The hardest conversation

Joe Greenheron
Practical Empathy
Published in
2 min readApr 5, 2019
Hostess bows to guest in a traditional tea ceremony. Japan, Oct 2017

Conventional wisdom in management is that the hardest conversation to have with an employee is the “termination”, where you’re letting an employee know that this is their final day at your company, usually due to an uncorrected performance problem.

I don’t want to minimize the challenges of having this conversation. It’s the worst conversation a manager can have. It’s soul-crushing. It never gets easier.

But the “termination” discussion is only the second-hardest conversation a manager can have with an employee. The hardest conversation is the one that precedes the termination, which I call the “job in jeopardy” (JIJ) conversation.

Here’s why:

If a manager screws up the termination discussion, the consequences could be pretty bad: the employee won’t leave the company with the dignity they deserve; the manager won’t communicate their own role in the situation (e.g. were they not coaching the employee effectively enough?).

But no matter how bad it’s botched, the result is mostly the same: the employee gathers their stuff, and is escorted out of the building. The manager gathers the remaining team, explains what happened, and reassures them that they’re not next.

On the other hand, the JIJ conversation is the last chance to pull up on the yoke before the plane crashes into the ground. In other words, the difference between a perfectly executed JIJ and a botched one is HUGE.

In the perfect situation, the manager is clear with the employee about what specifically needs to change about their performance and why (context), what change looks like (goals), the consequences of either path (turnaround or not), and pledges support through the process. And lets the employee know they can fix this!

In the botched situation, none of the above happens because, e.g., the manager is stuck thinking that ruinous empathy is the kindest way to approach this problem. That’s what the brains of conflict-adverse folks trick their mouths into believing, but the opposite is true: clear is kind.

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