Questions to ask CEO when interviewing at a startup


I've been through several rounds of technical (software developer) interviews at a start-up and have done pretty well. I've been invited back for the final round which will be with the CEO. I understand it will also be under NDA which will allow them to talk more about their plans, etc.

What sorts of questions should I ask?

Things I already know:

  • there will be options granted immediately (but not vesting for 3 years)
  • the company has been going for about 3/4 months and is close to delivering their first (software) product
  • I will be approximately the 4th software developer on board
  • the company is pushing for second round funding
  • they have a clear 5-year exit plan (although I don't know any more detail than that - they talk about "sitting on a beach" in 5 years)

I'd be interested to find out more about the exit plan and whether I will be "part of it". I'm also interested in how future funding plans will affect my options. But I'm not really a business guy, so I'm not sure what the right questions to ask are, or how to ask them without seeming rude!

Oh, and it's UK-based if that helps shape the answers.


Equity Interviews Exit Strategy

asked Sep 1 '12 at 18:22
13 points
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  • You can consider this failed business. There is no such thing as `exit strategy`. This is pure nonsense. Sitting on the beach in 5 years? You do not do such enormous (as for startup) planning, it's impossible. In 5yrs, sitting in job office I would say. – Andrew Smith 10 years ago
  • With company like this, you should really talk about the current situation, and current needs. Not the future ones. What product do they have now, and how much income they make now. If all of it is "none", you'd better start your own business. – Andrew Smith 10 years ago
  • @Andrew Jones - can't agree with you there. There are two kinds of startups - attempts to build a profitable business that will generate revenue quickly and be self-sustainimg, and attempts to build something that may not generate revenue for a while but is likely to be acquired by someone with more money quickly. Both are hard, though the latter is much harder. This company appears to be an attempt at the latter, and the OP wants to know what to ask to evaluate their chances of success. – Giles Thomas 10 years ago
  • @Andrew, thank you for your reply. I think you've missed the mark though. Surely all companies start with no product and no income? I'm currently working for a company which has been going for 5 years and has only recently started making a meaningful income and is not yet making a profit. I think the fact that these guys have a "plan" is a good thing. I've worked for too many places which just drift along with no really clear idea of where they're trying to get to. – Onmyway 10 years ago
  • Well good plan, or a very good push. Actually, for the start, far more effective is a very good push, and plan comes as second. Planning is good when the company is big, to not collapse it. But on the start, planning is harmful very often. I worked with number of companies who did planning from the start and missed all the goals, while the companies who did a good push at the start made a success but later on failed on planning, e.g. expansion. – Andrew Smith 10 years ago

3 Answers


Working for a startup, can be a very different experience compared to a well established company. Aside from the sort of questions you might expect about the compensation package, you should probably talk about the people, the work ethic/expectations, the culture they wish to build.

Additionally, talk a lot about the product, and about the "why" in the vision. If you're not excited by both, you should seriously consider whether this is the company for you.

Ask about the other roles needed to make this Startup a success, how will they get the product to market? If they don't have a clear strategy, be worried.

While talking about the details of the business, find out how much runway they have (how long can they survive until bankrupt). Fund raising takes time and energy and is rarely as smooth as you'd hope.

answered Sep 1 '12 at 19:43
Nick Stevens
4,436 points
  • Well, they've been quite open about working 12+ hour days :-) I forgot to mention in the question - I know their runway is around 2 years. This seems sensible to me, but I'm no expert (hence my question!). – Onmyway 10 years ago
  • So, I'm going to mark your answer correct Nick. All the answers I had were good (thanks guys) but I have to pick one and yours came first... – Onmyway 10 years ago


Usually, when you are talking to the CEO, at that point all the compensation and funding questions should have been asked earlier in the process. This is something head of engineering should have used to sell you on the position.
What I usually focus on when interviewing the CEO (yes, you are interviewing them as much as they are interviewing you) is long term vision and then dive deep into company culture questions.

answered Sep 2 '12 at 01:56
Apollo Sinkevicius
3,323 points
  • Thanks @Apollo. How would you assess company culture in a company which is currently only around 7 employees? – Onmyway 10 years ago
  • Company culture starts from founders. Even if it is just one founder, culture is already there. So what questions to ask? I would ask around what personality traits seem to work well and do not work well, get examples of how they have dealt with major mistakes, ask the hard question if they had to let someone go and how they did that, etc. – Apollo Sinkevicius 10 years ago


Some things come to mind immediately.

3/4 months old and pushing for second round already? How much was first raise? From credit cards / family friends? What is the amount of the second round - and who is leading (existing investors, or completely new)

Customer traction: they are just going to launch the product? How well do they know (validated know - not just a guess) what their target market wants? How large of a market is it?

Without good answers to these, the CEO might be sitting on the beach much earlier than 5 years (but likely not a Caribbean one).

answered Sep 2 '12 at 04:37
Jim Galley
9,952 points
  • So this is a B2B product rather than retail. I know they already have at least on customer "on board" who is driving the initial set of requirements and expecting delivery of a product fairly soon. Thank you for your thoughts. This is obviously really important, but I'm not sure I'd have thought about it off the top of my head in an interview situation! – Onmyway 10 years ago

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Equity Interviews Exit Strategy