Mel Savage Executive Coaching
Managing Relationships

How Leaders Make Difficult Conversations Less Difficult

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Here’s my 4-step strategy for how leaders make difficult conversations less difficult.

Who wants to have a difficult conversation? The answer is no one.

No one wants to have a difficult conversation.

My recommendation is to never have a difficult conversation. I say always avoid them if you can!!

Now… I’m not saying you should avoid giving constructive feedback, or aligning on expectations with a report, peer or boss.

Sometimes it’s imperative that you have those conversations. I’m just saying the “difficult” part is optional. And something I recommend avoiding.

“Difficult” is just a perception you’ve placed on the conversation.

Perceiving the conversation as “difficult” puts you on the defensive. And your anticipation of the “difficulty” increases your stress level as each day goes by.

And when you’re stressed and defensive, the other person in the conversation will feel it, and influence how they act in the conversation.

So why make it harder for yourself by framing the conversation as difficult?

You could frame the conversation in many ways.

It could be a “growth” conversation.

Or a “shared expectation” conversation.

But honestly, those words sound like B.S. jargon-y spin. They sound as unnecessary as the word “difficult”.

So I recommend keeping it really simple and boiling it down to what it actually is… “a conversation”. That’s all. Why do you need to qualify it in any way?

It’s just a conversation that you’re a little nervous about having. That’s fair. But why make yourself more nervous by labelling it as “difficult?”

Instead, put your energy into devising a strategy to make the conversation as effective as it can be.

Here’s my 4-step strategy for how leaders make difficult conversations less difficult.


Stop and ask yourself if you really need to have this conversation. And if so, why?

Sometimes you want the “difficult conversation” because you want someone to feel as bad as you. Or apologize. Or just know they offended you. And you think that by having a “difficult conversation”, you’ll feel better.

Sounds funny, doesn’t it?

I promise, there are easier ways to make yourself feel better than going through all of this. In fact, this type of conversation is likely to make things worse.

The best reason to have a “difficult conversation” is because you genuinely want to understand and support someone. Maybe you want to understand why they acted a certain way. Or why they aren’t delivering a certain thing. Or why they have strong feelings about something.

Sounds less difficult already!

Ask yourself why you want to have the conversation. And if the answer is focused on making you feel better, then you may want to revisit your strategy.


Now that you know the purpose of the conversation, decide what you want success to look like.

The key to success in step 2 is to make the result something you can control. This is harder than it sounds. When having a “difficult conversation”, you’ll often want the result to be something you can’t control. For example;

I want them not to be upset (or I want them to be happy).

I want them to stop doing what they’re doing

I want them to listen to what I’m telling them

You can’t control any of that. But what you can control is much more powerful. You can control yourself. For example;

I want to be clear on expectations or boundaries

I want to make a request

I want to understand their behavior

I want to let them be upset if they need to be

Make sure the result you want is something you can control and guides your focus for the conversation.


I know people who want to plan out entire “difficult conversations” in their head. And I understand why. You want to show up at your best. You don’t want to over-react and make the situation more difficult.

I love the intention. But the execution is way too much work. And honestly, there’s no way you can think of everything. Instead, I recommend an easier approach. Plan your emotional strategy based on likely scenarios. For example;

If they cry, I’ll let them by being patience and understanding.

If they get angry and defensive, I’ll stay calm and listen.

If they shut down, I’ll be caring and patient by giving them space to think.

If they blame others, I’ll be patient and coach them to see their role.

Grounding yourself in an emotional response strategy is not only easier, but allows your words and actions to come more naturally.


You might be glad the “difficult conversation” is over, but it may only be over for you. Even if you thought it was a great conversation, take the time to check-in. Sometimes what’s no big deal for you is harder for other people to process, and you’ll get longer lasting results if you double back and see how people are doing.

Bottomline: There’s no such thing as a difficult conversation. There are only the conversations you make difficult.

The minute you focus on being curious, supportive, understanding and clear, everything becomes easier. Instead of creating difficulty, you create connection.  


I have 20+ years working as a leader in the corporate world. I know what you need to do. And I combine that with four years of training as a cognitive behavioral coach. I know how to help you naturally think like the leader you want to be.

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