WHAT REALLY HAPPENS IN A COACHING SESSION: A Look Inside the Conversations That Make a Difference

When people come to talk to me, they’ve usually already done a lot of thinking. They’re often feeling the weight of responsibility, and a surprising amount of self-pressure. They've analyzed decisions, rehearsed and replayed conversations, weighed options, and tried to make sense of what’s in front of them. And despite their best efforts to reason it through, something still feels unresolved.

I always begin where my client is, and with the situation as it is: what happened, what was said, what didn’t land, who reacted and how, what now feels risky, uncomfortable, or unresolved. These details are necessary, and are often the most honest entry point into what’s really happening for them, and how I can help.

During that important first meeting, they’ll often describe their coaching objective as wanting advice or perspective, not because they don’t trust themselves, but because they’re looking for a way through a situation that feels risky, stubborn, or unresolved. In environments that reward decisiveness and momentum, it’s natural to want an efficient and responsible way to problem-solve, even when the terrain is complex or emotionally charged.

But as our conversation unfolds, something else starts to come into view. Alongside the situation itself, they begin to notice their interpretation of what’s happening, the assumptions they’re making, the habits of thought they return to, and the blind spots that may be shaping their reactions. Over time, many realize that changing other people, or waiting for the context to improve, isn’t what coaching is about, and wouldn’t actually help them be more effective or successful in what they’re trying to navigate.

During these early conversations, something subtle but remarkable takes place: the conversation gradually shifts without either of us forcing it. People begin to hear themselves differently. They notice where a particular frustration keeps reappearing, or how strongly they react to a certain powerful question. Sometimes they pause and say, almost to themselves, “Wow, I’ve never thought about it that way before,” or “I’ve been feeling this for so long, but I haven't been able to put it into words until now.”

What’s happening in those moments isn’t accidental. It’s the result of two unique perspectives coming together in service of the client. For the coach's perspective, it means careful listening (to what's being said, and what isn't), well-timed questions intended to create new insight, and attention to patterns the client may not yet be aware of. It also means creating enough room for them to think out loud and examine their patterns without feeling judged or rushed toward a solution. And from the client's perspective, it’s an opportunity to see themselves in the system more clearly, and to notice how their own wiring, assumptions, and patterns are shaping what’s possible. In that kind of space, behaviour, motivation, and context start to connect in ways that are almost impossible to access on their own, especially during a busy workday.

What often comes into focus next isn’t a neat answer, but a clearer sense of orientation. With a coach as a thinking partner, people gain new perspectives and start to see what matters most to them, what they’ve been protecting, and where they may have been holding back. That clarity is very practical. It shapes how they approach the situation, what they’re prepared to challenge, and what they’re willing to let go of.

I see this play out in small, ordinary moments all the time. A client will be describing a familiar frustration they have with a colleague or stakeholder, and I ask them what they notice about how that person is wired, what they tend to value first, or what reliably gets their attention. There’s often a pause, sometimes a laugh, and then something like, “Oh. I’ve been coming at them from my own perspective and preferences. Now I see why that wasn’t landing.” Nothing has been solved yet, but the person is suddenly inside the situation rather than just reacting to it.

Other times, someone has been circling an issue for a while, speaking carefully and professionally, sometimes even guardedly, when a word or phrase I offer really lands for them. I’ll offer it more as a mirror than a diagnosis or conclusion, and they’ll often stop mid-sentence for a long pause, followed by, “Yes! That’s it. That's how I feel!” In that moment, the issue moves from being a heavy, internal tangle to something clearer and more usable; something they can actually engage with rather than silently absorb.

And sometimes, the shift is even simpler. Some people arrive determined to make the right decision and are frustrated that they haven't been able to until now. As they talk through the trade-offs, the risks, and what matters most to them, I've seen many people stop mid-sentence and say, “I think I already know what I should do.” What they needed wasn’t a better answer, but enough space to trust the one that was already there, just out of sight.

Through the coaching process, people often come to realize that what they needed wasn’t direction, but permission. Permission to acknowledge doubt without immediately correcting it. Permission to name a value conflict they’ve been trying to smooth over. Permission to admit that something which looks sensible on paper doesn’t actually sit well with them in practice. Permission to experiment. Permission to do something outside of their comfort zone.

Language plays a central role here. Many people arrive with a strong sense that something isn’t right, but without the words to describe it clearly. When they find language for that experience, their relationship to it changes. It becomes something they can work with, rather than something that weighs on them in the background. Coaching doesn’t solve the puzzle for someone; it helps them see the shape of it more clearly.

My role as coach in these conversations isn’t to improve the question or guide someone toward a better answer. I stay with the question they bring. I listen for what seems to matter, and I help them stay with their own thinking long enough to understand it more fully. When insight emerges, it belongs to them.

Sometimes that insight leads directly to a next step. Sometimes it reframes the situation enough that the path forward looks different. Sometimes it simply provides steadier footing before any action is taken. When advice or perspective becomes useful in later coaching conversations, it lands because it’s connected to the person’s own understanding, not because it replaces it.

Near the end of a coaching session, people will often comment that they feel clearer or more settled, even though nothing external has changed. Their role may still be demanding. The decision they need to make may still be complex. That difficult relationship may still require care. What’s shifted is how they’re carrying it, and that shift alone can make the next step feel more manageable.

They leave with a stronger sense of their own judgment and a clearer internal reference point. That doesn’t come from being told what they need or should do. It comes from having time to think in a specific way that connects their experience with their values and their choices.

Many leaders and professionals are surrounded by input, opinions, data, and constant expectations, yet they are still expected to decide, act, and lead with confidence. Over time, this pressure can make it hard to see clearly what is actually asking for attention, or what part of the situation is truly theirs to own and work with. At its best, coaching helps people make sense of complex situations, work through difficult emotions without being overwhelmed by them, and arrive at decisions they can stand behind. That clarity shows up in very practical ways, in the choices they make, the conversations they have, and the steadiness they bring to moments of uncertainty.

YOUR COACHING CHALLENGE

Set aside 15 minutes of uninterrupted time to reflect or write about what is currently stretching, frustrating, or unsettling you in your leadership. Where you feel least at ease, most unsure, or preoccupied? How would you like to think, feel, and behave differently in this situation if you could? This reflection forms the foundation of your coaching topic.

Next, write down what you want to change in those situations, beginning with "I'd like to be more able to...". Here are some actual client examples of powerful coaching topics to use as inspiration:

I'd like to be more able to:

  • communicate clearly and calmly under pressure

  • enhance my influencing skills and leadership presence

  • step into my new role and lead my former peers with confidence

  • influence with steadiness and credibility when the stakes are high

  • manage my emotional interior when in conflict with others

  • build a strong relationship with my leader based on trust and clear expectations

  • balance my career strategy with my personal resilience

  • authentically and confidently embrace my full leadership role

  • make powerful leadership choices aligned with strategic business objectives

When you can write your coaching topic in one clear sentence, you’ve usually put your finger on the real work, the place where your leadership is being tested, and where focused coaching can make the greatest difference.

If you’re curious about what this kind of conversation could offer you, reach out for a free exploratory Executive Coaching conversation at www.leslierohonczy.com.