One of the hardest responsibilities of leadership is having a difficult conversation.
Most leaders don’t look forward to them. They know the conversation may be uncomfortable, emotional, or awkward. But they also know avoiding it rarely makes things better.
Eventually, they work up the courage to have the conversation. They rehearse what they want to say. They worry about how the employee will react. But they finally sit down and address the issue.
However, in wanting to avoid conflict or simply wanting to be kind, the message gets softened. A few concerns are mentioned, but the expectations aren’t communicated as clearly as the leader intended. The conversation ends, and both people leave with very different understandings of what just happened.
The leader walks away thinking, “I’m glad that’s over.” Maybe even, “I think I was pretty clear.”
The employee walks away thinking, ” Overall, I think I’m doing okay.”
Weeks go by. Nothing changes.
The leader becomes increasingly frustrated, while the employee assumes things must be improving because they haven’t heard otherwise.
In the absence of follow-up, both people naturally begin filling in the blanks with their own assumptions. Before long, they’re working from two completely different understandings of what’s happening.
The employee has no way of knowing whether they’re making progress, whether the issue is more serious than they realized, or what still needs to change. Meanwhile, the leader grows increasingly frustrated, assuming the employee simply isn’t improving.
Think about it: none of us wants to walk around with food stuck in our teeth while everyone else notices, but no one tells us. Yet that’s exactly what happens in organizations every day. People can’t consistently improve what they don’t clearly understand.
That first difficult conversation draws a new line in the sand and brings clarity to what needs to change. It creates awareness, and follow-up builds accountability. Together, they give people the opportunity to improve.
But too often, meaningful follow-up doesn’t happen. If you’re going to be an effective leader, you have to make the time to come back, continue the dialogue, reinforce expectations, and help people move forward. Only then can people genuinely improve. And if improvement still doesn’t happen, you’ll know the decision to part ways was made thoughtfully, fairly, and after every reasonable opportunity to succeed was given.