Saying the Thing About the Thing

Tackling difficult conversations is one of those things that sits firmly in the category of “I just don’t wanna” for many middle managers.

We know we need to talk to our people. We plan what we’re going to say… or we don’t plan at all and just jump in. And then somehow, it doesn’t quite go the way we expected.

• The conversation drifts.

• Or it gets tense in a way we can’t quite name.

• Or every time we speak to a particular person, it seems to veer wildly off course.

• Or we find ourselves stuck in a loop with the leader above us - having the same conversation over and over again, never quite getting what we need.

And we walk away thinking:

What on earth just happened?

Most difficult conversations don’t fail because of what’s said. 

Great leadership communication isn’t just about what you say - or even how you say it.

Sometimes the issue isn’t the content of the conversation at all. It’s the way the conversation itself unfolds. The patterns of communication over time. The things that sit just underneath the words.

Most difficult conversations don’t fail because of what’s said.
They fail because of what isn’t said.

And middle managers feel this all the time.

The mental loop we all get stuck in

When we’re preparing for a difficult conversation - or even just one that matters - most of our thinking goes into questions like:

• What should I say?

• What might they say in return?

• How will I respond to that?

Around and around and around we go, unstructured, unproductive imagining.

Then the conversation actually happens.

Something unexpected comes up.
The energy shifts.
We feel ourselves getting frustrated, defensive, or unsure.

So we react to whatever comes next. We follow the trail of connection… further and further off track… until we’re deep in the conversational wilderness wondering how we got there.

We’re focused on the content of the conversation - but we’re not actually leading the conversation itself. Unstructured, unproductive conversation.

The skill no one really names 

If you look at most leadership toolkits, communication is always there.

But it’s usually framed as:

• what to say

• how to give feedback

• how to structure a conversation

What’s often missing is this question:

What do you do when the conversation itself isn’t working?

Great leaders do know how to move past this. But many of us were never explicitly taught how.

This is an explicit, learnable skill.
It’s called metacommunication.

Saying the thing about the thing

Metacommunication is the skill of making the invisible part of a conversation visible.

Instead of skirting around the topic, we talk about how we’re skirting around the topic.
Instead of trying harder to land our point, we pause and name what’s happening in the conversation itself.

It’s about talking to the dynamic in the room - not just the item on the agenda.

Or more simply:

It’s saying the thing about the thing.

Naming the pattern.
Naming the dynamic.
Naming what’s happening between us.

Why this matters so much for middle managers

This is a game‑changing skill for middle managers in particular.

Because when you’re in the squishy middle of organisations, you’re often:

• leading downwards

• influencing upwards

• and collaborating sideways

…all at the same time.

In those dynamics, naming someone’s behaviour directly can feel risky, awkward, or just not quite doable - especially when you’re leading upwards.

But naming the pattern of communication?

That’s a different doorway.

It allows you to say something real without escalating the situation. It creates movement where before there was just… stuckness. And it lets you stay human‑first, curious, and grounded, even in difficult moments.

What it looks like in practise

This isn’t about having perfect words.

It’s about being willing to notice what’s happening — and gently bring it into the room.

For example:

• When a team feels stuck or is talking at cross purposes:
  “I think we might be solving two different problems here.”

• When things are moving too fast and everyone is agreeing too quickly:
  “Can we pause? I’m noticing we’re all agreeing quickly — does that feel real?”

• When there’s tension but no one is naming it:
  “I might be misreading this, but something feels a bit tense.”

• When a conversation keeps looping:
  “I feel like we’ve been around this a couple of times — are we missing something?”

These are small shifts. But they change the direction of the entire conversation. And in turn, they change what becomes possible. Structured, productive framework.

Case study: Interrupting the Pattern

A middle manager I worked with was frustrated that every conversation with their senior leader felt circular. They would raise an issue, the leader would agree in principle, and nothing would change. Over time, resentment built — but naming the leader’s behaviour felt risky.

Instead of pushing harder on the content, we worked on naming the pattern.

In the next conversation, the manager said:
“In our last few conversations, we seem to be in agreement on this issue, but it feels like we keep looping back around and having the same conversation. I realise neither of us really has time for that. I wonder if there's something we haven't figured out about this yet. Can we have a look at what's getting in the way of us taking next steps?”

That one moment shifted the tone of the conversation. It didn’t magically fix everything — but it opened a new, more honest dialogue about expectations and follow‑through. For the first time, the manager felt like they were leading the conversation, not chasing it.

The real shift

When managers lead with this skill, I see a noticeable shift in confidence.

They stop chasing the conversation… and start leading it. They notice when things are out of alignment - and bring people back towards the outcome they’re aiming for. They learn to distinguish between:

• a problem behaviour

• and a problematic communication pattern

And often, it’s the second one that’s quietly driving the first.

Most managers can feel when something’s off in a conversation. What they’re missing isn’t awareness - it’s permission and language to name it in ways that build trust through curiosity rather than judgement.

You don’t need to do this perfectly.
You don’t need a script.
You don’t need to name everything.

Sometimes middle managers don’t need better words. They just need to take a pause to think – to find the courage to elevate the conversation and say the thing about the thing. 

Because when we move away from judging what others should be saying, and instead focus on interrupting unhelpful patterns in real time, that’s when difficult conversations really start to change.