Job interviews are meant to be conversations. The interviewer asks some questions and the interviewee does the same. It’s never a good sign when an interviewee doesn’t have any questions. It shows a lack of interest. This is particularly true when interviewing for a startup job because there tend to be so many more unknowns at startups compared to more established, bigger organizations.

Recently someone asked me, “I’m thinking of taking a job offer from a startup. I’ll have to relocate. I have some concerns. What questions should I ask?”

That’s a great question. I immediately thought of Tony Wright’s post: Guide to Evaluating Startup Ideas. It’s definitely worth reading, but it’s also quite high level and doesn’t deal with some of the more nitty gritty issues of startup work life. So here are 8 questions I’d suggest you ask when interviewing at a startup:

1. What past success and experience do the founders have? Startups are driven by their founders. More experienced founders with past success have a better chance of succeeding again. That’s a good thing. The type of experience is important too. If they previously ran a completely unrelated startup in a completely unrelated industry, that’s less relevant than if they just exited a company in a similar area for $50M. A lot of my own decision as to whether I would join a startup or not would be based on the quality of the founders. Probe aggressively around this area.

   Incidentally, past failures are interesting too. Founders that are willing to discuss their past failures, what they’ve learned, etc. are probably more open, communicative and honest. That’s a good thing.

2. How much money is left in the bank? Let’s cut right to the chase. Find out how much runway the startup has left. Find out if they’re making money or losing money. Get a sense of their financial health, because this ultimately drives most of the risk in taking a job. I would be concerned if a startup is unwilling to share this information.
3. What’s the corporate hierarchy? Startups are generally very flat organizations. But it’s worth asking just the same. Who is the direct report? Do you have access to the founders and/or CEO? How does information flow through the organization? How are decisions made and at what levels? The startup’s corporate hierarchy – even if it’s only 2 or 3 levels deep – can have a significant impact on the day-to-day work environment.
4. How will performance be assessed? Startups often do a very poor job of reviewing employees. They may try and do employee reviews, and then skip them because they’re too busy. Employee reviews are sketchy at best in startups because things change so quickly. It’s not reasonable to do 3 or 6-month reviews and expect to get really meaningful results (both for the employer and employee.) You want to ask this question to get a feel for how the company operates and communicates internally.
5. What are the startup’s plans for the next 6-12 months? This is a very big, open-ended question. And that’s intentional. As Mark Suster’s points out, open-ended questions tend to draw the responder out more, get them talking, revealing things. This is important in job interviews. If the interviewer is speaking more than the interviewee that’s a very good sign. Granted, it might mean the interviewer is just a talkative person and wasting your time, but often it means they’re comfortable, warming up to you and eager to connect.

   There’s a good chance when an interviewee asks this question that they’re going to learn a lot about the startup. It might be difficult to judge the response received, but look for key points around financial strategies, user acquisition, spending of money, marketing & sales strategies, etc. Specifically, look for details tied to the job you’re interviewing for. If you’re applying to a web / graphic design job, look for information related to the work you’d be doing. How important is it? How often does the interviewer talk about it? In what context?

6. What’s the competition like? Again, this is a fairly open-ended question. It’s there to get the interviewer talking. It’s also interesting to see what the response is like to this question. If they pooh pooh the competition and don’t take them seriously that’s a red flag. If they’re panicked, that’s also bad. If they can speak intelligently about the competition and how their startup is different and unique, that’s good. This question can also draw some ire from interviewers; it’s interesting to see how people respond if they feel their back is up. That means there’s a risk asking a question like this, but it’s worth it.
7. How many more people is the startup hiring in the next 6-12 months? It’s always interesting (and potentially very, very important) to understand how quickly a startup expects to grow. If a startup is planning to hire too aggressively that’s a warning sign. They may be overly optimistic. They may run out of cash too quickly. If a startup is planning to hire too slowly that’s also dangerous, because it might mean the workload is overwhelming for each individual. It’s difficult to judge the right number of new hires a startup should bring on in any given period of time (especially as an interviewee looking from the outside-in) but getting a feel for a startup’s recruitment strategy is helpful nonetheless.
8. What are the key metrics for success in the next 6-12 months? Startups need very well-defined goals. The interviewer might speak about the startup’s future plans, but now it’s time to dig a bit deeper and get more specific. This question is intended to narrow down on specific metrics or targets that the startup is aiming to achieve in the relatively near future. The intent here is to understand whether those metrics exist, how they’ll be measured and whether they’re reasonable. Ultimately those are the metrics that all employees should be judged against.

A lot of this information can be collected through research. Do your homework! Don’t go into an interview cold, especially with a startup. It should be fairly easy to find information about the startup (amount of money raised, competitors, etc.) and find out about employees (or at least see who they are via their social media profiles.) But even if you know the answers to some of the questions above, ask them anyway. So you might find out that one of the co-founders recently exited their last startup. You don’t have to ask them, “Have you ever sold a startup before?” Instead, ask them specifically about that experience. You’ll get bonus points in the interviewee’s mind for having done your homework.

What else would you ask and want to know when being interviewed at a startup?