3 min read

How and why to interview your boss-to-be before accepting a job

How and why to interview your boss-to-be before accepting a job
Photo by Nathan Queloz / Unsplash

Sustain issue #64 (Get Sustain in your inbox next Thursday)

Last week we started to answer the question of how to find a company that cares about your well-being while job searching.

Today, we finish the conversation with what I believe is the most important step to ensure you accept the right offer. That is interviewing your boss-to-be after you have been given an offer.

This is a practice I have done before accepting my last two roles and has been really helpful in knowing what I would be walking into. Not everybody does this, but everybody should.


The interview process is all about the company interviewing you. Sure, you may get a couple of minutes at the end of each interview to ask some questions but it’s not enough time to gather all the details you need to make a critical life decision.

Interviewing your boss

After I receive the offer, I ask the recruiter if they can help me set up time with my boss-to-be to answer a few more questions about the role. They are always more than happy to help since both the recruiter and boss want to close you after the offer has been given.

These are some of the areas I typically probe into with this call (if it hasn’t been made clear already):

  • Work location: Is it remote, in-office, or hybrid (and how do they define hybrid)?
  • Team culture: What are the team norms? How do they work? (Remember, culture can vary within the company or even within the department)
  • Pace: What does the pace of work look like? What’s the rhythm of how decisions are made? How are new priorities and tradeoffs handled?
  • Well-being: Can you take a break during the day? Is there an expectation for you to be plugged in nights/weekends/PTO?
  • Success measures: Is it a culture where success is measured on work outcomes or hours worked?

In addition to collecting the final details to make your decision, this call is also the time to start laying the foundation for your needs so you’re in the driver’s seat on the first day.

For example, I might frame a question like this:

As somebody who previously experienced deep burnout from work, time to rest and recharge outside of hours is critical to producing the high-quality work we’d both want to see. Do you feel like the team culture I’d be stepping into and your philosophy support my need to take care of myself assuming I deliver the quality of work you’re looking for?

Learning from the call

You should have a pretty good idea if it will be a good fit coming out of this call. I ignored the warning signs of my boss-to-be in this call for a previous job I accepted. I stepped into a job that wasn’t supportive of my well-being and where I had a boss who wanted to assert their power over me. Needless to say, it wasn't a good fit. I knew the warning signs but I ignored them and stayed only 9 months.

Remember that interviews go two ways. It’s not just the company interviewing you. It’s just as important to make sure the fit is right on both sides. Taking time to explore the role before accepting saves both you and the company a lot of headaches.

Ready to downsize your relationship with work and quit burnout?

Hi, I'm Grant Gurewitz. I'm on a mission to eliminate burnout at work. I've been in tech for 10 years (ex-Zillow, current: Qualtrics) and suffered deep burnout and came back from it even though I never found a playbook for doing so. So, I'm writing it myself.

✉️ Want my top tips? I share my full step-by-step playbook in How I Quit Burnout, my premium newsletter. Get the next one delivered straight to your inbox >

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