Having the Hardest Conversations Requires the Deepest Caring

Leaders who care about people naturally want what is best for them. They do whatever they can to prop up, support, and encourage those on the team who underperform. They hope the optimism they project will become self-fulfilling over time, lighting a fire or burnishing new skills. 

At some point, however, reality takes charge. Over time, underperformers lose confidence. And the respect of their teammates. They struggle to add value to a team that has surpassed their skills and talents. 

Compassionate leaders often ignore the signs of a sinking ship precisely because they care. They rationalize that the best thing for the underperforming team member is to struggle through their setback and to do so in the midst of a team that values and cares about them. 

Unintentionally, leaders who travel this path hold people hostage. Despite the fact they cannot succeed in the current role, team, or assignments, they keep them in the seat because they care. 

Imagine waking up every day and looking into the mirror, knowing you will fail again today. The torture that must be. But leaders who refuse to make the tough call and have the hard conversation keep this nightmare alive. In their supposed caring about this team member, they refuse to acknowledge that what is transpiring is inflicting long-term damage on this person’s ability to succeed at anything, anywhere. 

That doesn’t sound like true compassion and caring. And it isn’t. 

As harsh as this might sound, the real reason many leaders don’t have the hard conversation is because they don’t care enough. If they truly cared deeply, they would be willing to say what needs to be said and to give this team member a new lease on life. 

Admitting that both the leader (in selection, coaching, or assignment) and the team member have failed is required. Working to find a better place for this underperformer is the real sign of deeply caring for their well-being. 

Good leaders don’t deny this reality with wishful thinking. The most humane and caring thing they can do is to force an end to the relationship and push people to other opportunities and organizations. 

With a fresh start and a new set of colleagues who are not tainted by past underperformance, good things can happen. Suggesting they find a role that matches their skills is yet another hard conversation to have. But that’s what truly caring leaders do. They want what is best for people and sometimes what is best isn’t on our team. 

The funny thing is that hard conversations only get easier when we don’t care. For those with a conscience, they are excruciatingly painful. But good leaders have them because they are compassionate people. They make the right call and have the tough conversations because they care enough to do so.