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Our Go-To List: 30 Interview Questions

Unconventional conversations can find you the needle in the haystack.

Doug LandisGrowth Partner
Tammy HanHead of Talent

One thing our team always gets asked about is what are the major catalysts to why companies fail, especially in the early days. By supporting GTM strategies, what we've witnessed is that early failure can often boil down to two things:

  • Lack of focus. Many startups try to be all things to everyone, like throwing spaghetti on the wall, waiting to see what sticks or push upmarket too soon. Staying focused and finding product-market fit is vital to long-term success.

  • Hiring the wrong people. Interviews can be awkward or feel generic, and not having the right process in place can lead to poor decisions.

Having interviewed thousands of prospects ourselves, we understand finding the needle in the applicant-stack is daunting. We've found that asking the right mix of questions - ones that get the candidate to think critically on their feet and dig a bit deeper - uncover unexpected aspects of a person’s character, what matters most to them, and how their passions could drive your team.

We've compiled our top questions to foster insightful conversations to help you find the right hire and build a winning team.

Our Top 30 Interview Questions

Skillset & Discovery

1. Imagine yourself 5 years from now. What would you have learned and taken away from this experience? What new skills would you have in your toolkit?What does your highlight reel look like? Are you still here? What role are you in?

2. What is something you'd be happy doing every single day for the rest of your career?

3. What's the biggest decision you've had to make in the past year? Why was it such a big deal?

4. In five minutes, explain something to me that is complicated but you know well?

5. Is it better to be perfect and late, or good and on time?

6. Who is your favorite superhero and why??

7. What are your superpowers?

8. If you could wake up tomorrow having gained one new skill, what would it be?

9. If you woke up and had 2,000 unread emails and could only answer 300 of them how would you choose which ones to answer?

    Work Experience & Culture Fit

    10. What excites you to come to work?

    11. What job made the most impact on your career today? How did it grow you?

    12. How would you sell hot cocoa in Florida?

    13. Why are you looking? What does your current role/opportunity lack that we could offer?

    14. Who was the best manager you worked for and why?

    15. Who is the best person (teammate, customer, client) you’ve ever worked with? What was/were their superpower(s)?

    16. Talk me through a bad professional relationship you've had. Why didn't it work?

    17. If I were to ask X [their last boss/manager] about your time at company Y, what are three words they would use to describe you? Words, not phrases.

    18. Now, what would your former colleagues say about you? Would these be different and if so, why?

      19. What were the best company cultures and the most productive work environment you’ve experienced?

          20. What do you feel attributes of the poor or negative company culture?


            21. Pitch me on a product you have sold/marketed previously. 

              22. How would you sell hot cocoa in Florida?

                23. Imagine you are the buyer of our product. What would compel you to use our product? What key customer logos are we missing? (allows them to demonstrate their knowledge of our customer base and value prop) 

                  24. Who of our competitors/incumbents should we worried about? Why?

                    25. Can you share your most memorable customer experience? What about it stands out from other experiences?

                      26. What aspect of Sales/Marketing/CS do you find the most interesting? Least?

                        Opportunity & Process

                        27. If there is anything you could change about this role/opportunity to make it your dream job, what would you add or remove?

                        28. What would your first 30, 60, or 90 days look like in this role?

                        29. If we don’t hire you, what do you think the reason would be?

                        30. What has surprised you about this interview process so far?

                        We're always looking for new conversation starters, so feel free to share your best (or worst) interview questions with us at @emergencecap.

                        Want more on hiring? Read our 5 best practices for executive employment agreements and visit our Talent Network.