Two Warning Signs Your Startup Needs A Chief of Staff
March 4, 2021

At this point, we feel pretty confident in saying that the Chief of Staff role is here to stay. But don’t just take our word for it. A simple search on LinkedIn for open Chief of Staff positions shows that there are currently over 8,000+ open roles across the world. Still not buying it? Maybe you’ll agree with us after seeing Harvard Business Review’s article from May of 2020 arguing why the Chief of Staff role is essential for top leaders today.

If we know the position isn’t going away anytime soon, the next question is, ‘How do I know if the Chief of Staff position is the right role for my team?’

It’s not an easy question to answer. Every new hire matters when you’re a startup. We had the opportunity to speak with someone in the role today who shared the challenges their company was facing that led to creating the position. In the clip below, Sydney Cummings shares the warning signs that led to Terminus opening up the position.


After listening to Sydney's explanation, there were two words that stood out to our team: communication and prioritization. 

Communication. If we had to guess, this is a topic you've examined over and over after 2020 forced the majority of the world to work from home. And there’s a reason for that. How companies discuss and share what they’re working on, why they’re working on it, and how it will push the business forward is critical to achieve any level of success.

When your startup is small, it’s much easier to be intentional about sharing what each individual is working on and how it fits into the bigger company picture. But as departments grow, natural communication silos begin to arise. 

Typically, it’s been the CEO’s job to break down these barriers and bring the entire business together. In today’s world, it’s become increasingly difficult for CEO’s to find the time to solve the day to day problems, while still casting that long-term vision for where the business is going. If your CEO is finding it nearly impossible to balance the two, it might be an early indicator that it’s time to start hunting for a Chief of Staff.  

If creating a centralized approach to communication is one of the problems a team is facing, then prioritization will be one that naturally follows. It cannot be overstated how important it is to ensure that each area of the business is working on the right things, at the right time, and that they all fit together on the same timeline.

Similar to communication, prioritization is much easier to tackle when your startup is small. As your employee count grows and the amount of deliverables your team is working on multiplies, it’s important to put serious thought toward how each area of the business determines what and when they should be working on something.

It’s not too difficult to determine if a company should be thinking about how to create a standardized approach to prioritization. If you’ve ever worked on a cross-departmental project only to find out other departments have been working on another project entirely, that is a sign prioritization should be an area to focus-in on.

Every business is different. There isn’t a one size fits all approach to knowing when the right time will be to create the Chief of Staff position. But if you're starting to find recurring problems regarding your team's communication and prioritization of work, it might be a sign that it's the right time for a Chief of Staff. And you might not have to look far. Some of the best Chief of Staff hires come from your team. But more on that later.

If you’re curious to learn more about what the day to day life of a Chief of Staff looks like, we’ve interviewed four different leaders on our Aspiring Ops series who are in the trenches daily. You can listen and learn from these leaders here.