It’s your last question, so make it a big one!

Make your last question count

Michael Hoeschele
Bootcamp
Published in
2 min readAug 22, 2022

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Until recently I used Steve Blank’s suggested last question in interviews. This question focuses on what should I have asked, but I found it only works with highly engaged participants.

I have had much greater success getting critical insights from people of all levels of engagement with this question that Jeff Callan shared with me.

What are you most concerned I didn’t understand or ask about?

Why this works so well

  • It borrows from Chris Voss’s “getting to no” approach that leverages how much easier it is for people to talk about negative things.
  • It allows people to highlight what is most important about the topic that you just discussed with them, whether or not you already asked about it.
  • People have the opportunity to correct others, which is an incredibly strong human desire (see any comments section) and you get more accurate insights.

How to use it

The end of an interview is a magical time, it is when the other person has done lots of thinking about a topic. If you have done your job well they have considered that topic from many different perspectives and come up with thoughts they couldn’t express or weren’t even aware of at the start of the conversation.

In this golden time, they are primed to hit you with their most profound insights, that's when I deploy this question. But right before I do, I make sure to review all the key points I heard in the conversation to remind the person of what we discussed.

Questions for other conversation types

This approach to the last question can be modified to fit other types of conversations and specific goals. Here are a few examples:

Job interviews

What do you see as the biggest risk in hiring me?

  • There is nothing worse than not getting a job because of a misunderstanding. This question uncovers those and gives you the opportunity to clear it up.

Choosing a course of action

What are you most concerned about making this decision?

  • This is great to identify if a concern is great enough that further analysis is needed to mitigate it or you can push forward.

Customer Success

What are you most concerned about using our product to get your work done?

  • I love this to identify those concerns that a person may not contact you about, but if they are already on the phone they will bring up if given the chance.

Retrospective

When I started using this question felt very forward, but I found that it really gives people the opportunity to step back and tell me what they heard in the conversation.

This mini-retrospective has proven to be incredibly powerful in checking my biases that result in misunderstanding people’s thoughts and what they see as most important.

Now get out there and make a difference!

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Writer for

Loves identifying problems through conversations and solving them with empathy & data. 10+ years @ NSA designing data collection systems and advanced analytics.