Is this company a sinking ship? And other things you should ask in an interview

Hindsight sure is 20/20, and none of us want to waste years of our lives on company that isn’t going anywhere. There are some ways (questions!) you can peer into the crystal ball and sidestep years of misery.

1. What is the company culture like?

Most companies (well, at least startups) will talk about happy hours and the kegerator. Good companies will have a culture that extends past drinking, though. They’ll all be different, but you may hear about bike clubs, board games, and hackathons in the way of events. Events are just a small part of culture. At a great company, you should hear things like: respect, blameless postmortems, encouraging innovation, curiosity, passion, etc.

2. What’s the story with investment?

Specifically, make sure the company has enough runway to make it to success. When was the last investment? If it was a while ago, is that because the company is cash-flow positive now and doesn’t need more money, or is nobody willing to invest more?

3. What recent press has there been?

If all the good press happened 2 years ago, why? If the company has been stealthy during a pivot, maybe that’s alright as long as you believe strongly in the pivot. If the company isn’t creating new press, though, it might not be innovating – and is likely to get passed by competition.

4. What do you think of the founders/company leaders (may be the same thing, may not be)?

Company culture and direction generally comes top down. Read between the lines of what people say. Do they respect the people at the top, or do they find them to be out of touch? Did these people have previous success? Previous failures? (Which could be a great thing – valuable lessons.)

5. Who are your customers?

No customers, no business. Everyone in the company should know who the customers are and care about them, from the Office Manager to the CEO. If not, the company either has major communication issues or major revenue issues; likely, both.

6. What do you like to do for fun?

Alright, this one could be slightly bordering on inappropriate for an interview, but I always try to sneak this in there in a non-creepy way. There’s no right answer -only one wrong answer: I have no time for fun. It’s one thing to work hard, but it’s another thing to completely lose yourself to work. That usually leads to burnout and doesn’t often translate into a great product.

7. What percentage chance do you think this company has at succeeding?

A CFO candidate looked me in the eyes and asked me that once during an interview. At first, it struck me as a ballsy question. However, I realized this was a candidate who knew what he was worth. He’d had a great track record of building up successful companies, and wanted to make sure the next place he landed would also hit it out of the park. Fair enough question. I answered honestly and he didn’t take the job.

Leave a Reply

two × one =