The Questions That Help Managers Coach Themselves

A story about how insightful questions can turn everyday working experience into a source of self-coaching 

Shane was an analyst. He solved problems for a living and was good at it. When a management role came up, he seemed a natural fit.

But managing people was a different kind of problem. There were frustrations and disagreements between colleagues, decisions from senior management he had to communicate, and situations where nobody was happy with the options. Promoted for being good at the work but without training for the people side of management, Shane was beginning to discover what the role involved.

A Conversation That Didn’t Go Well

That became clear when Michael, a member of his team, came to Shane unhappy about a change in the organisation he had been asked to explain.

The conversation didn’t go well.

Shane became defensive. He knew the reasons behind the decision, even though he hadn’t made it, and explained them carefully. But the more he explained, the more frustrated Michael became.

Afterwards, Shane told himself there was little he could have done. It was an unpopular decision, and some people were always going to be unhappy.

That was his first explanation. For a while, he left it there.

The Question That Changed Things

It might have stayed there, had he not had coffee with Louise, a colleague from HR.

He hadn’t arranged it for that purpose or thought to seek support. None had been offered: no programme, no obvious door to knock on. He didn’t want to look as though he couldn’t manage his own team, and he liked solving things himself.

He mentioned in passing that the conversation about the change hadn’t gone well.

Louise had oversight of a growing number of managers and wanted to support them, but there was little time for individual coaching. What she had was half an hour to listen, and one insightful question:

What else could it mean?

It was enough.

Shane realised her question wasn’t so different from the ones he asked every day in his analysis work. Louise had simply asked him to look beyond his first explanation.

Turning the Question on Himself

So he tried it on himself. What else could it mean?

Michael had questioned whether senior management understood the impact on the team. Shane had heard a problem to fix and given the reasons behind the decision. But perhaps the reaction meant something else.

He kept going, the way he would with any problem.

What did I assume? That Michael wanted the reasons.

What did he want? To be heard.

Three questions, and Shane had reached something the conversation itself hadn’t given him.

A Moment of Reflection

Shane understood he had asked himself three insightful questions and given himself effective feedback. In doing so, he had begun to coach himself.

By looking again at his own experience, he was becoming a better observer of his working life, developing greater self-awareness of his assumptions, reactions and decisions.

Reflection had helped him understand conversations that were already over. These questions could now help him shape the ones still in front of him.

The Forward Questions

Shane asked to meet Michael again.

He began the meeting by saying:

“I’ve been thinking about our last conversation. I don’t think I listened properly. What are your concerns about this change?”

Michael paused. Then he told him.

The team was already stretched. Two people had left in recent months and they had not been replaced. The change would mean more uncertainty, more questions from clients and more pressure on people who were already struggling to keep up.

As Shane listened, he noticed how quickly he had assumed Michael’s frustration was about the decision itself. It wasn’t. At least, not only.

“What do you need me to understand?” he asked.

Michael looked at him. “That we’re already at capacity. Everyone keeps telling us what needs to happen next. Nobody seems to be asking what we can actually manage.”

Shane felt his instinct to explain rising again. This time, he recognised it.

“What would help?” he asked instead.

Michael thought for a moment.

“Honestly? For someone to listen before deciding what the problem is.”

This time, Shane was fully present. He listened, noticed and responded to what was actually happening, rather than rushing towards the answer he thought he needed to give. Together, they considered what support the team needed and what Shane could take back to senior management.

A Little Input, at the Right Moments

Shane continued to catch up with Louise from time to time. Not on a schedule, and never for long. Usually, it was when he had reached the edge of what he could work out on his own: a situation he kept circling without resolving, or a decision he wanted to think through aloud with someone outside it. She asked the kind of questions that helped him find his own, and he left able to carry on.

That was the shape of it. Not a programme. Not a dependency. A capable manager doing most of the thinking himself, with someone who occasionally helped him see round a corner.

Learning from the Work We Are Already Doing

Many managers are promoted because they are good at their work and then discover that leading people asks something different of them.

Training and coaching is helpful. But when that’s not available, managers can also learnthrough the work they are already doing.

The difficult conversation. The decision that didn’t have the expected outcome. The disagreement between colleagues. The moment when they handled something better than they thought they would.

The challenge is not simply having those experiences. It’s noticing them.

Shane hadn’t found the learning in a course or handbook. He had found it by returning to a conversation and asking what else it could mean.

Self-coaching taught him to look more closely at the experience he was already having.

How HR Can Help Managers Ask Better Questions

Shane’s story demonstrates something useful for the people who support managers.

The intervention that helped him wasn’t a programme. It was half an hour, someone who listened, and one insightful question:

What else could it mean?

Sometimes managers need help recognising that their everyday experiences contain the material for development.

The aim is not to be needed every time. It is to help managers become better able to coach themselves, and to be there when they need another perspective.