My Product Management Toolkit (35): Effective One-on-One Meetings

Like all meetings, it’s easy to get little out of one-on-one meetings. Ineffective one-on-one meetings affect both managers and their direct reports. Ineffective one-on-one meetings are characterised by at least one party feeling that it’s been a waste of time. These are two examples of ineffective one-on-one meetings that I’ve observed over the years:

‘The generic disengaged one-on-one’

Manager: “How are things?”

Direct report: “All ok. You know, the usual.”

Manager: “Good stuff! That’s great to hear!”

‘The full frontal attack one-on-one’

Direct report: “I’m struggling with the delivery aspect of my role.”

Manager: “Yes, I’ve noticed your underperformance with respect to delivery.”

Manager: “You haven’t met my expectations in this regard!”

Direct report: “But what do you want me to do about?!” or “Does this mean that you’re going to fire me!?”

Particularly if you’re managing or mentoring another person, it’s worth knowing how to best facilitate one-on-one meetings. I strongly believe that valuable one-on-one meetings are important when creating great products and high-performing product teams. Here are some pointers designed to get the most out of your one-on-one meetings:

In preparation for a one-on-one:

I used to be unsure about one-on-one meetings, especially when I started facilitating them. I’ve since learned that preparing for one-on-one meetings goes a long way, both for me as a manager and the person that I’m having the one-on-one with.

  • Revisit what was discussed in your last one-on-one – For example: actions agreed on, topics discussed, feelings shared, particular challenges or opportunities raised, etc. I like to keep brief notes of one-on-one meetings with my direct reports, purely to make sure I come back to outstanding issues or agreed actions in the next one-on-one.
  • Ask the direct report for agenda items – Ask beforehand for any specific things that your direct report would like to discuss in the upcoming one-on-one; things on their mind, questions, challenges, recent events, etc. Having a (loose) agenda in place helps to avoid the awkwardness of what I call the “So, what shall we talk about today!?” moment and adds structure to your conversation.
  • Think about things I’d like to bring up – Even though a one-on-one is mostly about the manager listening, this doesn’t mean that you as a manager can’t bring up the things you want to ask or share as part of the conversation. For example: your concerns and issues, performance feedback, personal development or non work related issues or events.

Questions to ask during the one-on-one:

There are numerous questions one could ask during a one-on-one, and I particularly like the examples previously provided by Ben Horowitz and Claire Lew (see Fig. 1-2 below). These are some of the questions I often find myself asking during one-on-one meetings:

  • “How have you been feeling since our last one-on-one? Why?”
  • “In our last one-on-one you raised your concern about ____. How do you see that now?”
  • “What has been going well, what hasn’t?” Why?”
  • “What can I do to support you better? What can do I do more or less of? Why?”
  • “Is there anything stopping you from doing good work?”
  • “What can I do to help unblock you? Where can I support you best? Why?”
  • “What have you learned lately that might not be related to your day-to-day work but more focused on personal development?”

Following up after the one-on-one:

Make sure to follow up after the one-on-one; I believe it’s very helpful to reflect on what came up during conversation as well as act on any next steps or actions you agreed with your direct report. For instance, if you promised your colleague that you’d look into a specific question for them, I suggest prioritising this action to ensure you follow up on your promised action, well before your next one-on-one.

It doesn’t all have to come down to one-on-one meetings:

I always stress with my colleagues that they don’t have to wait until our next one-on-one to bring up any (critical) issues or questions, as I will always try to make myself ad-hoc conversations as and when needed.

Main learning point: One-on-one meetings can offer a great opportunity to take step back from the day-to-day and reflect. As the person facilitating the conversation, it’s important to prepare for one-on-one meetings and to follow up on them.

Fig. 1 – Example one-on-one questions to ask, from Ben Horowitz – Taken from One On One

  • If we could improve in any way, how would we do it?
  • What’s the No. 1 problem with our organization? Why?
  • What’s not fun about working here?
  • Who is really kicking ass in the company? Who do you admire?
  • If you were me, what changes would you make?
  • What don’t you like about the product?
  • What’s the biggest opportunity that we’re missing out on?
  • What are we not doing that we should be doing?
  • Are you happy working here?

Fig. 2 – Example one-on-one questions to ask -Claire Lew, Taken from: Managers: You’re not prepared for your one-on-one meetings. Here’s what to do.

Questions that uncover concerns / issues:

  • “When have you felt most motivated about the work you’ve been doing?”
  • “When have you felt bored in the past quarter?”
  • “Is anything holding you back from doing the best work you can do right now?”
  • “Is there any red tape you’d like to cut at the company?”

Questions that elicit feedback about work performance:

  • “Would you like more or less feedback on your work? Why/why not?”
  • “Would you like more or less direction from me? Why/why not?”
  • “What aspect of your job you would like more help or coaching?”
  • “What’s a recent situation you wish you handled differently? What would you change?”

Questions that help provide career direction:

  • “What have you been wanting to learn more of, get better at, and improve on?”
  • “What’s one thing we could do today to help you with your long term goals?”
  • “Is there an area outside your current role where you feel you could be contributing?”
  • “If you could design your ideal role in a company, what would it look like?”

Questions that foster a sense of personal connection:

  • “How’s life?”
  • “What have you been reading lately?”
  • “Been anywhere recently for the first time?”
  • “What have you been excited about lately?”

Related links for further learning:


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