One-on-Ones That Actually Build Trust

There’s a moment in every leader’s journey when they realize that leadership doesn’t happen in the big team meetings or the quarterly strategy sessions. It happens in the in-between. In the hallway conversations. In the quiet side chats. In the small, consistent touchpoints where trust is either built—or broken.

And at the center of that daily trust-building work is one of your most underused tools: the one-on-one.

Many leaders treat one-on-ones like status updates or glorified to-do list reviews. Others treat them as a casual chat, hoping that informal conversation will build connection over time. But here’s the truth: if you’re not intentional, your one-on-ones will drift toward mediocrity. And when that happens, so will your leadership.

In today's leadership challenge, you’re not just going to learn about effective one-on-ones. You’re going to experiment with them.

Rethinking the One-on-One

Most emerging leaders inherit the concept of one-on-ones without ever being taught how to make them effective. You’re told they’re important, that you should “check in regularly,” and that it’s a good time to “hear how your team is doing.” But no one explains what makes a one-on-one great.

Let’s be clear: one-on-ones are not for you to check off a box. They’re for them. Your team. The person across from you. That’s the mindset shift that changes everything.

Done right, one-on-ones become the heartbeat of your leadership. They’re where you build psychological safety, uncover tension before it becomes conflict, coach in real time, and reinforce clarity. They’re where your people feel seen—not just managed.

And in a world where disengagement is growing and trust in institutions is fading, that kind of leadership isn’t a luxury. It’s a necessity.

The Purpose of One-on-Ones

If you strip everything else away, a one-on-one serves three core functions:

Connection – Strengthening the human relationship between leader and team member.
Clarity – Ensuring alignment on priorities, expectations, and goals.
Coaching – Helping the individual grow, learn, and navigate challenges.

Anything outside of those pillars might be useful, but it isn’t essential. And anything that distracts from them—like micromanaging tasks or only talking about deadlines—undermines the trust you’re trying to build.

When you treat one-on-ones as a sacred space for connection, clarity, and coaching, your leadership shifts from reactive to relational.

The One-on-One Lab: A 3-Week Experiment

This is not just a post. It’s a leadership challenge. So here’s your experiment:

For the next three weeks, redesign your one-on-ones using the following model. After each one, reflect and adjust. You’re not aiming for perfection—you’re aiming for intention.

Week 1: Build Psychological Safety

Focus: Connection

Goal: Make the one-on-one a place where the other person feels heard, not judged.

Try This Structure:

Start with a check-in question beyond work.
Try: “What’s been energizing you outside of work lately?”
Ask: “Is there anything you want to talk about that’s been on your mind?”
Practice listening without interrupting for a full two minutes.
End with: “What’s one thing I can do to support you this week?”

Why It Works:

When people feel emotionally safe, they’re more likely to speak candidly, admit mistakes, or raise early flags. That safety begins with how you show up—not with how smart or prepared you are.

Week 2: Focus the Conversation on Clarity

Focus: Alignment

Goal: Ensure your team member is clear on priorities and expectations—and has the space to push back.

Try This Structure:

Begin with: “What’s feeling clear right now? What’s not?”
Ask: “What’s getting in the way of progress?”
Share any shifting priorities or new expectations.
Invite input: “What would you change about how we’re approaching this?”

Why It Works:

Leaders often assume clarity exists when it doesn’t. This week, you’re not dictating priorities—you’re co-creating clarity. That invites ownership and shows that you value their lens.

Week 3: Shift Into Coaching Mode

Focus: Growth

Goal: Use the one-on-one as a leadership development tool—not just a status update.

Try This Structure:

Start with: “What’s something you’ve learned lately?”
Ask: “Where are you feeling stuck or stretched right now?”
Use coaching questions instead of giving advice:
“What have you already tried?”
“What might be one small experiment to test next?”
“What would success look like?”
End with: “Is there a skill or area you’d like to develop more?”

Why It Works:

Coaching builds capability instead of dependence. It’s easy to give answers. It takes discipline to help people find their own.

What to Watch For

As you run this three-week one-on-one lab, keep an eye on the following patterns:

Are your team members opening up more over time?
That’s a sign of growing trust.
Do you hear more questions, pushback, or new ideas?
That’s a signal that psychological safety is increasing.
Are your one-on-ones feeling less transactional and more generative?
You’re moving in the right direction.

If not, don’t panic. Leadership is not about getting it right immediately. It’s about staying curious, adjusting, and committing to the long game.

Mistakes to Avoid

Even with good intentions, it’s easy to fall into old habits. Watch out for these common traps:

Using the one-on-one to only talk about tasks.
Save project updates for another format. Focus on people, not checklists.
Talking more than you listen.
If you’re doing 80% of the talking, you’re missing something.
Avoiding hard topics.
Transparency builds trust, even when the conversation is tough.
Canceling too often.
One-on-ones are one of the few protected leadership rituals you control. Don’t deprioritize them—they are the work.

Questions for Reflection

Do my one-on-ones create value for my team—or just for me?
What unspoken signals am I sending during these conversations?
How can I shift from checking in to actually connecting?

Actionable Exercise

Choose one team member this week and apply the Week 1 structure. Don’t overthink it—just show up with presence and intention. Afterward, take five minutes to jot down what you noticed:

What worked?
What surprised you?
What could be better next time?

Repeat with a different person next week, and continue the cycle.

Closing Thoughts

One-on-ones aren’t a leadership chore. They’re a leadership gift. But like all powerful tools, they only work when used with intention.

When you shift your mindset from managing tasks to building trust, from delivering updates to deepening connection, your one-on-ones become a foundation of your leadership identity.

In a world where people are craving real connection and real leadership, that foundation matters. So go run the experiment. Get messy. Learn something. And build the kind of leadership muscle that actually makes people want to follow you.