I think you're both right. These are interesting kinds of questions to ask, but they may be asking about the wrong metrics.

First, I disagree with a lot of the premises in the OP. I don't think startups are really that much more "dangerous" or "ruthless" than other companies. There's almost always a risk that you're joining a company with ****ty management and a path to failure. It probably didn't help my initial tone ITT.

Anyway, ignoring all the other aspects of joining a startup and just focusing on evaluating if the companies going to succeed here's what I'm thinking. Ideally a lot of these things would be covered before you have to ask about them.


* Where do you see the company/product in 6 months, 2 years, 5 years?

This is nice because a lot of startups have a short term idea with no idea of how to grow it, or have a great long term vision but no real idea of how to get started. What I'd be looking for in the answer is that there's something realistic, achievable, and high value in reach right away. This is something that will either make them profitable or let them get the next round of investment. But I also want to know that there's a big picture goal that we're always working towards.

If you're talking to the CEO or other high ranking person and they can't answer this question very well it doesn't bode well for their ability to raise funding since Investors definitely want to know the answers to these questions.

This can also lead into a good conversation about the company's plans to interact with customers (and if it doesn't lead into this you should probably follow up and ask explicitly about it). If their short term plan is to develop a product internally for 6 months and then release it to the world - you should probably run for the hills. Anyone not actively learning from customers while building out a product is probably doing lots of things wrong.


* Who are your competitors? Why are you going to succeed instead of them?

This is another good question for seeing how well the CEO knows their market. If they have trouble with this question, its obviously bad in its own right - but it again means they won't be able to get funding very easily.

This is also a question that you can do some homework on. Look into the companies they mention. Do a bit of research on your own for competitors. Compare what you find to what you're told.


* Why did you start the company? What's a home run?

Great startups often have a real problem that they want to solve or a core idea/concept that they want to bring to the world. For example the Harmonix people wanted to give people the ability to create/experience music without having to have a lot of technical skills. Having a good clear company mission makes it much more likely that the company will succeed. It means when one idea fails or isn't working the company is still in a good position to pivot into another approach for solving the same core goal.


* What's your ideal exit? Do you want to run a big company? Do you want to get bought? IPO?

I don't think there's a right/wrong answer here - but its interesting and you can judge a lot about who you're working for.


* What's your day-to-day and week-to-week like? How does what we work on get decided?

This is another question that's good for determining how well run the company is. If they talk about something like a practical light weight agile work flow - great. If they mention lots of meetings and the CEO setting out what's going to be built - not great.


* What's the team like now and what other positions are you trying to fill?

The bigger the company the less good I think this question is. But if you're talking to a company of less than 10 people it can be interesting to see what they feel their missing pieces are.



Anyway, I'm sure there are ton of other good questions. But I think you want to avoid getting into the financial weeds. The reality is that the vast majority of us don't have the knowledge or experience to really evaluate a company off of hard and vast financial metrics - so asking about them doesn't really help you and it can come across as you caring about things that you might not actually care about that much.

A lot of these questions aren't about just their answer. It's about asking open-ended questions that lead to good conversations. It's also about asking different things that you can compare to each other. If you're told that their 6 month plan is to build an enterprise application with 1000 customers and they don't have any sales people - probably not a good thing.

Finally, it can be interesting to ask every person you talk to some of these questions to get a feel for if everyone at the company is on the same page.

The main risk with joining a startup is that they wont be able to pay you one day, therefore the job security is pretty low.

For this reason asking if the startup is profitable and what financial backing they have are perfectly reasonable questions and very important questions imo!

I honestly don't know about this, there's so much uncertainty and in startup world 2 years is quite a long time, I think a good CEO could honestly answer "I don't know where we'll be in two years". I'm not sure what sort of answer you'd be looking for here, I'd be more worried about a CEO who told me they would be worth a billion dollars or something.

I also think a good question might be:

"Does this job come with any equity?"

The job doesn't have to come with or without equity, but the answer will reveal quite a lot about how the company see's itself, it's expectations and how realistic they are about stuff.

Gee... I'd be super worried about both answers.

If you don't have some sort of long term vision - I probably don't want to work for you (I'm sure there are exceptions). I want to see the balance between a long term vision and the ability to be flexible and pivot when needed.

You do the HTML games site, right? Are you telling me that you guys don't have a vision for where you'll be in 2 years? New technologies you'll support? Major features you want to add? Mobile platforms? Stand alone app? A good answer might just be listing out all the options you've thought about and the rough strategy for how you'll decide which ones are good.

As for 5 years, what are you goals for this? Are you just doing this as long as you can make money? Are you trying to build a big company? Do you want to become the next Zynga (but better)?

Our main product is nearing completion, and we have another product we want to release in around 1 years time, after that we don't know. Just going to see how it goes. In the coming year we'll probably discover lots of new opportunities and have new ideas.

1 year window we can sort of see where we are going, 2 years it's just guesses.

5 year window there's no way we could possibly say where we are going to be.

Factor in the fact that webdev is one of the fastest evolving industries as well, in the last 5 years it's changed dramatically, I have no idea what it's going to look like 5 years from now. Perhaps our products will be irrelevant and useless.

Maybe I'm misinterpreting your question, we have ambitions and ideas for exits but that's all we have. I couldn't possibly say where we would be in 5 years.

(Sorry if that doesn't make much sense I'm sleep deprived atm lol!)

For some reason that made me chuckle. Sounds like you're building the death Star :P

Ok... I mean this seems crazy to me. Maybe this is why we disagree on the question, because your answer in an interview is one that would definitely make my decision for me. I wouldn't work for a company that has a vision only 1 year out.

Again, its not about certainties. It's about educated guesses and things you guys are passionate about.

You don't have any idea what its going to look like 5 years from now? Doesn't that scare you? Even I can make some educated guesses about what its going to be like 5 years from now based on current trends. I can't imagine someone walking into an investor meeting and not having a forecast for their industry for at least greater than a year and I think at least 5 years. I definitely can't imagine the reaction when they shrug their shoulders and say - "We have no know idea what'll happen in 5 years. Hopefully we'll still be around. Can I have some money?"

I remember when our CEO was starting to meet with investors and he had to make up predictions and forecasts for the industry for 5-10 years out. A number of mentors mentioned that it wasn't about getting the numbers right but that showing you know the market and can make reasonable predictions.


Ok, lets ask this question then - if your ideal exit is greater than 1 year out, do you have a plan for getting there? When we're talking greater than 1 or 2 years out you don't need certainties or even really specific product ideas but you should have a general plan.

For example, there's a big difference between someone focusing only on web games and wanting to build a strong community there with free games (where your value is in your community) then focusing on lots of platforms and building some sort of revenue sharing model for games built on your platform (where your value is in being a marketplace). This is the sort of thing that I feel like you should have constantly in mind when deciding what to build now. Obviously you can totally change your mind and pivot when you get new information.

Anyway, I guess I'm rambling. But this is why I like my questions. They start a real conversation and they give me the information I need to make a decision (not saying my decision would be right - but it would be one I'm comfortable making). If you told me your revenue, costs, profitability, and investment information I don't have the financial background to evaluate that effectively.

I should add that I would totally ask about runway at a startup and what the plan is to extend the runway. I don't want you people to think that I don't care at all about the immediate financial picture of the company.

You're way over-thinking this. There's no way you can be sure about anything like this. Take the job because it pays well and is good for your career.

Start-ups usually have multiple rounds of financing. Sometimes there are delays and/or the money is not enough and people get laid-off. If you want to call that ruthless -- go ahead.

It doesn't sound like you're cut out for start-ups so just find something else.

Another perspective on all of this is to not worry about the initial plan because the view and purpose of your startup is likely drastically different within a year.

http://joel.is/post/30648299967/why-...-your-bad-idea

http://paulgraham.com/founders.html

This perspective is actually a pretty big pet peeve of mine.

First, I believe "likely drastically different" is often quoted and seldom proven (because talking about specific companies that made major pivots isn't proof).

Maybe its just a semantic issue - but if you look at most start-ups at two different points a year apart you're not going to see what I would call a drastic difference. Lots of times you're going to see the company working on a natural evolution of what they were working on before. Sometimes you're going to see the company working on a different product entirely but in the same domain and with the same general goals for the company. And sometimes, but not that often, you're going to see a company that's a made a major pivot into an entirely different domain.

Second, even if the first premise is true (that the company is likely to be doing something drastically different) there's a big difference between a company that has executed well on a well thought out plan and learned something that's caused them to pivot in a new direction and a company that just sways in the wind and continuously tries different ideas hoping something sticks to the wall and works. If you don't have a clear goal in mind for what you're trying to accomplish and how your company is going to evolve then how can you really decide if its not working and its time to switch directions?

Third, there's obviously a difference between a brand new startup with few or no employees other than the founders and a startup that has been around for a year or more and started gaining traction on an actual problem. The older and bigger the company the less reasonable it is to expect a drastically different company in a year's time.

I think I'm going to write about my experience with the start up I joined later tonight. I'll summarize what I saw which is what sparked this thread.

I agree with you. I think that the two points the articles are trying to make is that you need a ton of perseverance, and that those companies knew when to throw away an idea and start with a different idea.

I highly doubt any successful business owner has exactly one and one idea. A tunnel-visioned person simply cannot be nimble enough to succeed, and probably aren't open to gaining the requisite knowledge to succeed.

Sorry took me ages to reply to this, have been thinking about it for a while!

Maybe I misinterpreted your expectations on that question initially. I couldn't tell you where we will be in 5 years, but I could tell you where I'd like to be in 5 years. Is me telling someone where I'd like to be in 5 years useful information for anyone? We've been going for just over 1 year now, looking to the next 5 years represents so much time proportionately to the time we've actually existed I just don't think we could answer the question honestly or usefully.

It doesn't scare me at all. If someone throws a ball at you, to catch the ball you make a long series of small adjustments before you catch the ball. I think its the same in a fast moving industry, lots of small adjustments down the path which looks to be most beneficial.

I can tell you some educated guesses about what everything in the industry will be like in 5 years, but those guesses are going to be largely useless, you can't really act on them in a useful way in my opinion.

I've no idea how bad this is, but we're happy with how things are and are not actively seeking an exit or working towards one. (I know this contradicts a couple of business mantras). We're enjoying working, we're enjoying building the business, enjoying living for once! For now we're happy to carry on this way. Money isn't the only thing we care about. If an exit opportunity does come along later then we'll evaluate it for its worth at the time.

I honestly think it would be easier to evaluate security of a potential job through profitability than through the biased mouth of a founder telling you where they hope to be in 5 years!

Perhaps I'm wrong with all this though, I tend to get things wrong a lot lol.

I think the problem is with your question about the 5 year outlook is that it would be easy to interpret a fantasy over optimistic answer as a positive, and a more honest answer of "we're not really sure" as a negative, when it's probably quite dependant on the company.

Yes! Resoundingly, Yes! It says a lot about you and your company if you can describe all the cool things you'd like to be doing.

I don't want to work for a company that has no passion, hopes or plans for the future.


I don't love this analogy - but to (ab)use it - there are going to be times where you are standing nowhere near where the ball is going and small adjustments aren't going to work. I want to know that you have a reasonable reason to believe you're in the right proximity of where the ball is going to end up.

You don't think this is really important for a perspective employee to know and figure out? If you're offered equity the way the company approaches growth and exiting has a massive impact on how much worth you should assign to it.

I don't think what you're describing is good or bad - it can be both.

Meh, I already addressed that (quote below). This feels like a false choice. And the reality is that the same thing (easy to misinterpret) is true of profitability. A company that's not profitable because its reinvesting all its money in good solid growth opportunities is much better than a short term profitable company thats not going anywhere.