I strongly believe there are two ways to approach a hard conversation. You can be clear, or you can be liked.
The mistake I made was trying to be both.
I've read plenty of advice saying that radical transparency is the goal. But in practice, I often settled for polite avoidance. I waited for the perfect moment, the right mood, or the next performance review to say what needed to be said.
The assumption I made was that by softening the message, I’d be kind. I would wrap the truth in layers of context and compliments, hoping the other person will find the point buried somewhere in the middle.
But clarity is the highest form of kindness.
Trying to soften the blow doesn't actually make it easier for the other person. You’re just making it easier for yourself to deliver.
I struggled with this for a long time. I hated the idea of being the mean manager. So, I used the sandwich method: a compliment, the real issue, and another compliment. I thought I was being supportive.
What I was actually doing was being confusing. My team would walk out of the room thinking everything was fine, while the actual problem continued to grow.
That dynamic protects your reputation in the short term, but it destroys your team in the long term.
Difficult feedback isn’t an attack on someone’s character. It’s an observation of a gap between where they are and where they need to be. If you don’t point out the gap, they’ll never know they’re falling into it.
The problem is that we view feedback like an event. A big, scary confrontation. I think it's more useful to treat feedback like a temperature check.
When you wait until a problem is big enough to mention, you’ve already waited too long. By then, your frustration has built up, and the feedback feels like a judgment rather than a course correction.
One thing that has helped me is moving the goalpost. Instead of trying to make the conversation comfortable, I try to make it brief.
State the observation, state the impact, and then stop talking.
The silence that follows is the hardest part. It’s the moment where you want to jump back in and justify yourself, or tell them they’re still doing a great job, or take back half of what you just said.
The work of a leader is to sit in that silence and let the other person process the truth.
Have a good one.
- - Good Enough