A few more (not that they'll necessarily tell you, or offer you the job after you get done asking):

6. What percentage of the company are those XX,000 shares you're giving me?

7. What's the current valuation of the company?

8. How much runway do you have left? (Although you can probably infer this pretty easily by when they last raised.)

9. Since you're giving me a YY% haircut on my market-rate salary, what reasons other than the almost certainly worthless, say, 0.25% of the company you're giving me over four years should I be joining you?

10. I don't believe 60-80 hour weeks are productive, sustainable or healthy. What do you think about that?

#6 is super important. It's absolutely crazy that many companies won't tell you this.

#7 is a good question, but don't expect a tangible answer -- unless they just closed a round yesterday, it's truly impossible to say. That said, it's still a great question to ask to see how they value themselves, and what they feel potential acquirers or the public market would value them at.

#9 - I think that's a good question, though might be more diplomatically phrased. ;) (That said, be aware that "market rate" is extremely hard to pin down: for the same reasons you should expect an ambiguous answer to #7, your own "market rate" is similarly ambiguous.)

#10 - Agreed. I target 50, personally.

Re: 9, totally agree on phrasing a little more diplomatically ;)

But even with the ambiguity, I expect the answers would still be enlightening.

I always prefer an explicit answer on financial runway vs. inferring based on the company's last round. That provides a more meaningful picture since there are things you may not be able to piece together during the hiring process (current burn rate, future hiring plans or other significant expense shifts, etc.). E.g. knowing they raised 4 months ago can be deceiving if they only have another 4-6 months of funding left.

It strikes me that asking "Who was the last person to quit, and why?" is a big faux pas in this area. Am I wrong, or is it common/OK to ask this kind of question?

It's been my experience that very few people "quit." Separations from startups tend to be very neutral, leaving it ambiguous whether someone quit or was let go. It's not hard to read between the lines, but discussions about this are not very up-front.

That does strike me as kind of rude, plus companies tend to not want to discus HR issues pertaining to other people since it's a potential legal problem.

Asking about previous employees is no more rude than asking an employee for references. If a company has a history of lots of employee churn that's a big warning sign.

When you ask for a reference it's usually because the potential employee has said it is ok to do so.

You'll never get a straight answer on that. If a company told you the truth, I imagine they're opening a door for a lawsuit. You'll get the standard "left to pursue other opportunities / spend time with family / personal reasons" bullshit. Same reason that references are a waste of time: unless a reference really loved you, they'll forward you to HR to verify dates of employment. In my opinion, a reference is never going to give you even a tiny bit of negativity, and will only serve to reinforce a positive impression.

I generally ask any company about their "churn" rate. I think it would be pretty silly not to. You are interviewing them as much as they are interviewing you, why just ask easy questions that let them hide the actual situation?

Yeah, this is much less personal. An "average" over all people seems more appropriate (though still risks making some people feel a bit awkward, I think).

One reason to avoid these kinds of questions is because they can appear aggressive and people may not want to work with someone who is so up front on something that may or may not actually determine how well they can do their job, though obviously, churn can affect the over all work environment so it's good to know, but I think for most startups with <100 people you can easily figure this out on your own.

I've asked folks in interviews "have you ever had to fire anyone". It's an interesting question.

It's only a faux pas if the company you're talking to sucks. Great companies love hard questions.

I'd love to hear anecdotes from people who've actually asked this question and whether or not they got good answers and they ended up working/not working there because of it.

I disagree with 4 out of the 5.

> "How many people do you hire in a typical month?" Is there such a thing as a "typical month" in a startup? Isn't the definition of a startup that it's moving fast, things change and you have to roll with the punches?

> "Who was the last person to quit, and why?" Good luck getting a real answer out of this question. They're not going to say that "he hated the atmosphere", or "the pay was too low". They're going to say something positive-sounding and completely bland. It tells you nothing about the company at all, unless they completely trash talk the person who just left.

> "When do you intend to raise money, and why?" Again, you'll be lucky to get a real answer on this as well. If you get an "X months of runway before we need to raise again", there are a million assumptions built into that, and things change quickly. "Is the company primarily financed by selling product, or selling itself?" is probably a better question to ask.

> "Can I see where I’ll sit?" Seriously? Again: it's a startup, things change. In the 2 weeks it might take you to start, the seating plan may have changed 3 times. Ask for a tour of the office, sure! Depending on the startup, it's unlikely that you'll be spending 2,000+ hours a year sitting at the same desk. Offices will move, things will be re-arranged, etc. Look at how the workspace is set up, to be sure; but asking something this specific seems like an odd request.

> "What do I want to do accomplish in my life, and how does this help me down that path?" This one I agree with.

> "Can I see where I’ll sit?" Seriously? Again: it's a startup, things change.

I actually like this question. You can tell a lot about a company by whether they're thinking about how to integrate new people. If they say, "We put new people right here next to Michelle for the first few weeks so she can show them the ropes," that's a pretty good sign. If they say, "We'll find something," that's a sign that they haven't really thought about what to do once they have somebody on board.

I agree with most of what you're saying but you can easily deal with your second issue by contacting former employees and former co-workers of people working for the startup via linkedin. Many people feel this is a bit stalkerish but if I'm asked to provide personal references to a future employer I'm going to seek out personal references for the people I will be working with as well.

I think your pessimism is spot on for most companies. But I think you'll be pleasantly surprised with how great companies handle those questions.

Good list - Not too sure about this one

> How many people do you hire in a typical month?

1 per month? that seems low. Hiring is like everything else - subject to human cognitive biases. We all like to think that we can make the right decisions if we just put our minds to it, but the fact of the matter is a lot of it is just randomness. If I hired 4 people a month and I really fucked up on 3 of them I'd at least have 1 good employee left. That's a higher expected value than if I hired 1 person a month and screwed up just 5% of the time.

Another question would be how an all around p2p guy ends up running an expense management company :)

Heh, it was a long road:

1) Have a p2p startup get acquired by Akamai 2) Want to do something financial 3) Financial == PCI compliance == super super expensive 4) Use p2p to build inexpensive PCI compliance 5) ... 6) Profit!

I like where am i going to sit part.

Yes I like the blog article!