The Chief of Staff Interview: The Questions Founders & CEOs Need to Ask

I created a cheat sheet with the top questions that get to the heart of the candidate's fit for the Chief of Staff role

Interview processes for the Chief of Staff role can be lengthy. An example process looks like this:

• Initial screen with the external or internal recruiter

• Multiple rounds of virtual and/or in-person meetings with (nearly) every member of the executive team; sometimes a board member might be thrown in here

• Somewhere in the middle of the executive meet & greets, a take-home or live case study is slotted in to assess the candidate’s consulting and strategy & ops toolkit

• Final round (could be another quick call or meeting with the Principal)

• Background & reference checks

• Offer

• (Celebrate! 🎉)

A very common milestone in the Chief of Staff interview process.

The initial screen is usually a 30-minute call that’s commonly split into two distinct halves: interviewing and pitching. Particularly for more senior candidates, the interviewer might spend a good chunk of time pitching the role and the company. If time is left for questions, that means the interviewer really only has 10-15 minutes max to make a quick assessment of the candidate’s fit. They’re a significant gatekeeper, so impressing at this stage is critical.

While there are a ton of resources out there for how to interview well, there isn’t much on specific questions to drill into if you’re the interviewer, so I created a cheat sheet for executives to help. While this cheat sheet isn’t exhaustive, it does hit on specific areas that must be assessed for this particular hire. These are:

• Leadership

• Analytical & Critical Thinking Skills

• Decision-making

• Risk-taking

• Comfort with ambiguity

• Proactivity

• Role alignment

• Culture add

• Self-awareness

You can learn a lot by just asking the right question, so some of the questions are structured in a way such that they evaluate multiple areas at a time, which can be helpful when you’re time-strapped. So without further ado, check out the cheat sheet below! I can only paste images in Substack, so if you want this as a PDF, just respond to this email. :)

For folks who are interviewing, my top tips are to be clear and concise in your communication and to provide very concrete examples from your experience to answer the question. My suggestions in the “What to Listen For” column in the cheat sheet may also be helpful with respect to framing your responses.

One way of ensuring that you’re concise is to simply time yourself. If you’re talking for more than 2-3 minutes at a time, you’re taking too long: packing a punch within 1-2 minute soundbites using the STAR method and then pausing let’s the interviewer process what you just said and dig deeper where it’s relevant for them (which might be where you spent just 10% of your time talking about). Better yet, you can pause and let the interviewer know that you’re happy to dive into any area for example 1) your analysis of the problem, 2) how you got the team engaged, 3) what you learned. This accomplishes a couple of Good Things™:

1. Your interviewer is now engaged because you’re asking them a question or to react to something specific.

2. You’ve opened the door to the interview becoming more of a discussion with a back-and-forth dynamic, so both you and the interviewer become more relaxed.

3. It’s something that most candidates don’t do, so you’ll stand out.

I’m looking forward to writing more about this topic in the future, and I’d love to hear suggestions from my readers on what you’d like to learn more about!

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If you’re a candidate looking to get placed as a Chief of Staff with Right Hand, be sure to submit this Typeform.

If you’re a CEO hiring a Chief of Staff and want to learn more about the Chief of Staff role or need help accelerating your search, I’d love to talk. Just respond to this email or shoot me a DM on LinkedIn!

Finally, if you liked reading this, feel free to click the ❤️ button on this post so more people can discover it on Substack 🙏

Until next time, Right Hand fam! 👋