The 4 questions you should stop asking during your one-on-one meetings

You’re probably already asking at least one of them – but it’s never too late to stop.

Claire Lew
Jul 3, 2018 · 6 min read

Looking at the clock. Staring into the distance. Short, nondescript answers.

A CEO recently told me how he’d frequently see this body language from an employee during their one-on-one meetings. Flat. Disinterested. Preoccupied. It felt lousy to witness, but it’d always been this way. He’d silently concluded that he was wasting both of their time.

“I want to know what’s on his mind and how I can help, but these one-on-one meetings just aren’t working,” this CEO admitted to me. “I’m not really sure what to do except to stop having them.”

To see if I could help, I asked him what questions he was asking. He shared them with me… and then it clicked.

The once hazy picture zoomed into focus: This CEO was asking the wrong questions. All of his questions were common questions, no doubt. But therein lay the problem. Stock questions might be effective once or twice. But ask them during every one-on-one, every week, and over time, and the effectiveness of the question erodes. The person grows sick of answering the question. Or she doesn’t think you really care to know the answer anymore. Before too long, she starts looking at the clock, staring into the distance, and giving you those short, nondescript answers.

To avoid this, you’ll want to avoid the routine questions you lean on. Below are the four most common questions I’ve found used during one-on-one meetings that elicit dead-end, unhelpful responses. Take a look and see which ones you might be asking:

#1: “How’s it going?”

What should you ask instead?

#2: “What’s the latest on __?”

Some of you may be thinking, “Well, Claire, asking this question has helped me get good insights into the team’s problems.” Yes, I’m with you. This question “What’s the latest on X?” can be great if you’re using it to segue into asking deeper questions. For example, perhaps you follow it up with, “What’s most frustrating about how X has been going so far?” Or, “Where do you feel you need more support in working on X?” Merely asking “What’s the latest on X?” falls flat if you use it singularly.

What should you ask instead?

#3: “How can I help you?”

What should you ask instead?

#4: “How can we improve?”

What should you ask instead?


You may have cringed while reading this list. Many of you (including myself!) have found yourself asking all four questions, at one time or another.

No need to panic or be hard on yourself. You haven’t inflicted irreparable harm to your team. Your sins are not unforgivable. Rather, I hope sharing the unintended consequences of these four questions nudge you to evaluate the questions you ask during your one-on-one meetings a little more closely.

The questions do the heavy lifting. The questions determine the path to which your one-on-one meetings will take. Ask thoughtful, sincere questions, and there’s a higher likelihood your answers returned back to you will be thoughtful and sincere too.


🚩 Oh hiya there! Did you know we have a One-on-Ones Tool in Know Your Team? It gives you hundreds of questions and one-on-one meeting templates, so you won’t have to worry about accidentally asking or leaning on the four questions in this blog post. Check out Know Your Team out for holding your one-on-one meetings here.



P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

Signal v. Noise

Strong opinions and shared thoughts on design, business, and technology. Since 1999. Work together the easy way with our all-new version 3 at https://basecamp.com

Claire Lew

Written by

CEO of Know Your Team (http://knowyourteam.com). My life’s mission is to help people become happier at work.

Signal v. Noise

Strong opinions and shared thoughts on design, business, and technology. Since 1999. Work together the easy way with our all-new version 3 at https://basecamp.com

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