even through digital channels.

Evaluating EQ

Evaluating EQ can be tricky, but if you know what to look for when hiring, you can find the indicators. Ask situational and behavioral interview questions that prompt candidates to describe situations where they used emotional intelligence skills. Ask probing questions to understand their thought process. This reveals their self-awareness and emotional reasoning. Then, analyze their response for empathy, conflict resolution strategies, and emotional regulation. 

You can present candidates with hypothetical scenarios that might relate to the specific job role. Ask them to describe how they would approach and manage the situation. Evaluate their problem-solving skills combined with empathy and communication strategies. Pay close attention to soft skills displayed throughout the interview that can be indicators of emotional intelligence. 

A smiling woman wearing headphones looking at a laptop screen and waving.

Cultural Fit, Work Ethic, and Integrity

Physical distance can create challenges in fostering a sense of team spirit and belonging. This is where culture compatibility becomes even more important for remote teams. A strong company culture is built on a foundation of shared values, beliefs, and goals. When remote team members understand and embrace these values, it fosters cohesion and a sense of working towards a common purpose.

Company Culture

Culture compatibility promotes open and honest communication, too. This is essential for collaboration and navigating potential misunderstandings that can arise more easily in remote settings. A shared culture creates common ground and fosters a sense of psychological safety where team members feel comfortable expressing themselves.

Feeling like part of a team and aligning with company values boosts employee engagement and motivation. Remote workers who feel valued and supported are more likely to go the extra mile and contribute their best work.

When team members share similar work styles, expectations, and communication preferences, it reduces misunderstandings and potential conflicts. This encourages productivity. Still, a culture that values diversity of thought at the same time and encourages healthy debate can spark innovation and creativity. Culture compatibility ensures this diversity is channeled constructively towards achieving team goals.

Assessing Culture Compatibility

Before you can assess fit, articulate your company culture so candidates can self-assess their fit. Ask behavioral interview questions that reveal candidates’ work style, communication preferences, and values. You can also involve team members in the interview process so they can interact with candidates and gauge cultural fit firsthand. 

Assessing Work Ethic

You always want to hone in on candidates who have a strong work ethic and the right attitude towards remote work. To find them, ask candidates to describe past experiences demonstrating their work ethic.

As always, don’t settle for surface-level answers so you can really understand their thought process and motivations. Make sure you contact their references to get insights into candidates’ work ethic and reliability.

Ask candidates about their reasons for wanting a remote position. Ideal responses would indicate a desire for flexibility, self-management, or greater focus. These demonstrate an understanding of the remote work environment.

Be wary of candidates who seem primarily motivated by a desire to avoid a physical workplace. Look also for indicators of the ability to manage time effectively and work independently. 

If feasible, consider offering a short trial period where candidates work remotely on a specific project. This allows you to assess their work ethic and remote work style firsthand. 

a man on a videocall with a woman

Assessing Integrity 

Where physical supervision is limited, integrity becomes more critical to prioritize in potential hires. Trust is the cornerstone of successful remote collaboration. Ask questions that draw out examples of integrous conduct. Look for attitudes that foster a sense of reliability and dependability, which are essential for working effectively on teams.

Look for honesty, a cornerstone of integrity, which encourages open and transparent communication. Team members with integrity feel comfortable raising concerns, sharing ideas, and admitting mistakes.

Honest and ethical employees are less likely to cut corners or engage in misconduct that can lead to costly errors or legal issues. They also embody the company’s values, so look for that, too. Remote teams that display integrity are more likely to build strong relationships. Look for signs of eagerness in this area.


What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 


When you know what to look for when hiring, it becomes a smooth and even enjoyable process. By implementing a combination of these strategies, you can gain valuable insights into a candidate’s communication skills. This is how you identify individuals who can excel in your virtual work environment. Remember also to structure the communication skills assessment to be a positive experience for candidates. Provide clear instructions and avoid creating undue pressure.

Virtual Assistants

Ultimate Hiring Tips for Entrepreneurs: Mastering the Art of Sourcing Virtual Talent

Two people shaking hands to agree to outsourcing.

If you could get all of the best hiring tips in one place, would you grab the chance? If you answered, “Yes,” then you’re on the right page! This post aims to give you our take on the ultimate tips for entrepreneurs to find the best virtual talent. 

Understanding the Hiring Process

Let’s begin with clarifying the distinction between a recruiting and hiring definition. These are both crucial steps in the process of acquiring new talent for your organization, but they serve different purposes. 


Recruiting is an ongoing process of attracting a pool of qualified candidates. It involves activities like building your employer brand, sourcing potential candidates through various channels, and generating interest in your company and open positions.

Recruiting strategies encompass both inbound and outbound efforts. You might attract candidates who apply directly to your job postings, or you might proactively seek out top talent through targeted outreach.

The goal of recruiting is to create a large pool of qualified candidates with the potential to be successful in the role. This may involve considering candidates with a broader range of skills and experiences, assessing their fit with your company culture, and generating their interest in your organization.


Hiring is a specific and short-term process focused on selecting the single most qualified candidate to fill a current vacancy. It involves evaluating the applications and qualifications of candidates from the recruitment pool, conducting interviews, reference checks, and ultimately making a hiring decision.

The hiring process involves a more rigorous evaluation of a candidate’s skills, experience, and fit for the specific job requirements and remote company culture. This might involve assessments, skills tests, and in-depth interviews with various team members.

The goal of hiring is to identify the candidate who best aligns with the specific needs and requirements of the open position. This includes not only technical skills and experience, but also soft skills, cultural fit, and demonstrated potential for success in the role.

The Impact of Employer Branding on Attracting Top Talent

Your reputation precedes you, and it significantly impacts your ability to attract top talent. A strong employer brand acts as a magnet, drawing in highly skilled and experienced individuals who are actively seeking new opportunities. Top talent is more likely to apply to your company if they perceive it as a desirable workplace.

A well-defined employer brand also differentiates you from competitors. Candidates who identify with your company culture and values are more likely to prioritize your positions over others.

A well-crafted employer brand is transparent and authentic, showcasing the reality of what it’s like to work at your company. This fosters trust with potential candidates and allows them to make informed decisions about applying.

Importance of Writing Enticing and Inclusive Job Descriptions

Compelling job descriptions grab the attention of qualified candidates and spark their interest in the role and your company. Inclusive language expands your candidate pool by avoiding gender bias or unnecessary experience requirements. This allows you to focus on the skills and abilities needed for the role, not stereotypical assumptions about who can excel in it.

By using inclusive language, you attract a wider range of qualified candidates. This increases the likelihood of finding the best person for the job, regardless of background. Inclusive job descriptions also demonstrate your commitment to diversity. This appeals to top talent who value working in a fair and equitable environment. 

Hiring Tips for Strategizing the Process

Two women talking to each other over a video call using a laptop.

Knowing Your Company’s Value Proposition

A company’s value proposition is a concise statement that communicates the unique benefits and value your company offers to customers and potential hires. It’s essentially  why someone should choose you over your competitors. 

A well-defined value proposition acts as a guiding light. It quickly conveys what your company does and why it matters. It resonates with potential hires who are looking for a company whose mission and values align with their own. This leads to better recruitment and retention of top talent. When hires understand the value their company delivers, they are also more engaged and motivated to contribute to its success.

The first of all our hiring tips is to clearly articulate your value proposition on your company website and marketing materials. Ensure all existing and potential hires understand it and how their work contributes to delivering that value. Every interaction is an opportunity to communicate and drive home your value proposition. 

Leveraging Current Team Members in the Hiring Process

Your people have professional networks filled with potential candidates you might not reach through traditional channels. By encouraging internal referrals, you tap into a pre-vetted pool of qualified individuals familiar with your company culture. They are therefore more likely to be a good fit for the team dynamic and role requirements. 

Current team members can also provide valuable insights during the interview process based on their firsthand experience. Moreover, when teams feel involved in the hiring process, they become more invested in the company’s success. Referrals can also foster a sense of team ownership and pride in the team’s growth.

Use the following hiring tips to leverage your teams in the process:

  • Establish a formal referral program with incentives to encourage people to recommend qualified candidates from their networks.
  • Involve current team members in the interview process to provide unique perspectives on cultural fit and technical skills required for the role.
  • Solicit feedback from your team members after interviews to gain valuable insight for more informed hiring decisions.
  • Target referral requests to team members with relevant networks based on the open position to avoid overwhelming them.
  • Publicly recognize and appreciate team members who consistently refer strong candidates.

The Role of Social Media and Online Platforms in Vetting Applicants

Social media and online platforms can be a double-edged sword for vetting applicants. While they offer a wealth of information about potential hires, there are also drawbacks and privacy concerns to consider. 

Social media profiles can provide a more well-rounded picture of a candidate than just a resume. You might glean insights into their interests, work ethic, communication style, and soft skills. Online platforms can sometimes corroborate information listed on a resume, such as previous work experience or educational background.

Publicly available content can reveal a candidate’s professional affiliations, industry involvement, and personal brand, too. Look for red flags that might indicate a culture clash or integrity issues that could impact the job.

Respecting Privacy

Be mindful of privacy settings and only access publicly available information. Respecting candidate privacy is crucial. Remember that a social media presence rarely fully represents a candidate’s abilities or work ethic and can therefore be misleading. Be wary of unconscious bias based on a candidate’s online persona. Focus on relevant skills and experience, not personal opinions or social media activity unrelated to the job.

For transparency, clearly communicate in your job postings whether or not you’ll be reviewing social media profiles. Develop a consistent and standardized process for reviewing online information across all candidates. Only consider online content relevant to the required skills and experience for the position.

Crafting the Perfect Job Listing

4 Tips on How to Write a Kick Ass Job Post for a VA

One of our most valuable hiring tips is how to craft job listings that attract qualified candidates and accurately reflect the role. Before you begin, consider how potential candidates would search for a job like this. Include relevant keywords in the title that accurately reflect the responsibilities and required skills. Research popular industry terms and include variations to improve search visibility.

Title and Description

Make sure you write a title that clearly communicates the core essence of the role. Avoid both generic titles and excessive jargon that may confuse applicants. Aim for titles between 4 and 8 words so as not to deter potential applicants from reading further. Highlight the most appealing aspects of the position. This could be growth opportunities, impactful work, or a dynamic work environment. 

Use compelling words to convey the activities involved in the role to spark the applicant’s interest. For example, instead of asking for a Marketing Associate, try “Growth Marketing Specialist.” Change Customer Service Representative to “Customer Happiness Hero.” Try “Business Intelligence Analyst” instead of Data Analyst.

Additional Elements

When possible, weave elements of your company culture into the title to attract candidates who resonate with your values. Showcase the human element of the role. Highlight opportunities for collaboration, creativity, and personal growth. People want to feel like they’ll be working with others and making a real impact.

Instead of just listing duties, use action verbs to paint a picture of a typical day in the role. Move beyond responsibilities and emphasize the achievements made possible by the role. Write with enthusiasm for the role and your company. Your excitement will be palpable to potential candidates.

Interviewing for the Best Hire

We can’t call these ultimate hiring tips without talking about the importance of the vital interview stage.

Before the interview, clearly communicate your company’s mission, core values, and areas of focus for the role. Make sure candidates understand the job description, responsibilities, and required skills for the role. Don’t forget to send clear instructions to the candidate regarding the platform, format, and any materials they should prepare. 

During the interview, create a welcoming and positive virtual environment. Greet the candidate warmly, establish rapport, and smile! Maintain eye contact through the camera to simulate in-person interaction and show attentiveness. Pay close attention to the candidate’s responses, ask clarifying questions, and allow them time to elaborate on their experiences.

Ask questions that speak directly to your required skills and experience. Clarify why each candidate is interested in the position. Target strengths related to the job, and look out for weaknesses, considering whether they can be areas for development and growth.

Prepare behavioral interview questions and understand how candidates would respond using the STAR method (Situation, Task, Action, Result). Look for problem-solving skills and achievements. Take note when candidates give thoughtful answers and additional questions for you.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 

Final Hiring Tips

Be intentional about fostering diversity and inclusion in virtual teams. Top talent is more likely to gravitate to your company if you offer open opportunities. Be flexible in your approach to making the final decision. Try to accommodate candidates’ needs where it doesn’t compromise your needs. 

After choosing the best fit, don’t just ignore everyone else. It’s never an easy conversation, but you should communicate to them that they didn’t make to cut. Make sure you are professional and gracious when delivering a rejection. This begins with doing it as soon as possible. Respect for their time and effort is important. Always thank candidates for applying.

If you can, mention a specific strength or qualification that caught your eye. This shows you reviewed their candidacy seriously. Be honest and concise. If applicable, let them know you’ll keep their resume on file for future openings that might be a good fit. This way, your company will be spoken of within their networks in a positive light.

If you follow these hiring tips, we know that you will be closer to finding that gem of a hire that can propel your business forward.

Virtual Assistants

Hiring Definition Guide for Entrepreneurs and Virtual Teams

A sign on a door that says we are hiring.

What is your hiring definition? Have you noticed that it can be very different from someone else’s idea of what hiring means?

The Greek philosopher Heraclitus once said, “There is nothing permanent except change.” That definitely goes for language, maybe even more than anything else. So, as we grow into new things in the hiring world, we need to clarify what hiring is so we know what we’re doing. This helps us to avoid misunderstandings that can lead to poor decisions and unhappy hires.

Understanding the Hiring Definition in the Modern Workplace

Hiring in the modern workplace has evolved beyond simply filling open positions with resumes and interviews. It’s a strategic process focused on finding the right talent  to  achieve specific business goals in a dynamic and competitive environment. We see a few key characteristics that inform a common hiring definition in today’s workplace.

First, we see a focus on the search for skills and cultural fit. Modern hiring goes beyond traditional experience on a resume. Companies look for demonstrated skills and aptitudes relevant to the specific role, often using skills assessments or tests. Experience also comes into play here. Alongside capabilities is an increased value on cultural fit. They know that this can help ensure compatibility with the existing team dynamic, work style, and company values. 

Second, we see a lot of technology and automation intertwined with human labor. Many larger organizations use Applicant Tracking Systems (ATS). It helps them to screen resumes, filter candidates based on keywords, and manage the application process efficiently. Smaller companies that don’t have many hires tend to rely more on online assessments and interviews. Written test and video conferencing, for example, facilitate remote hiring and allow for a wider talent pool consideration.

Third, companies are more aware of how important branding is. They cultivate a strong employer brand to attract top talent that fits in well. This involves showcasing company culture, employee testimonials, and career development opportunities. Modern hiring, therefore, also focuses on creating a positive candidate experience throughout the hiring process. This includes clear communication, timely updates, and feedback to all applicants. 

The Shift

A lot of this has to do with a shift in the balance of power in the hiring world. Gone are the days when companies held all the cards. Now, companies have to woo the best talent if they want to make good hires. They can no longer simply put up a post and wait. They also can’t simply expect the best of the best to flock to them, each with their best foot forward. Companies need to make efforts to look good themselves.

In turn, a lot of this is due to the rise of the gig economy. This means that a hiring definition often includes a distinction between employees and freelancers and contract workers. Companies that want to fill specialized skills or project-based needs must consider how to attract these talents. Remote work options are also increasingly common. This expands the talent pool, but it also means that hires have more options. It also offers flexibility to both companies and candidates.

Here are a few more things that have changed over the past few decades. Modern workplaces strive for diversity and inclusion in their hiring practices to build stronger teams with wider perspectives and experiences. Companies value agility and adaptability in hires more than just doing the grind. People who can learn new skills and flow with changes are highly sought-after in today’s fast-paced environment. Companies also use more data and analytics to evaluate hiring strategies and track the success of different recruitment channels. 

The Hiring Process Explained

A man remote onboarding another man via a video call using a laptop.

Stages of the Virtual Hiring Process

The virtual hiring process has become increasingly common as technology facilitates remote work and geographically diverse talent pools. Here’s a breakdown of the key stages involved in hiring someone virtually:

Pre-Virtual Interview Stages

Clearly outline the job requirements, responsibilities, and skills needed in the job description. Use online job boards and your company career page to reach a wider audience. Shortlist qualified candidates based on resumes, cover letters, and initial phone screenings.

Virtual Interview Preparation

Ensure you have a reliable internet connection, functional video conferencing software, and a quiet, professional background for the interview. Develop a structured interview format with clear questions aligned with the job description. This ensures a fair and consistent evaluation process for all candidates.

Conducting the Virtual Interview

Dress professionally and maintain appropriate body language to project a positive image during the virtual interview. Minimize distractions, maintain eye contact with the camera, and allow the candidate time to respond to questions. Use the virtual interview to assess the candidate’s skills, experience, cultural fit, and communication abilities. Make sure that you have also taken the time to master virtual communication. This will help you make the most of every interaction.

Optional Additional Assessments 

Depending on the role, consider incorporating online skills tests to evaluate technical abilities or specific software proficiency. For some positions, requesting a sample work project or writing assignment can provide valuable insights into the candidate’s capabilities. Nore, however, than many freelancers sign NDAs, so they may not be able to show you actual samples.

Reference Checks and Background Screening

Contact the candidate’s references to verify their employment history, skills, and work ethic. Depending on the position and company policy, background checks may be conducted to verify qualifications and ensure a secure work environment.

Offer Negotiation and Contract

Present the job offer virtually, outlining the details of the compensation package, any applicable benefits, and your preferred starting date. Once terms are agreed upon, finalize a formal employment contract that outlines the job responsibilities, compensation, benefits, and legal terms of employment.


Develop a remote onboarding process to welcome the new hire, introduce them to the company culture, team members, and equip them with the necessary tools and resources for success. Maintain regular communication with the new hire throughout the onboarding process to address any questions or concerns and ensure a smooth transition.

Continued Support and Evaluation

Schedule regular virtual check-ins with the new hire to provide feedback, answer questions, and offer ongoing support during their initial adjustment period. Conduct performance reviews to evaluate the new hire’s progress, identify areas for development, and ensure they are meeting expectations in the remote work environment.

Advantages of a Virtual Hiring Process

When you go global, you have access to a broader range of qualified candidates, regardless of geographical location. You can also reduces the costs associated with traditional in-person interviews, like travel and venue expenses. Virtual hiring streamlines the hiring process, too, by allowing interviews and assessments to be conducted virtually. This works whether you are hiring remote talent or local talent. This process also enables scheduling flexibility for both interviewers and candidates. 

By following these stages and leveraging the advantages of virtual hiring, companies can attract top talent, conduct efficient interviews, and build successful remote teams.

Key Components of a Successful Virtual Hiring Strategy

People working together at a table.

In today’s digital world, virtual hiring has become the norm for many businesses. To ensure a successful virtual hiring experience, we see a few key components to keep in mind.


First comes preparation. Before you begin, clearly define the skills, experience, and qualifications you want to confirm for the role. This will guide your job description, interview questions, and selection criteria. Craft a compelling and informative job description that outlines the responsibilities, work environment, company culture, and applicable benefits. For example, define whether the work is strictly remote-based or if you require site visits. Develop a structured interview format with clear and consistent questions aligned with the job description. This ensures a fair evaluation process for all candidates.

Before scheduling a meeting, make sure you have the necessary technology and equipment to conduct smooth virtual interviews. This includes a reliable internet connection, high-quality video conferencing software, a professional background, and a functioning webcam and microphone. Provide clear instructions to candidates regarding the interview format, platform to be used, and any preparation materials they might need. For example, do they need to send you a resume or portfolio before you speak?


For the call, both interviewers and candidates should dress professionally. Appropriate body language is also important to project a positive image. Minimize distractions, maintain eye contact with the camera, and allow the candidate time to respond to questions without interruption. Use the virtual interview to assess the candidate’s skills, experience, cultural fit, communication abilities, and problem-solving skills. Look for indicators of success in a remote work environment, such as time management, self-motivation, and proficiency with communication tools.


After the interview, you might want to do some reference checks and background screening. Contact the candidate’s references to verify their employment history, skills, and work ethic. If you’re happy with them, present the final job offer virtually, outlining the details so they can confirm that they understand and accept. Once terms are agreed upon, finalize a formal employment contract that outlines the job responsibilities, compensation, benefits, and legal terms of employment.

Hiring Definition for Virtual Teams

A virtual onboarding meeting.

Unique Challenges

Building a successful virtual team comes with its own set of challenges compared to traditional in-person teams. One of the key hurdles to consider is communication and collaboration. Virtual communication can lack the richness of nonverbal cues and face-to-face interaction, leading to misunderstandings and misinterpretations. Spontaneous brainstorming sessions and informal chats are less likely to happen virtually, potentially hindering collaboration and team spirit. Remote team members might struggle to stay updated on project progress and company news, creating information silos.

Building trust and upholding company culture in this type of environment is, therefore, vital. Remote workers can feel isolated and disconnected from the team, impacting morale and engagement. Building trust and strong working relationships can be more challenging in a virtual environment. It can be harder to instill and maintain a strong company culture when team members are geographically dispersed. This means that you have to make all the more effort to connect intentionally, and keep team members connected, too.

Similarly, managers may have less visibility into employee workloads and daily activities. This can make performance evaluation more complex. The lack of in-person supervision can lead to micromanagement by some managers, hindering employee autonomy and trust. Working across time zones can create scheduling challenges and hinder real-time collaboration, too.


Despite the challenges, there are significant advantages to consider when hiring for virtual teams. Aside from the abovementioned advantages, virtual hires tend to enjoy the flexibility. Virtual work arrangements offer work-life balance, potentially leading to higher job satisfaction and reduced turnover. Studies also suggest that remote workers can be more productive. This is mostly due to fewer distractions and the ability to work during their most productive hours.

If you establish clear communication channels and protocols, you can mitigate the risks of virtual communication breakdowns. Look into email, video conferencing, and project management tools, for example, and establish your expectations to ensure smooth information flow. We recommend that you use online collaboration tools that facilitate file sharing, real-time document editing, instant messaging, and video conferencing. This has helped us tremendously at Outsource School to foster teamwork and collaboration.

Organize virtual team-building activities and social events to help remote workers connect, build rapport, and foster a sense of team spirit. Practice transparent management, provide regular feedback, and recognize achievements to keep remote workers engaged and motivated. Clearly outline work expectations, project goals, and deadlines for virtual team members to ensure everyone is aligned. Recognize the value of asynchronous communication to accommodate different work schedules and time zones within a virtual team.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 


The hiring definition of today’s modern workplace is a comprehensive and strategic process. It considers skills, culture, technology, employer branding, and evolving workforce models. By focusing on these aspects, companies can attract top talent, build strong teams, and achieve their business goals.

Virtual Assistants

Freelance vs Contract Workers: Which One Should You Hire?

Two people shaking hands to agree to outsourcing.

When hiring, every company nowadays needs to consider freelance vs contract workers. Virtual teams are the name of the game in this digital world, and functional distinctions are emerging. In this post, we’ll go over who freelancers and contractors are. We’ll talk about how they are different and how to hire and manage them effectively.

Understanding the Basics

Freelance Key Characteristics and Typical Work Arrangements

Freelance workers, also sometimes referred to as freelancers or independent contractors, are individuals who are self-employed. They work for themselves rather than for a single employer. They offer their skills and services to clients or businesses on a project basis, contract basis, or hourly basis.

Freelancers are responsible for finding their own work, managing their own time, and taking care of their own business expenses. This includes the equipment they use for work, their business taxes, and sometimes the software they need. Freelance work is typically not a permanent position. Freelancers contract with clients to complete specific projects or tasks, and the working relationship ends once the project is finished.

Freelancing encompasses a wide range of professions and skillsets. Writers, designers, developers, marketers, consultants, and many other professionals can find freelance work in their respective fields.

Perhaps the biggest benefit of freelance work is the flexibility and control it offers. Freelancers can choose their projects, set their own hours, and work from anywhere with an internet connection. They have the autonomy to make their own decisions and build their own business, too. Freelancing also opens up a wide range of project and client opportunities, which can keep work interesting. 

The main challenge with freelance vs contract work is income instability. Freelancers don’t receive a regular paycheck and their income can vary depending on the availability of work. Moreover, freelancers are typically responsible for their own health insurance, retirement savings, and other benefits. Freelancing also requires a high degree of self-discipline and time management skills. More than staying alive, freelancers must stay on top of deadlines and often manage multiple projects to be lucrative. 

Contract Worker Key Characteristics and Typical Work Arrangements

Contract workers, also known as independent contractors, share many similarities with freelance workers (defined previously). Both contract workers and freelancers are not regular employees of a company. They are self-employed, and typically don’t have permanent positions. They contract with companies or clients to complete specific projects or tasks. 

The term “contract worker” can sometimes encompass a broader range of workers compared to “freelancer.” Where freelance vs contract workers mainly differ is in their level of control, relationship with clients, and legal classification. 

Contract workers might have slightly less control over their work compared to some freelancers. For instance, a company might dictate specific work hours or require the contractor to be on-site for the project, even though they are not a permanent employee. The specific terms of a contract worker’s agreement with a company can vary, too. In some cases, the level of control a company exerts might be closer to that of a traditional employer-employee relationship, with the key distinction being the temporary nature of the work. 

The legal classification of a worker as a freelancer, independent contractor, or employee often has tax and legal implications. Because the specific distinction can be  blurry, it’s crucial to consult with a tax advisor to understand your obligations. 

Legal Considerations of Freelance vs Contract Work

A lady with a gavel on her desk writing on paper.

The legal distinctions between freelancers and contract workers can be nuanced, and the terms are often used interchangeably. However, there are some key factors that legal professionals and courts consider when classifying a worker.

Freelancers generally have more control over how they perform their work. They choose their methods, tools, and schedule. They are compliant as long as they deliver the agreed-upon results. A hiring entity likely dictates specific work hours and tools or methods for contract workers to use, though. 

Freelancers typically work independently and are not integrated into the company’s structure or hierarchy. They provide their services for a specific project and are not involved in the company’s daily operations. They may still be asked to comply with company culture, however. This is especially true if their work requires them to collaborate closely with others. Contract workers tend to be more integrated. 

Because they are usually considered business owners, freelancers are responsible for their own taxes and benefits, like health insurance. They typically receive a 1099 form from the companies they work with. The classification for contract worker taxes and benefits can vary. It usually hinges on the specific contract and level of control that the company exerts. In some cases, contract workers might receive a W-2 form and be eligible for certain benefits.

Here’s a table summarizing the key distinctions:

A table summarizing the key distinctions between freelance vs contract workers.

Note that the specific legal classification can be complex. Consult with a tax advisor or legal professional to determine the appropriate classification for your specific situation.

Some government agencies also offer resources to help classify workers. For instance, the US Department of Labor has an online classification tool. This keeps you out of trouble when the lines between freelancers and contract workers blur.

Pros and Cons

Advantages of Hiring Freelance vs Contract Workers

Hiring freelancers can be ideal for companies that value independence and a flexible work style. Freelancers often work on a wider variety of projects with different clients. This can be beneficial for companies who want to bring in some exposure from diverse assignments. This is also true in terms of teaching other team members about a faster-paced work environment.

In some cases, hiring freelancers might be a more cost-effective option for businesses. This is because freelancers are generally responsible for their own taxes and benefits. With contract workers, agreements might include some benefits. The freelance marketplace offers a vast pool of talent with niche specializations. This can make the cost of hiring a freelancer more palatable. For example, businesses can find freelancers with unique skills and expertise that might be difficult to source locally. That makes them invaluable. Sometimes, you can only find contractors through traditional hiring channels. Freelancers are all over the internet. 

Note that the specific advantages of freelance vs contract hires can vary greatly. Look at the nature of the work, the contract terms, and the individual preferences of both the worker and the business. Carefully assess your project needs and consider your budget and work style compatibility, too, when deciding between the two.

Disadvantages of Hiring Freelance vs Contract Workers

While freelancers offer benefits like the above, there are also some drawbacks to consider when comparing them to contract workers. 

Freelancers are self-directed, so managing their work can be more challenging. You might have limited oversight over their daily tasks and work schedule. This can be a concern for projects requiring strict adherence to specific protocols or deadlines.

Clear and consistent communication is crucial when working with remote freelancers. Time zone differences and asynchronous communication can create challenges in collaboration and project management. This is not true of contract workers, who are usually more readily available for real-time communication.

The quality of work can vary significantly among freelancers. While platforms and portfolios can help assess skills, in-depth screening and reference checks are important. This ensures that freelance hires possess the necessary experience for your project. Sharing confidential information with freelancers also requires strong security protocols. Consider putting non-disclosure agreements in place to mitigate security risks. 

Freelancers might have different work styles or approaches compared to your in-house team. Ensuring consistency in quality, tone, and formatting across projects can require additional effort and clear communication. 

Consider, as well, availability for ongoing projects or future collaborations, since freelance workloads fluctuate. They might prioritize other clients with more urgent needs if you don’t have a standing agreement, disrupting your project continuity. When that happens, transitioning the work to a new freelancer can be time-consuming and disruptive. This is especially true if a project requires institutional knowledge specific to your company. A contract worker who might be integrated more closely with your team can be the better option here.

Carefully weigh the trade-offs between freelancer advantages and potential  management challenges. For projects requiring strict control and long-term collaboration, contract workers might offer the greater advantage, but not always.

Hiring Process and Best Practices

People talking and shaking hands around a work table.

Before hiring, clearly identify the skills, experience, and deliverables you need for the project. This will help you target the right talent pool and write clear job descriptions. Consider the level of control you require and the benefits you’re willing to offer. Use a combination of methods like freelance platforms, professional networks, and job boards to find qualified candidates. 

During the hiring process, clearly and concisely outline the project scope, deliverables, timeline, payment terms, and required skills. Screen candidates thoroughly by reviewing portfolios, conducting interviews, and checking references. This is how you can evaluate skills, experience, and cultural fit before doing a trial run.

Always formalize the hire with a written agreement. Specify the scope of work, payment terms, ownership of intellectual property, confidentiality clauses, termination clauses, and the like. Set clear expectations on project goals, deadlines, milestones, and communication protocols, too, to avoid misunderstandings. Establish regular communication channels and touch points to keep the project on track. Maintain communication to address concerns promptly. Offer constructive feedback throughout the project duration and provide resources and support as needed.

Take advantage of freelancer tools and platforms to streamline the hiring and management processes. Consider starting with a smaller project to assess a freelancer or contract worker’s skills and compatibility. Then you can more safely commit to a larger engagement later. 

Management and Collaboration

Effective management of freelance and contract workers is crucial to ensure successful project completion and positive working relationships. 

Integrate all hires through proper onboarding. Invest the time to familiarize them with your company culture, project goals, workflows, and communication protocols. Provide clear documentation and resources to get them started quickly. Give them a detailed project scope document specifying deliverables, milestones, deadlines, and acceptance criteria. This minimizes confusion and ensures everyone is on the same page.

Set clear and achievable deadlines considering the freelancer’s workload and the complexity of the project. Factor in buffer time for potential revisions. Implement regular feedback mechanisms to provide constructive criticism and course corrections throughout the project. This improves quality and ensures alignment with expectations. Establish clear quality assurance processes to review deliverables and ensure they meet the agreed-upon standards before final acceptance and payment. 

Define payment terms in the contract, including payment schedule, milestones tied to payments, and payment methods. Consider using online payment platforms for secure and timely transactions. If you’re doing hourly projects, establish clear time tracking procedures for accurate billing. Reliable payment builds trust and encourages long-term collaboration.

Respect and appreciation go a long way. Treat freelancers and contract workers with dignity and thank them for their contributions. Value their expertise and communicate openly throughout the project. Implement periodic performance reviews and identify areas for improvement in the working relationship.

If you find a talented freelancer or contract worker, develop a positive working relationship to encourage ongoing collaboration. Most freelancers will commit if they see the advantage in building loyalty with you. If a freelancer or contract worker performs well, express your interest in working with them again on future projects. Building a pool of reliable freelancers can streamline your workforce management. This way, you get all the advantages of their broader experience and knowledge plus the stability of contract hires. Consider offering opportunities for professional development or skill-building resources to your freelance and contract worker network, too.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

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Hiring freelancers and contract workers can be a rewarding experience for businesses  of all sizes. By following these best practices, you can increase your chances of finding  qualified talent and building successful working relationships. Then you can manage projects effectively over the long term.  

Virtual Assistants

Freelance Invoice Templates: Streamline Your Payments with Ease


A lady typing a freelance invoice template on a laptop.

Having a good freelance invoice template for each service or set of goods you provide can be a game changer. Templates go a long way towards helping you streamline payments and declutter your workload. But not all templates are created equal, and not all tools are really going to help you. 

In this post, we’ll go through the basics of choosing the right freelance invoice template for each area. We’ll also get into the tools that go along with them and how you can get started using them seamlessly.

Understanding Freelance Invoice Templates

A freelance invoice template is a pre-designed document that serves as a standardized format for creating invoices you send to clients for the services you provided. It acts as a record of the financial transaction and ensures clear communication about the details and cost of your work.

Most importantly, templates simplify invoice creation. They save you time and effort compared to creating invoices from scratch every time. The pattern also ensures consistency in the look and professionalism of your invoices across all clients. A polished and professional image is good for any business. It demonstrates to clients your attention to detail and strengthens your credibility with them. 

This pattern can also provide transparency and clarity. You can clearly outline the services rendered every time, including descriptions, quantities, or rates. When you transparently communicate the total amount due, including any applicable taxes or fees, clients feel more at ease. The template also helps you to avoid confusion or disputes regarding payment expectations.

Digital templates and records can streamline record keeping. You have a standardized format for storing and organizing your invoice records for future reference. This also simplifies tax filing and accounting processes by having clear documentation of your income. 

Key Components of an Effective Invoice Template

The first section of any invoice template is the Header. It should include your business information. Add your business name and logo, prominently. Then add your contact details below that, such as your business phone number, email address, and website URL.

The next section is for Client Information. Clearly state the client’s name and contact information, including the contact person for invoicing. Make sure a unique invoice number is also clearly visible, for easy reference. This is usually placed to the right of the client’s information. Add the date that the invoice was issued under that.

Then comes the Body section. This is where you will have the bulk of your content. The main part of this section is the Description of Services. Clearly list the services you provided for the client. Be specific and include details like project name, deliverables, or time spent. Consider using line items for multiple services. Next to that, include columns for quantity, unit rate (e.g., hourly rate), and the extended amount for each service. Then have a more prominent subtotal calculated, which is the total amount due before taxes or discounts.

If you have applicable taxes and discounts, put these as separate line items. Then show the amount or percentage. Finally, prominently display the total amount due so the client can see at a glance what they owe. 

Below the details is the section for Payment Information. Clearly state the date by which the full payment is expected. Then outline your accepted payment methods and any specific payment terms you offer or demand, like late fees. You can include a Notes section below this for any additional information that’s relevant to the invoice. Finally, consider creating your template in a format. This will allow clients to easily fill in payment information, if necessary.

Benefits of Using Freelance Invoice Templates

Two men shaking hands over a document.

Time Savings

In the fast-paced world of freelancing, saving time translates to increased productivity and potentially more income. Freelance invoice templates can significantly reduce the time you spend on administrative tasks. 

Primarily, you reduced invoice creation time dramatically. With a pre-designed template,  you simply fill in the details for each project. This eliminates the need to recreate basic information like your contact details, payment terms, and invoice layout. Templates establish a consistent structure for your invoices, making the process of adding project details, calculating amounts, and generating the final invoice a breeze. This repetitive task becomes much faster and less error-prone. In line with error reduction, templates mitigate manual data entry errors by providing standardized formulas for calculations like totals and taxes. A standardized format makes proofreading your invoices a breeze, too. 

By having a template readily available, you can quickly generate and send invoices after project completion. Templates make it easier to track outstanding invoices and follow up with clients efficiently if payments are delayed. This ensures faster payments and improved cash flow. Some invoicing software with built-in templates allows you to schedule automatic payment reminders. These gentle nudges can encourage timely payments without being overly intrusive.

You can save frequently used client information, project descriptions, and service rates. With a few clicks, you can pre-populate these fields. Invoice templates can also indirectly contribute to efficiency by presenting accurate information. This minimizes the need to clarify details with clients, leading to less back-and-forth communication.

Many templates offer customizable features, allowing you to tailor them to your specific needs. You can add your logo, branding elements, or include specific service categories while maintaining the core structure, saving time compared to fully designing an invoice from scratch.

Professionalism and Brand Consistency

Projecting a professional image is key to attracting and retaining clients. Invoice templates can contribute significantly to your professional presence and brand consistency. This reinforces your brand identity across all client interactions. Consistent branding through templates also helps clients remember you and your business. Familiarity builds trust and fosters a stronger professional relationship.

Well-designed templates present information in a clear and organized manner. Clients can easily understand the services rendered, associated costs, and payment terms. This avoids confusion and fosters trust in your business practices.

Templates ensure a consistent, polished look for your invoices, replacing potentially haphazard self-made versions. This conveys attention to detail, creating a positive impression on clients. Minimizing the risk of errors like typos or inconsistencies in formatting also demonstrates your commitment to accuracy. This is crucial in financial matters.

A well-designed template can set you apart from other businesses who send generic or unprofessional invoices. This can give you a competitive edge and position you as a reliable and trustworthy service provider.

Selecting the Right Invoice Template

Choosing the right invoice template for your business hinges on understanding your specific needs and workflow. Below are some basic areas to consider.

Service Offering

If you offer a single service or have a limited number of service categories, a basic template might suffice. Just make sure you have clear descriptions and rates. If you offer a wider range of services or custom project packages, consider templates that itemize services and quantities.

Tone and Branding

For working with individual clients, a template with a professional yet somewhat friendly tone might be appropriate. For corporate clients, a more formal template that adheres to any specific invoicing requirements they might have is advisable. Either way, choose a template that allows for customization so you can maintain a strong brand identity. 

Payment Terms

If you have standard payment terms (e.g., net 30 days), a basic template outlining due dates might be sufficient. If you offer discounts, late fees, or deposit requirements, consider a template with dedicated sections for these details.


While the core components of a good invoice template remain consistent across industries, there can be some advantages to considering industry-specific templates. Clients in different industries might have specific expectations regarding invoice formats and information included. An industry-specific template ensures you’re providing the details they’re accustomed to seeing. For example, certain industries have specific terminology or breakdowns required on invoices. A construction client might need to include material costs on their invoices. A graphic designer might itemize software licenses used in the project.


If you work with clients who use different currencies, make sure that you can input the correct currency symbol. Decimal placement can also vary depending on the currency, so check that. If you use a payment gateway that supports multiple currencies, consider a template that integrates with it for easier processing. You might also need to include a note on the invoice about exchange rates used if you convert fees. Prioritize clarity in presenting the amount due in the client’s currency.

If you need to charge taxes based on the client’s location, choose a template with a customizable tax field. Consult with a tax advisor to ensure you comply with relevant tax regulations when working with international clients.

Additional Considerations

Make sure that the template you choose allows for all the customization options that you need. If you use invoicing software or outsource billing services, ensure the template integrates seamlessly to avoid data entry hassles. Consider as well if your needs might evolve in the future. Choose a template with enough flexibility to accommodate potential growth in your services or client base. 

Sample Freelance Invoice Templates

Here are some sample freelance invoice templates to give you an idea of the format and information you typically need.

Invoice Simple

Invoice Simple freelance invoice template


Wave freelance invoice template


Wise freelance invoice template

Recommended Freelance Invoice Template Tools


FreshBooks offers a variety of pre-made templates for different industries and purposes like simple invoice, contractor invoice, consulting invoice, etc. You can add your logo, branding colors and other details to personalize them. You get options for setting payment schedules, adding late fees and more. The free templates lack the advanced features of FreshBooks software itself, though. 

Invoice Ninja

Invoice Ninja provides a variety of pre-made invoice templates designed for different industries and purposes. These templates are free to use and can be customized to fit your specific needs. You can find templates for consulting, freelance work, products, services, and more. You can add your company logo, branding colors, and other details to personalize them.

If you prefer a more unique design, Invoice Ninja allows you to create your own invoice templates from scratch. You can use their drag-and-drop interface to add your logo, text, images, and other design elements.


Like FreshBooks, you can download free templates or create your own within the software. The QuickBooks library of free invoice templates includes various formats, like Word, Excel, and PDF. These templates cater to different business needs, such as simple invoices, contractor invoices, consulting invoices, etc. You can personalize these templates with your company logo, branding colors, and other information. Note that these also lack the advanced features available within QuickBooks software itself.

Zoho Invoice

Zoho Invoice offers a collection of pre-made invoice templates designed for different industries and purposes. These templates cover a range of scenarios, from simple product sales to service-based invoices. You can personalize these templates with your company logo, branding colors, fonts, and other design elements to create a professional look. If you prefer a more unique design, Zoho Invoice allows you to create custom invoice templates from scratch. They provide a user-friendly interface for adding your brand elements and tailoring the layout to your preference.

Legal Considerations and Compliance

Invoices are more than just requests for payment. They are legal documents that serve as records of transactions. To avoid any issues, ensure that your invoices comply with legal requirements. 

Proper identification is the first essential elements for legal invoices. Use your full legal business name, address, and contact information. The same goes for your customer’s details. Assign a unique identification number to each invoice to simplify tracking and record-keeping for both parties. Clearly mention the date the invoice is issued to establish the timeline of the transaction. Clearly specify the due date for payment and your accepted payment methods. You can also mention late payment penalties to encourage timely payments. These details are crucial in case of potential legal disputes. 

Provide a clear and detailed description of the products or services offered. Clearly state the quantity of items sold or the hours of service provided, along with the corresponding unit price. If you’re subject to sales tax, VAT, or GST, include the relevant tax rate and the total tax amount on the invoice. Accurate tax information is vital for compliance with tax regulations.

Make sure to consult with a local accountant or legal professional to ensure compliance with any regional regulations. Maintain copies of your invoices for the legal record-keeping period as mandated by your country or state.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 


Freelance invoice templates are amazing tools in and of themselves. They help you maintain a consistent visual style that aligns with your brand identity. Always remember to use clear language that shows professionalism but also your business’s style and character. Make it easy for your client to understand who you are and how well you can serve them. Yes, this is an invoice, but we know that you should never miss a chance to maintain a client’s confidence in you!

Virtual Assistants

Top Freelancer Tools for 2024: Boost Your Virtual Team’s Efficiency

A woman working on a laptop using freelancer tools to help her. Every business that hires virtually needs to know the best freelancer tools available. The right tools are absolutely essential for boosting virtual team productivity. Without them, work can become painfully complicated. This usually ends up hurting team morale and job satisfaction, too. That’s why we decided to give you our approved list of the top tools for 2024. We believe that they can help your teams stay at the top of their game. Moreover, they can keep the smiles on their faces, too!

Selecting the Right Freelancer Tools

Freelancer tools come in all shapes and sizes, but there are some key features that can make a big difference in your productivity, efficiency, and overall success. 

Project Management

Probably the most valuable freelancer tools we have used help us incredibly in the area of project management. With proper task management, our virtual teams are able to break down projects into manageable tasks. Then they can easily assign deadlines, and accurately track progress visually. Some of the features we like best are Kanban boards and Gantt charts.

Team collaboration is always smoother when you have tools that facilitate communication. This is very true for collaboration with clients, too. Features like shared workspaces, file sharing, and in-app chat can keep everyone on the same page. When you add in time tracking, you can monitor how much goes into different tasks and projects. This means that you will always accurately bill clients, which does wonders in the realm of loyalty. Moreover, this is valuable data you can use to improve time management and productivity across the board.

Communication and Client Management

Clarity in every interaction is the trademark of a truly professional company. If you can create professional proposals and estimates, you can show potential clients how well you will take care of them. They are more likely to trust you if you can properly outline project scopes and costs. To go another level up, choose a tool that offers secure file sharing and in-app messaging on their channel.

In addition, a good tool will make generating invoices and getting paid easier. In the best cases, the process is fully automated with options for customization as needed. This relieves the headache of tracking payments. One of the top features we look for is secure payments through whatever platform we invoice on.

On the subject of file sharing and storage, many available tools provide this for both project management and communication. It’s a common combination in the top tool picks. This makes organization and productivity just that much better. This way, you can securely store and share files with clients and collaborators on one platform. If they can provide cloud storage integration, that’s the best upgrade because it allows for access from anywhere.

We cannot do without easy and effective scheduling at Outsource School. So, we always recommend using a calendar system that helps you manage appointment bookings. Better yet, integrations with task management so you get deadline reminders. We love all the automation we can get, especially when it comes to repetitive tasks. This saves so much time and effort you wouldn’t even believe it until you saw it. Imagine not having to send follow-up emails or generate reports, just for starters. 


A digital map representing cybersecurity to prevent a path of attack.

You always want to have strong data encryption on whatever platform you choose. This protects your data and your clients’ data, both at rest and in transit. A very useful bonus is granular access controls. This allows you to restrict who can access and modify information at different levels. At the very least, look for two-factor authentication (2FA).

Check that the platform does regular security updates. This demonstrates a commitment on their part to vigilance and patching vulnerabilities promptly. Consider your industry or the type of data you handle. Depending on these, the platform might need to comply with specific data security regulations (e.g., HIPAA, GDPR).


In terms of scalability, your first consideration is pricing tiers. A tool that has them will allow you to start small and grow into better levels as you need them. Remember that different freelancer tools come with various pricing plans. Look deeper than what fits your budget and offers the features you need in the short-term. Many tools offer free trials, so you can try them out before committing to a paid plan.

The platform you choose should also be able to accommodate your growing needs. Consider things like adding more users, managing increased data volumes, and handling more complex tasks. This includes the ability of the platform to maintain good performance as your usage scales. Signs of greater flexibility include customization options within the different service tiers to adapt to your specific needs.


A feature-rich tool needs to be user-friendly, too. This depends on your team’s specific flow. For example, some people want a mobile app, or a web interface optimized for mobile devices, for flexibility and convenience. Prioritize this if you need to manage projects and tasks on the go. 

Consider what tasks you struggle with the most and what features would be most beneficial for your workflow. For instance, we like a clean, intuitive interface for easy navigation. This ensures smooth adoption by new users with varying technical skills. We hire virtually for a lot of positions, and we want to focus on core skills more than what tools they know. Of course, comprehensive tool documentation, tutorials, and customer support are great to have in case someone needs to troubleshoot any issues with the platform’s functionality.

Integration capabilities with existing systems

Look for tools that integrate with other apps you use, such as accounting software, design tools, or communication platforms. The ability to integrate with other tools and applications you use can improve your workflow and avoid data silos. Integration capabilities improve efficiency by automating data flow between systems. This eliminates manual data entry, reduces errors, and saves time. Automatic data transfer ensures consistency and accuracy across all your applications, too. You can streamline workflows seamlessly between different departments using integrated systems. I turn, this consolidated data provides a holistic view for better decision-making.

Ensure the platform offers robust APIs or pre-built integrations for your essential tools. APIs allow two applications to communicate and exchange data programmatically. Pre-built connectors are often user-friendly and require minimal technical expertise to set up. You can also get basic integration by importing or exporting data files between applications in a common format like CSV. This method is less automated but can be useful in a pinch.

When evaluating integrations, consider which specific integrations would be most beneficial for your workflow. Ensure the integration methods adhere to robust security protocols to protect sensitive data. Some integrations might require additional fees or upgrades, so make sure they are actually going to make things better. 

Top Freelancer Tools for 2024

Project Management


Asana website home page screenshot.

Asana is a project management tool that can also be used for communication. It allows you to create tasks, assign deadlines, and track progress. You can also use Asana to chat with clients and team members about specific tasks. Asana is a great tool for keeping track of project deadlines and ensuring that everyone is on the same page. It can also be used to document project history and communication. Asana offers a free plan with limited features, as well as paid plans with more features and storage.

Monday.cpm website home page screenshot. is a highly customizable project management tool that allows you to create unique boards tailored to your specific workflow needs. It offers a wide range of views like Kanban boards, calendars, and timelines. It also includes features like time tracking, automation, and integrations with various tools.’s high level of customization allows you to adapt the platform to your specific freelance processes. The visual dashboards provide a clear overview of project progress. offers a free plan with limited features for individuals, and paid plans with increased functionality and storage for teams.


Communication is a vital aspect of any successful freelance business. Here are some of the top freelancer tools for communication that we recommend. The right one can help you stay connected with clients, collaborate on projects, and ensure a smooth workflow.


Screenshot of Zoom website

Zoom is a popular video conferencing tool that allows you to hold meetings with clients and team members. It offers a variety of features, including screen sharing, recording, and breakout rooms. Zoom is great for face-to-face communication, especially when you cannot meet in person. It can also be used for presentations, training sessions, and other collaborative activities. Zoom offers a free plan with limited features, as well as paid plans with more features and meeting minutes.


Trello website home page screenshot.

Trello is a visual project management tool that uses boards, lists, and cards to represent tasks. It can also be used for communication by adding comments and attachments to cards. It’s great for visually representing projects and workflows. It’s also a great way to collaborate with clients who are not familiar with project management tools. Trello offers a free plan with limited features, as well as paid plans with more features and storage.

Time Tracking 


Clockify website home page screenshot.

Clockify is another user-friendly time tracking tool with a clean interface. It allows you to track time manually or use a desktop app for automatic tracking. Clockify offers features like timesheets, project budgeting, and reporting to help you visualize your time usage and identify areas for optimization. Clockify is a good all-around time tracking tool with a generous free plan that includes unlimited projects, trackable time entries, and basic reporting. Paid plans offer additional features like project budgets, team tracking, and customizable reports.


A screenshot of the Hubstaff website home page.

Hubstaff offers time tracking, screenshots, activity monitoring, and project management features in one platform. It can be helpful for freelancers who want to track not just time spent but also activity levels to ensure productivity. Hubstaff provides a comprehensive solution for time tracking, activity monitoring, and team management. The free plan offers basic features, and paid plans provide additional functionality like detailed reports and screencast recordings.

File Sharing and Collaboration

Google Drive

Google Drive website home page screenshot.

Google Drive offers cloud storage for various file types, including documents, spreadsheets, presentations, and more. Real-time collaboration features allow multiple users to edit files simultaneously, and version control ensures everyone is working on the latest version. Google Drive integrates seamlessly with other Google Workspace tools like Docs, Sheets, and Slides, facilitating a smooth workflow. The free plan offers a decent amount of storage, and paid plans provide additional storage for extensive file needs. Security features might be less comprehensive compared to dedicated business solutions.


Dropbox website home page screenshot.

Dropbox is a popular cloud storage service with robust file sharing and collaboration features. You can easily share files and folders with clients, set access permissions, and track file activity. Dropbox also offers real-time document collaboration and version control. Dropbox offers a user-friendly interface and is known for its reliability. The free plan provides basic storage, and paid plans offer increased storage and team collaboration features. Free storage space might be limited for extensive file sharing needs.

Financial and Invoicing 


FreshBooks website home page screenshot.

FreshBooks is a user-friendly invoicing and accounting software specifically designed for freelancers and small businesses. It allows you to create professional invoices, track expenses, manage client information, and accept online payments. FreshBooks also offers basic reporting features to analyze your income and expenses. FreshBooks is known for its intuitive interface and ease of use, making it a great option for freelancers new to invoicing software. The free plan offers basic features for a limited number of clients, and paid plans provide more features and higher invoice limits.


Xero website home page screenshot.

Xero is a powerful accounting software solution suitable for freelancers and businesses with complex financial needs. It offers comprehensive invoicing, expense tracking, bank reconciliation, inventory management, and financial reporting features. Xero also allows for payroll processing and integrates with various business apps. Xero is a robust solution ideal for freelancers who manage complex finances, have a high volume of invoices, or plan to grow their business significantly. The features and functionality come at a higher cost compared to some of the other options on this list.

Combination Tools


Slack website home page screenshot.

Slack is a popular messaging platform that offers a variety of features specifically designed for teams. It allows you to create channels for different projects or clients, share files, make video calls, and conduct polls. It’s a great tool for staying organized and keeping track of conversations with multiple clients. It’s also a great way to build relationships with clients and collaborate on projects in real time. Slack offers a free plan with limited features, as well as paid plans with more storage and functionality.


ClickUp website home page screenshot.

ClickUp is a powerful all-in-one project management tool offering a wide range of features. It includes task management with Kanban boards and mind maps, time tracking, team chat, document collaboration, goal setting, and reporting. ClickUp’s versatility allows you to manage projects of all sizes and complexities in a single platform. The free plan offers a generous amount of storage and features, making it a great option for freelancers starting out. ClickUp offers a free forever plan with limited features, multiple paid plans with increasing storage and functionality, and a custom enterprise plan.

Integrating Freelancer Tools into Your Business

Once you’ve chosen the right freelancer tools for your needs, effectively integrating them into your workflow is crucial to maximize their benefits. Below are some key considerations for successful integration.

Identify Your Workflow

First, map out your typical client workflow. From initial contact to project completion and invoicing, identify the steps involved and the tools that can improve each stage. Then, consider how you will communicate with clients. Integrate your communication tools (e.g., Slack) with project management tools for a centralized view. Be sure to explore automation features within your tools to streamline repetitive tasks.

Leverage Integrations

Many tools offer built-in integrations with popular platforms. Use these integrations to create a seamless flow of information between your tools. You can also use Zapier or similar automation tools if direct integrations aren’t available. Zapier also works to automate specific workflows like transferring data from a time tracker to an invoice.

Standardize Your Processes

Establish consistent procedures for using your chosen tools. This ensures everyone understands how to use them effectively. Create templates for invoices, contracts, or project proposals to save time and maintain consistency. Document your workflows to help onboard new team members and ensure everyone stays on the same page.

Prioritize Data Security

Understand the data security features offered by each tool. In addition, enforce strong passwords and two-factor authentication across all your tools. Don’t simply rely on cloud storage. Regularly back up critical information locally.

Training and Adoption

Provide training for yourself and any team members on the new tools and workflows. Encourage feedback from your team and continuously evaluate as your business grows or your needs change. Reassess your chosen tools and integrations to ensure they continue to meet your requirements.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 


When choosing freelancer tools, always read reviews. See what freelancers who actually use them are saying before making your decision. Ask your team members, too. Their input is invaluable. By considering all the feedback, your specific needs, and the key features presented, you can choose the right tools. This will help you to streamline your workflow, boost team productivity, and impress clients.

Virtual Assistants

Freelancer vs Self Employed: Understanding the Difference


A freelancer vs self employed man typing on a laptop at a desk.

Is there a real difference between a freelancer vs self employed individual? Here, we will define these two similar, yet nuanced, terms. You get to know the benefits and drawbacks of each and other tips and considerations before hiring. 

Definitions and Key Differences


Freelancers are individuals who do not work under a company or organization and earn a per-job income. Freelancers tend to work for multiple clients and can decide how much of a workload they want to take on. The type of work is usually short-term or project based. In terms of client relationships, they can interact with clients directly. However, some also work with an agency who interacts with clients on their behalf. This broad term encompasses multiple industries, skill levels, and specializations. Some freelancers have an array of skills within their respective field. Others focus on niches and prioritize honing their expertise in a single area. 

Self Employed

Many consider the term “self employed” synonymous with entrepreneur and business owner. While less traditional, freelancers have proven that they too belong in this category. What’s the difference? Self employed professionals (SEPs) can run their business with a greater level of autonomy. They have control over multiple aspects of their work. They can choose their hours, their work methods, and the type of work they do. 

Additionally, while freelancers tend to work alone, SEPs may hire other staff members. They also tend to work on long-term projects. They also interact with clients directly, though they may hire someone else to do this job as well. The self employed, by contrast,  rarely market their individual skills. They tend to focus on growing their brand as a company and what they have to offer as an entity.

Pros and Cons of Hiring Freelancers


There are several advantages to hiring freelancers for project-based work. Mostly, it relates to their flexibility and specialized skillsets. For one, you can find a freelancer that fits your budget and charges only the hours you need them to. This means you can hire someone as needed and scale only when necessary. You can also hire by skillsets and target hires to fit your niche needs.


However hiring on a per-project basis also has its disadvantages. These potential drawbacks include limited availability and continuity concerns. Freelancers tend to take on more than one client at any given time. This means they may only accept part-time offers. If you are looking for a freelancer who can work for you full time, that narrows down your options quite a bit. Otherwise, you might have to add a couple dollars to their rate. 

Another issue involves the challenge of maintaining consistent quality. Everyone works differently with varied work styles and methods. If you’re hiring different freelancers for different projects, you may run into problems with uniformity. Not only that, but transitioning to another freelancer can also be difficult. Compared to SEPs, there is a real risk of freelancers bailing mid project. 

A man gesturing with his hands in front of a laptop screen.

Pros and Cons of Working with Self Employed Professionals


The benefits of engaging self employed individuals for ongoing needs involve consistency and dedication. Long-term contracts are more common if you go with this option.

What happens if you complete a project and then choose to hire them again? While you might end up working with different freelancers the second time, you don’t have to worry about consistency as much with SEPs. This is because they usually have standard operating procedures and internal quality checks. Additionally, in contrast to freelancers, you are more likely to have the full attention of your self employed partners.


With SEPs, you’re looking at higher rates for higher quality service and stability. They can also be less flexible with pricing and services. SEPs often require legal contracts to proceed with bigger projects, which can be good for you both. However, if you want to maintain the flexibility that you have with freelancers, it can be challenging. This is because a contract protects the SEP’s pay. You can’t just close the project at any point without fulfilling the obligations of the contract. Just make sure that you are committed to whatever project you are signing a contract for, and all the inclusive terms.

Legal and Financial Considerations

A lady with a gavel on her desk writing on paper.

In a partnership, there’s usually a contractual agreement of shared profits between parties. How the split happens and how much is up for negotiation. Now if you compare freelancer vs self employed in this area, the former usually doesn’t have this. Freelancers usually only get compensation for the work itself and not the profits their work may earn the company. 

In terms of taxes, freelancers are in the same category as SEPs as far as US tax law is concerned. They have the same tax rate of 15.3% which includes Medicare and Social Security. Hiring companies are not liable to withhold these in both cases. Note that this may not be the standard universally. Companies are also under no obligation to provide worker benefits to freelancers or SEPs.

In terms of compliance, the best advice we can give is simple:

  • Identify the regulations
  • Create a plan and monitoring system for compliance
  • Train workers in compliance

How to Decide What You Need

When choosing a freelancer vs self employed individual, you need to establish guidelines that help you assess your business needs. Determining your operational requirements will help you select the best fit for your projects. Here are some factors you might want to consider before deciding: 

  • Project duration – Is it a short-term or long-term project? Is it one-off or do you need continued support after? 
  • Skill level – Are you looking for entry level talent, niche specialization, or a level of polish? Freelancers can provide a lot of flexibility in this area. On the other hand, you might consider SEPs for their unique services, style, aesthetic, etc. 
  • Budget – You can find freelancers at almost any price point. This tends to scale with their skill and experience level, specialization, and project scope. However, working with organizations tends to cost more. In exchange, you get something more reliable with a larger scope of services and support. On another note, financial projections can help you decide which investment is more feasible and profitable in the long-term. 
  • Long-term goals – Which decision will help you reach your company goals, mission, and objectives? Are you looking for longevity in partnership?

The Hiring Process

Here’s our checklist for finding, vetting, and contracting freelancers for your projects:

  • Create comprehensive job listings and job descriptions. This may require some research but you don’t have to make one from scratch. There are a lot of templates out there that can help you define and determine roles, responsibilities, and qualifications. 
  • Create a comprehensive list of interview questions. You can consider this part two of your vetting process. As you determine your needs, you’re going to want to tailor the questions to them. This list of questions will help you narrow down the best candidate. 
  • Research Platforms – There are many blog sites that help compile lists of reputable sites to find talent. In fact, we’ve made several lists you may want to check out after this one. See also: 11 Best Websites to Hire Latino Virtual Assistants for Your Business.
  • Vet through resumes, cover letters, ratings, and reviews – These help you find a trustworthy, enthusiastic, and competent hire.

You also need a set of guidelines before establishing partnerships and agreements. Entities enter into partnerships because both parties have something to gain from it. However, selecting the right partner is more than just finding someone who can help you make more money. You need to consider their mission, vision, values, and work ethic. Aligning these is crucial for a stable work relationship, brand consistency, and consistent quality output. 

Contracting is another matter. Creating contracts with freelancers may not require a lawyer. However, you should have a lawyer present when creating a partnership with SEPs and their respective organizations (if any). These agreements clarify the terms like profit-sharing and decision-making responsibilities. They also protect from potential liabilities on both sides. 

A computer screen and mobile phone screen showing virtual meetings via group video call.

Managing Your Virtual Team

Excellent project and team management begin with effective communication. Here are a few tips to help you maintain a strong working relationship with both freelancers and self employed individuals.

  • Provide all the tools, guidance, and information they need off the get-go
  • Schedule regular updates and progress checks
  • Set up communication channels early on and create feedback loops

Part of effective team management also involves knowing how to use the tools and technologies to support collaboration and productivity. This includes tools like Slack, Asana, Trello, and more.

Frequently Asked Questions

How do intellectual property rights vary between hiring a freelancer vs self employed professional?

Generally, freelancers and SEPs hold the rights to their created works. That is, unless there are stipulations within a contract or partnership agreement that say otherwise. For instance, a contract may state that freelancers own IP rights until they receive their full compensation. In partnerships, both parties usually have joint ownership. 

What are the best practices for resolving disputes with freelancers or self employed individuals?

First, step up and take responsibility first for your part in the dispute. Next, set a meeting to discuss what went wrong. Troubleshoot together to find a solution. If you had a good thing going, try to reconcile and save the partnership. If not possible, at least do your best to complete the project on good terms. 

Can I hire a freelancer or self employed professional from another country, and what are the implications?

Absolutely! A lot prefer to hire remotely because of the benefits of outsourcing, such as flexibility, scalability, and cost savings. Though there are also drawbacks, such as cultural differences, time zones, and communication challenges. 

How do I transition a freelancer to a self employed status or vice versa if business needs change?

You can move any freelancer over to self employed status at any time. As long as the freelancer is willing to transition to a more full-time position and schedule, you’re good to go. You can immediately have a conversation started around what the updated terms and obligations will be. Then you can get a contract drafted and finalized quite quickly. Just make sure that your business actually needs this level of change. By switching over, you could very likely lose the flexibility that you enjoy with freelancers.

Moving a self employed hire to a freelance position can be more challenging. You need to check your existing contractual obligations to make sure that this move will not violate any agreements. Of course, you also need to ask the hire if they agree to the shift. We strongly advise you to get that in writing, just in case, to protect yourself and your business. Ensure the hire that their status is secure as protected under the existing contract. However, if they are amenable, you would like to move them to freelance status. They will probably expect a higher hourly rate, so be being willing to take that on. Because they are being placed in a more unstable position, this increase helps to compensate for it.

What insurance should I consider when hiring freelancers or self employed professionals?

While there is no legal obligation, there are some freelancer insurance policies you can consider. This includes professional indemnity insurance and cyber insurance.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 


When it comes to choosing a freelancer vs self employed professional, there’s a lot more to consider than you’d think. Ultimately, it all comes down to what makes the most sense for your business goals. 

Virtual Assistants

10 Essential Executive Assistant Tools for Boosting Virtual Team Efficiency

Avoid Disappearing Virtual Assistants with executive assistant tools.

Executive assistant tools are super helpful when you want to boost the efficiency of your team. Since the best of these tools can be implemented digitally, they are great for virtual teams, too. In this post, we’ll go over our favorite picks in ten categories. These are communication, scheduling, project management, filing, productivity, finances, customer relations, personal development, security, and AI.

1. Communication Tools

Email and Messaging Platforms

Most companies will already have an email provider, but if you need one, our favorite is Gmail. Because we work with Google Workspace a lot, this makes the most sense. Of course, if you use a different suite of tools, we recommend checking out their native email system. It should do the job of sending emails, and will integrate better with yoru other tools.

Instant Messaging Apps

When it comes to messaging, Workvivo by Zoom is a powerful new option. This is an internal communication app, so it works really well for teams spread out all over the world. You can book a product tour on their website to learn more.

Slack is what we use at Outsource School for much of our communications. It’s super easy because it combines private as well as group communications, called channels. In these channels, you can share files, which we love. Plus, it’s all free and pretty much unlimited.

Telegram offers top-security messaging on desktop and mobile devices. They offer simplicity and speed for people who want to securely chat from multiple devices. Telegram does not limit the size of your media and you can have up to 200,000 members in your groups. A bonus we love is the ability to customize your messenger to reflect your branding.

WhatsApp is also known for its security, although it has come under some criticism for scammers using the platform. We love this one above other executive assistant tools for messaging because it’s completely free. Plus, you can create groups and do virtually unlimited voice and video calls. You have to use an actual working phone number, but that helps us keep track of hires.

Video Conferencing Software

Zoom, of course, is our top pick if you’re using Workvivo. This is a robust platform that offers more than just video calls, though. It has grown into a collaboration tool that offers team chats with an AI companion. The whiteboard feature has improved and it has phone connectivity options that other apps don’t. Zoom even has an email and calendar tool alongside an appointment scheduler, and virtual working spaces.

We love Microsoft Teams for any company that is already using this suite. The app works on both Windows and Mac devices. It got a revamp in October of 2023, and all users will be using the new Teams version by March 2024. Teams now supports third-party apps, breakout rooms, call queues, contextual search in chats and channels, and more. It performs much better and is more reliable and secure.

Free Conference Call offers only 40-minute calls for free, like Zoom. However, if you want to keep a channel open for people to jump in and out, it’s a great option. Their Unlimited Package is fairly reasonably priced for what it offers. This gives you access to their top-notch video and screen sharing for meetings. 

2. Scheduling and Calendar Management

A calendar with dates highlighted.

Online Calendar Tools

Of course, if you’re using Google already, Google Calendar is enough for most purposes. It integrates really well with many scheduling apps like Calendly, outlined below. 

The Asana team calendar is amazing if you use the Asana project management suite. Because it’s a shared team calendar, it’s super easy for you and your virtual teams to plan, manage, and visualize each work week.

Appointment Scheduling Software

Calendly is one of the executive assistant tools that makes appointment setting super easy. You share a simple link where anyone can book a time slot. No more back-and-forth emails to find the perfect time! You can not only set specific openings on your schedule, but also automate gaps between meetings. In addition, you can set a limit for the number of meetings people can schedule with you every day. This allows you to rest between meetings and keep a balanced schedule overall. 

3. Task and Project Management Tools

Project Management and Collaboration Software

If you have complex processes similar to a manufacturing facility, you’ll love Odoo. It allows you to simulate operations in real-time with capacity planning, components availability, and cost control. Odoo is a suite that has other cool tools like a CRM, helpdesk, accounting, inventory, marketing, and so much more. And it’s super affordable, too.

Aside from Asana and Odoo, is another of the more common executive assistant tools with multiple features. You can choose which features you want to use to manage small and big projects alike. 

ClickUp is our main project management tool at Outsource School. We love the versatility in the customization options within the different spaces and task lists.

4. Document and File Sharing

Cloud Storage Solutions

Again, start with the storage solution that comes along with whatever tool suite you’re already using. For example, Google Cloud or Google Drive, or Microsoft OneDrive. If you don’t have a suite or none of these work for you, you can try one of these:

IDrive offers online storage and syncing service at a great price. We love its archiving and continuous backup features. 

Box is great for business use with its features. It’s also free to use for up to 10GB of files.

Document Collaboration Tools

If you choose ClickUp for project management, you already have a robust document collaboration tool. If you need something more, check out Dropbox Paper. This integrates well with the original Dropbox cloud storage system. If you have a Dropbox account, Paper is free. This tool gives entire teams the ability to edit documents in real time, like Google Docs. 

Zoho WorkDrive is an online file management system for teams. It provides teams with a secure, shared workspace where they can collaborate without worrying about content leaks. 

Document360 is another real-time editing tool. What we love about this one is that it’s also a knowledge base. Teams can store information within the system to keep it in a centralized location. People can’t collaborate on documents, but they can still contribute through notes, the discussion feed, and other features. We also like the ability to set role permissions so you can set access for different people to different documents. Document360 has robust integration with tools like Slack and Microsoft Teams, too.

5. Time Management and Productivity

A man writing notes in front of a laptop.

Time Tracking Tools

We don’t necessarily use time trackers at Outsource School, but we have had good success with Time Doctor. It’s actually not just a time tracker but a complete analytics tool. You can use it to discover insights on your team’s productivity as well as the technology you use. The operations data you can gather will help you identify workforce issues and improve performance.

Hubstaff is another exceptional tool. It automates the time tracking process while it assists with workforce management and delivers productivity metrics. With this data, you can keep teams on track and close gaps in efficiency.

Many of our clients love Clockify. It’s a simple, free time tracker that helps you track attendance so you can monitor billable hours. It also helps with productivity through the timesheet, activity tool, and analytics reports.

Focus Tools

RescueTime is a time tracker that measures your focus so you know what distracts you. Focus Sessions block your access to websites that it notes can affect your focus. Afterwards, you get a breakdown of the session. uses a patented AI engine to play music that scientific research says should help you focus. More than focused work, this tool can deliver music to help you relax and sleep, too.

6. Financial Management Tools

Expense Tracking and Reporting

Expensify is an Android and iOS app that helps people quickly and easily track and submit multiple expenses. Your teams can scan receipts and record the expense. This tool can do mileage, GPS tracking, and automatic credit card importing, too. You can link it to bank accounts for easy logging. Expensify is secured by two-factor authentication and is compliant with Privacy Shield and GDPR requirements.

Invoicing and Payment Tools

Zoho and Odoo have great invoicing software. If you are using other tools in their suites, we recommend you stick to their compatible tools. We actually love Zoho Invoice anyway, even as a stand-alone tool. If you use PayPal for business payments, they also have an invoicing tool.

7. Customer Relationship Management (CRM)

CRM Software

Zoho CRM and are our favorite executive assistant tools in this category. Zoho features more robust automation while Monday is simpler. For customer-facing teams, Zoho is great. They can use comprehensive analytics and personalized solutions to provide more excellent service. Sign up and get started in no time—the fastest implementation in the enterprise CRM market.

HubSpot CRM is also pretty neat. This one gives you everything you need in one place to manage sales and marketing, content, operations, and customer service. 

8. Personal Development and Learning

A man wearing a headset looking at his laptop while resting his chin on his clasped hands.

Online Learning Platforms

LinkedIn Learning is our favorite platform for skills upgrades. It focuses on the most in-demand skills, which is what we want to target in our teams. They also offer highly personalized career coaching.

Udemy is probably the largest platform with hundreds of thousands of online video courses. You pay for only the courses you want. 

Coursera offers top-rates courses and job-ready certificate programs. It’s by subscription, though, so this is good if you want to pursue continuing education. 

9. Security and Privacy Tools

Password Managers

1Password has the most useful features and is compatible with a lot of sites and apps. It’s secure, which is what you want the most, and easy to use. If you want a free option that’s just as secure but free to use, we recommend Bitwarden.

VPN Services

If you need a virtual private network to encrypt your activity on the internet, we have a few recommendations. For general use once in a while, NordVPN and TunnelBear work well. Choose TorGuard VPN if you need to customize your options. If you need something more serious, Private Internet Access or Surfshark are best.

10. Digital Assistant and AI Tools

AI Personal Assistants

ClickUp AI is great for pulling in information on all your tasks, projects, and documents stored in ClickUp. There’s no need to use an outside tool. The same goes for Zoom AI Companion, if that’s the tool you’re already using. It’s free with a paid Zoom user account.

We love Google Assistant, too. You can use this one on various devices, and you probably already have it if you use an Android device. It’s voice powered and can do more than search the internet. We have high hopes for how this tool will improve over time, but it’s already an amazing tool today.

Voice Recognition Software

Go for Apple Dictation if you are already using an Apple device. Similarly, if you use a PC, Windows voice recognition is all you need for most cases. If you need something that everyone can use, Google Docs can type for you. Gboard works at pretty much the same level for Android devices. 

Frequently Asked Questions

What are the key features to look for in executive assistant tools?

The best features in these tools are ease of use and integration. First, you need to evaluate how intuitive they are for you. If there’s a high learning  curve, then it may not be worth the effort. Then, you need to make sure that the tool plays well with your other software. Otherwise, it’s not really helping.

What are the security considerations when using these tools?

You run the risk of data leaks when you use any kind of team app. For better security, go for the tools that have customizable access so you can limit permissions. The easier it is to give and revoke permissions, the better. Look into data encryption as well, especially if you have sensitive information stored in any of the tools.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 

Final Thoughts on Executive Assistant Tools

We hope that you found this list of our top executive assistant tools helpful. It’s just a start, but we believe it can springboard your journey towards virtual team efficiency.

Virtual Assistants

Freelancer Insurance Guide: Protecting Your Virtual Team and Business

A magnifying glass and cash on a freelancer insurance policy document.

Getting some freelancer insurance can be a smart move. Because freelancers are essentially business owners, they have a certain level of exposure to legal liability. Freelancers are responsible for running their businesses, which comes with responsibilities to the government. They are also responsible for the work that they agree to take on. This means that most work-related mishaps are their responsibility. Freelancer insurance protects freelancers in case something really bad happens.

Understanding Freelancer Insurance

Technically speaking, a freelancer does not earn a salary but instead gets paid per project or task. This makes them independent contractors. (Although there are differences between a freelancer vs contractor.) As such, they usually take on either short-term work. They can also take on recurring tasks for the same client that don’t make up a full-time job.

The government looks at freelancers as small business owners. Because they are not salaried, regular employees, they are basically self-employed entities. (Again, there are nuances between a freelancer vs self employed person.) Think of an independent dentist, accountant, or a private investigator. They all work for themselves. 

Freelancer insurance serves entrepreneurs and virtual businesses that do not have the protection of a mother company. Say a work-related incident causes some kind of damage or loss to a client. As an independent, a client may hold the freelancer liable. Insurance is protection for not only your business, but for yourself and your assets, too. This is vital for sole proprietors, who essentially run the business under their own names. 

Different professions carry different forms and levels of liability. The risks depend on the work being done. We do see basic insurance policies, though, that cover the most common ones that freelancers face.

Types of Freelancer Insurance

A smiling woman sitting on a bed with a laptop.

General Liability Insurance

This policy type provides protection against physical damage claims. Freelancers may need this insurance only if they rent an office or entertain clients at their place of business. General liability insurance basically protects a freelancer in case of third-party accidents. This generally covers client injury and accidents that damage client property. It also includes copyright infringement, however, and other damages relating to advertising. 

Professional Liability Insurance

We find this insurance, also known as errors and omissions insurance (E&O), to be very useful for most freelancers. The average policy covers mistakes or negligence on the job that negatively affects a client. It comes in handy when an oversight or missed deadline, for example, causes a client to lose money. When a client sues a freelancer, it takes care of legal costs. 

Business Owner’s Policy

We recommend this policy for freelancers who own their own business property. It adds the benefits of commercial property coverage to basic general liability insurance. You even get a discount, normally, when you buy them together. This gives you protection against business property damage. This includes stolen or lost equipment, damage from fire or storms. 

Cyber Liability Insurance

Cyber insurance secures freelancers against the general threats of working online. In the past, this insurance would benefit mostly IT professionals and others working in similar fields. Nowadays, it provides protection to a wide array of digital professionals

Data breaches and cyber threats can impact anyone transacting business online, especially if they store personal information. As more and more people transition to remote work, this policy type becomes more valuable. If a data breach or cyber attack should cause damage, this insurance helps a freelancer to recover financially. It mostly covers data breach notification and investigation costs. It can also help them with the costs of hiring a public relations professional help to repair a damaged reputation. 

Health Insurance and Workers’ Compensation 

Personal health insurance options for freelancers are much the same as any individual policy that offers personal health coverage. Many of these general health insurance policies do not cover all types of work-related medical bills, though. This is where workers’ compensation plans come to the rescue. Although mostly used by employers to cover lawsuits from employee injuries, workers’ comp works or freelancers, too. It even provides some disability benefits. 

Income Protection Insurance

Income protection policies come in different forms. Generally speaking, they secure freelancers against loss of income, mainly from illness or injury. It runs for a longer term than the other types discussed here. What income protection does is give a freelancer who cannot work a regular income until retirement or returning to work. 

Assessing Your Need for Freelancer Insurance

Two men sitting on a bench looking at a tablet computer.

Freelancers need different insurance bundles depending on the industry they work in and the size of their projects. Their specific roles can also call for different levels of protection. If you are a business owner who wants to purchase coverage for a freelance hire, you need to factor in the size of your business, too.

The guidelines for choosing insurance types generally relate to the coverage amounts a freelancer might need. Focus on weighing the types and levels of risk you face when pre-selecting bundles. 

In some cases, freelance contracts can determine what types of insurance a freelancer needs. Always check with clients if they have any specific coverage requirements before proceeding with applications.

Choosing the Right Insurance Provider

Many insurance providers offer the same or very similar coverage and premiums. So, what factors can help you when selecting an insurance partner? We think that the following qualities are most important.

Strength and Stability

Always shortlist only those providers who have a long-standing good reputation in the industry. A solvent company will best be able to fulfill its obligations. You want to make sure you partner with a company that can meet your needs. This means they can give you reliable coverage and promptly handle claims. No matter what happens, like the recent pandemic, they need to be able to protect your assets.

Service and Accessibility

An insurance company that cannot provide great service is not a good partner. Look into any prospect’s reviews from customers about their responsiveness and reputation around claims handling. You want a partner who is as accommodating throughout the claims process as they are when they are taking your money. Make sure that you will always have access to an agent in case you have questions or concerns. If you can, check out their online tools before you purchase insurance. The more robust their platform, the more likely they will be better at policy management and claims reporting. 

Policy Value

Don’t simply look at the price of a policy when comparing each one. Sometimes, you can get much better value in a more expensive policy. Sometimes, you don’t need all the coverage a policy provides, and can be better served with the lower-end one. Get quotes and compare them carefully, Look at items like the premium rates and deductibles. Does it fit your budget and coverage needs? 

Implementing Freelancer Insurance in Your Business Operations

A woman signing a freelancer contract while another woman helps her.

Note first that the law does not require freelancers to have insurance. Usually, a contract is enough to protect you and your freelance hires. The best route is to get a lawyer to prepare the contract as well as any other legal agreements you need. These documents will cover all the details of your working relationship, including compensation, scope of work, obligations, and the like.You should have a contract anyway, even if you hire a freelancer who doesn’t have insurance. Moreover, more and more US states and other countries are making contracts mandatory. 

When you want your freelance hires to have insurance, you need to make it a requirement. You can easily ask a freelancer to get insured, but you can’t be sure they will buy coverage. You need to put that as a non-negotiable in your contractual agreements. 

If you include insurance as a requirement, make sure that you state that in your job description. It should go right alongside any other non-negotiables you might have. Do not wait until the final cut to mention that they need to purchase insurance. Most freelancers who do not take on big money jobs do not actually get insurance as a rule. Insurance is an additional cost that does not make sense to them under most circumstances. They may not be willing to get insured after agreeing to a rate that won’t cover the costs. Always remember, they do not need to get insurance – it’s a choice.

If a freelancer asks you for health coverage or a stipend, you need to check the IRS’s Common Law Rules. They basically classify hires who get benefits like health insurance as regular employees and not independent contractors. This status change could mean that you will get charged employee misclassification penalties. 

Frequently Asked Questions

Can multiple freelancers be covered under a single policy?

Because freelancers are essentially separate legal entities, each one needs a separate policy. If you are purchasing insurance for freelancers as an agency, you may be able to negotiate group rates. You may also be able to get a discount if you form a group of independent freelancers. However, each freelancer will still have an individual policy.

How do claims work with freelancer insurance, especially in a virtual team environment?

Hiring freelancers from overseas can make insurance claims trickier, but not impossible. This is why we recommend working with a reliable partner who has more experience outsourcing work. They will know what to do and can offer protection when you transact through their agency. However, even if you are hiring independently, you can work it out. Just make sure that you know which insurance providers can work smoothly with overseas companies. Mainly, you want to specifically require providers that offer liability insurance with worldwide coverage. You should also check with your lawyer about any legal concerns around hiring overseas. 

What are the common exclusions to look out for in freelancer insurance policies?

The following are common exclusions for different types of freelancer insurance:

For Professional Liability Insurance, the main one is intentional acts or omissions, which includes fraud, misrepresentation, or willful negligence committed by the freelancer. This relates to Errors and Omissions Insurance, which also often has coverage limitations on claims relating to contractual obligations. For example, they may not cover a freelancer who fails to meet deadlines or fulfill agreements. This, again, is an area of concern, so weigh your choice carefully. Another common exclusion is claims where the freelancer provided advice or services that are outside their area of specialization. This makes perfect sense. It’s also another reason to never ask a freelance hire to do something you didn’t hire them for.

Cyber Liability Insurance also applies exclusions for intentional acts or omissions by the freelancer that lead to data breaches or cyberattacks. 

Claims around business interruption and loss of data that result from cyber incidents also include limitations.

In line with this, exclusions apply to claims involving negligence. For example, they won’t cover a freelancer’s failure to take proper security measures to protect against cyber threats.

Intellectual Property Infringement policies normally limit coverage for intellectual property rights infringement like copyright, and patent or trademark violations. Be very careful to check the actual coverage to make sure it fits your needs. Note that discrimination, harassment, and wrongful termination claims are also often excluded because it’s freelance work.

For General Liability Insurance, bodily injury and property damage exclusions apply. This makes sense since most freelancers do not have offices. Moreover, especially for overseas hires, clients are not likely to meet them in person, anyway. Protection for freelancers is also often excluded because digital work doesn’t require it. For example, protection against injury from the use of certain equipment or handling hazardous materials isn’t necessary. Similarly, pollution or environmental damage claims are not needed. Take particular note of exclusions around services provided by a freelancer. This may be where you actually need coverage. 

How frequently should insurance coverage be reviewed and updated?

We recommend a routine check-in for freelancer insurance coverage on an annual basis. This is because most policies last for a year. The terms and conditions of different insurance types vary, however. Always check the specific policy period stated. Usually, you will see an effective date and an expiration date. This shows you when the coverage begins and when it stops. If a hire purchases short-term insurance coverage, you will need to follow up on a renewal about a couple of weeks before the existing policy expires. That way, you won’t have to go through any interruptions in work or coverage.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 

Final Thoughts 

Don’t forget to tap into recommendations when you’re looking into insurance protection for your freelance business or virtual teams. Ask others in your industry about their experiences and do some online research, too. You can get some of the best referrals this way, and learn details that aren’t published on any pages. In the end, however, always make sure that the provider you choose aligns with your specific needs. 

Virtual Assistants

Hiring an Executive Assistant: Strategies for Entrepreneurs to Boost Productivity Virtually

A lady in semi-formal professional attire at a computer desk in an office hiring an executive assistant.

Are you thinking of hiring an executive assistant for your business? 

In this article, we’ll help you understand the EA, benefits of hiring one, and what that entire process looks like. 

Understanding the Role of an Executive Assistant

Definition and key responsibilities

An executive assistant is someone who directly assists a company executive. Their responsibilities range from business tasks to duties related to an executive’s personal or home life. 

Similar to secretaries, a lot of their duties are administrative in nature. This includes travel and accommodation arrangement, scheduling, email management, reporting, and more. 

The difference between an executive assistant and other administrative roles

One key difference between an EA and other types of admin assistants is their managerial function. As the name suggests, EAs have some executive power. This means they have the authority to delegate, lead, and supervise tasks and teams in certain situations. 

The Benefits of Hiring a Virtual Executive Assistant

Cost-effectiveness and scalability

Having an in-house executive assistant does have its advantages, but virtual EAs are more flexible price-wise. Their rates are more adaptable in that you can hire them for specific tasks and then scale up only when needed.

Access to a global talent pool

When you hire locally, the fact of the matter is that you have limited options. You may have candidates with excellent resumes, but they may not be the right fit for your business. Global talent gives you a variety so you don’t settle.

Increased productivity and focus for entrepreneurs

There’s an opportunity cost when you aren’t spending time efficiently. Hiring an executive assistant means you can direct your time and efforts elsewhere. EAs also act as a second pair of hands that helps you complete more complicated tasks faster. While you write meeting agendas, an EA will set a meeting date where all needed parties are available. 

Identifying Your Needs

A man in a suit sitting at a table thinking.

Deciding between a full-time vs. part-time assistant

Hiring full-time makes sense if you have a lot of work you want to outsource. Part-time hiring can be more economical. For instance, you might hire for specific tasks or only during a specific time of day. Examine what makes more sense for your business needs and hire accordingly.

Skills and qualities to look for in a virtual executive assistant

An EAs main duties revolve around calendar management and scheduling, communications, logistics, management, and other admin tasks. 

As such, they must possess valuable skills such as:

  • Organizational skills
  • Time-management
  • Good oral and written communication 
  • Research skills
  • Multitasking
  • Management skills 

The Hiring Process

Where to find qualified candidates

There are multiple places you can find vettable candidates. There are agencies, freelance marketplaces, as well as social/business networking sites. Some of these include Upwork, FreeUp, LinkedIn, and other EA hiring sites. Whatever site you choose, make sure they have some kind of rating or review system. 

Crafting an effective job description

This is an important step when hiring an executive assistant. This helps you communicate the roles, responsibilities, and qualifications clearly. You create one using  an executive assistant job description template

Screening and interviewing candidates virtually

Before you conduct your remote interviews, we recommend creating a list of interview questions. It’s also important to choose your platform ahead of time. We personally recommend Slack for interviews. 

Conducting reference and background checks

Candidates will usually have references to their previous workplace on their resumes. You can also explicitly request this on your job post/job description. If hiring through agencies or freelance platforms, check reviews and ratings. 

Onboarding and Training

A man and woman doing onboarding and training with a laptop looking at something and smiling.

Setting up communication and task management tools

We always say the remote onboarding process is crucial. It is during this process that you can familiarize people with the tools and software you use. The sooner you introduce it to them, the more time they have to adapt to it. 

Establishing clear expectations and goals

This part of the process is also where you can reaffirm what this partnership entails. Here you set the mission, communicate the vision and establish objectives. This also helps set healthy work boundaries in place as well. 

Training on specific systems and processes

You should conduct any training regarding proprietary software, SOPs, and the like early on. This may involve giving them instructional material and assigning someone to coach them through. 

Building a strong working relationship remotely

Integrating remote hires into your teams and workflows is key to healthy partnerships. You can do this through temperature checks and regular team-building activities. A healthy work environment boosts morale, which in turn improves the quality of their work. 

Best Practices for Working with a Virtual Executive Assistant

Effective communication strategies

We already mentioned that you should establish communication channels early on. 

Also, ensure that you reply to messages as promptly as you expect them to answer yours. Both sides should model active listening.

Setting up regular check-ins and feedback chains

Scheduling regular update calls can have a few benefits. For one, you can check progress and maintain a level of supervisory control. Second, you can gain insight into the inner workings of the project.

You do this by giving your EA opportunities to ask questions, provide feedback, and bring up suggestions. This is a key part of their role, as they can observe things much closer than business executives. 

Leveraging technology for collaboration and productivity

Partnering with technology can improve efficiency by a significant margin. Think about team management software that allows for communication, real-time collaboration, and progress checking. Consider other technologies that include automation features where you can set rules that save you tons of time. 

Ensuring security and confidentiality in a virtual setup

There are two factors involved in security: the data itself and those handling the data.

Any business that has dealings online (which is most), should know the most secure channels for relaying information. Additionally, you should consider investing in data security software.

When hiring an executive assistant, make sure they sign a data privacy contract andthat you bring them up to speed on your data policies. As a rule of thumb, only share the most necessary information on a need to know basis.. 

Legal and Contractual Considerations

Some documents on a clipboard.

Understanding employment laws for virtual employees

Naturally, if you plan on hiring internationally, you should also acquaint yourself with any laws related to that decision. 

One benefit of hiring remote workers is that you have no obligation to provide typical employer benefits. This includes healthcare, retirement bonuses, etc. You also don’t typically have to fill out tax papers or documents from that country. 

Drafting a comprehensive contract

Contracts protect both parties from disputes, misunderstandings, and abuses. When drafting a freelance contract, you can use templates or start from scratch. Always include important information such as names, dates, deadlines, scope of work, deliverables, and rates. Be as detailed as possible. 

While a lawyer isn’t necessary, they can’t help cover all bases and prevent loopholes. 

Discussing and setting up payment arrangements

You’ll notice that most freelancers will come with a rate upfront. On marketplaces you can usually see a rate range next to their profiles. Payment negotiations also happen during the interview process when narrowing down candidates. 

Once finalized, your contract should also include your payment agreement with the EA. This includes payment amounts, terms, channels, and dates. 

Frequently Asked Questions

How do I ensure my virtual executive assistant stays motivated and engaged?

There are three things we recommend

  • Equip them thoroughly with the tools and information they need 
  • Regularly check-in with them and listen to their feedback and suggestions
  • Implement good suggestions and provide positive reassurance 

What are the common pitfalls in hiring a virtual executive assistant and how can I avoid them?

Most bad hires are usually the result of poor research or poor management. 

When hiring, choose from reputable marketplaces, agencies, etc. Make sure you set clear expectations in your job description and ask proper interview questions for executive assistants

How should I manage time zone differences with my virtual executive assistant?

Time zone differences can be troublesome, but you can also use it to your advantage. For instance, EAs can work during your off-hours, so progress is continual. 

Can a virtual executive assistant handle sensitive or confidential tasks?

Yes, it’s a given that those in this position handle information with some degree of confidentiality. Hiring someone you deem trustworthy may not be enough. You must also have data security contracts and SOPs in place before hiring. 

What are the key indicators of success when working with a virtual executive assistant?

  • You have more time to get more done. 
  • Your processes are getting more efficient. 
  • You’re more organized.

What Is Outsource School?

outsource school

Outsource School helps you to unlock the potential of virtual assistants and accelerate your business growth.

This is the exact system Outsource School’s founders, Nathan Hirsch and Connor Gillivan, used to go from zero to 8 figures and 40+ virtual assistants with an exit in 2019.

Since being founded in 2020, Outsource School has helped 1,000+ business owners hire 2,000+ virtual assistants for their companies.

Schedule a free sales call to learn more

Free resources you might like: 


That concludes our “hiring an executive assistant” crash course. Hopefully, you now have a better grasp of the EA role and how to hire and manage one effectively.

If you want to learn more or think we missed anything, we recommend checking out our other posts related to this topic.