Interviewing at a startup? 25 questions to ask in 3 categories

Courtesy of Artotemsco. Metaphor: Make sure the startup you’re interviewing for isn’t full of hot air.

Candidates often forget that they are interviewing the company as much as the company is interviewing them. That’s the mindset you should go into any interview with as you are about to make a career bet on the company. Remember, you’ll invest the largest chunk of your time each day with these people. Interviewing is like dating and employment is like a relationship. You should help the company understand that if you’re the right person, that will help them be successful.

It’s even more important with startups because there is so little information about them. The interview is your best opportunity to learn because they likely have a low number of employees, they usually haven’t been around for long, and there is little to no public information about them. This all adds up to a high degree of uncertainty and it means the interview is that much more important.

So, how do you know what to ask them? What questions matter? Your mileage may vary, but these are the questions I like to ask. Not only to determine if the company values their customer, but also to determine if they treat their employees with that same empathy. So, here’s my question roadmap.

Warm up

Fastballs are easier to throw if you warm up. Don’t wear red though, it increases your odds of interview death.

I always like to warm up the conversation. To build rapport. This makes the conversation more personal and less professional, which leads to increased honesty on both sides of the table. Often, the first question I ask frames the other questions, but I always have backup questions that are generic enough so that they can apply to anyone.

Ask about them first:

1. <something I learned about them online, question about their education, history, company, or anything we share, e.g. music. this shows I am diligent.>
2. How funny is the office? How often do people laugh?
3. What are your top three favorite hobbies? What got you into them?

Then tell about you:

1. <something funny I’ve noticed recently or some industry news>
2. <something that I like to spend my free time doing>
3. <something generic that applies to both of us —weather, SF culture, shared background, thing I noticed about their tweets/background, etc>
4. <some small detail I really like about the place we are currently at (their office, coffee shop, any small detail, etc.)>

I try to prepare for this section for about 10 minutes. This ensures that I have relevant questions ready based on my research on the company and founders / hiring manager. It also ensures I don’t get nervous and I can let the conversation flow naturally. I don’t feel like I have to follow this structure.

Company

Traction/Growth:

These are growing chickens. The second chicken from the left may be Photoshopped :p

1. What is your month over month growth rate? Can I see a growth chart on your laptop or with the axises removed to maintain your confidentiality?
2. How many current paying customers do you have?
3. When are you projecting profitability based on current company size? Or are you profitable now?
4. What is the single biggest thing preventing you from growing?

Cultural:

Great cultures believe in harmony between work/life. Between listening and doing. A great culture knows that balance leads to stellar performance.

1. What are your two most critical pieces of customer feedback? How have you thought about addressing them?
2. What are your top three cultural values? (if empathy is not one of them, I consider it suspicious, because that’s important to me). What methodical steps do you see yourselves taking to get there?
3. Have you fired or laid off anyone? What’s your firing process look like? Or, if not, how do you communicate difficult news to someone?
4. What are the biggest gaps between your co-founder’s skillset and what the company needs right now? How are you hiring to help close those gaps?
5. Would you mind providing me with 3 references of people that have worked with you in the past? Or customer references that you’ve had support interactions with? I’d like to hear their thoughts.

Role:

How does your slice fit into the pie? Are you really the right missing piece?

1. What would success or failure look like in this role?
2. Where do you see this role in 6 months? 1 year?
3. What are your thoughts on work/life balance? What does success look like for the company at 20+ people? 50+ people? 200+ people?
4. What skills am I expected to come in with, what skills would I be expected to learn, and how do you feel about allotting company time to reading or learning?
5. What’s the compensation range for this position (this is a hard one to ask, and you’ll likely get a generic answer, but if they are way off of your number—and you should come in with one—ask if they are flexible for the right candidate.)
6. (At the end of the conversation). Based on our conversation are there any gaps in my skillset or things you’ve heard today that you have concerns about? Maybe also add… Would you hire me right now if you were the only person responsible for the decision? (This second part gives them a polite and easy out of the question.)

People

It’s really important for me to understand each person, because they will be running the show. What type of a person are they? How do they handle conflict? Are they aggressive? Empathetic? Responsible? Do they listen to feedback? Do they have the qualities of someone both that I would want to work for and I would want to hire if our roles were reversed?

1. Can you describe a specific incident in the past where you had conflict with a co-worker? What would that co-worker say about you today?
2. Who is your biggest net-detractor that you’ve encountered in your career and what one adjective would they use to describe you today? Do you still keep in touch?
3. What are your top three weaknesses as a team? How do you see the next person coming in to close those gaps?

It’s important to ask non-standard and difficult questions to understand if they are self-critical. The wrong person will get defensive or not have answers (either because they are the nicest person on the planet or because they are not self-aware.) The right person will tell you about their mistakes, be open about them, and tell you how they’ve changed.

The best types of people are able to take feedback, incorporate what’s useful, ignore what’s not, and be willing to listen with an open ear every single time. Even if, upon reflection, they don’t take action on some piece of feedback, it matters that they value the process.

Digging

Woofie knows that digging is the best way to find bones!

There is a caveat to all of these questions. If you find something you hear that sounds strange, dig, dig, dig! It’s actually the goal of these questions to unearth strange things! So, ask follow up questions. Say, “tell me more about that” so that they can elaborate what they are thinking and so that you aren’t directing their next response.

You should always deviate from this structure if there is a misalignment with what you think would be a good answer and what they said. Because, you’ll never get to understand someone from jumping from one question to the next, even hard ones. The only way you will ever tell if there’s gold or crap in the ground is to dig for it.

But, these questions should set you up to dig. Once you’re done digging, always follow your gut. If everything else says yes about the job, but your gut says no, don’t join the company. You won’t know why your gut is telling you this (maybe later you’ll learn), but I’ve found that it’s useful for me in making a decision based on only a small amount of information.

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