Difficult discussions

One of the hardest parts of leading any organisation isn’t the strategy, the OKRs, or the architecture decisions. It’s the conversations. The tough ones. The ones where you’re delivering bad news, addressing underperformance, or making a call that impacts people’s careers and in some cases their livelihoods.

Even seasoned leaders often stumble here. We soften the message. We delay. We package it in so much context and cautious language that by the time we finally reach the point, it’s diluted. Worse, the person leaves unclear on what’s actually happening or why. That’s a trust killer in any company, but especially in a large organisation where decisions ripple widely and quickly.

When you lead at scale, clarity isn’t optional it’s an obligation. People depend on you to say what you mean, early and plainly. Being direct isn’t about being abrupt or unkind; it’s about being fair and respectful. Clear is kind, unclear is unkind. The earlier you share the truth, the more chance there is for understanding, course correction, and preserving trust.

Over the years, I’ve found a few approaches that work, most of them shaped by failures and hard learned lessons, especially when the stakes are high and the conversation is going to be uncomfortable.

• Lead with the core message. Don’t bury it under context. If performance is an issue, say so early. If a decision has been made, make that clear before explaining the reasoning.
• Provide full context, not just the “what”. People deserve to understand the why, including business drivers, strategic trade-offs, or data that led to the decision. It doesn’t make the news easier, but it makes it make sense.
• Share responsibility when it exists. If leadership decisions, resource constraints, or organisational shifts contributed to the problem, own your part. It signals integrity and balance.
• Give a path forward where possible. A tough conversation should either end with clear improvement steps, support options, or clarity about finality. Leaving people in limbo creates unnecessary anxiety and speculation.
• Model the behaviour you expect. The way you handle these discussions sets the tone for your leadership team. Coach them to follow the same approach and make it safe for them to ask for guidance before, during, or after a challenging conversation.
• Avoid the “feedback sandwich”. Wrapping the bad news between two positives often confuses the message. Recognition has its place, but it should not dilute critical feedback or clarity of a decision.
• Choose the right setting. Delivering difficult news in a group setting or over a rushed video call shows a lack of respect. Privacy and presence matter so schedule enough time and avoid interruptions.
• Follow up in writing. In a large organisation, conversations can be misremembered or misinterpreted. A clear, respectful written summary helps align on what was said and the next steps.

Scaling this approach across an organisation requires more than personal discipline it requires cultural reinforcement. At companies like Unity, leaders were expected to treat direct communication as a core leadership skill, developing it through manager training, role-playing scenarios, and peer accountability for how messages are delivered. Post-mortems on major changes often include reviewing communication quality, not just the decision itself. This reinforces a culture where people see clarity as care, not conflict.

Being direct doesn’t mean being cold. It means giving people the truth they need to navigate their careers, understand the business, and decide their own next steps. It shows respect for their intelligence and their ability to handle reality. And over time, it builds a reputation for fairness that will serve you far longer than any single decision.

The next time you’re faced with a conversation you’d rather avoid, take a breath, step into it early, and say it straight. In leadership, the uncomfortable truth told well will always earn you more trust than the perfectly worded delay.