What to Look for in a Chief of Staff

A run-through of the ideal mindset and skillset for the role.

This is my second post on the Chief of Staff (CoS) role based on my experience as the CoS to our founding General Partner, Dakin Sloss. I spent about a year in that role before transitioning to an investing partner role. In my last post, I discussed when and why a CEO should hire a CoS. Today, I will go over the qualities I would look for in a Chief of Staff based on my experience.

Mindset

Like with any hire, it’s critical to understand why someone is interested in the role and how this role fits into their future career ambitions. It took me a long time to learn that a candidate can look perfect on paper and be excited about the job but it’ll never work out in the long run if you don’t support their why and future trajectory. From what I’ve seen, there are primarily two buckets of people that make for a great CoS.

1. Growth Layover: Individuals that are primarily motivated by growth and are using this as an expedited learning experience before moving on to something else. Typically, they’ll be in the role for 2–3 years and then will expect to evolve into a management position or leave.
2. Career CoS: People that are excited to be a CoS for the foreseeable future. They are much more likely to be driven by contribution and supporting their leader while still motivated by the growth and variety of the position.

Someone from either group could be a fantastic CoS but you should be explicit and aligned with the candidate on where they fall.

Skillset

Stack ranked by importance based on the typical CoS role.

• Empathy: As I discussed in the previous post, the crux of the position is learning to see the world and the company the same way the leader does. This is impossible without high empathy.
• Generalist: This role typically involves high levels of context switching and the ability to execute a wide variety of tasks. This is why I believe, early-stage former founders are a great fit for the role.
• Default to Execution: Someone who is comfortable making autonomous rapid decisions in ambiguous situations.
• Influence: The role often requires the CoS to make requests to team members or external parties to take action. This can be challenging internally because the CoS is not their boss and externally because the counterparty might have a diminished view of the CoS. Both cases require the ability to tactfully influence.
• Writing Ability: The CoS will be writing on behalf of the CEO to customers, the team, and investors. Clear and concise writing ability is non-negotiable.

Communication Style

Finally, this should be obvious but a CEO and CoS need to enjoy spending time with each other. A key part of enjoying working together is having similar communication styles. For example, do they prefer answers that are short and direct vs longer and more thorough answers? One good way to check for alignment here is with the DISC framework (discussed in this previous post).

Prime Movers Lab invests in breakthrough scientific startups founded by Prime Movers, the inventors who transform billions of lives. We invest in companies reinventing energy, transportation, infrastructure, manufacturing, human augmentation, and agriculture.

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