1-1 question generator

This is the set for a normal week, when nothing is on fire and there is no obvious topic. It works because it starts from the work the person is already holding and then makes room for whatever they have not said yet.

• What has taken most of your time since we last talked?
• What is the one thing this week that would bother you if it slipped?
• Is anything waiting on me right now?
• What part of the work felt good lately, and what felt like a slog?
• Anything happening in the team that I am probably not seeing?
• If you could change one thing about how we work, what would it be?
• What did you learn recently that surprised you?
• Is there a decision coming up where you want a second opinion?

Where it goes wrong. Used every week without variation, these turn into a script and people learn to answer them on autopilot. Swap two of them out whenever the answers start sounding rehearsed.

Bring these out once or twice a year, or whenever someone hints that they are thinking about the next step. They are slower questions and they need a full meeting rather than the last five minutes of one.

• When you picture your work a year from now, what is different?
• Which parts of your current work do you want more of, and which less?
• What skill do you want to be visibly better at by the next quarter?
• Who in the company does work you would like to be doing?
• What is the gap between where you are and the next level, as you see it?
• What kind of project would stretch you without breaking you?
• Is there feedback you have been given that you disagree with?
• What would make you say a year from now that it was a good year?

Where it goes wrong. Asking about growth too often, with no visible change between the conversations, reads as theatre. Ask once and then do something the person can see before you ask again.

The first weeks are the only time someone can see your team clearly, before the odd parts start looking normal. These questions try to catch that view while it lasts and to find the practical things that are quietly blocking them.

• What has been more confusing than you expected?
• Who have you talked to so far, and who should you have talked to already?
• What did you expect this job to be that it turns out not to be?
• Is your setup actually working, tools and access included?
• What is the first thing you would like to own end to end?
• How do you prefer to get feedback, and how often?
• Is anything about the team's habits unclear or odd to you?
• What would make the next month feel like a good start?

Where it goes wrong. Do not turn the first month into a daily audit. One of these conversations a week is plenty, and a new hire who is asked constantly how they feel will start giving you the polite answer.

Use this set when the signals are there but the person has not said anything: slipping deadlines, late night commits, a shorter fuse in reviews. The questions are deliberately concrete because someone who is buried rarely has the energy to describe the general shape of it.

• How many things are you holding right now, honestly?
• Which of them could be dropped or handed over this week?
• When did you last finish a day feeling like you got somewhere?
• What is pulling you outside working hours?
• If I took one thing off your plate today, what should it be?
• Are the interruptions coming from people, alerts, or meetings?
• What would a sustainable version of this month look like?
• Is there anything you have stopped saying out loud because it feels pointless?

Where it goes wrong. These only help if you can actually take something away afterwards. Asking what to drop and then dropping nothing is worse than not asking at all.

This is the hardest set and it belongs in a meeting you have prepared for. The questions are built so the person gets to describe the situation first, which usually surfaces context you did not have.

• How do you think the last few weeks went?
• Where do you feel you are strongest right now, and where do you struggle?
• What is getting in the way of the work you want to do?
• Is what I expect from you clear to you? Say it back in your words.
• What support would actually change the outcome here?
• What should we both see in four weeks to know this is on track?
• Is anything outside work affecting how this feels right now?
• What do you need from me that you have not asked for?

Where it goes wrong. None of this replaces saying the thing plainly. If there is a real problem, name it in the meeting rather than hoping a question walks the person into naming it for you.

Distance mostly costs people information, not motivation. These questions look for the gaps in what someone hears and the decisions that happened while they were asleep.

• Where do you feel out of the loop?
• How much of your week is meetings, and does that split feel right?
• Which decisions happened without you that you should have been in?
• Do you have enough contact with the people you depend on?
• What is harder for you remotely than it would be in a room?
• How would you like us to handle time zones for the next project?
• Is there anything you would raise in person that you skip on a call?
• What would make our written updates more useful for you?

Where it goes wrong. Do not use them to check whether someone is working. The moment a remote 1-1 feels like surveillance, you stop getting honest answers about anything else.

Wait a few days before using these. A hard week needs some distance before people can say anything useful about it, and the questions assume both of you have had time to think.

• How are you sitting with what happened?
• What is your read on it now, a few days later?
• What do you think the other person would say happened?
• What did I do or fail to do that made it harder?
• What would a good outcome look like from here?
• Do you want me to step in, or do you want room to handle it?
• Is there anything unresolved that will show up again next week?
• What should we agree on so this does not repeat?

Where it goes wrong. Avoid running the same conversation repeatedly. Once you have an agreement about what happens next time, close it and move on, otherwise the meeting itself keeps the conflict alive.

These assume you are not the person's direct manager. They stay on the team and the system rather than on individuals, which is what keeps the meeting from turning into a channel around someone's lead.

• What is the team good at that nobody outside notices?
• What slows you down that your manager cannot fix alone?
• If you were running the team, what would you change first?
• What are you working on, and why does it matter?
• Where do you think we are spending effort that does not pay off?
• How do you find out about decisions that affect you?
• What would you like to hear more about from leadership?
• Is there something you would tell me that you would not tell your manager?

Where it goes wrong. Anything you hear here needs handling with care. Acting quickly on a detail only one person could have told you is a reliable way to make sure nobody tells you anything again.