The Best Question to Ask in Interviews

Lilly M. Dobreva
Jul 23, 2019 · 3 min read

It’s hard to know if a company will be the right place for you while you’re still interviewing. Sometimes, the interviews are over, and you get the offer only to realize you are unsure. It has happened to me in the past. It just means I didn’t take the opportunity to dig deeper. Or worse, you think you have a clear picture, but once you start at the company, surprises start emerging.

To avoid this, next time you are interviewing, ask the CEO or whoever is present from the management team to answer this question:

Imagine it’s two years from now. The company has failed. What went wrong?

This is the classic pre-mortem question. It seems simple and it is, and at the same time, it’s an incredibly complex question. Let’s unpack it.

Illustrates knowledge and understanding

First, it’s essential to ask this question because it will reveal if the person answering knows the ins and outs of the business. Any business can fail for many reasons, some out of our control. But that doesn’t mean the company should not be aware of such dangers and actively work to mitigate the risk. As a leader, if you don’t know what can bring down the company, it’s hard to believe you fully understand what really brings the cash. That, in turn, signals potential strategy shortcomings. You’ve been warned.

Highlights problematic areas

Second, it shows you where the weak spot of this company is. Is the answer related to competition stealing their market share? Likely the company in question feels that they are not innovative enough and not able to go fast in comparison to other companies in the field. Is the answer related to the product? Culture? Costs? The answer tells you what scares the people at the top and likely will inform the strategy in the next few years. Now you know better what to expect.

Reveals character

Third, you can observe how your potential new leader tackles what is indeed an unexpected and tough question. Able to think on their feet? Is humble and objective enough to acknowledge failure could happen? Communicates well so even an outsider can understand the explanation quickly? The person is convincing and inspiring enough that you still want to work there even if you just heard a plausible way this company can go bankrupt? Happy to be vulnerable and open with you? Well, congratulations, they aced your challenge.

Bonus: It boosts your position

There is one other reason why you might want to ask this question in your interviews. Basically, it’s none of the standard questions people ask and it is a thoughtful and revealing question. Often, when I ask this question, I get the surprised look and then acknowledgment that it is an excellent question and no one else has asked this before. As a result, you stand out from the other candidates and it shows you are analytical and creative. These are all fantastic things to achieve with just one question.

Once you get the answer, don’t stop there. Keep asking thoughtful and difficult questions to fully understand if this company is the one you want to join. If you’re going after a Product role, make sure you also check out David E. Weekly’s awesome article on Acing Your Product Manager Interview and Andreea Nastase’s How I Prepared for a Product Manager Interview. Good luck!

Let’s be friends! Follow me on Medium for more articles on product management and startups.

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