You're sitting across from someone who might become your "force multiplier." That’s the buzzword, right? But honestly, hiring for this role is a nightmare because a Chief of Staff (CoS) isn't just a high-level assistant or a project manager. They are a proxy for the principal. If you ask the same generic chief of staff interview questions you’d use for an Operations Manager, you’re going to end up with a very organized person who has no idea how to navigate the political landmines of a C-suite.
I’ve seen dozens of founders hire a "mini-me" only to realize six months later that they didn't need a mirror—they needed a counterweight.
The role is weird. It’s undefined by nature. Tyler Parris, author of Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization, basically argues that the role varies so wildly between companies that the interview has to be about temperament and cognitive flexibility more than a specific checklist of skills. You’re looking for someone who can handle the "ambiguity of the gray space."
The "Day Zero" Reality Check
Most interviews start too soft. You need to know if they can handle the mess.
"Tell me about a time you had to tell a CEO they were wrong, and how did you handle the fallout?"
This is the gold standard for chief of staff interview questions. Why? Because a CoS who is a "yes man" is useless. You need someone with the backbone to pull the founder aside and say, "That's a terrible idea," without bruising an ego so badly that the relationship fractures. Listen for the nuance in their answer. Did they do it in front of the whole board? (Red flag). Did they bring data to back it up? (Good sign).
Then, pivot. Ask them about a project that failed specifically because of their oversight. If they blame the "market" or "the team," they don't have the radical accountability required for this job. A Chief of Staff often takes the blame for things they didn't even do, just to keep the gears turning. It's a thankless gig sometimes.
Navigating the Political Minefield
The CoS is often viewed as a gatekeeper. That’s a dangerous reputation. If the rest of the leadership team hates the CoS, the CoS cannot do their job.
How do you build trust with a department head who thinks your role is just an expensive spy for the CEO?
This gets to the heart of soft power. You want to hear about empathy. A great candidate might say they spend their first thirty days doing a "listening tour." They don't come in swinging a hammer. They find out what the VP of Engineering is actually struggling with and they fix a small, nagging problem for them. That’s how you buy internal capital.
- The "Low Information" Test: Give them a hypothetical. "I need you to oversee the merger of two departments by Tuesday. I can't give you any more details because of legal reasons. What are your first three moves?"
- The Prioritization Audit: "I give you ten 'Priority 1' tasks. You can only do three. How do you decide which seven people you're going to disappoint today?"
Honestly, the prioritization question is a trap. The right answer isn't a mathematical formula. It’s about alignment with the principal’s current "North Star." If the CEO is obsessed with fundraising right now, the pitch deck trumps the internal HR audit every single time.
The Technicality of Strategy and Execution
We often talk about the CoS as a "strategic partner," but if they can't build a spreadsheet or manage a cap table, they're just a glorified executive assistant. You need a "Special Projects" expert.
One of the most revealing chief of staff interview questions involves a real-world scenario. "We’re thinking about expanding into the DACH region (Germany, Austria, Switzerland). You have 48 hours to give me a go/no-go recommendation. What does your research process look like?"
You aren't looking for the right answer about Germany. You're looking for their mental model. Do they look at regulatory hurdles first? Do they look at talent acquisition? Do they immediately jump on LinkedIn to find experts? You need someone who builds frameworks on the fly.
Let’s Talk About the "Ego Gap"
This is the hardest part to interview for. The Chief of Staff role is often a career springboard. Many people use it to become a COO or a founder later on. That’s fine. Expected, even. But for the 18 to 24 months they are in the seat, they have to be okay with someone else getting all the credit.
"What happens when you spend three weeks on a board deck, and the CEO presents it, gets a standing ovation, and never mentions your name?"
If they look annoyed just thinking about it, they’ll burn out. The best Chiefs of Staff find professional satisfaction in the outcome, not the applause. It’s a behind-the-scenes role. You're the stage manager, not the lead actor.
Beyond the Script: The "Vibe" Check
You're going to be spending 60+ hours a week with this person. Sometimes in high-stress, late-night situations.
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- The "Travel Test": Ask them how they handle travel snafus. If a flight is canceled and the CEO has a keynote in three hours, do they panic or do they have a private car and a backup Zoom link ready before the CEO even knows there's a problem?
- The "Communication Style" Match: Do they prefer Slack, text, or face-to-face? If the CEO is a "voice note" person and the CoS is a "long-form memo" person, there’s going to be friction.
Making the Final Call
When you’re wrapping up the interview process, look at the gaps in your own leadership. If you’re a visionary who hates details, you need a CoS who is an operational hawk. If you’re a technical founder who struggles with people, you need a CoS who is a world-class diplomat.
The worst mistake is hiring someone exactly like you. You don't need two people dreaming about the year 2030; you need one person dreaming about 2030 and another person making sure the payroll clears on Friday and the Series B pitch deck isn't full of typos.
Actionable Next Steps for the Interviewer
- Audit your "Must-Haves": Before the next interview, list the top three things that currently fall through the cracks in your office. Ask the candidate specifically how they would have caught those three things last week.
- The "Shadow" Half-Day: Don't just do Q&A. Bring the top candidate in for four hours. Throw them into a real meeting. See if they take notes, if they speak up at the right time, or if they just sit there like a tourist.
- Reference Check the "Peers": Don't just talk to their former boss. Talk to the people who were equal to them. Ask if the candidate was a "bridge builder" or a "wall builder." A Chief of Staff who builds walls is a liability you can't afford.
- Review the "Ghost Tasks": Ask the candidate to describe a time they solved a problem before their boss even knew it existed. If they can’t give you a specific, granular example, they probably aren’t proactive enough for the level of support a true Chief of Staff provides.
Success in this role isn't about having the right answers; it's about asking the right questions before the crisis hits. If your candidate is already asking you tough questions about your weaknesses as a leader during the interview, you’ve probably found a winner.