I've been talking with some peers recently about strategies for succeeding in a job hunt. There's a myriad of discussion points, but one of my favorite topics was which questions to ask in an interview. I am mostly interested in working for startups, and when evaluating a startup I think that culture and financial progress are the most important things to know about. There's tons of other topics, but startups are so turbulent that it seems that most other things don't have lasting truth.

These are the questions that I came up with for a recent job search, and what my goals were in asking them. I used most (not all), and had pretty good success. They are definitely skewed towards a startup environment. They are also probably formatted a bit better for above entry-level roles, but I don't think any of them are dangerous to ask for entry level. You just might get different answers.

One last note: my real goal in any job interview is to get a discussion going. I'm never going to have all the questions to tease out the truth about working at a company - having a human conversation is the only way to get to the heart of it. I don't recommend asking all of these questions in one interview; it's better to choose the ones that fit best, and let them turn into conversation. Take notes on everything you hear!

How do you reward tenure?

Most startups won't really have an answer here. If they say equity, that's a bad answer (equity is worth at most $0). If they say something wishy-washy that's probably fine. If they have a real tenure program, that is amazing.

What cost center would have to be cut to be profitable today?

I've found that when I ask "what's your financial situation" of a startup, they give me some BS answer explaining that they're "reinvesting their profits to accelerate growth", and hint that they could be profitable if they wanted.

They aren't lying when they say this, but "reinvesting their profits" often times means things like "paying our employees" or "scaling up infrastructure". Those are things that the company would straight up fail if weren't paid for.

If the answer is "host fewer events" or "have a less aggressive ad spend" then things might actually be in good shape. If the answer is "slow down hiring" run for the hills. Over-hiring is the quickest way to kill a startup, in my experience.

What's the hardest challenge with selling the product?

Some products are just really hard to sell. I worked for a digital loyalty card startup, and the hardest selling point was that... small business owners don't have any money. No matter how awesome our product is, our target market was broke.

I want to hear that the problems in sales are solvable problems.

What's the hardest challenge with building the company?

Similar to the previous question, I want to hear that we can actually solve the problem we're trying to solve. If the problem is too technically hard for the team to accomplish, it's a no go. Most hard problems can be solved, but it requires the right team and enough capital. Uber is a good example here - their problem is seemingly impossible given the laws around ride sharing, but they have massive capital and a huge team. They can solve the hard problem (assuming their culture doesn't kill them first).

This actually may create some clarity around culture stuff. If the hardest company problems are culture related, that might be a red flag (unless they're addressing it well).

What's the end game?

I don't want to work for a company that doesn't expect to exist in 5 years. If you're targeting acquisitions, then your goal isn't to make your customers happy. Your goal is to make investors happy. That's a no go for me. Other people may feel differently, but I'm a customer-focused person.

Why is this an interesting business? Why is this an interesting product?

I'm looking for two things here:

• Does the interviewer think the business is interesting? Culturally, are employees invested in the product?
  
• Do I think the business is interesting? Often times things that look terribly boring are VERY interesting when you get into the details. Only insiders know that.

What is employee onboarding like?

This is probably the best indicator of company culture I know about. Startups that aren't thoughtful about culture don't spend any time thinking about onboarding. Startups that think about culture are usually proud of their onboarding (or proud of what it will be).

How is performance assessed? Has anyone had internal career growth?

Lots of startups get excited about being flat and having no hierarchy. That's cool, except it means that you will never get a raise and can only expand your career by finding another job. If you want a longer tenure at a company, they need to have internal career growth of some sort.

What caused you to open up this role?

There's probably two options here:

• Someone quit (or was fired), and they need to be replaced. This is a red flag, and should be explained.
  
• There is more work than there was before. This is usually a good problem, but knowing about it can give you some insight into what the role will be like.

What is the top priority for the company?

I ask this of everyone I interview with. I look for the answers to be mostly aligned from everyone. If they are not aligned, then it means that leadership isn't doing a great job of unifying everyone towards a common goal. That can create bad silos between departments.

How is the company performing on its goals?

The biggest red flag to look for here is if they don't know what their goals are. Run for the hills if that is the case.

The next concern would be if their goals are new. Lots of startups change their goals quarterly, because they aren't able to hit them. Obviously that's bad. Ask where they were at on metrics a year ago, and how they are progressing. Even if it's not going well, sticking to their goals is a great sign.

Tell me about the "low point" for the company?

This tells two things:

1. It gives some more insight into the biggest struggles with the company. If the low point is a problem that could easily happen again, that is trouble - it will be stressful for all employees. Startups are inevitably hard, but the struggles should be learned from.
   
2. Can the founders handle stressful situations well? Did they flounder, and make it out by luck? Or did they keep collected, and guide their team through the struggle?

To be clear, I would not join any company that can't tell me about a significant struggle. That either means they're untested or blind.

If you could sustain one thing about the company, but lose all others, what would you keep?

This is a weird one. I'm trying to feel out "what gets the founders out of bed" sort of thing, but without the easy cop-out potential. For most founders the answer here will be their customers - they are passionate about providing value to their customers. I love that answer.

I would also accept "my team" or "culture" as an answer.

Answers like "the cool tech" or "the money" or "the journey of a startup" are red flags to me. Those can be gained at any company, and are not lasting parts of any business.

How do they fit into the team? When was the last time you spoke with them directly? (Choose a random employee, either by pointing in the room, or prior research)

I haven't actually tried this one, but the point is to get a feel for how approachable the executive team is. Do people get to talk to them? Do regular employees get to voice their opinions?

What's your monthly burn rate? How much cash do you have in the bank? What was your monthly burn rate 6mo/1yr ago?

Burn rate is the only real metric that matter for a startup. Run way, cash on hand, CAC, etc. can all fluctuate up and down for a lot of reasons... but burn rate should be consistently decreasing. Unless there is a very very very good reason, you should hope to see burn rate trending down - that's how businesses stay alive.

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Like I said earlier, your best bet is to choose a few of these for each interview, and try to transition them into longer conversations. Not only will that give you more data to work with, conversations also give you more opportunity to show your (obviously stunning) personality, instead of just being a question machine.

Header Image Credit #WOCInTech

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