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The really important job interview questions engineers should ask (but don't)

Jun 22, 2022

Since we started PostHog, our team has interviewed 725 people.

What's one thing I've taken from this?

It's normal for candidates not to ask harder questions about our company, so they usually miss out on a chance to (i) de-risk our company's performance and (ii) to increase the chances they'll like working here.

This isn't desirable. People should be able to reduce the chances they end up in a situation like this, or this.

Disclaimer: These questions are direct, but a company that reacts badly to them may not be a good place to work. There are also a lot of questions here - think of them as themes, and you don't need to ask them all. Prioritize based on what you hear through the process.

If I were job hunting, these are the themes I'd be interested in – it's skewed towards (i) startup / early growth software companies, (ii) engineers and (iii) interviews with founders (I am one), but the concepts feel like they'd be useful beyond that.

Needless to say, but people who ask these kinds of questions often make great hires for startups, too.

Does the company have product-market fit?

This is the single most important thing a company can do to survive and grow.

  • "Do you ever question if you have product-market fit?"
  • "When did you reach product-market fit? How did you know?"
  • "What do you need to do to get to product-market fit?"
  • "What's your revenue? What was it a year ago?"
  • "How many daily active users do you have?"

It's ok if these answers show you the founder doesn't have product-market fit. In this case, figure out if they will get to a yes. Unless you want to join a sinking ship, of course!

Early stage founders are (or should be) super-mega-extra-desperately keen to have product-market fit – it's all that really matters. The ones that will succeed are those that are honest about this (or those that have it already) and are prioritizing it. Many will think or say (intentionally or through self-delusion) that they have it when they don't.

Low user or revenue numbers and vague answers to the example questions above are a sign that it isn't there. Product-market fit is very obvious.


  • Founders who aren't spending a ton of time talking and selling to users pre-product-market fit – it's a flag to attempt to outsource/delegate this

  • Companies where you don't understand the product or its benefits – if it can't be explained to you, others will struggle

  • Solutions looking for a problem

If there is no product-market fit, but you think the team could find it, it's very important the company has lots of runway (it'll be hard to raise more money without product-market fit, so time to find it is crucial), doesn't have a huge team (it's harder to make rapid changes in direction with a lot of people), and moves fast (look out for bureaucracy, management, or a team that can't work well with ambiguity).

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How much runway does the company have? Does their spending look within reason?

This means that the company whilst not profitable, is growing fast enough that it will become profitable ahead of running out of money.

This means:

  • Avoid companies that don't know if they're default alive or don't care about it, given the current climate – this may change in an easier fundraising environment for early stage, capital-intense business models

  • Avoid companies that you don't believe could get to default alive because they don't have enough time or are too slow to get things done

There are exceptions. For example, very low revenue numbers may lead to unrealistic growth rates – if I went from $1 to $2 of revenue yesterday, I'd be pretty darn rich if I kept that growth rate up.

  • "What's your runway?"
  • "What assumptions are you making to calculate this?"
  • "What are your fundraising plans?"

If a company doesn't have product-market fit, spending should be minimal so there's as much time as possible to find it. Spending a lot and having a big team just makes it harder to change direction rapidly.

If a company has strong product-market fit and has a ton of traction, a shorter runway is ok.


  • Companies that assume wild increases in revenue to survive, within a short timeframe

  • Companies that are fundraising as they'll otherwise run out of money, but haven't closed the round

What's the culture like?

  • "What are the company values, and why? Can you give me some specific ways you've followed them?"
  • "Who decides what to build?"
  • "What does a typical workday look?"
  • "What are the things or behaviors that would cause a person in this role to fail?"

We get the above a bit more often, they're good questions.

How strong is the team?

  • "Can you tell me about the team I'd be working with most closely?"
  • "How do you compensate the team?"
  • "How do you attract and retain really strong hires?"
  • "Do you share board slides with the team?"

If you want to learn in this role ask yourself: do you believe this company is able to attract people who are as good as or better than you?

You are trying to understand if they view engineering as a cost center (aka a higher chance you'll be miserable there!) or not. Thoughtful answers to how to hire and pay people indicate this is prioritized. Sharing more information rather than less shows trust and partnership with employees.

What's in store in the future?

  • "What motivates you?"
  • "What are you most proud of so far?"
  • "Do you plan to sell the company?"

You can't guarantee that plans won't change, but this gives you some indication of what is in store and it helps you understand the founders' motivation better.

  • "What's the company strategy and why?"

You are looking for a simple answer - otherwise the company and the product will end up a bit of a mess. At PostHog, we define strategy as simply "Nail X", where X is the thing we need to nail. We're currently focused on Nail Self Serve.

  • "How do you and the other founders avoid falling out?"

One of the most common ways for an early stage company to die is that the founders break up. Hopefully they've put some proactive thought into their relationship.

  • "What keeps you up at night?"

This will reveal perhaps what the hardest challenge will be, and where you could add the most value if you joined

Be reasonable, but buyer beware

Startups do not have everything figured out. The challenge is figuring out if they can get from where they are today to where they need to be to succeed – just don't shy away from asking to see if they're headed in the right direction.

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