Three Reasons to Look Internally for Your Chief of Staff 
March 8, 2021

In case you missed it, last week we shared the Two Warning Signs Your Startup Needs a Chief of Staff. With over 8,000+ open Chief of Staff roles the position is more popular than ever. We are fortunate enough to be at the forefront of this movement, working with the best of the best across leading high growth companies. 

As more and more companies look to hire for this critical role, we often get asked, ‘What makes someone a good fit for the position?’ And that’s a hard question to answer, because there are a number of qualities that a company should look for depending on the stage, industry, and goals you have in mind for your company. 

However, the place to start your search might be from within. If you haven’t yet looked internally for someone to fill this role, then you might be overlooking the best candidate for the job. 

Whether you’re a hiring manager looking for validation or an aspiring Operations Leader looking for guidance, here are three reasons why companies should look internally for their Chief of Staff. 

Built In Speed and Efficiency 

At a growth stage company, you have to be willing to move fast. In looking for a Chief of Staff, companies should expect that the role will improve your team’s decision making speed and execution through organizational processes. And who better to help you move fast than someone that already knows what’s going on? 

If you’re looking for someone to come in and ensure critical insights are being surfaced to the right stakeholders, then you need someone who can sift through information, understand the larger business implications of decisions, and has shown an ability to work across multiple teams. Ideally, someone who already has context and knowledge of your business, so they can prioritize effectively.  

The right internal employee can check every one of these boxes.

An internal candidate doesn’t need the 101 intro to your company. They know what’s going on, and understand how everything in your business is connected. An added bonus, they can get up and running in no time, and allow you to start focusing on the areas of the business that need your attention. 

Trust of Team Members 

One of the most critical qualities of a successful Chief of Staff is the ability to build trust. However, for anyone stepping into the role, it can be easy to make the mistake of only focusing on building trust at the executive level. Don’t overlook the importance and value of creating trust with employees throughout the company.

For a Chief of Staff that has grown with the company this can come naturally. Not only have they been around through the growing pains, they understand the day to day work being invested at a tactical level that drives the company forward. 

More succinctly put: they understand what is being asked of each individual and why it is being asked of them.

They also carry the validation needed to earn trust, because they’ve been there. Whether it is fielding customer support tickets, making cold calls, or closing the books, early employees can relate to the challenges of your team members. If you’re looking for someone who can earn your employee’s trust, and ensure there is alignment, collaboration, and transparency across teams, this seems like a pretty good place to start. 

Clear Understanding of the Company Vision  

As an extension of the CEO and executive team the Chief of Staff often serves as the connective tissue between leadership and the company. Starting with the CEO and reaching across every team, the Chief of Staff has to create complete alignment and ensure every team is rowing in the right direction. With aggressive growth goals every quarter, constant change, and new employees starting in waves, it can be easy for a company to lose sight of the bigger vision. 

One way to ensure this alignment is by having a clear understanding of the company’s vision and direction. So why not start with someone who’s already bought in? 

For early employees that join startups, they often believe in the leadership, the vision, or the opportunity presented to them. They are passionate about the company, and understand what you set out to achieve from day one. This passion can be your secret weapon in creating and harnessing momentum throughout your teams. 

As you think about how your company rolls out OKRs, annual goals, or new initiatives, ask yourself how you want your Chief of Staff to communicate expectations and drive accountability through teams. Further, are they doing so in a way that regularly reminds and emphasizes the company’s vision? 

Learnings from Some of the Best 

While internal employees might not have previously held the job title of Chief of Staff, we hope this article highlights just some of the reasons why your next Chief of Staff can come from within. If you’re interested in hearing first hand how companies like Terminus, Jellyvision, Trainual, and others have gone about hiring their first Chief of Staff, check out our Aspiring Ops Series.