Interrogation Time

A CEO has three primary functions — setting priorities, making sure the company is properly resourced, and getting the right people on the team. The best founders obsess about the third. They study, research, and experiment with the best ways to recruit, vet, and ultimately close the talent they seek.

I was chatting with one of our founders, who has been particularly adept at recruiting great talent, and he said something that grabbed my attention. “The best candidates ask the best questions, so I’ve learned to more heavily weigh the questions I’m being asked versus the answers I’m being provided.”

This seemed counter-intuitive to traditional HR dogma where the interviewer asks questions, there are clear right and wrong responses, and the sum of the answers will determine whether an offer would be extended. But the more I sat with my colleague’s quote the more it resonated. More than anything I believe that once you get past the functional skills for a role, there are two characteristics that are most predictive of a successful hire:

1) Is the candidate capable of receiving feedback, or do they shatter like glass at the mere hint of criticism?

2) Do they really, really, really want this job?

I’ve written about the first point recently. Startups have to move fast. Teams must collect, synthesize and act upon data quickly or perish. There are those who thrive in that environment and are accustomed to rapid, direct feedback. There are those who burst into tears or fly into a rage at even the hint of criticism. Avoid those people — they will drain you and your team until you’re just the founder of yet another startup turned to dust.

If the candidate is strong enough to listen to others, the next trick involves vetting whether someone truly wants a job. Most people are capable of putting on a good show through the brief and generally shallow interview structure. But one thing is hard to fake — the quality of prep a candidate brings to the discussion. And how does that prep present itself? …through the questions they ask.

Of course, what constitutes a good set of questions? You’re in luck. We developed a list. The more of these you hear from a candidate, the more confident you can be that they are really interested in the gig. These questions obviously are generic, and inquiries specific to your company’s market, product, economics, etc., should also be taken into account. Further, while asking these questions might indicate interest, it in no way informs ethics. So reference check accordingly.

The questions interested candidates ask:

For Vision:

— Why did you start this company?

— What gets you up and excited each day?

— Where can this go? What is the ceiling you see?

— How is the trajectory of the company different from what you imagined when you first founded it?

For Strategy:

— How do we win in this market (aka what are the most important things for us to do)?

— How have you thought about the market size?

— Who are the competitors you deem relevant and how can we be sustainably different from them?

— What comps do you see for our business? In other words — do we remind you of another type of business, and how so?

— If this business does not work out the way we all want it to, what are the biggest risks you see? (aka, why does this fail?)

For Tactical:

— How do we generate leads?

— What is the philosophy behind pricing?

— What expenses does the business have that flex with customer counts?

— How do we onboard a new member to the team? same question for a new customer/client?

— How are decisions made here? (describe for me the culture as you see it)

For Cactical:

— Do you have a philosophy on how you like to lead, manage or work with people?

— Any books or teachers you particularly have been influenced by related to building a team and a company?

— What are your most important personal values?

— If I were to ask someone who has worked with you for a long time, what is the best part about working with you, what would they tell me?

— In your opinion, where are your blind spots or weaknesses as a founder/leader/operator?

— Per the last question, can you share with me a time when that blind spot burned you?

For Role:

— What would be my mandate?

— Why is this role needed right now?

— How do you define success for the role?

— Given what you know about me  — What about my skills/background makes me a good fit?

— Similarly, what parts of my background make you nervous that this might not work out?

— How will this role change over time? Let’s imagine two years from now…


Here’s the real trick — if you want to wow the candidate intrigued enough by your company to arrive with a sheet of questions, then it’s up to you to have thoughtful answers. Because the truth is that for the best companies and the best talent, both parties play interviewer and interviewee.

Happy Hunting.

Learn more about Jonathan Lowenhar at