Recently, I got a chance to start a business with an old friend of mine. We went for ten months before I realized that particularly business was not the right for me.

In those ten months, I learned quite a lot, and it gave me proof that I have the stomach to handle the intense startup roller coaster. There were definitely some dark days…

Here’s what I learned from my “failed startup experience:”

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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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Actually, there are two equally strange pieces of advice I got. One was when I was 15 years old or so, and I joined a DJ pool (think of Birchbox for vinyl, but you get vinyl records 1-6 months before they go on the radio), and the manager of the pool told me “don’t f*** up!”…in front of my dad. I still don’t understand why he said that…

But we’re here to discuss a more relevant piece of advice I got…

I had to do a total of 6 co-ops/internships as part of the University of Waterloo’s Engineering program. One of these co-ops was at NexJ Systems as a Professional Systems Consultant in 2009 where I helped customize financial CRM software for clients.

It seemed like I got chummy (although I didn’t think this was the case) with a manager (whose name we will leave out) and he told me this:

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It’s a start of a new year and you may be looking for a new challenge as part of your New Year resolutions. When looking for a new job, you would usually look at other companies that build their own products for their own customers, and most importantly, have a Product Manager position. But now you have another choice: agencies.

I’m not talking about the traditional digital/media agency here. I’m talking about a different breed. These “agencies” offer Dev and UX resources to help others build products and tend to refer to themselves as any of the following: product consultants, product development firm/shop, design firm/shop, etc.

Their main goal is to help you build a product, not just a website or a useless app.

Some of these firms either started out as an outsourced dev shop and then added design/UX to their toolkit or started out as a design/UX shop and added development to their services. Now they are looking for Product Managers!

But why?

To answer this question, I’ve spoken with a number of these product development firms, including Neo, Happy Fun Corp., Fueled, Prolific Interactive and Thoughtworks, to understand why they need Product Managers. Here’s what I’ve learned during the conversations:

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From my personal experience, empathy is the one attribute that almost every single job descriptions depict as a requirement for their Product Managers.  This make sense since Product Managers are supposed to be the advocate of the user, and in order to do that, they must be able to empathize with their user, right?

Well, this author believes empathy is a piece of the puzzle, but another attribute is much more needed:

Let’s look at why:

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We use fits everywhere. You might say your pants fit you well or your two friends who are dating/married are a good fit for each other. Fit is also important in the startup and product development world where you have to figure out the Problem/Solution Fit and Product/Market Fit before even thinking about scaling, otherwise you risk wasting valuable resources (time and money).

Employers also look at fit. Sometimes they judge a bit too prematurely based on your resume, or perhaps rightly. They even use the word “fit” when rejecting you through their automated messages:

 

…we don’t think you are the right fit for this position at the present time.

 

It is just as crucial for you to look at fit when looking for your next move, especially in Product Management and UX where there are a lot of factors that you must take into account to increase your job satisfaction.

Here are the Fits you should consider:

1. You-Role Fit

You-Role Fit is about understanding what you are going to be doing on a day-to-day basis. Hopefully you’re applying to a job that fit’s your perfectly or in your zone if not the exact fit. Here are some questions to ask to help understand if the role if your fit:
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