An open leader's guide to better one-on-one meetings

The secret to better one-on-one meetings

Are your meetings as engaging, comprehensive, honest, and open as they should be? This checklist can help.

The secret to better one-on-one meetings
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How often do you have one-on-one meetings with your manager? Over my career, my managers have tended to provide bi-weekly one-on-one meetings. As a leader striving to work openly—and as someone who leverages the Open Decision Framework—I find bi-weekly one-on-one meetings insufficient for encouraging openness on my team.

Meeting more frequently helps me drive strategy and allows me to receive candid feedback at quicker intervals—crucial for teams that are always working in "release early, release often" mode. So in addition to giving micro-feedback as needed, I schedule weekly one-on-ones with all my direct reports. These meetings tend to be tactical checkpoint discussions, lasting about 30 minutes.

Here's my advice for making the most of them.

Make it transparent

Transparency is a key characteristic of an open organization, and acting transparently can help make one-on-one meetings better for both managers and team members.

To ensure transparency during one-on-ones, I ask lots of questions for clarity. The questions I'm willing to ask help people understand where I need more information. I explain that what helps me be a better manager is knowing what's blocking my team's work or what questions are most pressing for them. By asking questions and giving transparent answers as a manager, you're finding space to learn more about your team members—things like:

  • What are they working on beyond the work assigned?
  • What problems are they solving?
  • How are they deciding what work not to do?
  • What do they need to have unblocked in order to make faster progress?

In the end, however, my goal in one-on-one meetings is to listen more than I talk. I also want people to feel like I'm open to questions, too. Recently my team have seen lots of changes, so I have new people to meet with for one-on-ones. This change has reminded me that when you're working with someone for the first time—and neither of you knows the other well—it takes time for open dialogue to become the norm.

Building community takes time. While one-on-ones are tactical exercises for managers, they also give us time to reinforce shared values and principles—why we do what we do at work. This is important for creating community and driving collaboration.

The manager's performance is rooted in one on one meetings—so you have to come ready.

No specific amount of time that needs to pass before you've fostered the sense of community that allows a more open dialogue to form during one-on-one meetings. But at some point, you (as manager) should notice a shift in the conversation as team members open up and ask questions that demonstrate their willingness to deepen collaboration.

Waiting this indeterminate amount of time for community to develop might feel frustrating. I know it can be for me. When I feel frustrated, I focus on having empathy: I think about the 1:1 meetings I have with my manager. The initial 1:1s were focused on getting to know each other - specifically what results does my manager need to deliver and what's her strategy for delivering the results? I have had managers who were vague and directionless. Fortunately, those managers tend to move on quickly as they realize that they're not the best person to lead the team. For managers who are the best person to lead and manage a team, you have to have patience to show that you're here to stay. While time passes and you prove you're qualified, you can ask questions to show that you are paying attention. Team members respond to managers who pay attention and care about the work. As you show you are engaged, you'll see engagement from your team.

Eventually team members will likely start to test their managers to locate boundaries. Is venting OK? Can the manager listen and not react, or does every complaint trigger an unwanted action? Does the manager follow up on action items taken during discussions? Does the manager get distracted in one on one meetings with their computer or phone? Does the manager handle the sharing of personal information with respect and dignity? Employees want their manager to be a human being.

As a manager, you have the opportunity to step up and provide meaningful feedback that helps team members do their jobs. You have the opportunity to be tough and fair; responsible and accountable. The manager's performance is rooted in one on one meetings—so you have to come ready.

Setting the agenda

Everyone handles one-on-one meetings differently. So when team members ask for some structure and guidance for this meeting (since it's occurring more often than they're typically used to and they may not be sure what to expect or discuss), I offer a template to guide our conversations. That template is a guide for what I want to cover in the meetings, and it's stored in a shared document. Each meeting is a unique entry in that document, so we can go back and have a history of the one on one meetings.

Here's the template I offer my direct reports:

Date:

Reminder: I do not want you to spend a lot of time working on your 1:1 prep. This information ensures we spend our time wisely and don't miss anything.

Link to work tracking system:

Priorities for the week (no more than 3):

Things I'm not doing to focus on the priorities:

Things I am delegating (for managers and leads only):

Things I learned / surprises:

Roadblocks / bottlenecks:

Risks (and risk mitigation plans):

What do I wish I had more time to learn more about?

Action items from this meeting (with owner):

The template reflects a few core components of the one-on-one meeting.

Priorities and risks. For managers and team members, it's easy to think that things are going well, but there are often challenges. People want to give off an "I've got it all together" vibe to insulate themselves from risk. The thing is: Work is risky. Most jobs involve work that's ambiguous and uncertain. As employees, we're always making decisions that impact people who use whatever we're working to deliver. So the one-on-one meeting should always cover the priorities we're setting, a discussion of the impacts those priorities have, and the risks associated with those priorities.

People want to give off an "I've got it all together" vibe to insulate themselves from risk. The thing is: Work is risky.

Roadblocks and learning. Often, certain things will prevent us from moving our work forward—so managers need to know about those things in a precise and candid way. Even so, we can't always until we have everything we need to proceed with a project. So we need to work with a growth mindset so we, as a collaborative team, can share what we learn from mistakes and new information. The more trust and credibility a manager has earned with their team, the quicker team members can adapt to changes that are necessary for the business. For example, while a manager might not be able to answer every question that arises in a meeting, she can encourage curiosity. When dealing with ambiguity, identify people who want to answer similar questions and connect them. As you see people who don't know what success looks like, use the meeting to bring clarity to goals as much as you possibly can.

Writing all this without offering specific examples from one-on-one meetings might seem hollow. Relaying stories and anecdotes is difficult when I don't want to share personal details from people who've reported to me. I also choose to not share details about my own one-on-ones with my managers. At the end of the day, that reluctance to share publicly reveals another crucial truth about one-on-ones: No matter the frequency or duration, the meetings are tactical and personal. Not every meeting is going to be a home run—so focus on what you can control in the conversations, and act based on what you learn.

A checklist

To foster more open one-on-one meetings, managers should:

  • Establish a weekly cadence
  • Schedule 30 minutes for the meeting (allowing more time as needed)
  • Let team members drive the meeting agenda and direction
  • Provide template or some guidance if the meetings are not productive
  • Start with a question, listen, and provide clarity whenever possible

To foster more open one-on-one meetings, employees should:

  • Prepare by sending some type of notes or top-of-mind items before the meeting (use the template provided in this article as a guide)
  • Allow your manager to get to know you
  • Discuss the problems you need help solving to improve your impact and performance
  • Ask follow up questions if something is unclear (managers want engaged team members and questions can demonstrate engagement)
  • Let your manager know if you need to vent (be specific about what you're doing and when you'll be finished)

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About the author

picture of Angela Robertson
Angela Robertson - I lead and manage the development and publication of technical guidance for many of the Microsoft Azure products and technologies. As a member of the Azure Platform Experiences and Evangelism team, I work with cloud advocates, the team that develops docs.microsoft.com, and product groups throughout the company to publish content on our open platform. I learn from industry leaders about topics ranging from security, compute, identity, storage, networking, hybrid cloud, and numerous other...