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When to Hire a Chief of Staff?

As a CEO/Founder of your business, you’re probably used to wearing all the hats. From the visionary to the accountant, you’ve been juggling multiple roles and responsibilities to bring your business to life. While it may have seemed fun and exciting at first, as your business gains momentum, those hats can start to slip off, leading to potential disaster.

So, what’s the solution? Your natural reaction might be to hire an Executive Assistant (EA) to help you manage your day-to-day tasks. But hold on, have you considered hiring a Chief of Staff instead?

The Power of a Chief of Staff

A Chief of Staff is  someone who understands the intricacies of running a business, has a strategic mindset, and can act as your personal sounding board. They are your right-hand person, helping you navigate the challenges and opportunities that come your way.

When your business reaches a certain level of growth and complexity, it’s time to seriously consider bringing a Chief of Staff on board. Here are a few signs that indicate you might need one:

1. Overwhelm

If you find yourself constantly overwhelmed and struggling to keep up with the demands of your business, it’s a clear sign that you need support. A Chief of Staff can help alleviate some of that pressure by taking over certain tasks and responsibilities, allowing you to focus on the bigger picture.

2. Lack of Strategy

As the CEO/Founder, your primary role is to set the vision and strategy for your business. However, if you’re too caught up in day-to-day operations, it can be challenging to dedicate time to strategic thinking. A Chief of Staff can help bridge that gap by working closely with you to develop and execute strategic initiatives.

3. Need for a Trusted Advisor

Being at the top can be lonely. You may have a team of employees, but sometimes you need someone who can provide unbiased advice and act as a sounding board for your ideas. A Chief of Staff can fill that role, offering a fresh perspective and helping you make informed decisions.

4. Scaling Your Business

If your business is experiencing rapid growth, it’s crucial to have someone who can help you navigate the challenges that come with scaling. A Chief of Staff can assist in streamlining processes, managing resources, and ensuring smooth operations as you expand.

5. Time Management Struggles

Time is your most valuable asset as a CEO/Founder. If you find yourself constantly running out of time or struggling to prioritize tasks, a Chief of Staff can help you regain control of your schedule. They ensure your time is spent on the most important tasks.


As an entrepreneur or founder, it’s easy to fall into the trap of thinking you can handle everything on your own. However, there comes a point where the hats become too many, and something needs to change. Hiring a Chief of Staff can be a game-changer for your business, providing the support, strategy, and guidance you need to take your company to the next level.

So, don’t wait until disaster strikes. Bring a Chief of Staff on board and watch your business thrive!