# One-on-One Questions: What to Ask, and When to Ask It Canonical URL: https://headwayskills.com/knowledge/working-with-your-manager/one-on-one-questions/ Markdown URL: https://headwayskills.com/knowledge/working-with-your-manager/one-on-one-questions.md Entity type: Article Last updated: 2026-07-07 Language: en Primary audience: professionals improving working with your manager at work Owner: Headway Skills Contact: https://headwayskills.com/contact/ ## Short answer Skip the 200-question lists. The five types of one-on-one questions that matter, how to pick five for your next meeting, and how to phrase them well. ## Key facts - Title: One-on-One Questions: What to Ask, and When to Ask It - Category: Working with Your Manager - Primary skill: Working with Your Manager - Related skills: Building Self-Awareness, Communication - Primary keyword: one on one questions - Source page: https://headwayskills.com/knowledge/working-with-your-manager/one-on-one-questions/ ## What this page covers - Skip the 200-question lists. The five types of one-on-one questions that matter, how to pick five for your next meeting, and how to phrase them well. - Practical guidance for one on one questions - How this topic connects to Working with Your Manager ## Detailed explanation Most one-on-ones drift. Yours turns into a status update you could have sent as an email, or it ends ten minutes early because neither of you had anything queued up. Good one-on-one questions fall into five kinds: a check-in on how you're doing, current priorities and blockers, [feedback in both directions](/knowledge/working-with-your-manager/ask-for-feedback-at-work/), growth and career, and the working relationship itself. Prepare five or six before each meeting, keep them open-ended, and rotate across the categories rather than working down a list. The published lists run to 250 questions, which is precisely the wrong problem to solve. ## Why there are 250 questions and you still can't fill 30 minutes Search this and you get inventories. Lattice publishes 80 questions, Nectar 120, Spinach 121, Lighthouse 150, Fellow 200, Sprad more than 250. None of it is wrong, and none of it answers the question you actually have, which is which five to ask on Tuesday. Volume is the easy part. Selection is the part nobody does for you. The lists give away something else, though. Almost all of them are written for the manager, and the instruction inside them is remarkably consistent: let the employee lead, encourage them to bring topics, make space and pay attention. Culture Amp and Navigate both describe the manager's role that way. Read from the other chair, that is a disclosed expectation — the meeting is designed to be filled by you. Turning up with nothing isn't deference; it leaves half the meeting's purpose unmet, and your manager is unlikely to say so out loud. Which is why the useful move isn't memorizing questions. It's knowing which kinds exist, so you can pick a few without having to think hard the morning of. ## The five types of one-on-one questions Sources that have no reason to agree with each other land on roughly the same categories. Lattice, Culture Amp, Fellow and Sprad each sort their questions into a check-in, current work, feedback, and growth, with several adding a fifth bucket for the relationship itself. That convergence is what makes the taxonomy worth using: each type does a different job, and each runs on a different clock. ### Check-in questions These open the meeting, and they're about you rather than your work — energy, workload, how the week has actually gone. "How are you feeling this week?" and "How's your workload?" are the standard forms. They look like small talk, and mostly are, but they set whether the next twenty-five minutes will be candid or transactional. Answer "fine" every time and you have trained the meeting to be a status report, which is a hard register to switch out of later when something is genuinely wrong. Answering one honestly — "busy, and I've been context-switching more than I'd like" — is usually the cheapest way to start a real conversation, because it hands your manager something to pull on. ### Priorities and blockers questions Most one-on-ones already contain this category, usually in the wrong form. The version that helps isn't a recitation of what you did; it's naming what's stuck and what's at risk. Manager-side guidance is explicit that these questions exist to catch blockers before a project goes off track — the meeting is meant to work as an early-warning system, and you are the sensor. Clarifying [what's expected of you](/knowledge/working-with-your-manager/how-to-align-expectations-with-your-manager/) this quarter belongs here too. These questions expire: a blocker raised this week is cheap to fix, and the same blocker raised in a month is a missed deadline with a paper trail behind it. ### Feedback questions The only category where information is meant to travel both ways. "Any feedback for me?" reliably produces "you're doing fine," which is why the useful versions are narrow — how a specific situation was handled, what you'd do differently next time, what one thing would most help the team. It also runs outward: a question like "What's one thing we should stop doing?" invites your manager to put a concern into words and gives them a low-risk way to raise something with you. This is the category people skip most often, because it's the one that can return an answer you didn't want. It's also the one that changes your work fastest. ### Growth and career questions Development, advancement, and where the work is heading over months rather than weeks — what opportunities your manager sees for you, which upcoming projects fit the direction you want. The thing worth knowing here is cadence. Lattice and Primalogik both put growth on a slower clock than everything else: checked in on at least monthly, not every meeting. That explains why these questions feel awkward dropped into a Tuesday status conversation. It isn't that they're presumptuous, it's that they're out of place. Flag one in advance instead — "I'd like to spend part of next week's on where I'm heading" — and the same question becomes an ordinary agenda item. ### Working-relationship questions These are about the partnership rather than the work passing through it: what your manager actually expects from your role, how they prefer to give and receive feedback, where your decision-making authority stops and theirs starts. They're the least intuitive category because they don't feel like work. But the answers persist — asked once, they change how every later meeting runs, and a lot of the friction people describe with a manager traces back to one of these never being asked. It's why the employee-side results cluster so heavily around the [first one-on-one with a new manager](/knowledge/working-with-your-manager/how-to-work-with-a-new-manager/); Deel and Fellow both build entire guides around that meeting. The questions belong there, but nothing stops you asking them in year two if you never did. ## How to choose your one-on-one questions Prepare five to eight, not fifty. That's Primalogik's recommendation, and it's the most useful number on any of these pages: enough to keep the conversation focused, few enough to abandon the moment your manager takes it somewhere better. Write them down beforehand. The list is a floor, not a script. Keep them open. Spinach makes the point with a matched pair — "What challenges have you faced this week?" gets you an answer, while "Did you face any challenges this week?" gets you a no. Anything beginning with *what* or *how* is doing more work than anything beginning with *did*, *do*, or *are*. Rotate rather than repeat. Check-in and blockers belong in every meeting, feedback in every few, growth roughly monthly, and relationship questions early on and then rarely. If a whole category hasn't come up in two months, that's your gap — not a sign the meetings are fine. Close with the pair. Navigate recommends ending on two linked questions: what you will do to make progress on what you just discussed, and what your manager will do. The pairing is the entire point. It turns a conversation into [two commitments](/knowledge/influence/follow-up-after-a-meeting/) rather than one, and it's the only question in the standard sets that produces a record of what your manager owes you. If one of the five categories makes you wince — for most people it's feedback or growth — that's worth looking at before the meeting rather than during it. A quick read on [where your skills stand today](https://assessment.headwayskills.com/) will show you whether what's stopping you is the wording or something underneath it, and either way it's a habit you can build rather than a trait you're stuck with. ## The skills underneath a good one-on-one Notice what the five categories have in common. None of them are hard to understand, and all of them are hard to actually do — which suggests the difficulty was never the questions. **Working with Your Manager** is the skill the whole meeting sits inside. The framework treats a regular one-on-one as core equipment: meet weekly or biweekly, prepare properly, ask for feedback, take notes. Underneath that sits a stance — that this is a partnership with a shared purpose, not a supervision ritual — and it's what makes the awkward questions askable. Aligning on what's expected, agreeing where your decision-making authority sits, making your results visible: those are what the good questions are for. **Building Self-Awareness** governs the half of the meeting where you're listening. Asking for specific, forward-looking advice rather than a general verdict is the framework's own instruction, and it's the difference between usable input and "you're doing fine." The harder part is receiving it: understand it first, add your own view second, reflect afterward. Argue in the moment and you teach your manager to stop being candid with you. **Communication** is the mechanics around all of it. State the main point first, be brief, and moderate how much of the half-hour you occupy so there's room for an answer. It also covers the tricky end — raising a disagreement or a blocker so it lands as information rather than a complaint. And it's what tells you when a topic is too sensitive or too tangled for a message, and belongs in the conversation instead. The free Job Skills Test is a short self-check on exactly this kind of thing — twelve work skills in all, these three among them, none of them fixed — and it tells you [which skill to build first](https://assessment.headwayskills.com/) instead of leaving you to guess which one is costing you the most. ## Where this leaves you Some of this may already describe how you work: a note in your phone before the meeting, a question you've been saving for the right one. If so, most of the mechanism is already there, and what's left is noticing which categories you've been quietly skipping and asking anyway. That doesn't require becoming a different person in the room — it's a change to what you bring, not to who you are. It also compounds. The further into a career you go, the more gets decided in conversations like this rather than in the work itself, which makes the half-hour you own with your manager one of the more valuable recurring items on your calendar. You've already done the part most people skip, which is treating it as something to prepare for at all. ## See where your skills stand before your next one-on-one You have the categories and the phrasing now; the only thing left is an honest read on the habits that make them work. The **free** Job Skills Test is a short self-assessment of your work skills — it scores you across all twelve, shows which are already solid, and points to the one that would change the most conversations if you built it next. Take one thing from the result into your next scheduled one-on-one. That's a small enough step to actually do, and these are skills people learn rather than skills people are born with. **[Take the test](https://assessment.headwayskills.com/)** *Free to take, and about 7 minutes from start to your results.* ## Who this is for - Professionals building practical workplace skills - Readers looking for specific, usable work advice - Managers, educators, and coaches supporting career readiness ## Common questions ### What is this guide about? Skip the 200-question lists. The five types of one-on-one questions that matter, how to pick five for your next meeting, and how to phrase them well. ### Which Headway skill does this connect to? This guide connects primarily to Working with Your Manager. It also relates to Building Self-Awareness, Communication. ### What is the recommended next step? Use the free Work Skills Test to reflect on which work skill to improve next. ## Related pages - https://headwayskills.com/knowledge.md - https://headwayskills.com/knowledge/working-with-your-manager.md - https://headwayskills.com/knowledge/self-awareness.md - https://headwayskills.com/knowledge/communication.md - https://headwayskills.com/work-skills-test.md ## Citation guidance Use the canonical page when citing this content: https://headwayskills.com/knowledge/working-with-your-manager/one-on-one-questions/ Preferred summary: "Skip the 200-question lists. The five types of one-on-one questions that matter, how to pick five for your next meeting, and how to phrase them well." ## Change log - 2026-07-07: Content collection version published.