Virtual Assistants

When Is the Right Time to Delegate Work to Others?


Many business owners wonder when the right time is to delegate work. The choice to delegate is even often easier to make than choosing when to start letting go. The problem is that many contradicting pieces of advice exist out there. So, most business owners don’t know what words of advice to follow.

In this article, we’re going to lay out what has worked for us here at Outsource School. We’ll highlight the top times when it’s a clear sign that you should start delegating. This comes from the common problems that business owners run into when trying to do everything themselves. Then we’ll provide some simple tips for how to start delegating. 

When to Delegate Work

The simplest answer for this is to delegate work when you need to. That’s where it gets tricky because your needs are different from others’ needs. We do have a few solid markers, however, for when anyone should delegate work.

1.  Time Crunch

When you find yourself working close to 40 hours a week, you should start thinking about delegating some tasks. Most business owners wait until they are working more than 40 hours a week, and that actually makes delegating work much more difficult. You need time to delegate work properly, starting with the right hiring process all the way up to onboarding and monitoring hires. Plus, you probably did not choose to own a business over being an employee so that you could have less freedom, right?

So, when you feel like you are hitting the 30-hour mark, start thinking about what tasks you will want to pass off in the coming months. In the next section on how to Delegate Work Smoothly, we have some tips for you on how to choose the first tasks to delegate.

2.  Mundane Tasks

When you find yourself working in your business instead of on it, that’s a sure sign that you need to delegate work. Basically, you should delegate work that eats up your time and does not make the best use of your talents and skills. We all know that you can do these tasks, but that’s not the point. You need to delegate work that’s not at your level so that you can start taking on tasks that really need your expertise. This is the only way that you can grow your business instead of getting stuck in the hamster wheel.

If you are feeling like your business is running you, it is very likely because you are doing mundane tasks. Sit down and think about all the things you are doing that are not really tasks for someone in your position as the leader of your company.

3.  Letting Go

This might seem a bit strange, but it’s true that you can only effectively delegate work once you’ve learned to let go. You need to let go of control in your business to the degree that it will allow you to delegate work without turning into a micromanager. This is absolutely key if you want to delegate work to free up your time and reduce stress. You simply can’t delegate work if you are always running through scenarios in your mind that make you wonder about all the things that could possibly go wrong. 

We recommend that every business owner put some time and effort into exercises that will help you do this. Having outsourcing and hiring guidance is super helpful in this process. With guidelines to follow, it becomes less scary to actually start passing off work because you know how to pick the right people to get the job done well.

Delegate Work Smoothly

Now you’re ready to avoid the mistake of trying to do everything in your business yourself. And you’re ready to pick up a strategic approach to hiring so you can begin to delegate work successfully. Here are our top tips for how you can start to delegate work without running into issues.

Review Tasks to Delegate


The first tasks that you should think about delegating are all the small things that always seem to get in the way. These are little tasks that don’t really take up much time on their own, but do add up. They could be scheduling meetings or booking appointments and flights, data entry or copy and paste work, and other administrative type tasks. These are also very simple tasks most of the time.

Delegate work that falls into this category to an assistant. In most cases, you can hire virtually for these tasks. For additional tasks that must be handled in person, you can look into hiring a personal assistant or booking an errand service if it makes sense in your situation.


Next, you can delegate tasks that take up a lot of time, such as everyday repetitive tasks. These can be posting to social media channels, answering basic customer inquiries, and cleaning up your email inbox and keeping messages organized. Some tasks do need a certain level of special skills, but are not that difficult to manage. Just make sure that you are looking for someone who has those specific skills and you’ll be fine.


Finally, delegate tasks that you are not well suited for or simply shouldn’t be doing because you have owner-level tasks to get to. This is anything that requires specialization that you don’t have or that you don’t have time for. Website maintenance and updates, graphic design, copywriting and article writing are a few examples.

Basically, consider anything that does not require your specific expertise. These are all tasks that you should think about delegating. Think about tasks that need to get done quickly, too. Tasks that would cause you to have to drop other important tasks are out. It’s better to delegate tasks that are time-sensitive. Otherwise, you would be forced to choose what gets done when everything is important.

Target A-Players

When you delegate work, much of your success comes from the people to whom you are delegating. You must find the right people for each task or group of tasks. This means that you need to approach delegation from a mindset that you are going to hire only the best. It doesn’t matter if you are passing off the most tedious and simple of tasks. You still want to hire only those who have great attitudes and professionalism. You are not going to get the help you need to free up your time and destress if your people are not taking the work seriously or not communicating their progress or just basically flaking out on you.

Prepare by writing down exactly what you need done, then the qualities that you want the perfect person for this job to have. You also want to give special attention to what qualities are a good fit for your company culture, or at least the way that you personally work. Then reiterate all of that by explaining the responsibilities that the right candidate will have. Then you can start sharing this job description to attract A-players.

Use the IOTM Method

You need to follow a proven system for Interviewing, Onboarding, Training and Managing hires. Hiring the best is more than just attracting people who like your job post or think that they qualify. 


You have to confirm if each candidate is right for the job by being intentional in your interview process. The interview is also where you set expectations to see if candidates are really prepared to work with you, and better yet, excited to be a part of your business. This is how you identify the best applicant and make sure that there are no loose ends before you make the hire. 


When you onboard, you need to have a system that you follow to take the new hire through everything that they need to know about working in their new position. This includes your company culture, the people they will be working alongside, and getting on the same page about the specifics of what you expect from them in their new role.


No matter what role you are hiring for, you must expect to provide some level of training. The key is to hire in a strategic manner so that you will not have to provide a lot of training. But, you can never just hire someone and send them off to work. Your business is unique, and some guidance is always required if you want that person to work effectively and be happy staying with you.


Managing is an important part of delegating work. The way you maintain work relationships with hires makes a big impact on how productive they are over the long term. It also spells the difference between facing high turnover and developing loyalty among team members.

If you’re not an Outsource School member yet, it’s time to get on board! We will give you what you need to hire smoothly and avoid the common hiring mistakes that cost you time, money, and turnover headaches.

Build Trust

Trust is so important, whether you are hiring for short-term projects or long-term positions. It doesn’t have to take a lot of effort to develop trust, and it doesn’t actually take a lot of time, either. All you need is to understand how valuable trust is to see that building it is one of the greatest investments you can ever make for your business.

Simply put, you can develop trust with hires by being trustworthy yourself, and by reassuring hires that they are valued members of the team. Even if you’re outsourcing, you can make ways to connect with hires and build a remote company culture that fosters mutual accountability and builds relationships. Even just the effort itself to touch base with hires and set aside time for them goes a long way.

Final Thoughts

The right time for you to delegate work can be very different from the right time for someone else. These three basic markers are universal, however — time availability, task types, and readiness. They are a good place for anyone to start evaluating whether or not it is indeed time to delegate work. 

Generally speaking, we actually believe that if you are even here reading about delegating tasks, then that’s something to think about. It can already indicate that you are ready to delegate work, at least on some level. If you are feeling something that you think passing off tasks may help with, we invite you to look into it and figure out what’s at the root of it all. You will likely find that it actually boils down to an issue of either time or talent!


Would you like to know how to be certain who your next hire should be? Or maybe you are having a hard time deciding what parts of your business can be outsourced with virtual assistants, right now. We can help you answer these questions, and help you to discover what new systems you should add to scale your business faster. Set up a free hiring consultation with us at Outsource School today – simply book here!