Joining A Startup? Top 6 Questions You Should Ask

Joining A Startup? Top 6 Questions You Should Ask

In most of my experience with startups, I've been either a founder or an advisor to the founding team.  As such, I've generally been on the hiring/recruiting side of the equation.  It continues to amaze me how often people fail to ask the really important questions before joining a startup.  They get a lot of the basics (compensation, benefits, vesting, roles/responsibilities, etc.) right – but often fail to hit some of the important topics that are peculiar to startups.  

The reasons people don't ask the critical questions can be broadly categorized as:  "I didn't even to think to ask that" or "I would have liked to know, but didn't think it was appropriate to ask".

Here are the things that I think all individuals looking to join a startup should know about the startup before joining – but are in many cases, not asking.  I'm going to stay away from the standard questions that most people already know to ask and focus instead on the questions that often go unasked.  Note:  I'm not suggesting that you ask these questions "point blank".  I'm trying to really just surface the areas that should be covered in your discussion.

Top 6 Questions People Fail To Ask Before Joining A Startup:

  1. Will the founders get along when the going gets tough?  I think it's critically important to know what the background/history of the founders is.  How did they meet?  Have they worked together before?  What brought them together for this specific opportunity?  Too many startups fail not because of market forces, but because the founders simply could not agree on important issues.  You should ask questions to get to the heart of whether the founders are likely to get along.

  1. Will you get along with the team?  Startup teams are usually a very close-knit group.  There's nowhere to hide.  If you don't get along with just about everyone there, life is going to be hard.  Most recruits will determine whether they respect the founders and other team members (in terms of experience, accomplishments, intelligence, etc.) but just as important as all of this stuff is the simple question of:  "Do I like these people?".  If you can't see working along side them for 60+ hours a week for several years, think twice.

  1. What's the history of the basic idea?  What other ideas were assessed and discarded?  I get worried if the idea being pursued is too fresh and green.  Often the founders have not yet had a chance to really think through the idea fully yet.  Often, it takes a fair amount of "refinement" for most people to really settle-in on an idea that they are going to pursue seriously.  I'm leery of startup teams that come up with an idea in week 1 and start "recruiting" in week 2 because they're so enamored of their idea and can't wait to get started  This is almost always bad news. If I were joining a startup, I'd like to know how the founding team arrived upon the idea they're pursuing now (chances are, they went through several others before getting to this one).  Don't get me wrong, there's nothing wrong with being involved in a startup when it's very young – I'm just cautioning that you need to know what the status is and be prepared to have the overall direction shift on you pretty dramatically in those first few months.  Rarely have I come across a startup that can successfully think of a single idea very early in the game and then doggedly pursue that idea (and succeed).  I'd prefer seeing the openness to consider multiple ideas and pick the best one.  On a related note, it helps a lot if all of the founders are pursuing the same idea.  You'd think that this would always be the case, but it's not.  


  1. How much cash is there, where did it come from and how long will it last?  If a startup is venture-backed, it shouldn't be too difficult to find out who the investors are and how much capital was raised.  In most cases, this information is publicly available (some press release was likely issued) and if not, it is not inappropriate to ask.  For bootstrap and self-funded startups, this line of questioning can be a little uncomfortable.  If you're squeamish about it, then you can revert to the:  "What are the capital-raising plans for the company?  Do you expect to bring in outside investors?  If so, when?  This will give you a sense for where the company stands.  One thing to remember:  There is no real substitute for cash in the bank.  Though the fact that  "we have several investors that have expressed interest" is good, it will not pay the bills.  


  1. What are the founders looking to get from the effort?  Try and move beyond the platitudes and clichés.  Seriously, what do they really want to get from the startup?  Build a world-famous product?  Make a ton of money?  Take a company public?  Raise capital from top-tier VCs?  Get a chance to work with their friends?  There is no right answer, but the key is making sure there is some parity across the founders.  At some level, they need to have similar goals or there will likely be a fair amount of conflict.  

  1. What will the startup do for you?  Joining a startup is usually a pretty big risk and a lot of work.  In order for it to be meaningful, you need to really, really make sure that in addition to bringing a lot to the startup you'll be joining – it needs to bring a lot to you.  Are you looking to wear multiple hats?  Do you want to have a fair amount of discretion and control?  Are you hoping to work with a specific founder?  Regardless of what you attribute value to, make sure that you have a decent chance of actually getting this value.  One-way relationships in startup-land rarely ever work.  You need to be able to draw a lot from the startup – in addition to contributing a lot to it.  I'm a big fan of the growth opportunities in a startup – particularly for younger individuals earlier in their careers.  Nowhere else will you get the diverse set of experiences and visibility that you can get in an early-stage startup (whether your own or someone else's).  If you're not going to be benefit from this (or are not passionate about it), you're missing out on one of the biggest components of value.

Overall, it seems that the level of startup activity (particularly in the major markets) is really starting to pick up.  People are starting companies at a pretty good pace and those scarred directly or indirectly by the last bubble are starting to come out from under their desks and explore startup opportunities.  I, for one, think it's always a great time to look at startup opportunities.  But, it's important to walk in with your eyes open.  This is particularly true if you have never worked for a startup before.  Hope the above helps. 

What are your top recommendations for questions new recruits should be asking their startups?  Would love to hear them.

posted @ Wednesday, August 02, 2006 9:34 AM

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I'd have to echo the advice about getting along with the team as a whole, and not just the founders.

With the last startup that I worked with, I got along really well with the founder and most of the rest of the team. However, I really didn't get along with one of the other developers. Since startups work so close together, it is impossible to ignore such an issue like you could in a regular employment relationship. It may sound harsh to say it, but sometimes you just have to say "Either he goes or I go"- simply because if you both stay nobody will be happy (Internal conflict can kill the zeitgeist of a young company).

posted on Wednesday, August 02, 2006 at 10:25 AM by Erik peterson

This could not have come at a better time than the present. I am going to copy parts of this to my blog – we are looking for 3 key guys to join out team

posted on Wednesday, August 02, 2006 at 10:45 AM by Manoj Ranaweera

This subject is important.

I would ask one more question — How serious are the founders?

Are they betting their careers on the startup? Are they working full time on the effort, or do they have day jobs? Do they worry about their customers problems from when they wake up until when they go to sleep? Are they willing to do whatever is necessary (write code, print business cards, call the cable Internet company, and so on)?

Or, are they business school students who want to work on a startup over the summer to put it on their resume? Do they want to hire developers to do all of the tech work?

(This queston is similar to #5, but a little more narrow in focus.)

Writing this has led me to an additional question — Are the founders hackers?

posted on Wednesday, August 02, 2006 at 2:19 PM by Adam Smith, of

I'd like to echo Adam Smith (xobni)'s comment. I've seen "start-ups" where the entrepreneur got a piece of the lat '90s .com boom by being early in a start-up and they think that doing it part-time is sufficient and working 8 weeks of the year out of the Caribbean is OK — because they've done it before. Not a recipe for success if you ask me.

posted on Wednesday, August 02, 2006 at 7:25 PM by David Catalano


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