Having courageous conversations with your team

Published 27 October 2026

Having courageous conversations with your team: what to know

Managers often avoid difficult conversations out of fear of making things worse. It's a natural instinct, and it's usually wrong. Avoiding a difficult conversation rarely prevents the problem; it lets it grow, sends the message that you don't notice or don't care, and damages trust that then has to be rebuilt later at greater cost. Courageous conversations, done with care, strengthen trust and resolve issues early.

Prepare, but don't script. Get clear on what you want to understand and what you want to achieve — these are different things. Understanding comes first; resolution follows. Choose a private, neutral setting, allow enough time, and bring your full attention. Don't have a hard conversation in a corridor, between meetings, or in front of others.

Open with specific, non-judgemental observations rather than labels. 'I've noticed you've missed the last two deadlines, and I wanted to check in' is a door. 'You're unreliable' is a wall. Describe what you've seen and heard, then invite their perspective. The aim is a shared understanding of what's happening, not a verdict delivered from your side of the desk.

Listen more than you speak. This is the hardest part for most managers, because the urge to solve is strong. Ask open questions, reflect back what you hear, and resist the impulse to fix immediately or fill silences. Often the act of being genuinely heard is itself most of what is needed; solutions frequently follow naturally once someone feels understood.

Stay calm if the other person doesn't. Strong emotions in response to feedback are normal, and your job is to absorb them without matching them. Acknowledge the feeling ('I can see this is frustrating'), keep your tone steady, and keep the focus on understanding. If emotions run too high, it's fine to pause and return to it — it's not fine to abandon it.

Close by agreeing on concrete next steps — ideally co-created, not imposed. What will each of you do, by when? Write it down if it helps. Vague endings produce vague follow-through. A specific, shared plan turns a difficult conversation into a turning point rather than an event.

Follow up. The conversation is the beginning, not the end. A brief check-in a week or two later shows that you meant it, that you're paying attention, and that the relationship is intact. Consistency over time is what builds the trust that makes the next courageous conversation easier — for both of you.