What should you ask instead of “how’s it going?”
Pick three questions before the meeting, in an order, then ask the first one and follow it up properly. A workable default trio: what took most of your time since we last talked, and was that the right place for it?, then what are you waiting on right now, and how long have you been waiting?, then what do you need from me before we talk again? Swap the middle one for whatever you actually noticed that week. The follow-up matters more than the opener — a question you do not follow up on is small talk with a clipboard.
The rest of this page is how to choose those three, and what to do when the answer is “fine.”
The meeting is fine. The question isn’t.
You already hold the one-on-one. It is in the calendar, it recurs, and you show up. The failure is upstream of all that: you get to the meeting without having decided what you want out of it, so you open with the only question that is always available, and the answer comes back the same shape every week.
Then you fill the gap with status. Status is a perfectly legitimate thing to discuss and a terrible thing to build a recurring meeting around, because it is already written down somewhere and because neither of you learns anything from saying it out loud. Six months later the meeting has a reputation, and it is not a good one.
The fix is unglamorous and takes about two minutes: arrive with three questions you picked on purpose, ask the first one, and follow it up properly.
The four questions worth retiring today
| What you ask now | Why it fails | Ask instead |
|---|---|---|
| How’s everything? | Too wide to answer — the honest response would take twenty minutes, so you get “good, yeah.” | Narrow it to a week, a project, or twenty minutes: what was the most annoying twenty minutes of your week? |
| Any blockers? | A yes/no question that invites the no, and “blocker” is a word people reserve for emergencies. | What are you waiting on right now, and how long have you been waiting? |
| Any feedback for me? | Asks somebody to invent a topic and criticize their manager in the same breath, with no warning. | What’s one thing I should start doing, and one I should stop? |
| Are you happy here? | The answer is usually yes — right up until the day it isn’t. | If you were still doing exactly this job in two years, how would you feel about that? |
Each replacement does the same two things: it narrows the scope so an answer is actually possible, and it asks for something specific rather than a verdict.
Start from what you noticed, not from the plan
The most useful input you have is not the project tracker — it is the thing you observed and have not mentioned. Late-night messages. The fourth week of “all good.” A name that comes up with a sigh attached. A deadline that slipped at the seam between two teams rather than in the middle of the work.
Each of those points at a different set of questions, and the routing matters more than the questions do:
- Messages arriving late at night, more than once this week. Get the real number first — how many hours are you actually working in a normal week right now? — then cut something yourself. Do not ask a person who is underwater to prioritize their own rescue; that is the hardest possible task in the worst possible week.
- “All good” for four weeks running. Do not ask harder, ask smaller. A twenty-minute window is difficult to deflect in a way that a whole week is not. If four weeks of narrow questions still return nothing, name the pattern out loud — as an observation about the meeting, not a verdict about them.
- A lot in flight and nothing shipped in two weeks. Usually a blocked dependency or a decision nobody has made, not a motivation problem. Ask what they are waiting on, and how long.
- A project just landed. Within the week, while the detail is sharp. Ask what surprised them before you ask how it went.
- A strong performer passed over again. If your name came up for a bigger role tomorrow, what would someone argue against? Then separate the fair objections, which are theirs to work on, from the visibility problems, which are yours.
The follow-up is the whole thing
Published lists of one-on-one questions tend to stop at the question. That is the half that is easy to write and the half that does the least work.
Take the standard opener. What took most of your time since we last talked? On its own it produces a summary of the week, which you mostly knew. The second question — what would you have spent that time on instead? — turns a summary into a judgment, and the judgment is the useful part. And if the first answer is a list of tasks rather than a judgment, there is a third move: make them rank it.
The pattern underneath every good one-on-one question is the same five steps.
- Ask the question, word for word. Nobody minds that you prepared.
- Listen for the specific — a name, a date, a number, an example.
- Follow up with the second question you decided in advance.
- Capture it out loud, in one sentence, in front of them.
- Close on who does what by when.
Silence is a technique, not a failure
A real question needs thinking time. A pause that feels endless to the person who asked it barely registers for the person thinking. The reflex to fill that gap — softening the question, offering two options, answering it yourself — converts a real question into a multiple-choice one, and multiple choice hands back the answer you already had.
If the silence holds, say “take a minute” and look at your notes instead of at them. If it is still empty, let it go kindly — “fair enough, I’ll ask again next time” — and then actually ask again next time. Repetition is what makes a question safe to answer.
What to do when the answer is “fine”
“Fine,” “nothing really,” and the shrug are the normal case, not a failure, and there are three moves that work better than asking again in a firmer voice.
Shrink the window. The most annoying twenty minutes of the week is much harder to deflect than a whole week, because it asks for one concrete thing rather than a summary.
Take a number and a plus-one. Rate the week one to ten, then ask what would have made it one point higher. The number itself is nearly useless; the plus-one is the whole question, and it is far easier to answer than “what’s wrong?”
Ask by proxy. Someone who will not complain on their own behalf will often speak fluently for the team. “If someone else on the team were sitting here, what would they say is going wrong?” gets you the problem without asking anyone to own it.
One thing that is not a move: putting the three questions out of sight. Put them where you can see them, on the table or beside the laptop. Reports tend to take a visibly prepared manager more seriously than one who improvises, and nobody has ever minded that their manager thought about the meeting first.
Close the loop between the meetings
Two of the steps that decide whether any of this holds up happen outside the conversation itself.
Ask what they need from you, and get a date on it. “Nothing” is a common answer and rarely the whole truth, so offer two concrete kinds and let them pick: a decision, or an introduction. Either one is small enough to say yes to.
Then open the next meeting by reporting on what you promised — kept or not. This is the unglamorous half. Trust in a one-on-one is built as much by the follow-through between the meetings as by the questions inside them, and a brilliant question followed by nothing teaches a report to give you a short answer next time.
It is also what makes the non-answer moves work over time. Someone who has watched you act on the last honest thing they said will give you a second one. Someone who hasn’t will keep saying “fine” — and “fine” is not a personality, it is a verdict on what happened to the last answer.
How often should you ask about career and feedback?
There is one predictable way this decays even when it is working. Workload questions are easy to ask and urgent to answer, so they tend to crowd the agenda. Career, feedback, and wellbeing questions are neither, so they get postponed — and a whole quarter can pass in which nobody on your team has been asked a single question about where they are going.
The fix is bookkeeping, not willpower: keep a note of which kind of question you last asked each person and roughly when, glance at it once a month, and go wherever the gap is largest. Four categories are enough — workload, growth, feedback both ways, and how they are actually doing.
Where to get the questions already written
If you would rather not compose these from scratch every week, the free twelve 1:1 questions card sheet gives you one question from each of twelve situations, each printed with its follow-up, on cards you cut out and keep by your notes. No email, no signup.
The full 1:1 & Coaching Question Deck is 108 questions across those twelve situations, and every card adds the two fields the free sheet leaves out: the moment to use it, and the specific move for when you get a non-answer. It also adds the routing — twenty-two observed signals, each mapped to three named cards in order with the reading behind that order — twelve pre-sequenced trios for the meetings you already run, and the rotation log described above as a printable grid.
If you are weighing this against a subscription tool, the question deck versus a one-on-one app comparison covers which half of the problem each one actually fixes.
Where the answers go is a separate job. The 1:1 Meeting & Goal-Tracking Workbook keeps a running log per report, carries action items forward until they are closed, and flags who you are overdue to meet with. If you have just been handed a team, the New Manager’s First 90 Days Playbook covers the wider job this meeting sits inside.
A note on what belongs in the room
These are conversation prompts, not legal, HR, or employment-law advice. Some of the best questions touch on workload, wellbeing, and pay. Use your own judgment about what belongs in a one-on-one, follow your organization’s rules on records and on compensation conversations, and route anything beyond your role to whatever support your organization actually provides. Notes about a named person are an employee record wherever you keep them, paper included — keep them factual and somewhere only you and HR can open it. If an answer names somebody else, record the issue rather than the characterization, and remember that a conversation touching conduct, a protected characteristic, an accommodation or a grievance is an HR conversation before it is a management one.
