As a leader the only way to get better at letting people down is to understand which persona you’re addressing and why.

The legendary manager of Arsenal FC, Arsene Wenger – a personal leadership hero of mine – was interviewed on Desert Island discs. Wenger is a veteran coach and speaks several languages with equal eloquence.

David Dein, his one-time business partner, once told me: “Arsene is the cleverest man I ever met. An incredible leader.”*

Arsene was talking about how every match he would have to explain to players who expected to be in the side that they would instead be on the substitute’s bench. Here’s what Wenger said: “When you speak to a player you are speaking to three people.”

To the child: “he just wants to play, and gets frustrated and angry when he’s not chosen.”

To the teenager: “everything is black and white. You are either a genius or an idiot. There’s no room for reasoning.”

And to the adult: “this is the grown up who has to reconcile all of these warring emotions, who recognises that throwing their toys out of the pram is not the answer but who still feels deeply hurt by rejection.”

And it really resonated with me. As leaders we give people bad news every day. Their work isn’t up to scratch; they can’t have that promotion they so richly deserve; there’s no budget for pay rises this year. Sorry.

Yet we still have to keep them onside, make sure their motivation stays high.

So how do you deliver the bad news and still make sure their effort and commitment doesn’t flag? I have five suggestions:

Before you deliver the news, remember that all three people are in the room.

1. Acknowledge the disappointment

Too many managers rush straight to the explanation. Start with the emotion instead.

“I know this isn’t what you wanted to hear.”

The child needs to feel seen before they’ll listen.

2. Explain the decision, not the person

Separate the outcome from their worth.

“You weren’t selected for this project” lands very differently from “you’re not ready.”

The teenager is already looking for evidence that you’ve written them off. Don’t give them any.

3. Be clear, not diplomatic

When leaders feel uncomfortable, they often become vague.

People can cope with bad news.

What they struggle with is uncertainty.

The adult wants clarity.

4. Give them a path forward

Bad news without a next step feels like a dead end.

Bad news with a plan feels temporary.

What would they need to do differently? What would success look like? When will you review it again?

Hope matters.

5. Leave their dignity intact

Nobody remembers every detail of difficult conversations.

But they do remember how they felt when they walked out of the room. Make sure they leave the meeting with self-respect still intact.

Wenger understood that every difficult conversation is really three conversations happening at once.

The child feels hurt. The teenager feels angry. The adult is trying to make sense of it all.

Your job as a leader is to deliver bad news in a way that allows all three people to end the meeting believing they still have a future.

*For more of David Dein’s wisdom, read Chapter 24 of Next Gen CEO where he talks about how to successfully motivate some of the best paid people on the planet – Premiership footballers.

Best, Mike