Understanding your position in a job interview

Jon Dobrowolski
3 min readNov 28, 2014

Companies are extremely complex, and the individuals representing them can have skewed perspectives. However, there are some tools at your disposal to offset potentially misleading information while assessing employment opportunities. With the help of colleagues and other hiring leads I’ve compiled the thoughts and questions below to aid you in your job search.

Reframe the job interview

Remind yourself that we are lucky enough to be in a talent market — they want you. Interviews are just as much for you as they are for your future company. When I’m on the other side interviewing candidates, I make sure they’re onboard and excited with the possibility of the position. If your prospective employer doesn’t lead with that, make sure you put them in a position to sell you on the job.

Questions to ask in an ‘Employer Interview’

There’s nothing worse than hearing all the right things in a job interview, only to find out that what you heard wasn’t necessarily accurate. I’ve found that some red flags can present themselves when you dig deeper asking questions like these:

The Product Process

How do your teams currently capture software requirements?

How have you recently improved your product development processes? Can you describe your process step by step?

Why do you really need [job title/function]? What problem are you expecting it to solve?

What’s the size of the Product team? The Engineering team? The org as a whole? (i.e. are they beyond the 50 or 150 mark?)

What’s the history of the Product team? (i.e. size, change over time, recent re-orgs)

How has the team scaled?

Ask about the Business

Can I see your current roadmap? (Alert: If they can’t produce this in some fashion you should question how badly you want this opportunity)

How does your revenue stream breakdown?

What’s your platform penetration breakdown? (i.e. what platforms is your business on and what are the percentages)

How is this business defensible? (Alert: a lot of companies will bullshit you here… A lack of defensibility will make your job a lot harder and cause a lot of shiny objects to materialize)

Which business unit would you say is the driver of the organization?

Questions to ask yourself

You should continually ask yourself questions as you assess employers to make sure that you’re not blinding yourself. Optimism is great, but sometimes it can mislead you when you’re trying to ‘win’ the job. Here are the questions I try to keep in mind as I go through the interview process.

What’s the growth potential of this company?

Will this company be attractive to other talent as it scales? Is this the only exciting opportunity here?

Is there really a possibility for exit here? (Is this a factor for you? Mega alert if its all the company is talking about and they seem pretty far off)

Notes

These questions are focused on finding the right business. Finding the right cultural fit is a different story (maybe a future post) and you should be thinking of that at the same time.

Remember that the only way this list is effective is to have an opinion on the answers you want to these questions.

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Jon Dobrowolski

Multifinality / Concept / Product / Process / Design / Development