How did you meet the people you work with in your startup (past jobs, school, randomly, etc...)?

How do you solve disputes within the team?

If you were not doing startups or technical things, what types of things would you pursue?

Was the original idea for the startup the one you stuck with?

Was there any AHA moments within the team that were notable?

How many monitors do the programmers use?

Not because I need a bunch of monitors, but it seems like a rough indicator of how much programmers are valued in the company. A company looking for code monkeys isn't going to find the marginal return of another monitor worth the investment.

I used to work at a company where the programmers got basically whatever scrap monitors could be found - usually a single 15" or 17" CRT - while some of the secretaries had dual 19" LCDs. That was as recently as a year and a half ago. (I think things got better since then, but I didn't stick around).

So, yes. Excellent question.

This might be a very difficult question to get answered, but I think it could be very interesting: In retrospect, how closely (or not) did the allocation of ownership (between founders, and also founders vs. employees) match the contributions people ended up making to the company?

Bonus points if you can ask several people at a company and get different opinions about the relative values of each other's contributions. :-)

I think this question is fascinating, and it's one I've asked several people at various startups I know. Because you're comparing extremely different types of work to each other, it's very hard to answer.

OK, honestly, what kind of schedule & hours do you guys (and ladies) really keep?

Most consistently 10-8 ish. If there's a big design or feature being worked on, ill probably get reeeled back in from 12-3. Very easy to get lost in photoshop.

Why would someone sacrifice their secure job with good benefits and plunge into the startup world?

Have you ever watched Scoble interview startup founders? It's completely unscripted, yet he does a remarkable job (in my opinion). You can tell he's passionate about discovering neat technology, and he always gets excited over some cool features. It's very authentic. You might want to check out his style. This is a good example:

http://www.fastcompany.tv/video/a-really-useful-way-take-not...

What was your biggest time waster?

news.ycombinator.com ;)

1- how will you make money? What if that doesn't work? What about your plan C to generate revenue?

2- What is your exit strategy?

3- What if Yahoo, Google or Microsoft launchs a competitive product?

4- What would you do if you were not startupping?

5- What other startup do you like?

Which advice have you ignored at the outset, only to regret it later?

Do you hang out together outside work?

In retrospect, did you do it the hard way, or the easy way (whatever each constitutes in your context)?

What will you do differently next time?

How transparent are the founders in their info-sharing?

If you have paying customers, how did you find them? And how are you planning to get more?

What a great question. I'm particularly interested in the marketing and customer gathering methods of startups who have gone the bootstrap route instead of receiving investor money.

1. Why did you start your company(ie. what problem are you trying to solve)?

2. Has your original idea/product changed over time?

3. Have you started a company before?

4. What are your funding goals (if any)?

5. Where do you see your startup in 1 year?

6. What is your best advice to other entrepreneurs?

Some more questions:

1. How do you ensure that ideas are listened to?

2. How do you find technical, business and recruiting talent?

3. What are the 1 - 3 central tenets to your business? What do you do if people stray from these ideas?

4. Are people expected to work 12 hours a day, or is there a work-life balance?

5. Will the company make a reasonable effort to accommodate the requirements of techies, such as a quiet office, or are you expected to sit in a bullpen next to salespeople or tech support?

6. Do I get my own printer / second monitor / fast pc / team morale budget / software budget / 20% time etc.?

(1) What are you doing? (2) What is important to you?

If (1) doesn't directly contribute to (2)....

For CEOs, "What are the last three important things about engineering/development that you didn't hear from the VP-Engr?

For VP-Engr/managers, "What are the last three important things about the biz that you heard from your reports?"

In both cases, the followup is "What did you do with that information?"

1) What are the weaknesses of your startup?

2) How do you manage between letting people have a say in product versus micro-management?

What keeps you up at night?

What was your biggest mistake? We want the gory details.

DO you have an exit strategy?

If so, when did you formulate it?

If early on, how has it affected your product?

Man, these are awesome questions.

Talk about success story in crowd-sourcing.