Most of the time during the interview process I've been reluctant to ask a lot of questions about the company I'm interviewing with, generally happy to have the opportunity. Sticking with that kind of approach I'm not sure what or if I'm missing out on anything. Likewise, I'm not sure if it has any effect on negotiating a position with a company if I'm interested in joining them.

In your opinion, what are the most important questions to ask when interviewing with a startup?

I can't remember the last time I interviewed. This is from the point of view of a hiring manager and the questions I like to hear from candidates. Think like an investor.

Some general themes: company direction, competition, culture and job reqs.

Personally, I prefer it if the questions show that the candidate has done some research and knows the space the company is in. For example, for a competition themed question at an up and coming startup, instead of asking "Who are your competitors?" you would ask "Company X and Company Y are also in this space. How do you see your company in relation to them?" or "If Company X (who isn't in your space right now) started selling the same product, how do you think that would affect your company?"

Of course, those questions are generally best directed at someone higher up in the company but it's always interesting to see how people at different levels respond.

For a hiring manager, avoid too many questions about culture. Focus more on generic and overused but useful questions like "What keeps you up at night? What is your biggest problem right now?"

As for how it would effect the negotiating, I think the goal is to come out of the interview looking like a strong contributor who will have a long term positive effect on the company. Questions that demonstrate that will increase your value, where questions like "How much vacation time?", "Can I work from home five days a week?" could reduce your value.

The outcomes that the hiring manager is trying to achieve are: How "good" on a scale is the candidate and do we want to hire someone on that scale. Once they've determined what scale they think you're on, the range of negotiations isn't very wide. If they already think you're awesome, you can pretty much ask whatever you want and it won't have any effect on how much they will pay you.

Also remember, you're a hot commodity right now. Don't let it give you a big ego, but keep it in mind. Even though you're under a time crunch, you're still a good hire and they should know it.

As with Jeremy, I've not actually formally interviewed in a long long time, so take this with a grain of salt.

I would agree that culture should be a focus and you should spend some time going over how the team works together. I'd get into specifics: is there a lot of process? Are people empowered to make decisions? is risk and failure acceptable? etc. You want to know if you'll like working with them, but also want a good idea of the day to day work environment.

I would also be tough on job reqs. Some startups aren't sure what they're looking for, be honest about what you can and can't do and make sure they're still interested. If they want more for you ask about training and timeframes, etc.

I agree with Keith on job description & reqs.

I tend to ask what department I report to and how product decisions are made, customer feedback prioritized. What's their commitment to users or community?

These are somewhat specific to the roles I go for, but in general getting the idea of the priorities and decision making of the company is great.

Just want to tack on to Laura's point about how product decisions are made and how customer feedback is incorporated. I feel like that's important. Might be a slightly off-topic (related to the relationship between product/community and support) but I know that's important to be as a designer and something I'd be concerned about as well.

(An aside: I'm working on writing up some thoughts about how community/support works with and influences product. My support team here is one of my best resources.)

Quick hits from my game PM interviews lately

1. Who owns the product? If it's me, what's the reporting structure with with engineering and design?

2. What's the product road map? How are you going to differentiate yourselves from X? (X is a close competitor).

3. Do you have any other PM's? If so, can I speak with them? Generally I then ask those people to take me through their average day.

These are questions I wished I had asked before my last startup experience:

1. How much runway do you have at your current burn rate? Is that including my job? Is it including any business deals that are not closed yet?

2. What does X shares mean in terms of % of the company? Are there different share classes?

One way that i've tried to ask the culture questions (it's tricky because i don't want to come off as lazy) is as such:

"Hey, coming from Z (my current job), i'm clearly not afraid of long hours, but it's not necessarily the healthiest ongoing situation. What are your thoughts on ideal work culture as it relates to team health?"

The trick here is: usually no one will tell you "I'm going to grind my team to dust no matter what." But as people start to talk about their own work habits, you get an idea of what they expect from others. One CEO i talked to said that he really believed in work/life balance, but he personally worked from 4AM to midnight, and he thought his CTO worked so much that he made himself constantly sick.