What questions should I ask in my interview process?

Part IV of what I wish I'd known before leaving consulting to join a Series B start-up

Greetings! Welcome to Part IV in a series about transitioning from consulting to start-up—Part I was whether you should leave consulting for a start-up, Part II was on how the hell to figure out what you’re supposed to do next, and Part III was a breakdown of the merits and detractors of business school. So at this point, you know you want to leave consulting and have started to piece together a shortlist of what you want to optimize for in your next role. Now, you’re interviewing. What could go wrong?! Here I’ll cover my favorite questions to ask during the interview process and what you should listen for in a response.

We all know change is hard. There’s a reason Fortune 500 companies cough up millions to retain consulting firms to help them navigate change (or, depending on how much Kool-Aid you’ve drank, ✨transformation✨). Even good change—change that we wanted!—is still scary. So changing jobs, especially if you’re early on in your career, can be incredibly anxiety-inducing. As someone who had a full-fledged, imposter syndrome-fueled panic attack the night before starting my new role, let me tell you, I get it.

Unfortunately, you can never be fully prepared for change. You can know nine months in advance that you’re going to have a baby, decorate a nursery, try to acquire a vague semblance of responsibility, and still totally shit your pants when the aforementioned human creature / tax dependent lands in your arms. You can even be one of those rare, insane people with detailed 5-year personal roadmaps and know with conviction each milestone ahead, yet still experience night terrors about the future. So, don’t try to ‘fully prepare’ for the change coming with your new job. And don’t set yourself up for inevitable disappointment by holding onto the expectation that your next role will be perfect, or check all the boxes in Tier 1 of your personal priority stack.

But whatever your next job is, you will be spending a great deal of your precious time advancing the goals of this organization, so it’s well worth the effort to try to really understand what you’re getting yourself into: both the good and the bad. Being the Type A people pleaser that I am, I often to struggle to remember this myself but the goal is not to get offers from every company you interview with. The goal is to find the best fit. Read that sentence again. The fit, people. Not 100 offers! Do not forget that you are interviewing each other. You should feel totally empowered to ask the tough questions, and to dip mid-process if you feel like this job doesn’t offer you what you’re looking for. So, here are the interview questions I personally like to ask to weed out bad fits early or the ones I wish I had asked for further insight before taking the role.

In early stage interviews, ask:

• Can you give me an overview of how the organization is structured? Have there been any re-orgs recently?

  • The organization should, at a high-level, make sense. If you’re struggling to follow along and it’s not because you skipped your second cup of coffee, this might be an indication of overlapping scope or poor leadership.

  • I’d also listen for frequent and/or recent org re-structures. Reorgs, as we know all too well, can be a necessary and positive thing as a company scales and as business objectives shift. However, too many might mean that this company just has chaotic energy. A follow-up question is to ask about executive / management turnover. If a lot of high-profile execs (levels may depend place to place, but generally Senior Director / ‘Head of…’ roles and up) have churned in the last year, this may turn into a red flag.

• How big does the company expect to get by the end of the year? Which teams have been staffing up the most? How many people have joined this team in the last six months?

  • There’s no right or wrong answer here, but hiring up teams is the real litmus test of how fast a company is growing. If they’ve got plans to double or triple headcount in the next year, you may be seeing the material proof of a #rocketship (a term that is all-too-often hijacked by non-rocket, regular ships). What teams they’re focused on hiring may also give a tangible clue as to where the company itself is investing—or on the flip-side—lacking.

  • If everyone else on the team has only been at the company for a very short amount of time, you may want to proceed with caution and take whatever they say with a slight grain of salt. For instance, if you’re chatting with someone who’s only been at the company for two months and they are gushing about the culture, I’d want to get a bigger sample size from someone who’s been there for a couple years to compare against.

• What are the company’s big goals for the year?

  • Your hiring manager should be able to articulate this in a relatively pithy way. Ideally, the mandate for your role should ladder up quite nicely to support one or more of those goals. If not, probe a little more.

• What three adjectives would you use to describe the [Team or Company] culture?

  • This may be a hot take, but “collaborative” can be a double-edged sword. This may very well just indicate that the culture is very collegial and people are friendly. But it could also be a veiled signal that things are bureaucratic, move slowly, there are lots of approval layers, etc. I also find “work hard, play hard” to usually be code for high-burn, intense work culture. So is “ambitious,” “intense,” and “driven”.

In mid-stage interviews, ask:

• If you could wave a magic wand and change anything about your job, what would it be?

  • Obviously if they start listing a laundry list of shit they would change—um, run. But other than that, listen really closely to make sure whatever this is is something you can tolerate / wouldn’t drive you absolutely bonkers. I’d also just have your bullshit detector on and listen for really authentic, specific responses.

This is a pop culture reference to the film, Get Out.

• Can you give me an example of a recent project you’ve worked on? (Optional follow-up: How did this idea come to be?)

  • A good answer, for me, entails the person describing end-to-end ownership of the project all the way from discovering the need for a project themselves and then seeing it through to execution. If the person describes the project as a pet idea from their boss’ boss (I call that person your grand-boss) or the CEO, then that might raise some questions on how much ad-hoc work will be flying your way from the top-down. Consulting folks, you might experience a little PTSD here.

• Can you give me an example of a project that I’d be likely to work on?

• In an ideal world, what would you like to do more of? What would you prefer to do less of?

• What surprised you when you first joined [Company]?

  • Some positive signs include access to and mentorship by senior leadership (ideally in some structure set up by the People org of the company itself), transparency about what conversations are had in the board room, investment in professional development and mental health, meaningful and open conversations about difficult things like racial injustice, etc.

Once you’ve got the offer in-hand, ask:

• How often do people switch teams internally?

  • Be careful about asking this question—I’d avoid asking your would-be boss or even anyone on your direct team this. You don’t want to raise any concerns that you’re just using this role as an ‘in’ to get to the role that you actually want. Even if that is the case. Rightly so, they don’t want to go through the trouble of hiring and training someone only to have them try to shift gears after 6 months or even a year to another team or function. But if you have the opportunity to ask someone that’s more of a peer but on another team, go for it. If they reply that it’s really rare, they haven’t seen anyone do that, etc. be sure that you’re really stoked on the role itself because internal mobility appears low.

• What’s your long-term vision for this role?

  • In a start-up world, your hiring manager might not be able to give you a concrete answer but that’s not necessarily a bad thing. You may even get a response that’s something along those lines. However, it’s a good indicator of how thoughtful your manager is when s/he is able to articulate what your role will eventually fully own vs. what projects s/he needs immediate help with.

• Can you tell me more about how performance evaluation is done at [Company]? Are there defined career ladders?

  • Start-ups tend to not heavily invest in their performance management until they’ve reached a certain stage of maturity, so this is a tell-tale signal on how far along they are. Know that career ladders don’t necessarily mean that you’ll be promoted more quickly or slowly; it’s clarity around what it takes to get promoted and what you’ll have to demonstrate or tie your performance to make a sound case.

• Who should I be chatting with about my compensation package?

  • Never fear, dear reader, I’m planning on a whole post dedicated to understanding the mumbo jumbo / fine print of start-up compensation packages. But here you’ll want to understand whether it’s the HR person (= recruiter) or your manager that’s holding the purse. If it’s your manager, that’s just another signal that there isn’t a fully developed recruiting org.—not necessarily surprising for an earlier-stage start-up—so take that as you will. You can also avoid some awkwardness by negotiating directly with the HR person instead of trying to play hardball with your manager if s/he doesn’t even have the decision-making authority.

• [To your prospective manager] Would you be comfortable sharing a short list of people who have worked for you that I could contact and get a better sense for your management style?

  • By the way, this is far from the only due diligence you should be doing on your would-be boss. Whether having a great manager is a Tier 1 consideration in your personal priority stack or not, it’s completely worth your time and energy to reach out to any mutual connections or even slide into someone’s DMs to ask for an unbiased opinion of your boss, since whatever references they supply are likely to give them a glowing review no matter what.

So from now on—when the interviewer looks at their watch and says, “Looks like we’ve got five minutes for questions”—that’s your Super Bowl, baby. Go get em.

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🎁 What other interview questions have you found to be super insightful? Please drop your wisdom on us via the comments below!

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