One-on-One Healthcheck

Team one-on-ones are a great way to feel your team’s pulse — whether you subscribe to the manager-ownership or the team-ownership school of thought. Here’s a bunch of questions I like or have used over the years to measure the pulse. I tend to pick one or two of these and ask them over and over. The team get used to them and turn up prepared. If you want some variety, pick your every-week questions and then add something different.

Life Balance

People over process. People over all. Everything is people. It’s important to begin by recognizing our teams as people rather than resources. To achieve your goals and to help your team achieve their own goals, they need to have a healthy life outside work.

How are you … really?

What you’re really checking here is whether life outside of work needs some attention. The first answer you get will be trite and quick until your team is used to being asked. Dig deeper. If you need to, provide a scale. “From absolutely rotten, to top-of-the-world, how are you doing outside work?”

If the answer you get here is not positive, ask a follow up like “Is there anything we can do to help”. But don’t ask this unless you’re willing to help.


The cynic in me enjoys this take on a popular aphorism: Choose a job you love and you’ll have to work every day of your life – because you just turned your favorite hobby into a job and now you can’t escape.

But if you’re turning up to work each day, it would be nice if it was more than a paycheck, right?

What one thing are you most proud of this week?

This is one of my two favorite questions. It’s a great way for you to understand how your team views their own work (you might be proud a feature was released, they might be proud they learned a new way to implement linked lists). But almost more importantly, it’s a good way to force your team to stop a minute and think about their week, recognizing that they achieved something during the week.

What is one thing another team member did this week that they should be proud of?

This is my other favorite. It forces your team to think beyond themselves and to recognize the contribution the rest of their team makes. This has the effect of building cohesion and trust. But here’s the kicker: it gives you a great source of positive feedback you might have otherwise missed.

Did you feel challenged this week?

It’s important to have weeks where we are challenged to stretch beyond our comfortable limits. But like a piece of elastic, it’s important to have weeks where we aren’t, and never to have weeks where we are beyond our capacity. Neither being stretch or being relaxed is healthy in the long term, so this question lets you monitor your team’s challenge levels over time.

Do you feel you got the time to produce your best work?

The ugly truth in most tech companies is that the answer to this question is rarely an honest and emphatic ‘yes’. You’re looking here to uncovering stress and helping your team manage it. As managers we are responsible for a lot of deadline related stress, but we need to uncover anything else that is affecting our teams. Follow up question: how does that make you feel?

Culture and Communication

These questions are around arresting negativity before it becomes an entrenched problem. They require trust, so until you’ve asked them a lot, expect fairly benign answers. But if you want answers, don’t stop asking.

Has anything made you uncomfortable or worried? or Are you hearing any rumors that I can address?

Your team talk to each other and to other teams. Are they hearing rumors that you can address? In an open environment there’s no need for rumors as they can be answered openly. Get on top of issues before they become problems.

Did you have any challenges or conflicts with other team members?

Most people, not just in tech, are terrible at dealing with interpersonal problems. In a work situation they’ll often ignore it until they can’t. And at that point they’ll either leave or attack. Fight or flight. Neither are productive and neither give closure or deal with the issue. As a manager building trust relationships with your team, you are perfectly placed to be the mediator. But until the issues are brought into the light there is nothing to mediate.