Difficult Conversations
Leadership Coach, Front of Room Leader and Systemic Change Guide

I remember playing doctor with a friend as a young girl. I am not sure how old I was, I don’t even remember the friend, but I do know in which house in our neighbourhood we played. The memory is just a flash of light. And I am pretty sure my patient had no pants on.

The reason I remember so little so vividly is shame.

The shame I felt when his grandmother entered the room, scolded me for examining my friend, and had us stop.

Perhaps that is the reason that I don’t like role playing. I do it anyway, as a coach, because it is a powerful, powerful tool when it comes to preparing for difficult conversations.

Here’s something that happens frequently when we are co-leading a room full of team leaders in one of our experiential leadership programmes. When we get into the topic of difficult conversations, we ask:

“What makes a conversation difficult?” Boom. A buzzing room goes tense.

I can literally sense the group’s energy drop, even through zoom. This question connects participants to difficult conversations they’ve had in the past, and to difficult future conversations they dread. Their answers point to no shortage of ingredients for what makes a conversation difficult. The all evolve about one word:


The anticipation of strong emotions, based on past experience. The anticipation of defensive behaviour, tactical maneuvers, lies, of getting accused, and so on. In short: not getting anywhere, or perhaps even getting hurt. There’s also the long-term anticipation: the fear of demotivating someone and in that process, getting even poorer results or civility from them than up until then.

Now, you can teach people all sorts of techniques.

And there are many good ones out there to help you keep difficult conversations calm or de-escalate them when necessary.

But one team leader tells me: “You see, Regina, they have practiced their game for twenty years…

… This is what they do! But we have many other things to do and don’t have time for these tough conversations every other week.” Fair enough! So how can you deal with an avoider, a bully, or any other person on your team that is really difficult to align with?

And here re-enters role play.

Get yourself a coach, or find yourself a trusted peer, enlist your partner, in short, find someone you trust with whom you can role play the situation until you are confident that you can be in charge of the conversation, not hijacked by your own emotions, but clear about what you have to say, and prepared to listen to what they have to say.

I want to give you a few pointers as to how to set yourself up for role play that prepares you well for a conversation:

  1. Reflect on your situation and define the goal of the role play: Gain confidence? Get clearer around what you want and need to say?

  2. Find your role-play partner just enough of the details: enough so that they can get into the role, and not too much, because that creates distraction. Err on the side of not enough detail before the first practice round. Then add more detail, if necessary, before the second practice round.

  3. Define what a successful conversation would look like. Would you like to just advocate for your own position with clarity and ease? Or would you like to get someone to commit to something? Be clear about the desired outcome of the conversation you role-play.

  4. Decide who plays which role: Will you play yourself? Or will you play the person you need to have a conversation with?

  5. Start role playing

  6. Pause at crucial moments, so your coach or role play partner can give you immediate feedback on how you are doing. Then resume or start the role play again.

  7. Re-play as often as it takes to get so good at this conversation that you know what message you need to deliver, and how you want to go about it. The feedback loops will help you with this.

Role playing yourself is powerful, because you get a lot of practice for your upcoming conversation. You also become clearer and clearer about what you really want and need to say.
Role playing the other person is eqiually powerful because it helps you experience the conversation through their perspective as you step into their shoes.
Role playing both yourself and the other person allows you to both practice your conversation, and to experience how another person would handle the conversation in your place.
The more we practice, the less we are afraid of the actual conversation.

At the end of the day, what makes them difficult is our fear of emotions, our own and those of others. And the more we experience those and learn to dive through them, the less grip they have on us.

For leadership coaching and developement, get in touch

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