How To Interview Like A CEO

How To Interview Like A CEO

No man — or woman — is an island. The most successful people surround themselves with great teams and co-leaders. But how do they get those people? Obviously hiring is a big ecosystem of factors that involves assessments, interviews, referrals, previous work with the person (or knowledge of their work), and more. High-level hiring is obviously different than rank-and-file, entry-level hiring. But what does overlap in so many different hiring contexts is the interview, which has long been a cornerstone of the process. So how can you get the most out of the interview process and your time in front of a candidate? Consider using some of these interview questions lauded by famous CEOs to help you stay a step ahead of the competition. 

What didn’t you get a chance to include on your resume?

Who said it?: Richard Branson, Virgin CEO

Branson mentions this question in his book about leadership. His logic is this: If you are going to hire someone based solely off what they say about themselves on paper (i.e. what a resume is), you wouldn’t even need to do interviews. So, ask them what they had to leave off to keep the resume roughly a page. See what they highlight but didn’t feel was resume-worthy. It can teach you a lot about the candidate sitting in front of you and their priorities.

Three adjectives

Who said it?: Michelle Peluso, IBM and Gilt

Peluso is currently the SVP of Digital Sales/CMO at IBM. Her question is, “If I asked a bunch of people who knew you well about you, what three adjectives would I hear the most?” This question can be “gamed” or “hacked” by the candidate, sure — “Well, all my friends would say I’m a perfectionist…” — but it can open up a chance for you to see their self-awareness and their relationship to others, both of which are integral factors for success in most modern jobs. 

Read more: Swap out these traditional interview questions to improve candidate experience

When did you solve an analytically-difficult problem?

Who said it?: Laszlo Bock, Google HR/Humu

Bock ran HR and People Operations at Google for years. Now he runs his own startup at Humu. Google, in its early days, was famous for brain-teaser type questions like “How many tennis balls can fit on a 787 airplane?” Over time, they shifted to more behavioral questions, and that is what Bock does for his own company now. As for why, here’s his reasoning:

“The interesting thing about the behavioral interview is that when you ask somebody to speak to their own experience, and you drill into that, you get two kinds of information. One is you get to see how they actually interacted in a real-world situation, and the valuable ‘meta’ information you get about the candidate is a sense of what they consider to be difficult.”

Knowing what people find challenging will help you better align the right role to the right person. It also might give you some insight into their last job and how they handled challenges there.

When did you have your first paying job?

Who said it?: Hannah Paramore, Paramore interactive ad agency

Paramore asks this to see how far back a candidate’s sense of work ethic goes. “I love people who have to patch success together from a number of different angles,” she admits. Asking a question like this will help you gain a better sense of a candidate’s work history and drive. Talking about their personal history and work experience is also a good way to ease candidate’s into the interview process and help them relax a little before diving into deeper, more complex interview questions.

If we’re sitting here in 12 months, what did we achieve together?

Who said it?: Randy Garutti, CEO of Shake Shack

This is a great question because you get to see what a candidate thinks success in a role would look like. If it doesn’t quite align with your definition of success in that role, you two can have a conversation around what would even define “success” in this job. Plus: it forces a candidate to speak in specifics around certain metrics, as opposed to general ideas like “growth.”

The one-mile question

Who said it?: Elon Musk, Tesla/SpaceX

Here’s the Q: “You’re standing on the surface of the Earth. You walk one mile south, one mile west and one mile north. You end up exactly where you started. Where are you?”

There are two common responses: North Pole and South Pole. The interesting thing is that Musk doesn’t actually care about the right or wrong answer; he uses it as a guide to see how candidates approach problem-solving and how they process information. He primarily uses this question with lead engineers but has used it in other roles. 

By the way, if you were wondering about that other brain teaser above, if someone asks you about tennis balls in a 747 — not a 787 — the correct answer is apparently 7,894,917. Who knew?

Who or what has shaped who you are?

Who said it?: Karla Gallardo, Cuyana

This question allows for a deeper personal understanding of the candidate and, in Gallardo’s words, allows them to “show vulnerability without ego.” Again, this can also point to a candidate’s self-awareness and understanding of others. If someone answers, “No one I got here all on my own” that tells a recruiter a lot about how that person views the world and how they might potentially interact with others. Someone who has a ready list of supporters or mentors may indicate a deeper sense of awareness and a better team player.

Pro-tip: Hiring at a startup or small business? Try these questions instead.

What have you failed at?

Who said it?: Carly Stein, Beekeeper’s Naturals

This one is a twist to the standard, “What’s your greatest weakness,” question candidate always prepare for. Instead, framing it this way makes candidates think of specific examples of times they have stumbled. Failure is a common reality in business, especially if you’re trying to grow or embark into new markets. So … why wouldn’t you ask a candidate where they’ve failed and what they’ve learned from that failure? It gives you a healthy understanding of how they process and contextualize times when things aren’t going well. It also let’s you see if they shift the blame or if they are able to step back and evaluate their own performance with a critical eye.

How many messages are in your inbox right now?

Who said it?: Andy Crestodina, Orbit Media

This question is designed to see how they manage email — a challenge for many — and how they work through a sense of overwhelm and a priority list. While we have a narrative right now that Slack and other tools are “killing email,” the reality is that they are not — business email sends have increased almost every year since 2008. People still need to effectively manage asks and projects across email, which makes this a good question. And again, there’s no one great answer here, the point of this question is to see how people approach a typical work problem and what that indicates about their work ethic and performance.

The main layers of interviews

While peppering some of these question into a traditional job interview might help you learn new information, none of these questions, in isolation, will get you a slam-dunk, A-Player hire. It’s a much bigger ecosystem than that, of seeing where they are in their career, what challenges they’re ready for, their personality, their company culture fit with your organization — and an understanding of their past work and references/referrals. A hire is a big decision, especially at larger compensation levels. Single questions won’t get you all the way there, but these questions above could guide some of your thinking about what to include and how to structure an interview. From there, try to make use of behavioural based questions within the context of a structured interview to help you find the best candidate. And keep in mind, assessments or work-based tasks can also help shine more light on who your candidate is and what kind of future potential they have. The hiring process isn’t always easy but asking the right questions can help a savvy hiring manager find the great talent they’ve been looking for.


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