What Questions Should I Ask When Interviewing at a Startup?


The ten years I've worked since graduating college have been for companies with more than 40,000 employees. I am being interviewed by a startup. The job seems to suit me and I am ready for the culture difference from working for a giant company.

  • The founder is interviewing me
  • They have a hardware & software product
  • 3 or 4 employees and is looking at hiring 3 to 4 more
  • The hiring is contingent on completing their first sale

[Edit]: I have a relationship with the founder and have been following his progress for six months. He has founded at least three successful startups (independently verified) and I have no reason to doubt the "first sale" story.[/Edit]

What questions can I ask the founder so I understand the company and my place in it?

What can I expect in terms of benefits?

I like a lot of things about my corporate job. Like paid vacation and great healthcare.

Is it appropriate to ask for a signing bonus?


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asked Jan 21 '10 at 07:07
Dean Brundage
256 points

7 Answers


In your position, there are several questions you need to ask. Some are for the startup and some are for you. For the startup, I would recommend asking things like:

  • Cash Position and Burn Rate: This is pretty critical since you need to determine how long they have money for.
  • Types and number of investors: It's good to know if you are dealing with Angel, Strategic or VC investors.
  • Equity Stake in the Company: How much stock will you get for signing up.
  • Your Main Role: Exactly what will you be doing and who you will be reporting too
  • Culture: What's the culture like? What do they value? It's probably best to talk to the other founders about this and get a sense of what people are like.

The questions you should ask yourself are:

  • Why do I want to do a Startup? Your own reasons for doing a startup are just as important as picking the right one.
  • What am I willing to Sacrifice? This may be time, money or both. It all depends on what you value as important.
  • Is your Spouse/Partner Bought In? Critical to your startup success is that whomever your partner in life is, are they ready to take the ride with you.

In terms of asking for a signing bonus, that is usually not done. Benefits should be competitive. If not, then that is kind of a red flag. What I mean by competitive is that they offer the standard medical, dental, 401k, etc.

answered Jan 21 '10 at 08:58
Jarie Bolander
11,421 points
  • +1, but re "equity stake", remember "how much" means "percentage", not "number of shares". At an established company, equity will likely be in the form of stock options. So be sure to ask about acceleration on change of control, strike price (ie. What's the basis for the current fair market value?), and vesting schedule. – Joe 14 years ago
  • That is true. You do need to make sure you know what you are being offered. – Jarie Bolander 14 years ago


I am sure that there are a lot of guys/gals on this site who will give you some excellent questions to ask. Having moved from a Multinational to a small (20 people) company in the past - the biggest thing was to make sure you are ready for the major culture shock. Gone are the long standing set processes that you have been programmed to adhere to for the last 10 years and they are replaced by much more fluid and sometimes chaotic environment. As well as asking them questions, make sure in your own head that you can cope with this huge change.

Good luck!

answered Jan 21 '10 at 07:24
Dr. Phil
86 points
  • Agreed... OP should be careful of what he's asking for in going to work at a startup... He just might get it :-) – Gabriel Magana 14 years ago
  • Thanks for the advice. Good riddance to the processes & policies that feel like they are hindering my work. (-: – Dean Brundage 14 years ago


Questions to ask:

  • How would you describe the culture here? (At a startup, there's so few people that if you don't match the culture you will not have a good time.)
  • How do you make money / find new customers / determine what to build? (If you don't understand and agree with the answer, you're not going to fit in!)

For "expectations" for benefits and salary, there's no rule. It just is what it is! You will almost surely not get "great benefits." That's part of what you're giving up by being at a startup.

answered Jan 21 '10 at 08:53
16,231 points


I currently work for a small startup (current team is 4). A few quick things to keep in mind as you go into this:

You will be working a lot, a normal week will most likely be 55-75 hours. Make sure you are ok with working some crazy hours, 1 day is a long time at a startup :-)

You will be paid less then you are making now, possibly a lot less, this will be made up for in stock mostly, and some of the perks.

Per the last one, asking for a signing bonus (in my mind) is way out of line. At a early startup cash is really tight, the capital is just not there to be tossing it around like that. Note, unless you really are THAT good, we are talking you are the difference in making it big or failing.

You just need to go into this knowing that it is a high risk, high reward job. I am pretty young and love the excitement, so the risk is totally worth it for me. Also make sure you have a backup plan for when the startup goes under, because 9/10 will.

Best of luck, and if you do take the job... Work hard, there is nothing better then building a product from scratch and seeing it grow beyond your dreams!

answered Jan 21 '10 at 18:02
131 points

answered Jan 21 '10 at 07:47
Martin Hn
234 points
  • Might be helpful for OnStartup if you include questions here you find valuable, rather than just sending readers away to other blogs... – Matt 13 years ago


I would ask the founder these type of questions and I would listen carefully to the answers.

  • What are your vision and future plans for the company?
  • What qualities and values are you looking for in the employees you hire?
  • What qualifications and expertise are you looking for in me?
  • What are your expectations of me?
  • How would you describe the company culture and atmosphere?

I think the start up would pay a signing bonus if you are being recruited and the start up really wants you.

Startups generally have minimum benefits because cash is extremely tight. Expenses are more than revenues and any cash is put back into the business to keep it going. People who thrive in a start up environment like the excitement, freedom and creativity of doing things from scratch, things that have not been done before and are made up as you go along. In the startup I worked at, there was a critical two and a half year period where everyone in any supervisory management position did not go on vacation!

answered Jan 21 '10 at 09:00
Starr Ed
948 points


I'd try asking some of the employees what the culture is like before your interview on Twitter/email. Suit no suit.

Just curious "The hiring is contingent on completing their first sale" does this seem a little fishy?

answered Jan 21 '10 at 07:36
279 points
  • I already have a relationship with the founder and have been following his progress for about six months. He has founded at least three startups (independently verified) and I have no reason to doubt the customer/sale line. – Dean Brundage 14 years ago

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