Questions you should ask when interviewing at a startup

Jevon MacDonald
Nov 29, 2022
5 min read

Interviews... interviews... If you've ever switched jobs then you know there can be good interviews, and there can be really bad ones. Sometimes a bad interview means it's a bad company. Sometimes it means you aren't the right hire for them.

Interviews are typically structured as a 1-way conversation. Sometimes there is a cursory "do you have any questions for me?" as the interviewer glances at their watch with a few minutes left before your time is up.

The truth is that it's very hard to stand out in an interview when you are responding to questions. The best you can hope for is to check a few boxes in an otherwise obscure and fuzzy process.

How can you turn any interview from boring to engaging? From mundane to exciting? Asking great questions!

Interviewees who ask great questions stand out from the pack and they look and sounds like leaders. Asking good questions is a skill for you to develop. For the person on the receiving end, a good question demonstrates that you have a depth of understanding, an earnest interest, and that you have leadership skills and the ability to influence.

The right questions to ask are going to be different in every situation, but there are a few that can be helpful in any situation when you are interviewing with a hiring manager.

1. What is the team culture like? Why is it like that?

You'll never get a consistent answer on this one, and sometimes it might be hard to get a truthful answer. What you are told may speak volumes about not only the company, but more importantly how the person you are asking perceives the company itself. Asking "why is it this way?" may open up a discussion about values and leadership, or you may find some subtle finger pointing going on. Keep an eye out for 🚩🚩🚩 red flags.

Other questions you could ask:

  • How do decisions get made?
  • What happens if there isn't consensus?
  • How often does the entire company meet? Who leads that meeting?

2. What do you think sets this company apart from its competitors?

This is a broad question. Product and goto-market differentiation are subsets of this. The interviewer may focus on one or the other, or ideally they will be able to speak more broadly about what makes a company special. It might be a visionary CEO (Marc Benioff, Salesforce), it could be a particular cultural environment (Spotify), or it may be a special and defensible technology (Google). Whatever it is, listen for the signs that the company really is special and that it's a place where you truly want to invest your time and career.

Other questions you could ask:

  • Do you have product-market fit? When did you find it? What has changed since then?
  • Do customer's help shape the roadmap? What kinds of requests do they make?
  • Who does support? How do they share feedback/requests/requirements with the rest of the company?

3. What is the company's mission and vision?

Boring right? Wrong! This is the right question to ask if you are speaking with multiple people. Their ability to give you an answer that is consistent with their peers is a useful indicator of the level of cohesion within the company. A great leader spends a significant amount of time making sure everyone is playing from the same sheet of music. It can also be a good topic for you, your skills and how your role will contribute to things the company has prioritized.

Other questions you could ask:

  • Does this mission statement/vision/values change often?
  • How could they change over time?
  • Does everyone in the company have a hand in crafting the vision, or is it shared by leadership?

4. What challenges has the company faced and how did it overcome them?

Startups often face significant challenges in their early stages, such as funding, market fit, and product development. Asking about the specific challenges the company has faced and how it has managed to overcome them can give you a better understanding of the company and its ability to succeed.

  • How much runway does the company have?
  • Do you plan to raise more money? Do you have a rough idea of when?
  • Is the company profitable, or does it plan to be profitable? How are you balance growth with stability/runway.

5. What is the company's growth strategy?

In order to be successful, startups need to have a go-to market strategy. Asking about this will help you to understand the company's plans for the future and how you can contribute to its success. It will also help you to determine whether the company is a good fit for your skills and experience. Are they focused and specific in their answers? Or you do you get a "you're in engineering, you don't rreeallllyyy need to now this stuff, right?" kind of vibe.

  • What metrics are you focused on?
  • How do you decide which work to prioritize to support growth?
  • How important is account expansion vs new business?
  • How did you come up with the current pricing? Is it working as-is or do you have plans to change it?

There are many ways to handle an interview. Sometimes you'll simply want to find an opportunity to demonstrate your skills, other times you'll find yourself being evaluated for "cultural fit". Whatever situation you find yourself in: remember to ask good questions. Be specific, expect precision. It's your your change to be certain you are going somewhere exciting, and it may uncover the red flags that would otherwise get glossed over.