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Have an upcoming one-on-one with your boss or employee? Let's take a look at this guide to have an amazing meeting!
Think back to the one-on-one you had last month.
You both sat down. They asked how the project was going. You said “good, on track.” They nodded. You filled the rest with the same updates you’d already typed into the tracker. Twenty minutes later somebody said “great, let’s do this again next month,” and you both walked out having said nothing you couldn’t have put in an email.
Sound familiar?
It doesn’t have to go that way.
Knowing how to walk into a one-on-one and actually make it count is one of the most underrated skills at work. These meetings happen between managers and their direct reports, or peer-to-peer. And the good ones do real work: they clarify questions, surface honest feedback, and yes, sometimes they’re just a chance to swap stories about the weekend visit to the in-laws.
So what separates the one-on-one that moves your career forward from the glorified to-do list readout? That’s what this guide is for. Here’s where we’re headed:
- What one-on-one meetings actually are
- Why they’re worth your time
- How to prepare as a manager
- How to prepare as a team member
- Questions to ask, plus ready-to-use meeting templates
What Are One-on-One Meetings?
A one-on-one is an informal, private conversation between a manager and a direct report. The whole point is to build trust and catch issues or concerns early, while they’re still small. A performance review is technically a kind of one-on-one too, but that’s a different animal, so it’s not what we’re talking about here.
How often should you hold them? That depends on the relationship. As a general floor, though, at least once a month.
And both people should walk in with something to talk about. That could be
- things that have gone well,
- a check-in on goals,
- a general catch-up,
- areas for improvement, or
- questions on upcoming projects.
This is your moment to check in on the longer-term goals and trade real feedback. It’s an open conversation, and both people should feel free to put their thoughts and ideas on the table.
Why Are One-on-Ones Beneficial?
The payoff isn’t a hunch. Gallup found that employees whose managers meet with them regularly are nearly three times as likely to be engaged as those whose managers don’t.
Nearly three times. From a recurring slot on the calendar.
Whether you’re the manager or the team member, the wins stack up fast:
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You get to know each other as people. You hear what’s actually going on in their life and how they really feel about the work. And once you’ve talked about more than the project tracker, the trust goes up.
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You get a much clearer picture of where they want to go: their goals, their aspirations, what they’re hoping the next few years look like.
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Your team member gets a safe place to raise a concern without bracing for blowback. A problem with a colleague, something rough in the workspace, whatever it is, it has somewhere to go. And when people can say the hard thing without fear, productivity climbs.
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It flows both ways. Your report can give you feedback on how you’re doing as a manager, which is gold for spotting where you could be offering more support or guidance.
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And honestly? People feel valued when their manager carves out regular time just for them. That alone is worth a lot.
How to Prepare for Your One-on-Ones as a Manager
If you’re the manager here (and we have our full guide for managers here), a little prep is the difference between a meeting that lands and one that drifts. Here’s what to think through.
Step #1: Have a goal
Before you sit down, get clear on what you’re after. Is this about reconnecting? Clarifying something? Giving feedback? The more specific you can be, the easier it is to walk out knowing the meeting actually did its job.
Use a casual opener
Resist the urge to lead with the “serious stuff.” Your team member might be a little nervous walking in, so easing in with something non-work usually works best. A few openers to keep in your back pocket:
- How was your weekend?
- How do you like the working environment here?
- Did you go to [a company event]? How did you enjoy it?
Be fully present
Try not to treat this as one more box to check. Make “fully connect with this person” one of your actual goals for the time. That means putting the distractions away, phone, laptop, the lot.
And the signal travels fast. If you’re glancing at messages or taking calls mid-meeting, your team member reads it loud and clear. They feel like they don’t matter.
Ouch.
Step #2: Develop a meeting agenda
Got your goal? Now break it into a few agenda items. If your goal is to build trust with a new hire, you might ask about their background and what drives them. If your goal is to help someone push a project across the line, you’ll spend more time on what they’ve actually gotten done versus the plan, and where they’re stuck.
(There’s a one-on-one meeting template waiting for you further down, by the way.)
Jot those points as bullets, then hold them loosely. You can absolutely flex during the conversation, just steer it back if something urgent needs a course correction.
Step #3: Schedule recurring meetings
Cadence is everything. Set up a recurring rhythm, weekly or biweekly, and your relationship with your team member grows on its own over time. Drop them on your calendar so they don’t quietly slip away.
And when life happens and something collides with the next session? Reschedule, don’t cancel. Canceling sends a quiet message that the meeting was optional all along. Rescheduling says it still matters.
Step #4: Think about the logistics
Can you do a coffee chat, a lunch, or a walk?
Who said one-on-ones have to happen in a conference room? A coffee shop or a shared lunch can be a great swap. People tend to loosen up outside the office, it feels less like a meeting and more like catching up with a friend, and you’ll often build a closer relationship this way. Bonus: healthy foods even make people happier!
And if you or your team member are the restless types, take a walk. You’ll talk easier and sneak in some steps while you’re at it.
Who else do you need to invite?
Yes, it’s a one-on-one. But if you can see the topic coming, it’s worth asking whether a third person should be in the room.
Say you’re heading into sensitive territory, a raise, a severance package, garden leave, an unusual promotion, and you’re not 100% sure on the details. That’s a good moment to loop in someone from HR.
Or picture a different scenario: your team member is struggling to settle into a new environment, or feels shy about meeting new people. Bringing in someone with a shared background (same home country, same hobbies) can change the whole vibe. Your direct report might be genuinely glad to connect with a peer.
One rule, though: tell your employee ahead of time if someone else is joining. Don’t catch them off guard. They may have reservations about opening up beyond just the two of you, and that’s fair.
Get the right tools in place
Sort out the logistics before you’re in it. Meeting virtually? Pick your video app ahead of time. In person? You might want a whiteboard handy in case you need to sketch something out.
Step #5: End on a high note
Leave time for them to ask questions
You might be itching to confirm whether that deadline next week is on track. Fair. But leave room for them to ask you things, even the stuff that has nothing to do with the task list. A good manager often doubles as a life and career coach, and those questions are where it happens.
End with action steps
You’re holding these meetings for a reason. So close the loop with concrete action steps.
- Feeling overworked? Redistribute the load or help them prioritize.
- Feeling unsupported and overwhelmed? Point them to company resources, a meditation app, a therapist, maybe some paid leave.
- Unsure about the best next move? Recommend a couple of good books, introduce them to someone who’s been through the same thing, or make “let’s revisit this” the plan for your next one-on-one.
Then move on those steps quickly. The worst outcome is your team member walking away thinking that opening up led nowhere.
Action Items for Managers:
- Schedule weekly/bi-weekly one-on-one meetings with your direct reports and put them in your calendar.
- Spend 5 minutes thinking about the agenda for your next one-on-one meeting.
How to Prepare for Your One-on-One with Your Manager
Now flip the chair around.
Imagine you’ve got fifteen minutes with your boss on Thursday. You can spend it reading your task list out loud. Or you can spend it telling them where you want your career to go in two years, and watching them start to clear the path.
Same fifteen minutes. Wildly different payoff.
If you’re the one meeting with your boss, these conversations can do a ton for your career, but only if you treat them as more than a check-in. Here’s how to make the most of yours.
A one-on-one meeting is your opportunity
Any time you get face time (or Zoom time) with your manager, it’s a chance to show what you can do, float an idea, or just get to know them better. So think about your goal going in. What would help your manager understand and appreciate you a little more? Pre-plan with a few questions like these:
- Is there anything you want your manager to know?
- What do you wish your manager understood about you?
- Do you need any help or advice from your manager?
Send regular updates before meetings
Whatever you do, don’t let the meeting become a status readout. This time is for career planning, goal setting, and deepening the relationship. The fix is simple: send your updates ahead of time, and often, so there’s nothing left to “report” in the room. Two ways to handle it:
- A few weeks before the meeting, update them through email: Send your status update in emails frequently and some reminders if necessary. You can even make this a weekly email check-in. Or,
- do frequent stand-up meetings. Daily or weekly stand-up meetings will enable you and your team to update your manager on the work status.
Whichever one you and your manager land on, go with it.
Here’s why this matters: the more your manager already knows, the less tempted they’ll be to spend your precious one-on-one time rehashing it. And that frees you up for the bigger, hairier career stuff, your long-term goals, the areas you want to grow.
That’s the good part. Protect it.
Pro-Tip: Send your goals or questions for the meeting ahead of time. Something like:
- In our one-on-one next week, I would love to discuss ____.
- One thing I would love to chat about in our upcoming one-on-one is future growth opportunities at the company. I want to be doing more ____.
- If you are building an agenda for our one-on-one next week, please add the item of remote work/flex time / a new time management strategy / ______. I would love to discuss this possibility with you.
Write out your talking points
Once the meeting’s on the calendar, write out what you want to cover. Drawing a blank? Here’s a starter list to pull from:
- your career goals,
- personal growth trajectory,
- roadblocks,
- ideas for team improvement,
- personal topics, interpersonal issues.
Your manager can’t read your mind. If you don’t say it, they don’t know it. The whole point of a one-on-one is connecting and talking through the things, sometimes the tricky things, that matter to you.
Keep track of notes
We’ve all been here. Your manager asks how that thing from last month’s one-on-one turned out, and you go blank.
Awkward.
Worse, it can leave them thinking you don’t really value these meetings.
So bring a notepad, paper or digital, and take notes. Even better, keep a running template for the topics you revisit every time.
Try this one:
Last quarter work goals:
Future goals:
How’s my current work performance?
Questions and issues that have come up:
Pro-Tip: Save your talking points from every meeting and bring the whole stack with you. It’s a handy reference, and it quietly shows your manager just how far you’ve come.
Highlight progress & share your work confidently
A one-on-one is the perfect place to put your progress on display. What have you pulled off this quarter? This month? This year? Over your whole time here? Don’t make your manager guess. Share it. Own it.
And when you do, share it like you mean it. Sit broadly, keep the fidgeting in check. Your body language matters just as much as your words here, sometimes more.
Need more of a confidence boost? Check out our 11 Strategies to Up Your Confidence.
Ask for a meeting reschedule, and try not to have them cancel
One of the biggest things that derails a one-on-one? A manager who keeps canceling. It happens a lot, especially with bosses who live in client meetings. And when they reschedule or cancel on you, rest assured, it’s almost never about you.
So be consistent and ask to reschedule. That persistence quietly signals that you’re proactive, serious about your work, and that you’ve got something worth their time.
And if they ask when works best to slot it back in? Check their calendar first, then suggest a time that’s easy for them to say yes to.
Action Items for Team Members:
- Spend 5 - 10 minutes thinking about what you’d like to discuss for your next one-on-one.
- Be sure to include your achievements and questions.
- Make a sticky note reminding you to bring a notebook/digital pad before the meeting.
One-on-One Meetings Templates
The right questions shift depending on the goal of the meeting and who’s across from you. So here are a few ready-to-go agendas to borrow.
First one-on-one with a new employee
Trying to build a relationship with a new employee? These questions are great for sparking a real conversation:
- Tell me a little bit about you.
- What made you choose this role?
- What are your professional aspirations?
- How can I support you better?
- What are your motivations?
- Tell me about your working habits—are you a morning person or a night owl? Are there essential activities/family traditions you want to ensure you have time for?
- What are your hobbies?
- Is there anything else you’d like to talk about today?
Regular check-in
For a regular check-in, you’re after two things: building trust and clearing roadblocks before they grow. Try these:
- How has the past week been for you?
- What will you say you are proud of?
- Is there anything stopping you from achieving what you want?
- Do you need support?
- Where can I help?
- Is there anything else you’d like to talk about today?
Goal setting meeting
Goals land better when they’re built together, not handed down. So make it a true collaboration and walk through these:
- Let’s understand why we set goals.
- What makes a good goal?
- How did the goal we set go?
- Let’s take a look at our priorities.
- Let’s discuss how the current goal will add to our team development/client objectives.
- What is the next step to take in achieving our goals?
Template Action Item:
- Pick one of the templates above and customize it for your next one-on-one.
One-on-One Meeting Takeaways
If you remember nothing else, remember these:
- Write your agenda ahead of time so the critical, time-sensitive stuff actually gets covered.
- Use the time for goal alignment and feedback.
- Schedule them with your direct reports, ideally weekly or biweekly, and keep them recurring.
- And if something comes up, reschedule instead of canceling.
One-on-ones are one of the simplest ways to lift productivity and build real relationships at work. The investment pays off. Want more on leading well? Go grab our guide on How To Be A Good Manager.