How to ask good questions in an interview

The promise of Playbooks is that you will get insights and strategies straight from my 1:1 coaching sessions. And this month, I’ve been talking a lot about interviews.

Asking good questions is such an overlooked opportunity to demonstrate your ability as a candidate, as well as an opportunity to steer the conversation where you want it to go. But it can also feel hard to know: are you actually asking good questions, or just asking what everyone else is asking?

People like people who ask great questions. People like to talk about themselves and what they’re passionate about, and a lot of hiring managers are passionate about their work. Getting someone talking is a great cheat code to getting them to think well of you.

A great interview feels like a conversation, and conversations are two-sided. Don’t let your interviewer drive with their pre-written questions that feel awkward and stilted. When you give them your answer, ask a question back, don’t hold them all for the end. Treat them like any interesting person you’re meeting for the first time.

But don’t use up all your questions during the interview. Save a few toward the end so you can leave them with a strong impression.

Asking good questions is a mark of confidence. It proves that you’ve done your research, that you know what you want, that you’re not desperate and that they also need to meet your needs.

Ask questions at a level that prove you understand Customer Success. Questions like “What does the handoff from Sales to CS look like right now, and where does it tend to break down?” Use the questions you ask as an opportunity to prove yourself, not just your answers.

Ask questions that show you’re evaluating them as much as they’re evaluating you. Questions like “What are the common traits of your current CSMs? What about CSMs that have left?” You need a job, but they also need a hire. Don’t let them make you feel like they have all the power.

Now typically I don’t love a hard and fast rule, so think of this more like a challenge. If you weren’t allowed to say “you answered all my questions,” and you had to ask something, what would you ask? Challenge yourself to ask something. Ending with a thoughtful question leaves a strong impression.

Prove you’re thinking on level two or three. Save the basics for your interview prep and your limited interview time for the good stuff.