As a leadership coach, I often hear complaints from team members about check-in meetings with their leaders:
- The meeting gets canceled more often than not.
- My boss just talks at me and doesn’t save time for my questions.
- The meeting has no structure, and we end when we run out of things to talk about.
- It’s the same thing every week: He asks if I’m okay. I say yes. He says good. Meeting over.
Sound familiar? One-on-one meetings often become routine, whether they’re scheduled check-ins or spontaneous chats in the hallway. By following the boring routine, we’re missing opportunities to show care, develop our teammates, provide guidance and build trust.
(For more on routine and other signs your conversation is stuck, see this article on the RUTS: conversations that need help because they are routine, uncertain, tense or serious.)
Now is a good time to revisit how you handle one-on-one meetings with your direct reports. Here are six do’s and don’ts, along with corresponding questions, to elevate your one-on-ones.
While these are tailored for individual meetings, they’re applicable to any interaction.
DO: Begin with the person.
DON’T: Begin with tasks.
Yes, there’s work to discuss, but the person across from you is more than their to-do list. Start by connecting — ask how they’re feeling, what’s new in their life or whether they’ve seen the latest episode of a popular show.
Leading with task signals, “I care only about the work.” Leading with the person shows, “I care about you.” This simple shift can set a tone of mutual respect and rapport.
Person-oriented talk should be culturally appropriate and reasonably contained. (We’ve all had that coworker who doesn’t know when to stop chatting.) Keep it within appropriate boundaries, but don’t overlook it. Talking human-to-human is a great way to build relational trust.
Questions you can use:
- What’s going on lately?
- What’s new outside of work?
- How are you feeling about ___?
DO: Bring a plan.
DON’T: Wing it.
I’m amazed at the number of leaders who don’t require an agenda for their scheduled one-on-ones with their direct reports. Without an agenda, a meeting becomes just a chat with no clear direction. Whether it’s formal or informal, outlining key topics or questions ensures focus and efficiency.
An agenda conveys that you value everyone’s time and are prepared. Showing up unprepared sends the opposite message: that their time — and, by extension, their contributions — don’t matter as much.
This doesn’t have to make more work for you. Ask your team members to prepare the agenda, providing links to supporting documents. Then, do your homework before the meeting — read through the agenda and all the supporting resources so that you can spend the in-person time discussing ideas rather than them bringing you up to speed.
“A shared agenda doc is my favorite thing for managing up and down,” a vice president recently told me.
Personally, I think the agenda should always include a few key questions:
- What are we celebrating from the last week?
- What are your top priorities right now?
- What help do you need from me?
- Do you have any feedback for me?
DO: Ask thoughtful questions.
DON’T: Dictate orders.
The era of barking commands is long gone. Research suggests that high-performing teams use questions to foster dialogue and collaboration.
Questions help us truly understand each other’s perspectives and ideas; that means we build connections and identify risks faster. No wonder questions contribute to high performance in teams.
When you lead with curiosity, you unlock new ideas and empower others to take ownership of solutions.
Try asking questions like:
- Take me a layer deeper in your thinking.
- What options have you explored?
- Is there anything worrying you?
- What do you recommend and why?
DO: Focus on the future.
DON’T: Dwell on past mistakes.
Feedback should be part of most check-ins, even when they happen weekly.
Remember — feedback can be positive or constructive. When offering positive feedback, be specific. Name with detail the behaviors or mindsets that you observed, and encourage your team members to use these approaches again in the future.
When constructive feedback is necessary, frame it around growth and opportunities rather than critiquing past errors. Forward-focused language reduces defensiveness and encourages accountability.
For example, instead of saying, “Your presentation didn’t land well with the audience,” try, “Next time, let’s work on making the presentation more interactive. What’s your plan for that?” This approach communicates your confidence in their ability to improve.
To prepare for sharing constructive feedback, use these questions:
- What is the problem I’ve identified?
- What is the positive alternative I want?
- How will changing this help the individual’s work or reputation?
DO: Listen to understand.
DON’T: Hear and dismiss.
Actively listening shows that you respect others’ perspectives. Respond thoughtfully to their ideas, even if they differ from yours.
When you genuinely listen, you create an environment of psychological safety — a key factor in high-performing teams. Ignoring ideas, however, stifles collaboration and innovation.
Thoughtful follow-up questions are an important way to show you’ve listened carefully and want to know more. Adapt these questions to dig deeper and show you’re listening:
- Tell me more about ___.
- I hear you saying [summarize]. Did I get that right?
- How will this impact [another aspect of our work]?
DO: End with clarity.
DON’T: End with confusion.
Have you ever left a meeting unsure of what just happened — or worse, what comes next? Concluding with clear action steps prevents confusion and keeps momentum moving forward.
“Ghost commitments” are the unclear, unspecific commitments we make in meetings. They happen when two or more people agree something needs to be done without assigning responsibility or a deadline.
Don’t ghost your team. Instead, Before ending the one-on-one meeting, confirm decisions, next steps and deadlines. Record them in your agenda as a shared record of the commitments so that everyone is aligned and ready to execute.
The questions that help bring clarity to the end of your meeting are obvious:
- Who will do what, and by when?
Six steps to better one-on-ones
| ✅DO | ❌DON’T |
| Begin with the person | Begin with tasks |
| Bring a plan | Wing it |
| Ask thoughtful questions | Dictate orders |
| Listen to understand | Hear and dismiss |
| End with clarity | End with confusion |
These six strategies can transform your one-on-ones, whether you’re a senior leader, a new manager or a trainer. But there’s one last thing that’s required: consistency.
Remember the complaints from the start of this article? Well-intentioned leaders often fail their team members by making their check-in meetings too routine, unstructured, preachy or likely to be canceled. But if you apply these six ideas with consistency, you’ll transform the one-on-one time into a robust conversation that drives high performance.
Opinions expressed by SmartBrief contributors are their own.
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