Sent on August 26th, 2022.

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A follower recently reached out to me on LinkedIn with this request:

“Read your articles, and they are quite informative. Appreciate it. Would you be able to write a blog on things to do/ask before joining a startup as an employee?”

That was the best request I’d received in ages, so I immediately got to work on a piece about the questions you should ask, especially from the founders, when you are interviewing for a startup job.

Note that these questions will apply from a startup of a few people to over a hundred people. They are all relevant, and founders can easily fail on these. Or, as I call it, raise red flags.

You should also be aware of these things:

First-time founders, who’ve never employed people, will be learning people management as they go along, building their business.

The great thing about VC-backed startups is that the management gets professional help from investors and advisors.

From my personal experience, a single founder, the bootstrapped company is the most prone to suffer from not-so-great company culture. The founder is alone, and when times are tough, the issues can become lashed at the founder.

An employee shouldn’t feel awkward asking the company the same questions that an investor would ask. Also, you’d want to ask about such details that might not come up in an investor conversation.

Okay, let’s start with the questions. What are the questions to ask?

Do you have stated the company values?

Having values stated is the cornerstone of excellent company culture. It is what the founders want as the default behavior of people in the company.

If the answer is that” we haven’t yet stated the values,” it can be a red/yellow flag since the founders seem to be more focused on making progress on their games or other priorities than the culture.

Without the values stated, how do you know if the company is the right fit for you?

Do you have a meeting policy?

Great companies have thought about everything. The answer will reflect on how they’ve thought about meetings, maybe they have a policy, or perhaps they don’t. You want to get a feel that they are conscious about how people spend their work time.

I’ve previously written about meetings here.

Do you openly talk about the runway?

One of my favorite culture-building and accountability exercises is that founders share their runway with the team, preferably weekly or whenever they have regular all-hands meetings.

It creates a feeling of transparency that the entire team is in the same boat. Founders often tell me that it’s hard for them to be so open about the situation with the team; how will the team handle “bad news?”

A negative answer to this question can be read as a red flag. If the founders haven’t been sharing the runway actively with the team, what else could they be hiding?

Sahil Lavingia, the founder of Gumroad, talks openly about everything happening in his company, including how bad things are sometimes. In this piece, he talks about how the company works, titled “No Meetings, No Deadlines, No Full-Time Employees.”

Why did the founders start the company?

You want to see if your motivations for your reasons to be in gaming and work on something that has meaning align with what the company founders are thinking. – This question is an excellent follow-up to asking about the values since it will uncover more about why the founders are doing what they are doing.

These four are the most important ones. Then I’ll add two bonus ones:

  • How do you prefer to compensate employees? Do you like to give out shares or stock options versus a competitive salary?
  • What great company is an inspiration for you?

What else?

As you are interviewing, you should go outside the company to ask about the founders. Investors do reference checks on the founders by talking to ex-colleagues, ex-bosses, and previous investors. It would be best if you did the same.

Here’s a list of questions you should ask:

  • What are they like to work with?
  • Did they do what they said they did?
  • What are some areas for further development?
  • Are there any red flags I should know about?
  • How good are they at what they are going to be doing?
  • Is there anything I haven’t asked that you would like to share with me about them?

Here’s a piece I found helpful for developing more questions to ask in an interview. The questions aren’t explicitly aimed at startup interviews where founders are put on the spot, but these will also come in handy.

(Photo by Ekaterina Bolovtsova)