How to Prepare for a Difficult Conversation at Work

I stood in a bakery queue the other day, distracted by checking out the delicious pastries, when I overheard a man in front of me speaking.

He was on a conference call, right there between pastries and people waiting for their morning coffee. He believed the leadership team on the other end were making the wrong decision. He challenged their strategy and questioned their intentions — and in between, placed his order.

He was nervous. I could hear it in his voice. But, oh my, he was determined. And clearly came prepared.

I found it incredibly powerful.

How often do we fear the moment where we want to express our opinion or ask for something, and shy away at the last minute because it feels too hard? When we feel it’s time for a career progression review? When something is bothering us? When we intend to resign because the environment no longer works for us?

These kinds of conversations really carry weight for most of us. They feel risky.

And often, they come with that same visible nervousness I saw in him.

Some of my coaching work sits right here. In preparing for the conversations that ask for change. The ones that create movement, even if the outcome is uncertain or even risky.

There is a structure we follow which looks like this.

We start by getting clear on the outcome.

What do you actually want from the conversation?

Of course, ideally we would want our managers to hand us the promotion right there and then. But that’s not how it works. So this question is more about planting seeds. Perhaps establishing a step ladder that gets you to the promotion you want.

Without such an anchor, it’s easy to drift halfway through the conversation.

We consider scenarios.

What’s the best case scenario?
What’s the worst case?

This reflection is intended to take some of the power out of the unknown outcome. When we’ve already seriously considered certain outcomes, the actual reaction doesn’t come as a surprise and allows us to prepare for a response in advance.

We practise.

We go into a bit of role play and practise the conversation. We pay attention to where the client stumbles or where the message becomes vague.

This rehearsal isn’t intended to script every word of the conversation, but rather to identify gaps and insecurities that the client can reflect on while preparing.

We play with metaphors.

If clients are open to it, we anchor their intention in a small object that has a particular meaning for them. Something that reminds them why they wanted this conversation in the first place and of its importance.

I was truly inspired by the man in the bakery queue. He didn’t look comfortable, but he was determined.

We hardly ever feel ready for these types of conversations. But we can calm our nervous system by preparing and considering the outcomes. 

If you want a space to think it through or practise it, you’re always welcome to schedule a discovery call.

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