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Tips For Leaders On Running Successful One-On-One Meetings

“How’s everything going?” 

“It’s fine.”

If your one-on-one meetings sound a lot like a car ride with an angsty teenager, you’re doing them wrong. As a manager, it’s your responsibility to ensure that these regularly-scheduled conversations are valuable—for both you and your direct reports.

But, while one-on-one meetings seem simple and straightforward on the surface, they can be surprisingly difficult to run. 

How can you make sure you’re digging into the topics that direct reports really want to talk about? Should you be asking the questions, or letting your direct reports steer the conversation? How much ownership should you be taking over that meeting? 

You have questions and this guide has answers. 

Do You Actually Need One-On-One Meetings?

Let’s start with the hard truth: most of us hate meetings. They can be major time and energy depleters, with 67% of employees saying excessive meetings prevent them from making an impact at work. 

That makes putting yet another recurring meeting on the calendar feel not only unnecessary, but maybe even a little detrimental.

The reality is that frequent and predictable one-on-one conversations with your employees are important. “One-on-one meetings are a dedicated space in your calendar to talk about your direct report’s priorities, challenges, and professional development,” explains Manuela Bárcenas, Marketing Manager at Fellow.app. “These are conversations that can’t take place in a team meeting or chat app, and that wouldn’t happen in a remote setting unless you intentionally schedule them.” 

When they’re run well, these conversations give you an opportunity to: 

  • Build and maintain trust with your direct reports
  • Proactively identify and fix challenges and sticking points
  • Provide support and encouragement
  • Celebrate and recognize accomplishments
  • Solicit feedback and make necessary improvements

All of these can lead to boosted employee engagement, improved morale, and ultimately, a high-performing team that exceeds your expectations.

What Should You Talk About During One-On-One Meetings?

Okay, you get it. One-on-one meetings with your direct reports are important. However, simply having the meeting isn’t enough—you need to be prepped and ready to run it well. 

That all starts with knowing what to talk about. You don’t want this recurring meeting to become a glorified status update that wastes time. Instead, you should 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 

Bárcenas says that you likely won’t talk about all of these things during every single one-on-one, but having these types of prompts will help you focus on the topics that your conversations should be dedicated to. 

In addition to those work-related topics, make sure that you also take time to connect with employees about what’s happening with them personally. You’re all humans, and your direct reports want to know that you care about their lives outside of the office. In fact, research from Gallup shows that employees who feel as though their manager is invested in them as people are more likely to be engaged. 

Questions To Ask In Your 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 proves that you’re prioritizing your employee’s needs and concerns (which we’ll talk about more a little later).

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 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? 

Tips For Running Effective One-On-One Meetings

Knowing what you should be discussing and what questions to ask goes a long way in helping you host a beneficial one-on-one. However, there’s plenty more 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. Here are a few more tips to keep in mind. 

1. Create A Collaborative Agenda

Every single meeting deserves an agenda, and that includes your one-on-ones. Both you and your direct report should know what will be discussed. 

This works best if it’s a collaborative process that starts ahead of the actual conversation. Create a shared space (a Trello board works great for this!) where both of you can drop talking points throughout the week. It helps you document things as they come up, rather than getting to that meeting with nothing but crickets and blank stares. 

“Know that things will evolve. The questions you ask will change. That’s totally normal and okay. But, having a starting point will help guide the conversation better,” says Hiba Amin, Senior Marketing Manager at Soapbox

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.

“Your employee owns this meeting. That means you should let them own the agenda and cover their items before covering yours,” explains Amin. 

This doesn’t give you a hall pass to show up unprepared, sit back, and watch the conversation unfold. Amin warns that you should still show up ready with your own questions and talking points (cough, they should be on the agenda too, cough). The point is that you shouldn’t jump right in and steamroll your direct report without allowing them to have their own input. 

3. Remember That One-On-Ones Are Personal

You know now that you should use some of your one-on-one time to connect on what’s happening with your employee outside of the office.

Additionally, keep in mind that this conversation is about that specific employee, and nothing else. This isn’t the time or place to chat about company updates or team-wide concerns. Those are usually better saved for your team meetings where everybody can chime in and ask questions. However, it is a good time to ask your employee if they are having any interpersonal issues with co-workers.

4. Schedule Enough Time

Even though your one-on-ones are frequent, there’ll likely still be quite a bit to cover. You don’t want the conversation to feel rushed as you try to cram these important topics into just a few minutes.

Make sure you’re allocating enough time to these meetings. There isn’t a perfect formula here, but in general: 

  • Half an hour is adequate for weekly meetings
  • One hour is adequate for biweekly meetings

If your discussions feel either too short or like they’re dragging, you can always adjust. It’s also wise to ask your direct reports how they feel about the duration of your meetings to make sure they’re getting the time they need from you. 

5. Wrap Up With Action Items

The best, most productive meetings end with clear action items. “Assign next steps to keep you and your direct report accountable. Are they expecting an update on their salary next week? Add it to the agenda,” says Amin. 

There will likely be plenty of topics that you’ll follow up on in future meetings. That’s another benefit of having a shared agenda—you can make sure that you continue to check-in and don’t let those talking points slide off the radar. 

6. Resist The Urge To Reschedule

Finally, there’s one seemingly small thing to keep in mind: avoid constantly rescheduling these meetings with your direct reports. 

These recurring conversations should be in your calendar, which means you should be able to plan around them in most cases. When their check-ins continue to get bumped, employees can quickly feel like they’re at the bottom of your priority list—and that’s 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 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?


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