Cartoon of two remote workers having a one on one meeting

Transform one-on-one meetings from afterthoughts into relationship-building, productivity inducing, inspiration-fests! Or, at least make them a helluva lot better.

You’re powering through a few of your to-do list items when you see a notification pop up: You have a one-on-one meeting with a direct report in 10 minutes.

Oops. You quickly try to remember what happened over the course of the past week. You jot a few random notes on a sticky note. You had a question for this person, didn’t you? What was it again? Oh well. You hop into the meeting feeling completely unprepared and a little frazzled.

Sound familiar? You’re not alone. Planning for a one-on-one meeting can feel like a low-priority commitment compared to the rest of your workload. However, done right, one-one meetings can be productive, worthwhile, and most importantly, build trust and rapport with your team. 

The key is to have just enough structure so that both the planning and the meetings themselves become easy and intuitive. Here’s how to pull it off. 

What are one-on-one meetings for, anyway?

One-on-one meetings as most people know them are regularly-scheduled, relatively short conversations between a manager and a person they supervise.

But that’s the textbook answer. Digging deeper, these meetings provide a chance to check in with your direct reports—both professionally and personally—and reinforce psychological safety. During these routine conversations, sure, managers can get insight into an employee’s progress. But they also provide an opportunity for the employee to ask questions, share challenges, and benefit from the full, individualized support of their supervisor. 

In other words, if you’re the manager, it’s not about you. It’s about them.

There’s a delicate balance to strike with these cadenced discussions. They shouldn’t be rigid status updates or a quick run-through of completed to-do’s. On the flipside, they also shouldn’t be “so unstructured, so casual that there’s no real aim or follow through,” says Leah Ryder, former Head of Marketing here at Trello.

We’ll talk about how to queue up those meaningful interactions in just a minute. First, let’s talk about why they’re so important. 

What are the benefits of one-on-one meetings?

Even if they’re short, one-on-one meetings take up a decent amount of real estate on your calendar—and that’s particularly true if you lead a larger team. Are they worth the time and effort? Absolutely. When they’re run well, these conversations are an opportunity to: 

  • Build and maintain trust with your direct reports
  • Understand your employees on a deeper level
  • Proactively identify and fix challenges or sticking points
  • Provide support and encouragement
  • Celebrate and recognize accomplishments
  • Solicit feedback and make necessary improvements

All of this open communication and increased trust leads to a number of other meaningful benefits in terms of productivity and employee engagement.

For starters, one-on-one meetings give employees clarity about their roles and what they should be focused on. Particularly when you wrap up with action items, people know exactly what they need to prioritize for the week and can use their time as productively and efficiently as possible (without wondering what on earth they’re supposed to do next).

Close and candid conversations with managers also give a big boost to engagement. Research from Gallup found that employees whose managers hold regular meetings with them are almost three times as likely to be engaged as employees whose managers don’t hold regular meetings. That same research found that employees who feel as though their manager is invested in them as people are more likely to be engaged.

All of that means better morale—and even less burnout. Employees who genuinely feel like they’re cared for are a whopping 71% less likely to report a lot of burnout. 

Pretty powerful stuff for a modest and unassuming one-on-one meeting, right? 

How often should one-on-one meetings be held?

Frequency is key for one-on-one meetings. Generally, they’re held weekly or every two weeks. 

Before you think of them as inevitable clogs on your already-packed calendar, take comfort in the fact that these one-on-one meetings can be relatively short. Particularly with a thoughtful and collaborative agenda (which we’ll talk about below), you can usually get through all of your discussion topics and action items in about a half hour. 

In research published by Harvard Business Review, meeting once a week for 30 minutes or so was the most desirable option among employees at all job levels. But if you decide to meet more infrequently—such as every other week or even monthly—plan to set aside at least an hour.

What should you talk about during one-on-one meetings?

You won’t reap the benefits of a one-on-one meeting if it sounds like nothing more than a car ride with an angsty teenager. “I’m fine … everything is fine.”

While this meeting ultimately belongs to your employees, you need to be prepared to lead the discussion and connect on a variety of topics including: 

  • Career goals and growth
  • Concerns and challenges
  • Confidence
  • Energy levels
  • Positive and constructive feedback
  • Team dynamics and relationships
  • Wins and celebrations
  • Workload

You likely won’t talk about all of these things during every single one-on-one (remember, they’re relatively short conversations), but these provide plenty of inspiration for different topics to chat about. 

Questions to ask in one-on-one meetings

Still stuck on how to get the conversation rolling?

Start your one-on-one meetings with this question: What would you like to cover today? That prioritizes your employees needs and concerns, which is exactly why this meeting exists in the first place.

If you’re looking for some other ways to keep the discussion flowing in a positive and productive way, here’s a long list of one-on-one meeting questions in a variety of categories that you can use to solicit helpful feedback and encourage team members to be candid. 

Questions about your management style

  • Do you have any feedback for me or the team?
  • Is there anything I could do better as your manager?
  • What can I do to support you better?
  • What can I stop doing that will make your job easier?
  • How can I help you enjoy your job more here?

Questions about their role and workload

  • What are some recent wins or positive news you’d like to share?
  • How’s your workload? Do you need any help from me?
  • What are some challenges you’ve encountered recently? How can I help?
  • What skills or professional development opportunities would you like to work on next?

Questions about their engagement and happiness

  • How happy are you in your current role?
  • What do you love about your job? What do you dislike about your day-to-day responsibilities?

Questions about professional growth and development

  • What have you learned recently in your role?
  • What’s the biggest lesson you’ve learned in the past week?
  • What career goal(s) would you like to work toward next?

Questions about their personal life

  • How are things outside of work?
  • What’s energizing you this week? What’s depleting you? 

What do you discuss in a first one-on-one meeting?

It’s usually not long before you get into a good groove with your one-on-one meetings—but there’s something nerve-wracking about that very first one.

Whether you just stepped into a leadership role or have a new direct report on your team, think of that first one-on-one as an introduction. While you absolutely can use some of the other questions above, lay the groundwork with a few other basics like: 

  • Overviews of each of your roles and responsibilities
  • What to expect from your one-on-one meetings moving forward

Even if it feels a little unnecessary, that quick rundown is helpful context as you both settle into not only your one-on-ones—but your entire working relationship. 

4 tips for running effective one-on-one meetings

Knowing the right questions to ask goes a long way in helping you host a beneficial one-on-one. But there are a few more things to know to make sure these conversations are a safe space for your employees to talk openly and honestly about their roles and your team. 

1. Create a collaborative agenda

“All throughout the week you’re logging things in your mind that you want to remember for the following meeting,” says Ryder. “That’s a heavy mental load to carry especially if you have half a dozen of these meetings or more every week.”

That’s why it’s helpful to create a collaborative agenda where both you and your direct report can drop discussion topics as they come up throughout the week. Our one-on-one meeting agenda template is a private, shared space where you both can add things to the “to discuss” column.

Trello template for 1-1 meeting agenda

When something is added, you can jump in and ask questions or do a little research—or save it all for your upcoming meeting if a topic doesn’t need immediate action. Either way, this living agenda helps you and your direct report head into your meeting with a clear idea of what you’ll talk about (and spare yourselves crickets and blank stares).

2. Let your employee drive the meeting

Here’s the most important thing to remember about these conversations: they belong to your employees, not to you. Anything that your direct report wants to discuss should be covered first. 

Of course, this doesn’t give you a hall pass to show up unprepared, sit back, and watch the conversation unfold. You still want to come ready with your own questions and talking points (those should be on the agenda, too). The point is that you shouldn’t jump right in and steamroll your direct report without allowing them to steer the conversation first. 

3. Wrap up with action items

The best, most productive meetings end with clear action items—next steps to keep both you and your direct report accountable. 

On your Trello meeting agenda template, Ryder recommends creating an action list for any follow up that comes out of the meeting. You can drag cards there, assign due dates, and collaborate via comments.

If a topic needs to come back to the table in a future one-on-one, drag it back to the “to discuss” list so that no important talking points slide off the radar. 

4. Resist the urge to reschedule

Finally, avoid constantly rescheduling these meetings. These conversations should be a recurring commitment in your calendar, which means you should be able to plan around them. 

When their check-ins continue to get bumped, employees quickly feel like they’re at the bottom of your priority list—which is the exact opposite of what you’re trying to achieve.

Sometimes things happen. However, rescheduling should be the exception and not the rule. 

Win together by getting your one-on-ones right

One-on-ones are frequent and usually pretty short, but that doesn’t mean these meetings should be haphazard or afterthoughts.

These conversations are a valuable time for you and your direct reports to connect about all sorts of important topics—from their career growth and happiness to their workload and challenges.

When they’re done well, they help you fix issues, achieve goals, and build a team of happy and supported high-achievers. That’s more than worth the half hour every week or so, don’t you think? 

Stop forgetting about one-on-ones and start creating meetings worth having