I have, in the last six years, sat on the other side of a 1:1 from about forty different managers. Some of them were great. Some of them were not. The difference between the two groups, more than anything else I can identify, was the questions they asked.
The bad managers asked the same three questions every week, and they were not the questions I wanted to be asked.
The great managers asked specific, slightly uncomfortable, almost embarrassing questions. The kind of questions that, when I heard them, made me realize that this person had been thinking about me as a person, between Thursdays.
Here are eight of those questions. Not all of them are right for every meeting. But if you're a manager and the last few 1:1s have felt thin, I'd bet at least one of these is the one your report has been waiting for you to ask.
1. "What's been on your mind that you haven't brought up?"
This is the most useful question in the whole list. It's almost a cheat code.
Your direct report is, almost certainly, sitting on something. Some thought they've been turning over for two weeks, that they haven't surfaced because it didn't seem urgent enough, or because it felt awkward, or because they were waiting to see if it would resolve on its own.
Asking this question — and then waiting through the silence after you ask it — gives them permission. The first answer is often "no, not really." The second answer, after a pause, is often the real one.
A variant that works at first 1:1s with new reports: "What have you wanted to bring up but weren't sure if you should?"
2. "What's something you'd like me to give you more or less of?"
Most managers ask "any feedback for me?" That question is too big, too vague, and arrives with too much social cost. The honest answer is rarely "yes, here is structured feedback for you, my boss."
"More or less" is a better frame because it pre-grants the answer a structure. More of something, less of something. Your report can name a specific behavior, no matter how small, and the framing makes it feel like calibration rather than criticism.
Most common honest answers I've seen: more context on why decisions get made, less involvement in the small stuff, more direct feedback, less back-and-forth before you give me a yes or no.
3. "What's a thing you did this month that you're proud of, that I might not have noticed?"
Your direct report has done something good this month that you don't know about. There's no chance this isn't true, unless they did literally nothing.
Asking this is not just a feel-good move. It's also the only way to see the invisible work — the mentoring, the cross-team coordination, the hard pull request review that turned a junior developer's career around, the document that got passed around quietly. None of that lands on a dashboard. Most of it lands in this question.
Bonus: the answer to this question is exactly the kind of thing that, six months later, becomes a sentence in a promotion case.
4. "Is there something I think is going well that you don't?"
The dark twin of question 3.
Sometimes a manager believes a project is going well, or a relationship with another team is going well, or a process is working — and the report knows it isn't. They've been quiet about it, partly because correcting your manager is hard, and partly because they're not sure if their concern is real or just their own anxiety.
Asking explicitly tells them: it is okay to disagree with my read of the situation. It also calibrates you against their reality. It is rare that the answer is "no, everything's fine." More commonly, you find out that the thing you were celebrating in the all-hands has a quiet hairline fracture in it that the person closest to it has been seeing for weeks.
5. "What does the next year look like for you, if it goes well?"
Career conversation, but framed in a way that doesn't feel transactional.
"What do you want next?" is the question most managers reach for, and it's a hard one to answer in real-time. People haven't worked it out. They feel pressure to give a tidy answer — a title, a promotion, a project — when the actual answer is fuzzier.
"What does the next year look like, if it goes well?" gives them room to describe a felt sense rather than a job posting. The answer might be "I want to feel less stretched" or "I want to actually finish something I'm proud of" or "I want to work with that team I keep hearing good things about." Those are the real answers. They are also the actionable ones.
6. "Is there a conversation we should be having that we're not?"
This is the meta-question.
It tells your report: I'm aware that there are conversations we are avoiding. I'd like to know which ones you think we should not be avoiding anymore.
Often the answer is no. But when the answer is yes, it is almost always a load-bearing yes. They have been waiting for you to ask. The conversation that emerges is, often, a conversation about money, or scope, or whether the relationship is working, or whether they're going to leave. These are the conversations that move things; you want to invite them.
Don't ask this question every week. Once a quarter is about right.
7. "What's something you've been working on that you wish was harder?"
A question for your high performers specifically.
Your strongest reports often have a quiet problem you don't see: the work has stopped stretching them. They don't say so, because they don't want to seem ungrateful, and they're not sure what they'd want instead. So they keep delivering. Then, eight months later, they leave.
This question gives them an opening to admit that the project they're crushing is a project they've outgrown. The answer is data. Use it.
A close cousin: "What's something you used to find hard that doesn't feel hard anymore?"
8. "Is there anything going on outside work that I should know about?"
Used carefully, this is the question that builds the deepest trust. Used badly, it's invasive.
The right time to ask: when you've noticed that something has shifted — energy, focus, response time, demeanor — and you'd rather check in than guess. The right framing makes clear you don't need details, and that "no" is a complete and accepted answer.
I usually say something like: I'm not asking for specifics. I just want to know if there's anything going on that means I should be giving you a lighter hand right now, or covering for you, or just being aware. That phrasing makes it possible for someone to say "yes, my dad's sick" without feeling like they've over-shared, and possible for someone else to say "no, I'm just tired" without it being a lie of omission.
Your report does not owe you their personal life. They do, sometimes, want to be able to hand you a small piece of it so that the work makes more sense, and they need permission to do that. This question is the permission.
What none of these questions look like
A pattern, in case it helps: none of the eight questions above are the ones most managers reach for. None of them is "How's it going?" or "What are you working on this week?" or "Do you have everything you need?"
Those questions are not bad. They're just neutral. They produce neutral answers. They allow the conversation to remain at the surface, and the surface is not where the most useful 1:1 conversations live.
The questions in this post are slightly more uncomfortable. They take a beat longer to answer. They sometimes produce an awkward silence before the real answer comes out.
That silence is a good sign. It means you asked something that mattered.
How to actually use this
Don't ask all eight in one meeting. That's an interview, not a conversation. Pick one. Ask it, then close your laptop and listen. If the answer is short, follow up gently — "say more about that" works almost every time. If the answer is long, say less. The whole point of the question was to make space for them.
Next week, pick a different one.
In a year you'll have asked each of these eight questions a half-dozen times, in different contexts, of different people. You will know your team in a way that the other managers in your org do not. And the people who report to you will know, without you ever having to claim it, that they work for someone who is paying attention.
That's the bar.
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