Good Leaders & Tough Conversations

Maxwell Wessel
3 min readJun 17, 2022

Good leaders care. They care about their customers, they care about the quality of their work, and, most importantly, they care about their people. And because of that, it can be difficult for good leaders to have performance conversations with employees. Anyone who cares struggles with sharing bad news — especially when it’s personal.

But avoiding tough conversations is a short term kindness that leads to a long term cancer. It’s a diet heavy on ice cream and low on vegetables. Every day, I find myself coaching the leaders on my team on people topics. Rarely do they need guidance on how to celebrate their team’s successes — and not because there aren’t wins (the wins are numerous!), but because it’s easy to celebrate the rock star performers. Instead, more often than not, these leaders are looking for help on how to best address performance challenges.

When a leader is struggling to talk to an employee about failing to meet expectations, I remind them of three things I’ve learned over the years:

If people don’t know they have an issue, they can’t fix it.

No one wakes up in the morning and thinks, I want to be shitty at my job. No one wakes up hoping their manager and teammates won’t trust them. Often, someone who is failing to meet expectations may not know it — or may not realize how bad it is. As a leader, you owe your people the opportunity to understand their failures and take steps to do better. It may be a tough conversation to have, but it’s a fair one to the employee. Because you care, you will give them the opportunity to understand the issue — and explain what happened, make improvements, or move on.

Tolerating mediocrity weighs on the team.

It’s awesome to give high performers a pat on the back. But when we don’t challenge everyone to contribute equally, everyone else notices. The rest of the team has to pick up the slack — and can easily reach burnout. This is too real and too infrequently talked about. It often goes unnoticed by leaders. Often a team’s high performers get tasked with more and more responsibility. And they won’t complain until the day they walk out the door for greener pastures. A players hire A players — and A teammates want A teammates. A great team wants to rely on everyone for contribution. As a leader, don’t sacrifice the good of the bulk of your people to spare you the pain of an uncomfortable conversation.

Talent density raises everyone’s output.

Finally, I remind my leaders that the juice is worth the squeeze. When you build an organization that takes performance seriously, the benefits have expansive impact. If a team tolerates weak performance, every employee will be waiting for the next ball to drop. This expectation of failure is a distraction that fosters a culture of second guessing and siloed operations. On the other hand, a team focused on talent density will have increased trust, speed, and diversity of ideas. Employees will have an easier time trying big things — and succeeding — knowing that their teammates will amplify their efforts, provide good feedback, and independently manage their own responsibilities. When performance is well managed, everyone performs better.

Performance conversations can be immensely uncomfortable. But often the most critical step that a leader can take on their path to building a strong team is having them openly and often. Not because they don’t care about the happiness of their people — but precisely because they do.

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Maxwell Wessel

President @ Degreed. Believer in human potential. Repeat founder. Recovering VC. Faculty member. Lucky recipient of great friends, family, and colleagues.