Difficult conversations

Are you avoiding having a difficult conversation right now?

Because you’re worried about hurting someone’s feelings?

Or anxious the relationship might sour?

A big part of my work is supporting leaders with difficult conversations.

Sometimes that means:

• Planning the conversation so the language lands well.

• Reframing it so it stays professional, not emotional.

• Positioning it tactically, so it becomes a with conversation, not a to conversation.

Most of the time, that preparation means the conversation goes well and achieves the outcome the leader wants.

But recently, I worked with a leader facing a different kind of dilemma.

She had a new CEO who was driving significant change, including reducing people’s roles and responsibilities.

My client had recently been off work, in fact she had been hospitalised. On her return, she was called into a meeting with the CEO because of her absence record.

Unsurprisingly, she was angry.

She is highly committed, works long hours, goes above and beyond, and rarely takes time off. When she does, it’s because she’s genuinely ill and following medical advice.

Our session wasn’t about how to confront her CEO.

It was about whether to have the conversation at all.

We explored every angle.

We considered how different approaches might land.

We talked honestly about power, timing, risk, and consequences.

And she made a conscious decision to pick her battles.

She chose to calmly explain her ill health and reaffirm her commitment, rather than escalate the situation into conflict.

She didn’t want to mark her cards.

Which made me pause.

Are difficult conversations always the right answer?

Or can they sometimes create consequences that outweigh the benefits?

In my experience, many workplace conflicts and grievances come not from avoiding difficult conversations, but from having them badly, at the wrong time, or when another approach would have served better.

So if you’re weighing up whether to have a difficult conversation, you don’t have to do that alone.

Message me at info@claireplattcoaching.co.uk to arrange a free discovery call.

I can help you prepare for a courageous conversation, or help you decide whether a different path might be wiser.