Signs Your Team Would Benefit from a Chief of Staff

As a leader, you may think you want to do it all when it comes to your business, but you shouldn’t. And at some point, you just can’t. Once you’ve established your strategic priorities, recognize that anything outside of those parameters is just extra noise in your day and can easily be delegated to other team members. However, if you and your team are already at maximum capacity, you may have reached a point where you’re looking for another option to take back more of your time. If you’ve reached this tipping point, it may be time to consider hiring a chief of staff for your organization.


Perhaps you’ve already reviewed the potential a chief of staff could add to your organization but haven’t taken action yet. Or maybe the chief of staff role outside of the political realm is a new concept for you and you’re curious to learn more. As a leader who has seen organizations thrive under the direction and guidance of a chief of staff, I am an advocate for adding the role to your staff roster because of the numerous benefits that come with having a chief of staff.


In order to determine if now is the time to bring on a chief of staff, you may be curious about what kind of work a chief of staff can do. Especially in our current environment, where many have shifted to work from home status indefinitely, and many are planning to continue with the virtual workspace in some shape or form going forward, you may be reevaluating how to improve efficiency even more so as you muddle through what may be uncharted territory for you and your team. I’ve been an advocate of remote work for five years now, and I have seen firsthand how a chief of staff working in a virtual capacity can be an incredibly efficient use of your company’s resources.


While I’ve covered this topic extensively on our blog and even had a featured post on Forbes, here’s a quick summary:

  • Communications Management: Responding to emails, keeping up with Slack messages, and answering or returning phone calls on your behalf; alerting you when high priority messages need your response

  • Presentations: Organizing all the administrative details involved in presenting (scheduling, communicating with sponsors, preparing materials, follow-up surveys), writing the first draft and/or editing your presentation

  • Project Management: note taking during meetings, assigning project-related tasks out, and communicating project details

  • Budget Creation and Management: serve as a liaison between the office of the CEO and the finance department; in smaller organizations and startups, the chief of staff often manages the entire budget creation process (planning, reconciling expenses, monitoring revenue monthly)

  • Hiring and HR Systems: sorting through resumes, scheduling interviews, following up with candidates on hiring status, on-boarding new hires


Another common question that we hear is “What’s the difference between a chief of staff and an executive assistant?” It's a valid question as both roles support an organization's leader in a personal, high-touch way. While both the CoS and EA are inherently tied to keeping an executive organized, prepared, and focused, there are some key differences:

  • The role of the chief of staff is that of a senior-level strategic partner. A chief of staff might manage projects across the entire organization, working with a variety of stakeholders and staff. If the leader is traveling or unavailable, the chief of staff makes decisions on their behalf—so there's a real level of nuance required. Chiefs of staff often have experience in strategy and project management, and can help leaders create strategic plans, but they also need to be generalists, with experience in many different areas. As an executive's spokesperson, the chief of staff also must hone in on the leader's communication style and be able to write things like emails and reports in his or her style.

  • The role of the executive assistant tends to be focused on logistics, such as travel, scheduling, and expense processing—things that require a very strong eye for detail. It's an incredibly important role as the smallest mistake can have huge implications for an organization's leader.


So when does that “aha” moment set in, when an organization or entrepreneur realizes it is time to seek out the kind of help that a chief of staff can provide? Many of the indicators come down to time and efficiency:



While there is no one assessment that will dictate to you whether you need a chief of staff or not, take a minute to self-reflect on these questions:


  • Am I spending enough time on the high-priority items on my agenda, or am I bogged down by items lower on the list?

  • Do I have regular planning time for business development and investigating future opportunities, or is most of my time spent reacting?

  • Do I feel fully prepared for important meetings or making important business decisions? Do I have all the information I need well ahead of time or do I find out information I should have known after-the-fact?

  • Do I hear back on actions to be taken or data to be collected in a timely manner, or do I need to prompt and/or give reminders?

  • Are problems identified early enough that action can be taken to minimize or eliminate damage, or do problems occur unexpectedly? And when they do, does senior staff also seem unprepared?


I cannot stress enough how important it is to step away from the mindset that you need to do it all, control it all and be it all for your business. You will exhaust yourself and your business will suffer as a result. Instead, consider reaching out for support through a thought partner who can back you up and give you back the time you deserve to work on your business and make it the absolute best it can be.