How to deliver difficult news
Jun 10th 2025 | leadership | management
I first became an engineering manager while at Twitter. Like most new managers, I knew nothing about the role. Fortunately, Dick Costolo, CEO at the time, personally ran a class for new managers - and my god, I needed it.
One part that burned itself into my mind is regarding something that every manager dreads - delivering difficult messages. Whether it's a layoff, some difficult feedback, a disappointing performance review - this is where you can make or break relationships with your team. Dick's message:
Your job is to deliver the message, not to make them feel better in the moment.
Optimise for clarity.
This sounds blindingly obvious and is written about in mountains of management literature but still, in my experience, too many managers do the opposite. They care about their team (good!), and they want to soften the blow (understandable), that instinct often undermines your objective - that they've actually understood the message. That's categorically not showing care for that person.
Here’s how to do it properly:
DO:
- Deliver the message clearly. Fewer words are better. Ensure they understand the message.
- Own the decision and explain why this is happening.
- Answer questions about what it means for them. Ensure they know what happens next.
- Once you've done the above, end the meeting.
DON'T:
- Get drawn into litigating the decision.
- Pass the buck - you are delivering the message, it's your message now.
- Draw out the meeting by adding uneccessary commentary or platitudes.
Let them process. Give space. Follow up later—maybe with others—to support them through whatever happens next.