👓 Jensen Harris tweetstorm about startup hiring on Twitter

Read When you're leaving a big company to interview at a startup, there are some hidden questions you might not know to ask. by Jensen Harris (Twitter)
When you're leaving a big company to interview at a startup, there are some hidden questions you might not know to ask. Not all startup jobs are created equal; without the right info, you could make a bad choice. Here are 4 questions you should ask in a startup interview loop:

1) How much money does the company have in the bank?

OK, yes: this sounds super crass... an embarrassingly direct question. But it is also incredibly crucial, because without this info, you have no idea what kind of situation you are potentially walking into. You would never ask this question at a megacorp because, well, the answer is usually "infinite money." The cash position of a public company is also usually freely available. Besides, you probably wouldn't be talking to someone who could give you a direct answer anyway!

But at a startup, everything is impacted by money. For example:
* How free is the company to build towards its vision?
* How likely is the leadership to make desperate/rash decisions?
* Will you have access to the resources you need to do a good job?

There are lots of less-gosh ways to ask this question, like: "how strong is the company's financial position?" And be prepared, the answer might sound more like "here's what % of our Series B is still in the bank" or "here's how many more months of runway we have." These are ok! But by not asking, you have no idea what you are signing up for. And if a founder/senior member of the team isn't willing to give you *some sort of answer here*, that is a big red flag. They may be hiding something you won't find out about until you start work.

2) Tell me about a time the founders disagreed. What happened?

In any startup with multiple founders (most of them!) the founder working relationship can make or break the company. If it is wonderful, the company may thrive whereas if it is toxic, nothing can save it. Notice the phrasing of the question. As a candidate, just like as an interviewer, you must practice behavioral interviewing. Don't ask "how do the founders handle disagreement?" Any smart person can answer that well: “They talk, hear each other's perspectives, and work it out!” Instead ask the question the behavioral way: "Tell me about a time..." This forces the answer to be specific and real. Founders always have some disagreement; if they own that and show they know how to handle it, it is a powerful positive signal about the company. Note: Be especially wary if you are interviewing with a founder and they repeatedly answer your specific questions about this by taking the topic back into the abstract. This could show that they are not transparent, not self-aware, deceitful, or all three.

3) What is the role of the company’s board of directors?

I'll be honest. During the 16 years I worked at Microsoft, I am not sure I could have named anyone on the board. Bill Gates? The Netflix guy? It just wasn't in any way germane to the day-to-day of working there. In a startup, however, the company's relationship with its board could have a huge impact on whether you want to work there. If you are talking to a founder or senior exec, look for words of alignment and respect. Not snark or # or "ugh, the board, don't get me started.” If interviewing with a more junior employee, a great answer might well be "No idea, I’ve only seen them in the office once.” A board that is out of the way operationally, helping behind-the-scenes but not interfering, is a good sign that there's a healthy relationship there. Fun story: I once interviewed for a senior job at a tech startup. I went with the CEO to meet the board for a last round of interviews. The first board member got me into a room and started with: "Hi! FYI. you can't tell him, but we are firing the CEO." AWKWARD. Um, kthxbye.

4) Tell me about the changes you’ve experienced at the company over the last year.

A big company is pretty much the same year after year. Working there in 2017 is the same as working there in 2018. The best startups, on the other hand, are growing, changing, strengthening. The single best way to predict the future is by analyzing the past. And so by asking your interviewer not "where do you expect to be in a year" but "what have you experienced in the last year", you get a window into what the actual the pace of growth is at the company. A great, thoughtful answer about the ways the company is growing is a huge plus. A positive is often: "wow, I can't believe how much we've done/grown/changed/built when I think about it."

A worrisome answer is "honestly, it's about the same." When startups stagnate, they die. Hear the stories about what the last 12 months were like, and use that to gauge whether it would be an exciting place to spend your next few years. Companies that are thoughtfully growing employ people with a strong growth mindset, creating an amazing place to learn and build. Last thing: Don't be afraid to ask these things. You have the right to ask direct questions in your interview. As a founder, I relish being able to share info about our company. If you get vague answers/hostility, especially from senior people, this is a bad sign. Run away!

Startup interviews require you to probe differently than megacorp interviews. This is a good thing! What you learn will help you find the place that's a strong match for you.

Be prepared to ask the right questions, and you'll be one step closer to landing your dream startup job.


Published by

Chris Aldrich

I'm a biomedical and electrical engineer with interests in information theory, complexity, evolution, genetics, signal processing, IndieWeb, theoretical mathematics, and big history. I'm also a talent manager-producer-publisher in the entertainment industry with expertise in representation, distribution, finance, production, content delivery, and new media.

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