The Calendar Management Playbook

Pass Calendar Management and Scheduling Off Your Plate

In this playbook, learn how to hire and train a virtual assistant to manage your calendar, scheduling, and booking with our step-by-step processes and worksheets.

Is managing your calendar taking up too much time?

At a certain point, everyone’s calendar becomes a time-strain and it distracts you from focusing on what’s most important to growing your business. 

The great thing is that you can quickly and easily hire a virtual assistant to take it all off your plate. All you need is the right processes to make sure they understand how you want your calendar managed and meetings scheduled. You’ll learn all of that in this playbook. 

Is this playbook for you?

Whether you’re in the early stages of your business or you’re completely slammed every single day with calls, this playbook will help make you more productive. 

In the playbook, we teach you the exact processes and systems you can set up with an affordable virtual assistant so that they will manage everything to do with your calendar. Once implemented, you’ll never look back!

Here's what you'll learn...


A Calendar Management System

Learn how to use our unique worksheets to fill out how you want your calendar managed and when certain things should and shouldn’t be booked. You’ll then be able to give this to your virtual assistant so they can manage it. 


Proven Processes for Calendar Management

Learn the step-by-step processes for having a virtual assistant manage your calendar and scheduling. They’re all super simple to implement and will save you hours each day. 


Proven Steps to Hire a Virtual Assistant for Managing your Calendar

Learn how to apply our unique IOTM Method for interviewing, onboarding, training, and managing to a calendar management virtual assistant. We give you interview questions, training tips, and management hacks for making it a success. 

What you get with your purchase...

PDF: Calendar Management Playbook

  • Getting Started → an overall breakdown of the entire Calendar Management system.
  • Step #1: Setting Up Your Calendly Account 
  • Step #2: IOTM Method for a Calendar Management Virtual Assistant
  • Step #3: Set Up a Cheat Sheet with Calendar Rules for your VA
  • Step #4: Go Over the Exact Steps your VA Should Take to Book a Meeting
  • Step #5: Setting Up a Feedback Loop
  • Final Calendar Management Tips

Worksheet: Calendar Management Preferences

  • A built out worksheet (Google Sheet) that you can easily edit to match your scheduling preferences so you can easily communicate what you want to your virtual assistant. 

Video: Calendar Management Walkthrough

  • Video: Over-the-shoulder screen share of the entire Calendar Management system. It will walk you through filling out your preferences to sharing the preferences with your virtual assistant to managing them once they’ve been set up. 

Who are Nathan and Connor?

Nathan Hirsch and Connor Gillivan are 10+ year entrepreneurs. They built their first eCommerce business to $25 million in total sales using virtual assistants. Then, they scaled and sold their second company, FreeeUp, with a 100% remote team of virtual assistants. They have been recognized on 250+ podcasts such as Entrepreneur on Fire and were on the Entrepreneur 360 List for two years in a row commending them as one of the best entrepreneurial companies in America. At their core, they are systems entrepreneurs always looking for new ways to automate and outsource to virtual assistants and talented professionals.

Calendar Management Playbook

A system to outsource your calendar management with ease.
$ 97 one time fee
  • The Calendar Management Playbook: The playbook PDF, a worksheet to set your calendar management preferences with your VA, and an over-the-shoulder video explaining the entire system and how to use it with a virtual assistant.
  • Email Support: Get in touch with us at any time as you progress through the Calendar Management Playbook.

3% of all sales go to charity

By supporting us, you’re supporting the Teach for the Philippines nonprofit.

30 Day Satisfaction Guarantee

Try the Calendar Management Playbook for 30 days…

…100% risk free.

If you don’t find real, actionable value in the playbook content and materials, reach out to us at within the 30 days and we’ll issue you a full refund…no questions asked.

Frequently Asked Questions

While it will vary depending on how in tune you are with your calendar and working with virtual assistants, it should only take 2-3 hours to get through reading and implementing the Playbook PDF and watching the Playbook videos. 

Since this playbook is only $97, there is not currently a payment plan for the Calendar Management Playbook. 

If you have any questions about the price of the playbook, feel free to reach out to us at 

The Calendar Management Playbook will always be available for sale on the Outsource School website. 

Additionally, you will gain access to the Calendar Management Playbook and all other playbooks and formulas if you decide to join the Outsource School Insider membership program. 

We’re always available to you and we work hard to provide quick responses. You can always reach us at with any questions, inquiries, or feedback. We look forward to hearing from you 🙂 

We have a 30 day satisfaction guarantee on the playbook. If for any reason you feel that the playbook has not delivered on its value, reach out to us at and we’ll submit you a full refund. We’re not looking to cheat anyone and we want you to feel confident in the playbook’s value.

Join Outsource School for ONLY $97 per month