How Do I Run a One-on-One That Actually Develops Someone?

The one-on-one belongs to the employee

This is one of the first things I would change. A one-on-one is not really the manager's meeting. It belongs to the team member. The manager's role is to create the conditions for the employee to:

• think more clearly;
• speak honestly;
• reflect on what has happened; take greater ownership;
• and leave knowing what they will do next.

The manager's job is not to prove how clever they are. It is not to become the first source of every answer. I sometimes say: The quality of a really good one-on-one is not measured by how much the manager spoke. It is measured by how much the employee thought. And that thinking should begin before the meeting even starts.

Make the employee prepare first

I recommend that the employee completes a short pre-one-on-one worksheet before the meeting. Questions might include: What's working well? What needs attention? What are you concerned about? What did you commit to last time? What did you do? What happened?

What would you like help thinking through today? What would a successful conversation today look like for you? Now their brain is engaged before they walk through the door. They have reflected. They have reviewed their previous commitments. They have thought about what matters.

They have begun taking ownership. So instead of the manager starting with: "Here's what I think we should discuss." the employee can begin with:

"Here's what I think is going well. Here's where I'm stuck. Here's what I committed to last time. Here's what happened. And here's what I'd like to think through with you." Now you have something useful to work with.

The manager should prepare questions, not answers

The manager should prepare too. But differently. Review the notes from the previous meeting. Refresh yourself on priorities. Remember previous commitments. Think about what you have noticed. And, if you are going to do any serious preparation, prepare some questions. Not answers. Ask yourself:

What do I want this person to think about? What assumptions might I be making? What do I need to understand so I can see this through their eyes? Where am I likely to be tempted to rescue them? That last question matters.

Capable managers often walk into one-on-ones already knowing what they think the employee should do. Then the meeting becomes a slightly disguised attempt to guide the employee towards the manager's answer. That is not really curiosity. It is advice wearing a one-on-one hat.

Start with what's on their mind

You do not need an elaborate opening. Try: "What's on your mind today?" Then listen. Really listen. Not listen while mentally constructing your answer. Not listen until you find a gap to speak. Listen to understand what they are actually saying. And perhaps what they are not saying.

Then ask: What's really going on here? What concerns you most? What have you noticed? What have you already tried? What do you think the real issue is? Then stop talking.

Silence is one of your most powerful management tools

Managers are often terrible at silence. A pause appears. The employee looks thoughtful. And the manager jumps in to save them. They rephrase the question. They offer a suggestion. Or they turn it into multiple choice: "Well, do you think it's A, B or C?"

Now you have interrupted the very thinking you were trying to create. Sometimes the most useful thing you can do is: ask the question; and shut up. If you do not fill the space, the other person often will. And that is frequently where the useful thinking appears.

It is surprisingly rare for an adult to have the opportunity to speak uninterrupted from the beginning of a thought, through the middle, all the way to the end. Give them that opportunity.

Don't accept "I don't know" too quickly

"I don't know" is sometimes completely genuine. But not always. It can also mean: "I haven't thought about it yet." Or: "I'm frightened I'll get the answer wrong." Or: "I know what I think but I'm not confident enough to say it." Or even:

"If I say I don't know for long enough, perhaps my boss will answer for me." So don't rescue too quickly. You might ask: "Humour me. If you did know, what would the answer be?" Or: "What's your best guess?" Or:

"If somebody else was sitting here with this problem, what would you advise them to do?" Or: "Let's write down some options." The point is not to bully somebody into pretending they know. It is to help them get beyond the first barrier and hear themselves think. As they articulate their own thinking, confidence often begins to grow.

Move beyond the status update

A lot of one-on-ones never get beyond: "How was your week?" "What are you working on?" "Where is that project up to?" That information may be useful. But it is not really development. Go deeper. Ask: What patterns are you noticing? What's getting in your way?

What might you be avoiding? What do you now know that you didn't know before? What are you learning? Now information starts turning into insight. That is where the one-on-one becomes developmental rather than merely administrative.

Don't catch the problem ball

Suppose one of your managers says: "One of my team isn't performing." It is very easy for the senior leader to reply: "Put them on a performance plan." Perhaps that will eventually be the right answer. But what thinking happened?

What does "not performing" actually mean? What is the gap? What's the evidence? Have expectations been made clear? Have there been previous conversations? Is this:

• a skill problem?
• a training problem?
• a behaviour problem?
• a motivation problem?
• a system problem?
• a clarity problem?
• or simply the wrong person in the wrong role?

Instead of giving the answer, try: "Can you unpack that for me?" "What exactly isn't happening?" "What would good look like?" "What evidence do you have?" "What have you already said to them?" "What do you think is causing the gap?"

"What are your options?" "What are you recommending you do?" Now the manager has to think like a manager. And that's the point. Your goal isn't to give them the answer. Your goal is to help them become the kind of manager who can increasingly find the answer for themselves.

Keep them driving the taxi

I use a taxi analogy for this. Imagine one of those London black cabs. The employee is driving. The manager is sitting in the back. Between you is an opaque glass panel with only a small window through which you can see. You are not in the driver's seat. You cannot see the whole road.

Your job is to ask the driver: What can you see? Are there any signs? Are you at a crossroads? Do you think you should turn left, right, keep going or turn around? What you cannot do is get out of the back of the taxi, open the driver's door, pull the employee out and take the wheel yourself.

But managers do this all the time. The employee arrives with a problem. And the manager leaves saying: "I'll speak to HR." "I'll check the numbers." "I'll rewrite the document." "I'll call the customer." "I'll work out what you should do next."

The employee may feel supported. But they are carrying less than when they arrived. They have not learned very much. And the manager has added another five things to an already ridiculous to-do list. That is rescuing. Support is different. Support helps them think without taking the problem away.

The employee stays in the driver's seat.

Ask what success looks like

A developmental one-on-one should also have a direction. What is this person trying to become better at? What should they be capable of doing three months from now that they cannot do comfortably today? What does success look like in their role? How does their development help the business?

Without some kind of destination, a one-on-one can become an endless weekly conversation with no visible progress. Development should be observable. Not perfect. Not linear. But observable. Over time, you should be able to ask: What can this person do now that they couldn't do three months ago?

That is a much more useful question than: "Did we remember to have our one-on-one?"

Come back to previous commitments

One-on-ones should have continuity. If somebody made a commitment last time, come back to it. What did you say you would do? By when? What happened? What did you learn? That is not about catching people out. It is about making the meeting meaningful.

If commitments disappear between meetings, employees quickly learn that the commitments themselves are optional. And managers lose valuable evidence about patterns over time. Does this person generally follow through? Do they repeatedly avoid the same type of task? Are they developing?

Are they stuck? Are they taking more ownership? Those patterns matter.

End with their actions, not yours

At the end of the meeting, ask: What are you going to focus on first? What are you going to do? By when? How will you know you've made progress? What's the one commitment that matters most? Make sure it is a genuine commitment. Not: "I'll try." Not: "If I get time." Not:

"Hopefully next week." If it has been agreed, write it down. Not because anybody needs more paperwork. Because memory is unreliable. And vague memories create arguments later.

One-on-ones should build capability over time

A useful one-on-one changes the conversation from: "How was your week?" towards: "What are you working on?" "What are you getting better at?" "What are you learning?" "What can you do now that you couldn't do a few months ago?"

That is building capability. That is building stronger shoulders underneath the leader. The whole point is that the person gradually becomes more able to think, decide, act and follow through without needing you to provide every answer. What about underperformance?

One-on-ones are not only for encouragement and development. They are also where issues should become visible early. If performance is below standard, use the same discipline. What does success look like? What is actually happening? What does the evidence show? What is causing the gap?

What has already been tried? What does the employee think needs to change? What are they committing to now? By when? Then follow up. That approach helps prevent performance concerns from sitting untouched for months before suddenly becoming one enormous "difficult conversation."

Don't let the meeting become your rescue mission

After your next one-on-one, ask yourself: Did I listen more than I spoke? Did my questions open up their thinking? Did I leave enough silence? Did I help them identify what mattered most? Did I make decisions they were capable of making themselves?

Did they leave better equipped to think than when they arrived? And perhaps most importantly: Who left driving the taxi? If it was you, you may not have run a developmental one-on-one. You may have run a rescue mission.

A simple one-on-one rhythm

Before the meeting — employee

Reflect on:

• what's working;
• what needs attention;
• previous commitments;
• concerns;
• what you need help thinking through;
• what you want from the conversation.

Before the meeting — manager

Review:

• previous notes;
• previous commitments;
• priorities;
• relevant evidence;
• what you've noticed.

Prepare questions, not solutions.

During the meeting

Start with: What's on your mind? Then explore. Listen. Ask. Wait. Challenge where useful. Do not rescue.