How to interview a company while they interview you

Tevi Hirschhorn
5 min readJun 23, 2020

When I started my career, I didn’t know how to consider company culture in new jobs. I was more anxious about how I presented myself. I realized it was like looking for love and never thinking about what I wanted in a mate. My journey has taken me through the agency world, enterprise, and startups of varying stages — fast moving rocket ships to traction-less duds. Now, I vet companies I want to work with, and take a hard pass if I have any doubts about culture.

Here’s what I learned:

1. Company culture is the most important thing you verify during the application process.

They want to know if you have the skills, and if you’ll be a good fit for the team. But if you take that as a given, your time at the company will be very different if the company suffers from poor culture. Culture has nothing to do with bean bag chairs, snacks or ping pong.

You can still dread going to work each day, even if the work is interesting, the company pays well, and you have a great list of benefits. In a bad environment, you can be miserable.

2. Look out for red-flag buzzwords.

“We have an open door policy.” If executives can’t take the time to seek out issues and consciously build good communication methods, then those are not priorities for them. “An open door policy” demonstrates lazy leadership.

“Work hard; play hard.” This is code for “work hard and try to find the time to play without impacting your hard work.”

Any use of “Ninja” or “Rockstar” is not necessarily a deal-breaker, but make sure they have a good collaborative environment, and are not just looking for Twitter-, IG-, or Dribbble-stars to make their team look good in PR.

“We’re a family.” No you’re not. My family provides unconditional love and support. A company is probably more like a team. How do you all work together? How do you support each other?

When you hear a buzzword, try to find out what they actually mean by that.

3. Where does the role lead in 1 to 5 years? What does the company look like in 5 years?

It’s common for hiring managers to ask where you, the candidate, expect to be in 5 years. But have they put the same thought into the role they’re trying to fill? What does advancing in the company look like? Where does the company hope to be in 5 years? How will this role impact the company? If they hope to be a global unicorn but don’t know how this role will advance, then you’re just a cog in their big machine.

4. Be careful how you ask questions

You want your new company to have rational expectations about work-life balance. But if you ask that straight out, you could be sending a signal that you don’t want to work hard! Don’t send negative or incorrect signals!

So how do you ask about work-life balance? Keep reading…

5. Think about the role itself and what faulty processes could end up causing you to pull an all-nighter or work through the weekend.

As a product manager, I would ask things like:

  1. What’s the release schedule?
  2. What are your support processes?
  3. How do new features get prioritized?

Answering those questions would give me some insight, and arm me with information for follow-up questions: If the releases are Friday afternoon, that could be a red flag.

6. What mistakes were made? What areas could be improved?

This is a common questions hiring managers ask of candidates, and for good reason! Nobody’s perfect, everybody makes a mistake every now and then. Just like they want to know how you own up to mistakes, you want to know what trouble spots exist, and who’s taking responsibility for them.

7. Ask open-ended questions about who else is on the team.

I’ve asked things like, “What types of people does Company Corp hire?” and “How do you balance hiring for ambition AND compassion?”

When I’ve hired, I looked for candidates who were ASK: Ambitious, Skilled, and Kind. If someone is unkind but ambitious, they’ll step on others to get ahead. A good question to ask is, “If you have a tight deadline, and a coworker seems to be behind in work you need to hit your own deadline, how would you navigate that?”

8. Ask the interviewer to describe the management style of the executives.

Drama starts with the leadership allowing it. If the executives are not clear in their direction, or don’t prioritize communication and culture, then the culture will suffer. Listen to what is said and what is not said about how the company is led and managed.

9. Any new hire is a change to the team. Don’t assume you’re a welcome addition.

Ask everybody you interview with at a company how the new hiring will affect the team dynamics, and if everybody is on board. Ask what team changes might occur in the future.

I once had 2nd interviewed for a role where it was clear I would be more senior than the person interviewing me, based on conversations from the first interview. It was one-on-one and extremely uncomfortable. The interviewer was clearly bitter the whole time. I didn’t make it to the next round, thankfully.

10. How are decisions made?

Ask your interviewers how decisions are made, but be specific. Ask about how decisions are made regarding the type of work you’re doing. Again, since I’m a product manager, I would ask things like, “How are product decisions made?” and “How are design decisions made?” You should also ask how decisions are made regarding company direction and culture. And ask for examples.

You’ll learn if leadership respects it’s hired experts, and if they ever had issues in the past — and how they learned from it.

For example, if all decisions are made by the CEO, and they’re approved or vetoed at her whim, then you can assume there could be friction to truly do your best work.

11. Do your homework!

Don’t start and stop your interview questions with the interviewer. Do your homework! See what current and former employees say on Twitter and LinkedIn. Reach out to current and former employees for an information interview and get their thoughts.

One hiring manager I stumbled across on Twitter appeared so venomously opinionated I was slightly freaked out. Another contact I reached out to had just changed roles, and had a lot to say about friction doing his best work at his former employer.

Also, see what leadership, the hiring manager, and other people you might be working with are sharing! If they’ve given talks, been on podcasts, or have other interesting content, it can let you know how the company encourages professional development.

See what the leadership and company stand for. What passion projects does the company have? Are there any team building activities they’ve publicized? How do they give to their community?

12. One last thing — go with your gut!

My friend Jennifer Aldrich wrote about going with your gut here (read the story about the murderer!!). The point here is obvious, though: if something seems a bit off in the hiring process, trust your gut.

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