One Interview Question Every Founder Should Ask When Hiring Their First 10 Employees, To Build a Healthy Culture that Scales

Hiring is hard. Culture is even harder. The good news is that you can make it easier by asking the right questions in interviews.

After building my first team of 10, I’ve learned to screen for something specific to make sure I don’t bring in a “bad egg.” It is: how does this person behave when they disagree with someone? I love digging into this topic because it touches on many critical behavioral aspects. By digging into this, you can understand how someone navigates conflict, how self-aware they are, and how they talk about other people (REALLY important).

I have a question that I ask in every interview to screen for this. This question works based on i) my own experience and ii) insights from a fantastic book on hiring, WHO (I highly recommend reading this).

You can ask this question many different ways — here’s how I ask it:

Tell me about a time you disagreed with a coworker. How did you handle it?

Consider the following when evaluating their answer:

• Pay attention to how they navigate conflict. Are they able to demonstrate that they successfully resolved the dispute? If the answer is no, not good.
• Do they acknowledge that the person on the other side had valid reasoning? You may need to ask a follow-up question to dig into that specifically. If the answer is no, not good.
• Are they getting overly emotional when telling the story? Emotions aren’t a bad thing, but you want them to keep it professional. If they’re getting overly emotional, not good.
• Does it sound like they disagree with ideas, or do they take things on a personal level and disagree with people?
• Do they recount the story more in terms of fact or more in terms of opinion? You want people that can resolve conflict in a fact-based manner. If their story is primarily opinion-based, not good.
• MOST IMPORTANT: Do they bad-mouth people they have worked with in the past? If the answer is yes, very, very, very not good. In most cases, this is an immediate disqualification. You can’t have people in your company that talk bad about others behind their backs; this is toxic for your culture.

You need people that can disagree respectfully. You need people who stay motivated and commit to decisions even if they disagree. You need people who aren’t prone to gossip and bad-mouthing. That’s why it’s essential to ask this question.