1:1 Meetings: The Secret Superpower of Great Leaders  

Think about the best boss you’ve ever had—the one who believed in you challenged you, and made you feel like your success was their top priority. What made them stand out? Was it their guidance through challenges, the trust they built with you, or how they helped you grow in your role and career?

Chances are, they didn't become your best boss by accident. They created intentional opportunities to connect, listen, and support your growth. In my experience, these magical moments often happen in 1:1 meetings—a powerful but underutilized leadership tool.

1:1 meetings may not be flashy, but they are a leadership superpower I've relied on throughout my career to help teams grow, solve problems, and build trust.

Outstanding leadership isn't about giving orders; it's about enabling others. Your job as a leader is to create the space for your employees to thrive, and there's no better way to do that than by having consistent, meaningful 1:1s.

I often emphasize this when mentoring or working with new managers. One of the first things I do is hand them my well-worn copy of Glad We Met: The Art and Science of 1:1 Meetings by Steven Rogelberg. It's been one of my most frequently loaned books because it demystifies what makes these meetings so powerful and how to get them right.  

I've even lent my copy to my immediate supervisors—managing up, delicately but intentionally. I wanted to ensure they knew what I hoped to get from our 1:1s. It wasn't about taking control of the agenda but making the most of our time together.  

But lessons on leadership and connection go far beyond one book. Some of the most valuable lessons I've learned—from experience and great books—have shaped how I approach every 1:1. Here are a few lessons, each with a story.

Lesson #1: Care Personally, Challenge Directly  

(Kim Scott, Radical Candor)  

When I mentored first-year teachers, I learned early on that the key to trust is showing that you care about someone's success—not just their performance. But caring doesn't mean sugarcoating things. One teacher I worked with had an incredible passion for teaching but struggled with classroom management.  

During our 1:1s—which often took place while we walked around campus—I had to find the right balance between encouragement and honesty. At first, I hesitated to give direct feedback, afraid I'd hurt her confidence. But avoiding the truth wasn't helping her grow.  

So, one day, I said: "I believe in you. Here's what's not working and how I can help you fix it." She was surprised at first, but something clicked as we worked through the challenge week by week. She felt supported, not judged. Over time, her confidence grew, and so did her classroom skills.  

Kim Scott calls this Radical Candor—caring personally while challenging directly. 1:1s are where that balance lives. They're where you build the kind of trust that allows you to hold people accountable while showing you're fully invested in their growth.  

Lesson #2: Ask Better Questions  

(Michael Bungay Stanier, The Coaching Habit)  

If there's one thing I've learned, asking the right questions is far more powerful than giving the correct answers. Early in my career, I often fell into the trap of solving problems for my team. It felt efficient at the moment—until the same issues kept showing up.  

Then I found one of my favorite questions from The Coaching Habit: "What's the real challenge here for you?"  

I used it in a 1:1 with a relatively new staff member struggling to meet deadlines. His first response was about workload—he felt overwhelmed by how much he had to do. But as we dug deeper, the real issue was his discomfort with asking for help. He didn't want to appear like he couldn't handle his responsibilities.  

Once we uncovered that, we worked on strategies for delegation and collaboration. That question helped shift the conversation from a surface-level complaint to the heart of the problem.  

Lesson #3: Keep a Record, Track Growth  

(Steven Rogelberg, Glad We Met)  

I never walk into a 1:1 without an index card in my hand.  

Why? Nothing erodes trust faster than promising to do something and forgetting about it. Every promise, follow-up, and key takeaway goes straight onto that card. It ensures I follow through and creates a living record of our conversations.  

A few years ago, I noticed a recurring theme across multiple 1:1s. Different team members kept bringing up issues related to onboarding. It wasn't something I would have spotted without my notes. Those records helped me realize we had a system-wide gap, which led to a broader solution.  

These notes aren't just helpful for problem-solving but a powerful way to track growth and celebrate progress. One of my favorite moments in 1:1s is flipping back a few months to show someone their early goals or challenges and reflect on how far they've come.  

Lesson #4: Create Ownership  

(Camille Fournier, The Manager's Path)  

At one of my previous jobs, we used BambooHR to manage 1:1 agendas. It was a simple tool, but it transformed how I prepared for meetings with my boss. I'd populate the agenda in advance, ensuring we focused on what mattered most.  

But not everyone knows how to do this instinctively. For newer employees, learning how to own their 1:1s is a skill you have to teach.  

When onboarding someone new, I explain that this meeting is theirs—it's a space for them to get what they need from me. We start with simple questions: What's going well? What's challenging you? Where do you want more support?  

Over time, they get more comfortable taking ownership of the conversation. Once that happens, our 1:1s go from routine check-ins to high-impact strategy sessions.  

Lesson #5: Listen and Be Fully Present  

(Brené Brown, Dare to Lead)  

Brené Brown reminds us that vulnerability and courage are the foundations of trust. In 1:1s, that starts with being fully present.  

Turn off your notifications, close the laptop, and make eye contact—or look into the camera if you're on Zoom.  

Even a few moments of deep listening can change the tone of a conversation. It shows your team that they're worth your undivided attention.  

I'll admit it's not always easy. There are days when leadership demands pull me in multiple directions. But every time I've chosen to be fully present, the result has been powerful. It's the foundation for everything else we do.  

When I Was the Direct Report: Flipping the 1:1 Script

1:1s aren't just valuable when you're the manager; they're equally powerful when you're the direct report—if you use them well. Early in my career, I realized that how I showed up to 1:1s could be just as important as how my manager prepared. I made it a habit always to end my 1:1s with two questions:

1. What can I do to make you look better?

2. What are you reading?

At first glance, these questions might seem unusual, but they were game-changers for building strong working relationships with my managers and tapping into deeper conversations.

Why "What can I do to make you look better?" matters:

No one thrives in a vacuum. This question served two purposes: it helped me understand how to support my manager's priorities better and opened the door to conversations about broader organizational goals. More importantly, it signaled that I wasn't just there for personal development—I was invested in the success of the team and the leadership around me.

One boss's response to that question fundamentally changed how I approached my work. They said: "Help me anticipate problems before they happen." That answer pushed me to shift my focus from execution to strategic thinking, turning me into a more proactive team member.

Why "What are you reading?" matters:

I've always been a voracious learner—it's my top CliftonStrength, and it shows up in everything I do. This question wasn't just a conversation starter but a window into what inspired my managers and how they stayed on top of trends in their field. It often led to deep conversations about leadership, innovation, or completely unexpected topics.

One manager's response to that question introduced me to Michael Bungay Stanier's The Coaching Habit, which has influenced how I approach 1:1s. Another introduced me to Brené Brown's work on vulnerability and leadership, which fundamentally reshaped my understanding of trust in teams.

For me, this question wasn't about checking off another book on my list; it was about understanding how great leaders think and evolve—and then applying those insights to my own growth.

"Yeah, But Another Meeting? I'm Already Really Busy."  

I get it. We're all drowning in meetings. When your calendar feels like an endless loop of calls, reviews, and updates, adding another meeting—especially a 1:1—can seem impossible. I've felt that pull to reschedule or cancel countless times, thinking I'll just catch up with them next week.  

But here's the thing: 1:1s aren't just another meeting. They are the meetings that can make all the others more effective—or even unnecessary.  

When you prioritize consistent 1:1s, you:  

• Reduce random interruptions because your team knows they'll have dedicated time to discuss priorities and questions.  

• Prevent avoidable crises by catching miscommunications and challenges early before they snowball into urgent problems.  

• Build long-term trust, which means more autonomy for your team and fewer requests for micromanagement.  

Most importantly, 1:1s are at the core of what it means to be a leader. Your job isn't just about strategy, deliverables, or responding to the latest crisis—it's about leading others and enabling their success. It's about asking: What does my team need from me to thrive? How can I support their growth and make their work easier?  

That's the same question I would ask as a direct report at the end of every 1:1: "What can I do to make you look good?"  

At first, it seemed small, but it always led to meaningful conversations. This question wasn't about flattery—it was about alignment and support. I wanted to know what mattered most to my manager and how I could help them achieve their goals. In return, I gained clarity on what moved the needle, which helped me focus on the right things.  

It also reframed my role as part of something bigger than my responsibilities. By helping my manager succeed, I wasn't just growing my career but contributing to the entire team's success.  

As a leader, that's your job in reverse. You need to create the space for your team to ask you how they can make you look good—how they can help you hit your goals—and then guide them toward the answer. 1:1s are where you create that space.  

And they don't have to be long! Even 20 minutes every other week can be transformational if focused and intentional. It's not about the length of the meeting—it's about the quality of the connection.  

So, next time you're tempted to cancel, ask yourself: Is there anything more important than enabling my team's success?  

Because your success as a leader is tied directly to theirs, and when they succeed, guess what? Soon, they'll be the ones asking how they can make you look good.  

Why It's All Worth It  

Leadership isn't about grand speeches or sweeping changes. It's about small, consistent actions—the promises kept, the honest feedback given, and the moments when you listen without judgment.  

1:1 meetings are where these moments happen. They're where we remind our teams—and ourselves—that growth is a process, not a destination. They're where trust is built, one conversation at a time.  

So, next time you're tempted to cancel that 1:1, ask yourself: What opportunity for connection or growth might you miss?  

1:1s are your leadership superpower. Use them well.  

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What's your favorite tip for making 1:1s meaningful? Share it in the comments—I'd love to hear how you use your superpower!