Irfan Ebrahim

Previously, I shared some of the questions I like to ask when interviewing with an organization for a Product Manager position. One thing I quickly realized while interviewing back in the day was that interviewing at an established company or former startup is quite different than interviewing at a startup, and that’s because the startups deal with a lot of risk around viability.

You might say that all organizations, whether they are startups or not, deal with risk, and risk comes with working anywhere. But, as a Canadian working in the US on a work, I knew that if I wanted to work for a startup, I needed to understand for myself whether the startup in question had the potential to succeed. I took this aspect seriously because if I joined a startup that tanked, I would have to leave the US promptly and then try looking for a job in the US from Canada…and that’s something I wouldn’t be very excited about doing. In addition, I wanted to find an organization that I could be with for the next couple of years.

So how could I understand whether a startup had potential to succeed (or at least survive for the next 12 months)?

Well, by having an honest and open conversation with the founders of the startup and asking these questions:

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Interviewing for a Product Manager role is not an easy task, especially since there are just so many factors that can make a company either the best place to work at or the worst place to work at. A year ago, well pretty much exactly a year ago, I wrote about the 6 Fits every Product Manager should consider before accepting a job, to help understand if this job is the job for you. This article became my second most popular article, behind the slightly controversial Waterfall vs Agile vs Lean post.

We’ve all heard how important it is to ask questions during interviews, not only for you to figure out if this role is for you, but also because it shows your prospective manager/company that you are thoughtful and care about what you do with your life. But coming up with good questions in not easy, especially if you are new to Product Management and are not sure what to ask, or you’ve been out of the interview game and are a little rusty.

The side benefit to asking good questions makes you look like a candidate who wants to work there

Over the last three years, and after interviewing with ~50 organizations, I’ve developed a list of questions for me to ask, in case they were not answered during the interview, to help ensure that I understand the role and company as much as possible, and most importantly, whether a specific role and company are the best for me.

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