Dave Bailey, the CEO of Founder Coach, discusses the unique value that a chief of staff brings to start-ups.

The majority of investors I know have their own personal assistant to help manage their busy schedule and take care of their admin. Until recently, it wasn’t even a question for a start-up CEO to have an assistant.

The trend towards start-ups hiring a chief of staff seemed to come out of nowhere. And can’t smart productivity tools, such as AI assistants, achieve the same thing?

Way beyond admin

While the chief of staff role varies greatly between companies, I’m referring to someone who acts as an extension of the CEO—a true right hand.

Having a chief of staff can make a start-up, or scale-up, CEO and leadership team more effective. Here are some of the ways:

  1. Tracking actions in meetings. The chief of staff attends all meetings that the CEO attends, with the additional responsibility of writing down action items. When a commitment is made, it’s often down to the leader to follow it up and check that it actually happens. Offloading this allows the CEO to remain present and focused, reassured that the necessary actions will be tracked and followed up.
  2. Pre-screening meetings. When a chief of staff arrives at a meeting before the CEO, they can check the agenda, start the meeting off—and quickly summarize things when the CEO arrives. And if the participants aren’t sufficiently prepared? Well, the chief of staff can glance at their phone and say, ‘Oh I’m so sorry, the CEO can’t make it—we’ll have to postpone,’ while simultaneously texting the CEO, advising them not to come. Genius, right?
  3. Playing bad cop. Giving direct feedback is difficult, even for CEOs. I’ve often spent too much time trying to find the least confrontational way of delivering it and losing a clear message in the process. A chief of staff can play bad cop to your good cop. They can say things like, ‘Okay, let me translate for you: this needs to be done by Friday or there’ll be trouble!’
  4. Playing good cop. As a CEO, it’s hard to get used to the fact that words have added weight. Something intended as an innocent suggestion can leave the team in a state of confusion, turmoil, or even panic. The chief of staff can take the time to calm people down and ensure your message is correctly interpreted.
  5. Feeding back information. It’s scary for people to give feedback directly to the CEO— after all, their job may be at stake. The chief of staff can provide a safer channel for CEO feedback. Moreover, the chief of staff can also provide their own candid feedback, based on what they observe in meetings and hear around the coffee machine.
  6. Co-founder facilitation. Relationships are hard, period. It’s inevitable that co-founders will battle from time to time. When passions are high, discussions can get personal, especially behind closed doors. Having another person at the table is sometimes enough to keep co-founders on their best behaviour, making it easier to reach an amicable conclusion.
  7. Acting as a sounding board. Have you ever asked someone for help, but when you started talking your problem through, you solved it yourself, with no help needed? Sound-boarding is an effective way to structure ideas and solve problems. A good chief of staff is a good listener, and a great chief of staff asks innocent questions, and innocent questions are routinely the best ones.
  8. Sharing the operational burden. There are countless operational tasks that fall into the CEO’s lap because they have nowhere else to live. The chief of staff can take over some of these administrative burdens. In scale-ups, one such area is recruiting and culture — especially at the stage before a full-time HR team exists.

‘The chief of staff can take the time to calm people down and ensure your message is correctly interpreted.’

What to look for in a Chief of Staff

The chief of staff needs to be someone that the CEO can relate to and trust. Their characteristics may include:

  • Diplomacy
  • Organization skills
  • Great interpersonal skills
  • Listening and coaching skills
  • Trustworthiness
  • Facilitation
  • Project management.

It’s a difficult role with long hours, but it can be highly rewarding. The chief of staff learns directly from a business leader and gets a unique insight into the challenges of scaling companies.
And yes, there is a real return on this role. My own reports show CEO productivity rising by 20–50%, enabling the CEO to focus on where they can add the most value.

Give it some serious thought. How could a chief of staff help you become a more effective leader? And how would you measure their return on investment?

Dave Bailey is the CEO of Founder Coach, a coaching company dedicated to helping scale-up founders become great leaders. Dave previously co-founded three VC-backed companies, invested in 50+ start-ups and writes The Founder Coach Blog.

Further Reading

Bailey, Dave, ‘How to Resolve a Conflict Where Both Sides Are Right’, The Founder Coach https://medium.dave-bailey.com/how-to-resolve-a-conflict-when-both-sides-are-right- 1f375bc82f7f (1 April 2020)

Bailey, Dave, ‘This Technique Can Help You Listen More Carefully’, The Founder Coach https:// medium.dave-bailey.com/this-practical-technique-can-help-you-become-a-better-listener- b5ce3238c6aa (13 January 2021)