Difficult Conversations

Almost every leadership problem I encounter in coaching eventually traces back to a conversation that didn't happen. The feedback that was softened into meaninglessness. The accountability that was avoided to preserve the relationship. The boundary that was implied but never stated. The anger that was swallowed instead of channelled.

Most leaders know they should have these conversations. They don't avoid them out of laziness - they avoid them because they're genuinely hard, and the stakes feel high, and the risk of making things worse feels real.

These posts aren't about toughening up. They're about having difficult conversations with skill and in a way that's direct without being destructive, honest without being harsh, and accountable without losing your humanity.

If there's a conversation you've been putting off with a team member, a peer, or a boss, that's often the very place where coaching creates the most leverage. I can help you prepare, practise and follow through. 

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Accountability and being nice: trade-off or allies?
Accountability and being nice: trade-off or allies?

Here are a few ways to approach ways of working accountability without losing “niceness” as a leader.

5 ways to keep your cool when someone is angry at you
5 ways to keep your cool when someone is angry at you

Sometimes pushing back can be particularly challenging when a stakeholder is angry and/or powerful. It requires a delicate balance between maintaining the relationship and respecting your own limits. Here are 5 strategies that you can use to push back effectively in these difficult situations.

How to set boundaries when your stakeholders won’t listen
How to set boundaries when your stakeholders won’t listen

Recently I ran a workshop for in-house lawyers and was asked for tips on how to assert healthy boundaries and push back on work demands when your stakeholders refuse to hear it. Here’s my take…

I need your help fixing my team
I need your help fixing my team

From time to time I will have a meeting with a potential client about working with them or their team.

Want to know a big red flag?

3 questions to ask yourself before a high stakes conversation
3 questions to ask yourself before a high stakes conversation

When a client is feeling stuck or stressed about an upcoming conversation, these 3 questions have often proved to be a real game changer.

Being cruel to be kind
Being cruel to be kind

Lately I've been thinking about "being cruel to be kind". I'm against it. Why not just be kind? That might (will) mean making decisions other people don't like, but that's very different from treating people with contempt and indifference.

If there's a conversation you've been putting off with a team member, a peer, or a boss, that's often the very place where coaching creates the most leverage. I can help you prepare, practise and follow through. 

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