Useletter3 November 2026Culture3 min

Avoiding a difficult conversation?
Picture them naked.

Readsomething to read

Next time you’re tempted to avoid a difficult conversation, try picturing them naked.

Metaphorically speaking.

There’s an old cautionary tale about two swindlers who come to town with an offer to the emperor.

They promise they’ll weave him the finest cloth outfit in all the land. The cloth is so fine it’s invisible to anyone unfit for their role, or (in their words) to anyone who is extraordinarily ‘simple’.

Fearing the consequences if he checks it himself, the emperor sends his faithful old minister. The minister stares at the empty looms, sees nothing, and decides no one can ever know, so he praises the colours and the pattern. A second official does the same. When the emperor finally goes, he can’t see it either and worries he’s unfit to be emperor, so he calls it charming.

Putting on these new ‘clothes’, the emperor walks through the streets until a child in the crowd finally has the courage to say what everyone can see.

Yeah, this guy is naked.

Most teams I’ve worked with have their own version of the emperor’s clothes. Those seemingly small behaviours everyone notices but nobody names.

I know because, in the research for Let’s Talk Culture, only one-third of people leaders said they feel empowered to speak up when they see a misalignment with their culture and values.

We stay quiet because fitting in feels safer than being honest. And speaking up when it risks belonging feels scary. We might also tell ourselves someone closer to them will say something.

The problem is that silence is a loud teacher.

Silence costs your culture.

When you tolerate a behaviour, you communicate “we are ok with this”.

Steve Gruenert and Todd Whitaker put it well: “The culture of any organisation is shaped by the worst behaviour the leader is willing to tolerate.”

The conversations you don’t have end up reinforcing a culture you don’t want.

Silence costs you personally.

I’ve lost count of the arguments I’ve had with people in my head. The frustration we carry is like a lit fuse. Stamp it out early and you avoid the explosion. Leave it burning and it’s only a matter of time before it goes off, usually with collateral damage.

Silence isn’t fair on the person either.

The emperor didn’t find out in a quiet room from someone he trusted. He found out, in a very public way, something that could have been addressed early.

Silence costs the team most of all.

They’re the ones living with the behaviour every day and watching to see whether anyone will do anything about it.

You always end up having the conversation. It only gets harder with time.

The kindest time to have it is early.

Here’s a simple way to start:

  1. Say what you see. Point to the behaviour you observed, not what you assume. “I noticed you spoke over a few people in today’s meeting.”
  2. Say why it matters. Link the behaviour to the team culture you’re trying to build. “We agreed we want everyone to feel heard and contribute in meetings, and when people get cut off, they tend to withhold their ideas.”
  3. Ask for their input. You might only have part of the story. “What do you think about that?”

It doesn’t need to be polished. It does need to be said. I’ve always believed it’s better to say it clumsily than not say it at all.

Next time you’re tempted to avoid a difficult conversation, picture them naked, walking down the street with everyone watching.

Leaving them that way doesn’t help them. It makes everyone else awkward, and pretty soon other people will think it’s ok to do the same.

Staying quiet can feel like the kind thing to do, but from a lot of experience, I can assure you it isn’t.

Thinksomething to think about

Dosomething to do

Write your script

Think of one conversation you’ve been putting off. Write the three lines you’d say, in your own words.

When will you have it?
Your script

Your lines will appear here as you write them.

Read it once before the conversation, then put it away and talk.

Yousomething from you

What everyone's saying

When you notice something that’s off, what most often stops you saying it?

One tap, and you see where everyone else landed.

Got a question or thoughts? Let me know

Whatever you write comes to my inbox and nowhere else: what it made you think, what you would add, what happened when you tried it. I read all of them and I reply to most.

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