So far in my LinkedIn Client Management series we’ve looked at managing expectations (the foundation of strong relationships) and building trust to become a true partner.

This time, we’re diving into one of the trickier – but unavoidable – aspects of client management: handling difficult conversations.

Why they matter

Whether it’s delivering bad news, pushing back on a request, or addressing a misalignment, tough conversations are part of every client relationship.

It’s natural to feel uncomfortable. But here’s the thing: handled well, these conversations don’t damage trust – they deepen it. They show clients that you’re honest, reliable, and willing to have the conversations that matter.

Principles for navigating tough conversations

✔ Start with intent – Ask yourself: What’s the outcome I want here? If your intent is genuinely to help the client, it will shape how the conversation unfolds.

✔ Prepare, don’t script – Think through the key points you need to cover and how you’ll phrase them, but avoid over-rehearsing. You need clarity, not a script.

✔ Be clear and kind – Don’t wrap bad news in so much padding that the message gets lost. Clients appreciate directness – provided it’s delivered with empathy and respect.

✔ Listen as much as you talk – Clients may react emotionally, or raise concerns you hadn’t anticipated. Give them space to respond. Sometimes the listening is more important than the message.

✔ Focus on solutions, not just problems – If you’re bringing bad news, bring options too. Showing you’ve thought about ways forward demonstrates care and proactivity.

✔ Stay calm under pressure – Tone and body language matter. A calm, steady presence reassures the client, even if the message is difficult.

When things go wrong

We’ve all had conversations that didn’t land well. The key is not to avoid them in future but to reflect, learn, and adjust.

Difficult moments don’t have to end relationships – in fact, they often strengthen them when clients see your resilience and integrity.

This month’s challenge

Think of a conversation you’ve been putting off with a client – maybe it’s an awkward update, or a pushback on a request.

And given it’s just after the summer period, there may be plenty of reasons why expectations have slipped: projects delayed, decisions postponed, actions missed while people were away.

Pick one of those situations and lean into it. Reach out with empathy (“I know summer holidays may have delayed things…”) while also bringing clarity and focus on how to get things back on track. Prepare your intent, plan your key points, and have the conversation. The relief (and trust) that follows is often far greater than the worry beforehand.

Next time: We’ll explore the art of spotting opportunities in client relationships – how to see beyond the immediate brief and add value that drives growth.

Until then, I’d love to hear your experiences: what’s worked (or not) for you when handling difficult conversations with clients?