How to Know When a Session Has Actually Gone Well

by Lorraine Hamilton | Jun 23, 2026 | Coaching, Coaching Craft

You hang up the call and sit with it for a moment. Something happened in that session (you felt it) but you’re not entirely sure what. The client seemed engaged. She said a few things that felt real. Nothing broke down.

And yet you find yourself asking the question you’ve asked after hundreds of sessions: was that actually good?

I’m Lorraine Hamilton, and this question is one I’ve heard from coaches at every level of experience. It arrives for people just starting out, and it arrives just as persistently for coaches with a decade in practice. The uncertainty doesn’t always diminish with competence. Sometimes it just gets quieter, or more sophisticated in how it presents itself.

I want to offer a different frame for thinking about how to know if a coaching session went well, because the one most coaches are using is working against them.

Why the usual ways of knowing if a coaching session went well don’t hold up

The most common measures coaches reach for are visible ones. Did the client leave with a clear next step, or say the session was useful? Did she have a breakthrough? Were my questions any good?

These are not useless measures. But they are unreliable as a primary assessment of session quality, and relying on them heavily does two things that gradually erode your confidence rather than building it.

First, they make you dependent on the client’s visible response as feedback. A client who doesn’t visibly shift, doesn’t arrive at a clear action, or who leaves thoughtful rather than energised can look like evidence of a poor session. In reality, some of the most significant coaching work is quiet, slow, and not immediately apparent, to the coach or the client.

A session that asks someone to sit with a hard question rather than answer it quickly is doing something real. It just doesn’t look like a breakthrough.

Second, measuring a session by its highlights (the incisive question, the powerful moment) puts you in the position of performing coaching rather than practising it. When you’re tracking whether this session produced something worth noting, you’re partly tracking your own contribution. That’s a natural instinct, but it pulls attention in the wrong direction: toward your insight rather than the client’s experience.

How to know if a coaching session went well: the honest answer

A coaching session has gone well when the client was thinking thoughts she hadn’t thought before, in a space that felt safe enough to think them. That’s it. The thoughts don’t need resolution. The session doesn’t need to produce a decision. It doesn’t need a visible moment of clarity.

It needs to have created enough safety and enough productive disturbance that the client’s thinking moved somewhere it wasn’t when she arrived.

A coaching session has gone well when the client was thinking thoughts she hadn’t thought before, in a space that felt safe enough to think them.

You can often sense this without the client telling you. The quality of the silence between questions. The moment when her pacing changes and she slows down. The shift in how she’s describing something, when the language becomes less rehearsed and more uncertain, which usually means she’s arrived somewhere closer to what’s actually true.

A session that produces that kind of movement, even in a single moment, has done something useful. That’s a session that went well.

What this means practically is that the question “how do I know if a coaching session went well?” is often better asked after the next session than the current one. The client who left thoughtful last time sometimes arrives next time with something that shows you exactly what the previous session moved.

Coaching is not a series of standalone events. It is a relationship with its own arc, and you often can’t see from inside a single session how much it contributed to that arc.

What the uncertainty about session quality is usually about

There is something else worth naming here, because it sits underneath the technical question and shapes how coaches experience it. For many coaches (especially those past the early-learning stage, when there is always another skill to acquire) the persistent uncertainty about whether a session was good is not really about the session. It is about not having a stable enough sense of their own practice to trust their own judgement.

This sounds harsh. I don’t mean it as a criticism. It is the pattern I see most often in coaches who have been in practice for three to seven years and are doing genuinely good work, and who still feel, at the end of a difficult session, that they don’t know what they’re doing.

The skill is usually not the problem. The self-trust is.

The skill is usually not the problem. The self-trust is.

Self-trust in a coaching practice is not confidence in the sense of certainty. It is the capacity to hold not-knowing without needing to resolve it into a verdict. A coach who trusts her own practice can sit with “I don’t know if that was as useful as it could have been” without that uncertainty becoming a statement about her worth or competence. She can hold the session lightly, learn what there is to learn, and move on.

That capacity doesn’t develop in isolation. It develops through peer conversation, through supervision, through the accumulated experience of having other skilled practitioners reflect your work back to you with honesty. Not to tell you whether your sessions are good, but to help you build the internal reference points that make it possible to evaluate them yourself, with less noise, and with more accuracy.

A more useful question to ask at the end of a session

Instead of asking whether a session went well, I’d suggest asking: where did the client think? Not where did she arrive, not what did she decide, not what was the best thing I said. Where was the thinking alive?

There is usually a moment (sometimes several) where you can feel the quality of the client’s attention shift. Where she’s no longer giving you the pre-formed answer and is working something out in real time. Where the sentence she started is not the one she finishes, because she found something different in the saying of it.

That is the moment the session is for. It may not look dramatic from outside. It rarely does.

If there were two or three of those moments in your session today, it went well. If there were none, if the whole conversation felt rehearsed, or like the client was waiting for you to tell her something rather than finding it herself, that is worth noticing and worth bringing to supervision.

Not as failure. As information about what you might try differently next time.

The question of how to know if a coaching session went well is ultimately a question about what you’re trying to do in the room. Getting clearer on that is its own kind of ongoing work, and it’s the kind of work that The SWITCH Coaching Collective is built to support.

Lorraine Hamilton is an ICF PCC coach, founder of The SWITCH Coaching Collective, and creator of The Coaching SWITCH, an ICF-accredited coach training programme based in New Zealand. She has worked with coaches at every stage of practice for over 20 years.

The Client Who Argues With Everything You Offer

by Lorraine Hamilton | Jun 9, 2026 | Coaching, Coaching Craft

You offer a reflection, and the client disagrees. You reframe it, and she disagrees with that too. You try a question, and she answers it by explaining why the question doesn’t quite apply to her situation. Twenty minutes in, you’re beginning to wonder if anything you say will land, and a quiet voice at the back of your mind is asking whether she actually wants to be coached at all.

I’m Lorraine Hamilton. I’ve been coaching for over twenty years, and the coaching client who argues with everything you offer is one of the most useful kinds of client to sit with, not because it’s comfortable, but because she is almost never doing what it looks like she’s doing.

What a coaching client who argues with everything is usually doing

A client who argues with every reflection you offer is usually not disagreeing with you. She is disagreeing with the version of herself you are holding up. The pushback is not about you and, frequently, it’s not even about the content of what you said. It is about how it feels to have something true held in front of you when you’re not quite ready to look at it directly.

She is disagreeing with the version of herself you are holding up.

This reframe matters because the coaching response to resistance looks completely different depending on how you understand what the resistance is doing. If you interpret it as the client being difficult, or as evidence that you’ve said the wrong thing, the instinct is to either back down or try harder.

Neither is useful. Backing down confirms that the reflection wasn’t solid. Trying harder increases the pressure, which almost always increases the pushback.

When a coaching client argues with everything you offer, the craft move is not to retreat or to push. It is to get genuinely curious about what the arguing is protecting.

The pushback is a signal. Something in the vicinity of what you said is landing more accurately than she’d like. The question is what she’s protecting, and why she needs to protect it right now.

How to work with a coaching client who argues with everything: the direct answer

When a client argues with every reflection you offer, slow down rather than escalating. Don’t defend what you said, and don’t immediately replace it with something softer. Instead, name what you’re noticing without making it a problem: “You’re not finding much that fits so far — what feels off about it?”

This hands the client the pen. She now has to articulate what isn’t working, which moves the conversation from reaction to reflection. Often, what she offers in response to that question is closer to what’s actually true than anything you could have said directly. The resistance has done its job: it’s kept her engaged, pushed back on easy answers, and moved you both closer to something real.

This approach requires you to not need your reflection to land. That’s the actual craft requirement. If you have a stake in being right, or in appearing insightful, pushback will feel like failure.

Genuine curiosity about what the client is protecting turns that same pushback into useful information. The capacity to make that shift (away from being seen and towards being useful) is one of the clearer markers of good coaching under pressure.

There is also a tempo consideration. Arguments have a pace to them, a rhythm of offer and counter-offer that can accelerate without either person noticing. When you feel that happening, slowing down deliberately is useful.

A longer pause before your next question. A slower, quieter delivery. Not to signal defeat, but to change the energy of the exchange.

Argument escalates when both parties are moving at argument speed. When the coach steps out of that tempo, the client often steps out of it too.

When the arguing isn’t resistance, and what that looks like instead

Not all pushback is the same. Some clients argue with everything because they are genuinely analytical and need to test an idea before they can accept it. These clients are not protecting anything. Disputing is how they engage, and if you sit with it long enough you’ll notice they eventually land somewhere.

The arguing is their process, not their defence. These clients often make the most rigorous progress, precisely because they won’t accept easy formulations.

Other clients argue because they have had coaching before (sometimes quite directive coaching) that told them what to think rather than asked them to think, and they’ve learned to protect themselves from being told what their experience means. With these clients, it helps to name the dynamic explicitly: “I’m noticing I keep offering reflections that don’t quite fit. I want to make sure I’m staying with your experience rather than bringing mine. What would it be useful to explore here?”

This is not a technique. It is a genuine reset, stepping back from the presumption that you know what’s going on and returning to honest inquiry.

The client worth watching carefully is the one who argues with everything as a way of staying in motion without arriving anywhere. She will dispute each reflection, offer a counter-reading that is also not quite right, and redirect to a new topic before anything settles.

This pattern is different from resistance or analytical rigour. It’s avoidance with high verbal fluency. Here, the most useful move is often to slow the conversation right down and name what you’re observing across the whole arc: “We’ve covered a lot of ground today. I’m curious, where does it feel like we actually are?”

What a coaching client who argues with everything is teaching you

Coaches who find a consistently argumentative client difficult tend to be coaches who rely on the quality of their reflections as evidence of their own competence. When a reflection lands, it feels like good coaching. When a client pushes it away, it feels like failure. This is understandable, but it’s also a sign that the feedback loop being used is the wrong one.

A client’s willingness to receive your reflection is not a reliable measure of your coaching quality. Some of the best sessions I’ve witnessed have involved a coach offering twelve things that didn’t land before the client worked her way to the one that did, and the coach being entirely at ease throughout.

The willingness to stay with the friction, without needing it to resolve, is what made the session safe enough for the client to arrive somewhere real.

The willingness to stay with the friction, without needing it to resolve, is what made the session safe enough for the client to arrive somewhere real.

An argumentative client you hold with patience and genuine curiosity often becomes one of the most committed clients in a practice. She has spent the relationship testing whether you’ll hold your ground, whether you have something solid enough to be worth disagreeing with, whether you’ll still be there when she finally comes around. When she finds out that you will, the work deepens considerably.

This is the craft that doesn’t fit on a framework. You build it through practice and, usually, through working alongside coaches who have already learned to stay when the session gets hard. That kind of peer environment is one of the things The SWITCH Coaching Collective is built around.

Lorraine Hamilton is an ICF PCC coach, founder of The SWITCH Coaching Collective, and creator of The Coaching SWITCH, an ICF-accredited coach training programme based in New Zealand. She has worked with coaches at every stage of practice for over 20 years.

What To Do When a Client Cries and You Don’t Know What To Say

by Lorraine Hamilton | Jun 2, 2026 | Coaching, Coaching Craft

The client goes quiet, and then her eyes fill, and you notice the shift happening before she does. Something just cracked open. And in the three or four seconds before you respond, a small but distinct internal question arrives: what do I do when a coaching client cries?

I’m Lorraine Hamilton. I’ve been coaching and training coaches for over twenty years, and I want to say plainly: this question arrives for every coach, including experienced ones. It arrives not because you’re underprepared, but because the moment asks something of you that no amount of training quite gets ahead of, the capacity to stay, without flinching, in the presence of someone else’s feeling.

What follows is not a crisis protocol. It’s an account of what I’ve found actually matters in these moments: the craft beneath the technique.

What to do when a coaching client cries: the first thing

The first thing to do when a coaching client cries is nothing. Not nothing as in absence (nothing as in non-intervention). Don’t move quickly to fill the silence, reach for the tissue box, or change the subject. And don’t begin your next question.

There’s a coaching reflex that kicks in here, the urge to do something useful, to demonstrate competence, to help the client feel better. That urge is worth noticing, because it’s usually about you, not her. It’s the discomfort of witnessing someone else’s emotion and wanting to resolve it.

But the emotion doesn’t need resolving. It needs witnessing.

The emotion doesn’t need resolving. It needs witnessing.

Sitting with a client who is crying, without visibly tensing or reaching for a strategy, communicates something no words can: that this is allowed, that you are not alarmed, and that she does not need to manage her feelings for your benefit. That is the first, and often most important, piece of the work.

On the practical question of tissues: offering them can be a kindness, but it can also be a subtle signal that you’d like the crying to stop. Pay attention to which is true for you in the moment before you reach for them.

How to know what the tears are about, and why that shapes what comes next

When a coaching client cries, the tears are information. Not about the topic she was discussing a moment ago, necessarily, but about where in herself she has arrived. The question worth holding is: what just happened, and what is this feeling telling us about what actually matters here?

Sometimes a client cries because she has touched something true. A recognition. Something she has known but not said aloud before.

In those moments, the last thing to do is redirect. The recognition is the work. Let it land. When she’s ready, you might simply reflect back what she said just before the tears came, not as analysis, but as an invitation to stay with it.

Other times the tears come from frustration or exhaustion, the weight of something that has been carried too long. This is different. There may be more space here for a question, for gentle curiosity about what’s been accumulating. Not to fix it. To see it more clearly together.

And sometimes (not often, but occasionally) tears in a coaching session are a signal that the conversation has moved into territory that belongs in therapy rather than coaching. If a client has moved into grief about a loss, trauma, or something that consistently overwhelms the coaching container, the most useful thing you can do is name that gently and honestly. Referring a client to a therapist is not a failure. It is good professional judgement.

The craft question when a coaching client cries

Here is the direct answer to what to do when a coaching client cries in a session. Don’t try to stop the tears or fill the silence. Stay present without flinching, which signals that the emotion is allowed and does not need to be managed. Give the client time.

When she’s ready, reflect back what was true just before the moment, not to analyse it but to help her stay with what she’s just touched. Ask a single open question if she seems to want direction. Stay curious rather than clinical.

The feeling is information. Your job is to help her hear what it’s saying, not to resolve it on her behalf.

What I want to add to that: this is easier to describe than to do, because it requires you to have a settled enough relationship with your own emotional responses that someone else’s feeling doesn’t pull you off centre.

That settledness is a craft skill. It develops. It is not the same as being unfeeling or detached (it’s the opposite). It is the capacity to be fully present with an emotion without being swept into it or away from it.

Coaches who are new to practice sometimes tell me they’re afraid of making things worse in these moments, that a clumsy response will damage the client or the relationship. In my experience, what damages the relationship is not a clumsy question. It’s the coach visibly needing the client to be okay again.

Clients are surprisingly forgiving of genuine human response. They are less forgiving of feeling like their emotion has become your problem.

Before that, a word on what happens in the moment when you genuinely don’t know what to say. You have gone quiet, you are present, and still nothing arrives. No question, no reflection, just the two of you in the room with the feeling between you.

This is fine. More than fine. A coach who can be present in silence without manufacturing something to say is offering something rare. The impulse to speak (to fill, to reframe, to demonstrate that you are doing something) is very strong in coaches, particularly in moments that feel charged.

Silence with full attention is not the same as silence from uncertainty.

Resisting that impulse is a skill, and it is one of the more important ones you can build. Silence with full attention is not the same as silence from uncertainty. Clients can feel the difference.

After the session: two things worth your attention

After a session where a client has cried, there are two things worth doing.

The first is a brief debrief with yourself. Not to evaluate whether you handled it correctly, but to notice what the moment stirred in you. Where did you feel pulled to intervene? What did you want the client to do with her feeling?

These are windows into your own patterns as a coach, the places where your presence is slightly conditional. Good supervision material, if you have it.

The second is a note in the client file about where the session went. Not a clinical account: a reminder to yourself of what she touched, so that you can return to it with intention in the next conversation rather than stepping over it as if it didn’t happen. Clients notice when you carry the thread of the work. It builds trust in a way that technique alone does not.

The coaching sessions that matter most to clients are often the ones with the most feeling in them. Not because feeling is the goal, but because feeling is what happens when someone arrives close enough to what’s actually true. The moment when a coaching client cries is not a complication to be managed. It is, more often than not, exactly where the useful work is.

If you’re interested in working with coaches who think this carefully about craft, The SWITCH Coaching Collective is where those conversations happen.

Lorraine Hamilton is an ICF PCC coach, founder of The SWITCH Coaching Collective, and creator of The Coaching SWITCH, an ICF-accredited coach training programme based in New Zealand. She has worked with coaches at every stage of practice for over 20 years.