What are Your Favorite Job Interview Questions?

As a team we’ve been doing tons of interviews in our efforts to match remote professionals with great companies over at Dynamite Jobs.

We’re exploring ways to ask more elegant and efficient questions. What can you ask someone that reveals the most about their potential in a job?

Recently, I asked Kean Graham, founder of Monetize More, a company with over 100 remote employees, about it.

Here’s his favorite question:

“Say I were to grant you three promises related to working [for us]. What would you want those three promises to be?”

I asked how people generally respond.

They take a while to think, and they give what we found to be much more genuine answers… things that they value the most, whether they want autonomy to use certain strategies… [or] want the access to resources for self-improvement. Sometimes they want to be promised fair compensation.

Sometimes they want to be promised vacation time. Sometimes they want the ability to take time off whenever their kid is sick. It can be very specific, it can be very broad.

What we’ve found is the discrepancy between their answers and what they actually believe in, what they actually value, is very small.

Kean’s found the question is difficult to game and tends to get at something authentic in the candidates.  He also mentioned that it works well when you’re getting to know a new team member. So even if you’re not hiring at the moment, give it a try.

Here are some of Kean’s other favorites:

What motivates you to do your best? What would you advise MonetizeMore to do differently? What could you teach MonetizeMore? Tell me about a time in your life when you actually failed at something. How did you deal with the failure and where did you go from there? On a scale of 1 to 10, how weird are you? What book do you think everyone on the team should read? What was the first experience in your life when you realized you had the power to do something meaningful?


Other tips for interviews:

Perhaps because I’ve interviewed 100’s of candidates over the years (not to mention 100’s more for the pod) I only come to interviews with one stock question, asked towards the end of the call:

Do you have any questions for me? 

If the interview went well, I modify it to do you have any other questions for me? (If you’re a candidate reading this, check out “10 Tips for Getting Your Dream Job.”

So instead of a list of questions, I have some rules of thumb:

  • Try to arrange for a video call if possible. I find tremendous value in seeing the other person when talking. We do this for our podcast interviews as well, even though we don’t publish the video files.
  • Good questions tend to be inversely proportional to the number of words they contain. Although often some groundwork in the conversation needs to be laid. The GOAT question is probably “why?” See how many times you can get to it in an interview.
  • Avoid giving candidates easy ‘question outs’. Once you know about this mistake, you notice it everywhere. The harder the question, the more likely we are to give others some help answering. ‘Why did you quit your job?’ is a tough question. In casual conversation, we typically offer outs like, “was your boss a jerk or something?” Avoid doing this in professional interviews by getting comfortable with the silence that often accompanies difficult questions.
  • Try to have a conversation around and in a previous professional experience. Often candidates won’t have enough specific knowledge to offer quality commentary on your business practices (certainly there are exceptions). I find it’s more useful to try and warp myself into professional situations they’ve had in the past and to get a sense for how they behaved and made decisions. I believe the past is the best predictor of future performance so I try and uncover things that would be relevant in their professional and personal life, ie, what they actually did in a previous job is more important than their big ideas for your business. See: “The Charisma Trap.”
  • The best questions are almost always follow-ups. You won’t need too many stock questions if you get comfortable listening and asking simple follow-ups. “Can you say a little more on that?” and “how did you feel?” and “do you wish you would have done it differently?” and of course “why (….)” are the most lucrative questions.

If you have any favorite hiring questions or approaches to interviews, we’re all ears. We’ve been testing all sorts of approaches lately as we continue to ramp up our matchmaking services at Dynamite Jobs.

See you next Tuesday, where I’m answering some TMBA reader questions ([email protected]). regarding wealth timelines (ref: 1,000 Day Principle) and more. Got a question or a prompt, let me know!



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