Lesson 5: One-on-Ones Done Right

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One-on-Ones Done Right

One-on-ones are often ignored by old-school leaders - but they are one of the most important things you can do for yourself as a leader, and for your team. Done right, the one-on-one is your primary venue for developing your people, building trust, surfacing problems before they escalate, and demonstrating that you actually care about the person sitting across from you.

Done poorly - treated as a status update or cancelled when things get busy - they signal the opposite.

Setting the Right Conditions

For a one-on-one to be genuinely useful, it has to feel safe. The person needs to trust that what they say will be treated with respect and discretion. A few principles that make that possible:

• Treat 1:1s as private conversations. Be explicit that what is discussed stays between you. Open the floor to honest feedback - including feedback about you and the organization. Initially, people may not trust this. Over time, if you honor the boundary, they will start to open up.
• Never get defensive when someone is honest about something difficult. Defensiveness shuts people down fast.
• Eliminate distractions. Close the laptop. Put the phone away. Be fully present.
• Invite reflection with open questions: "What is working well?" and "What challenges are you facing?" Signal that concerns and needs are welcome.
• Check in on the whole person - not just the work. "How are you feeling about your workload?" and "How are things going outside of work?" matter.
• Practice active listening. The 1:1 is a perfect time to listen more than you talk.

What to Cover

I typically do 1:1s with everyone on my team on a weekly or bi-weekly basis. The agenda generally follows this structure:

• Anything the employee wants to discuss. I often lead with "What is top of mind for you today?"
• Things I have on my list - project updates, news from my manager that is relevant to them, coaching on topics they are working on.
• A feedback question for me: "Is there anything I can do for you? Something I can do more of or less of?"

Notice: the agenda is primarily theirs, not yours. This is their meeting. Your job is to listen, ask good questions, and help them move forward.

Best Practice Tips

Set a Regular Cadence

Consistency builds trust. Schedule one-on-ones on a recurring basis - weekly, biweekly, or whatever cadence you and your team member agree on - and stick to it. Canceling a 1:1 is like telling someone you do not care about them. If you have to move one, reschedule it. Junior team members may benefit from more frequent check-ins; senior staff often prefer more space unless issues arise.

Have an Agenda

Even in casual 1:1s, prepare some talking points around ongoing projects, performance, or development. Invite the team member to suggest topics in advance. My personal preference is to vary the focus - some weeks work-related topics, some weeks focused on coaching or development. In stressful periods, the 1:1 can also simply be a moment to connect as humans.

Take Notes

If action items are discussed, write them down. Referring to notes from previous 1:1s keeps conversations forward-moving and creates accountability. If you are ever in a situation where you need to address performance or behavior issues, those notes may become important. Just do not let note-taking get in the way of being fully present.

Be Flexible

Not every meeting has to be driven by your agenda. Encourage team members to bring their own concerns, questions, and goals. Invite them to talk first: "What is on your mind this week? Do you have anything for me?"

Focus on Development

Use the 1:1 to discuss long-term career goals, not just current tasks. "Where do you want to grow?" and "How can I support your career development?" are questions most leaders do not ask often enough. Balance constructive feedback with recognition, and offer advice and mentorship on areas the person wants to improve.

Tackle Problems Early

If there are performance issues or team dynamics concerns, the 1:1 is the right place to bring them up in a non-confrontational way: "I have noticed X - let us talk about how we can work through it." Involve the person in the solution by asking "What do you think could help?" or "How can I support you with this?"

Follow Up on Action Items

Write down any decisions, feedback, or goals discussed, and follow up on them in the next meeting. Review whether the goals or issues discussed previously have been resolved. "How are things going with X?" keeps momentum and builds accountability.

Honor Your Commitments

If you commit to showing up in a certain way - staying open to feedback, not getting defensive, following through on something - keep that commitment. Nothing erodes trust faster with direct reports than a leader who does not honor their own commitments.

End on a Positive Note

Conclude by highlighting something the person has done well recently - reinforcing their strengths and making them feel seen. Ask "Is there anything else you need from me?" so they leave feeling supported, not just debriefed.

Do this well, and your team engagement will soar.