15 engaging questions for your next 1:1 meeting

In this article we list 15 one-on-one questions that you can use in your next one-on-one meetings.

15 engaging questions for your next 1:1 meeting
Jeroen Fiege
Jeroen Fiege
Founder Strateamic
April 12, 2023

There are a number of things to consider when running one-on-one meetings as a manager. One of them is asking engaging questions. In this article, we list 15 one-on-one questions that you can use in your next one-on-one meetings. But first, let's explore what makes a question engaging.

What makes a question engaging?

Open-ended vs closed

The fundamental aspect that makes a question engaging is that it should be open-ended instead of a closed one. Closed questions are questions that can be answered with a simple yes or no. Open questions, on the other hand, need a descriptive answer. Let’s look at this example: “Did you have a good weekend?”. This can question can be answered with a simple “Yes”, which isn’t very helpful for a meaningful discussion or interaction. If we change the question to be open-ended like this: “What was the most enjoyable part of your weekend?”, we get a much better conversation.


Another aspect that makes a question engaging is that it should be thought-provoking and encourage the recipient to do critical thinking. They require the recipient to consider different perspectives, analyze information, and draw conclusions. Engaging questions should challenge the recipient to think deeply about the topic at hand and consider their own beliefs and experiences in relation to it. This will lead to more meaningful conversations and a deeper understanding of the subject being discussed

Make it Personal

And finally, an engaging question should be personal. When a question is personal it taps into the experiences en emotions of the person being asked, making the question more meaningful and relatable to them. It encourages the person to share their thoughts, feelings, and opinions on a topic that is relevant to them. This creates a deeper level of engagement and connection between the person asking the question and the person answering it.

15 questions you can ask in your next one-on-one meeting

Now that we have a clear understanding of what makes a question engaging, let’s dive into the gist of this article. We have divided the questions into 3 meetings. Every meeting we start with a conversation starter, and we end with a question that encourages feedback. In between we ask questions about career goals, alignment with team and company goals, and job satisfaction.

Meeting #1

  • Tell me about your weekend activities.
  • What’s a recent situation you wish you handled differently? If given the chance, what changes would you make?
  • What work are you doing here that you feel is mostly in line with your long-term goals?
  • Who would you like to work more often with? Why?
  • What can I do to help you achieve your current goals and priorities?

Meeting #2

  • Tell me about what you’ve been working on recently.
  • What, if anything, did you used to do that you find you don’t have time for at the moment?
  • What other roles at our team/company could you see yourself in down the line? Or what areas would you like to explore?
  • Do you feel adequately supported by other team members? What makes you say that?
  • How do you prefer to receive feedback?

Meeting #3

  • Tell me about last week.
  • What’s an area of your work you want to improve?
  • Is there an aspect of your job you would like more help or coaching?
  • What are some ways we could improve teamwork? What makes you say that?
  • At what point since our last 1:1 were you most frustrated with or discouraged by your work? What can I do to help you manage that?

Want more questions?

Strateamic offers team leaders a way to boost their 1:1s. We’ve identified 300+ questions which you can use in your next 1:1s. Questions are randomly picked for new meetings and are never asked twice. We also offer easy scheduling and send smart reminders. Your 1:1s have never been better, try now (free)!

Strateamic for structured 1-on-1 meetings
Strateamic helps tech leaders structure their 1:1s. After you've invited your team, you can create a meeting schedule with your direct reports. Strateamic automatically prepares meeting questions, or you can add your own talking points. Ahead of the meeting, your reports are asked to go over the questions and answer them. Because they already put thought into it before the meeting, they will be better prepared during the meeting, which makes it more effective for both of you.

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