The 4 One-on-One Meeting Questions You Should *Not* Ask Your Employee

If you're wondering why your one-on-one meetings tend to feel unproductive, these questions might be why.



“I think my team isn’t enjoying our one-on-one meetings,” said the CEO of a 15-person remote company to me, recently. He was having a hard time engaging his team during their one-on-one meetings. An employee would give one-line answers. Another seemed to keep looking at the clock. This CEO would stare down at his one-on-one meeting agenda, racking his brain, wondering if these seemingly “essential” meetings were actually becoming a big waste of time.

To see if I could help, I asked him what questions he was asking. As he told me, the underlying issue revealed itself: This CEO was asking completely the wrong questions, in my view. Below are the questions he asked and that you should learn from. They are the four questions you should not ask during a one-on-one meeting.

“How’s it going?”

Ah, the perennial one-on-one meeting opener. How many of us have found ourselves asking this question? It seems like a solid way to break the ice and initiate the one-on-one meeting. While “How’s it going?” seems innocent and innocuous enough – that’s exactly why you should not ask it. It’s filler. It rarely elicits anything meaningful. Consider, that the answer most people tend to give to “How’s it going?”, nine times out of ten is “It’s fine.” Do you learn anything with an answer of “It’s fine?” No, you don’t.

What should you ask instead? If you’re looking for a casual, open-ended way to kick off a one-on-one, instead ask, “How’s life?” Asking “How’s life?” gives permission for someone to talk more interestingly and personally about how their feeling, what they might be up to, what’s on their mind (vs. just “How’s it going?”). With “How’s life?” you also show you care about their well-being, and not just their work output.

“What’s the latest on __?”

It can be tempting to use your one-on-one session as a time to get caught up on what’s going on. However, keep in mind that having a status update be the focus of your one-on-one squanders the purpose of a one-on-one, to begin with. A one-on-one meeting isn’t a reporting session – it’s a unique, invaluable opportunity to get to the bottom of what someone is actually thinking and feeling.

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, “Can you tell me about what’s been most surprisingly about working on this project so far?” Merely asking “What’s the latest on X?” falls flat if you use it as the end all be all for the meeting. What was once an opportunity to uncover a hidden blindspot, or unearth a potential issue, now became a status update meeting. You probably could’ve gotten the some information asking them that question via Slack or an email. And instead you just spent 40 minutes of both you and the other person’s time on it.

What should you ask instead? Make sure to use this question sparingly (if at all). And when you do, that it’s a segue into something more probing about the project, instead of an update on the project.

“How can I help you?”

The intention behind this question is fantastic. You want to help, you want to get out of their way, you want to figure how what you can be doing better. However, this question is the absolute worst way to signal that. Why? It’s lazy – it makes the person receiving the question do all the hard work of having to come up with the answer. It’s also a very hard question to answer, especially on the spot — you’re asking the person to critique you across all spectrums and come up with something actionable for you to do. It’s not surprisingly that often when you ask this question, your employees reaction will be to silently roll their eyes.

What can you ask instead? Suggest something specific yourself you think you can be doing to help, and then ask – what do you think? For example: “I was thinking I’m being a little too hands-on on this project and creating a lot of bottlenecks for you. Should I back off and check-in with you only bi-weekly? What do you think?” By being specific in what you suggest, you open the door for critique and make it a whole lot easier for that person to share exactly the ways in which you can help them.

“How can we improve?”

The problem with “How can we improve?” is that it’s a vague question. And when you ask a vague question, you invite a vague answer. You cause the person to think in generalities and broad buckets, instead of nuance, actionable items, and specific insights. Ask an employee “How can we improve?” and they think, “Man, from a business development perspective? Marketing perspective? Leadership perspective? Where to even begin?” Now, some employees you work with will be able to craft a thoughtful answer from this question. But it’s rare, and it’s a lot of work for them.

What can you ask instead? Focus your efforts on asking specific questions, instead of defaulting to general ones. For instance: “Is there anything we’re not doing right now that we should?” “What do you think is the most overlooked area of the business?” “Where do you think we’re behind in, that other companies are excelling at?” “Where in the company have we fallen short, and need to pick up the slack again?” Notice how specific each of these questions are. The more specific the question, the more effective they are.

When you start evaluating your one-on-one questions more critically, the more you’ll start to get out of your one-on-ones. The questions do the heavy lifting. The questions determine the path to which your one-on-ones will take. Ask well-thought out, meaningful questions, and there’s a good chance your answers returned back to you will be well-thought out and meaningful too.

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