Difficult Leadership Conversations Matter: Stop Avoiding Them

Difficult Leadership Conversations Matter: Stop Avoiding Them

Being a leader sucks most of the time. If you think it’s easy or fun, you either aren’t one or you’re not a good one. Recently, my 8-year-old son declared he wanted to be a leader “to boss people around…like you.”

“But if I’m the boss,” I replied, “why don’t you ever listen to me?”

This innocent exchange highlighted a harsh reality: many people, even adults, have no idea what leadership truly entails. The image of a leader commanding a room, making decisive calls, and driving a team to success is alluring. But the reality is quite different—it’s a constant battle with discomfort. And quite often, I lose.

The Uncomfortable Core: Difficult Leadership Conversations

The most critical skill for a high-performing leader in a high-impact organization isn’t strategic vision or charismatic communication—it’s the willingness to confront anything in your organization that doesn’t drive results.

Here’s what real leadership looks like:

  • An employee is giving it their all, but the output is mediocre. Their dedication is unquestionable, but the results aren’t there. Recognition of their limited capability means a salary cut.
  • An employee has a family dependent on their salary but needs to be let go. The personal ramifications are heavy, but keeping them on board could be detrimental to the team.
  • The senior leadership team is afraid to speak the truth, creating a culture where problems fester instead of being resolved.

Now, I know what you’re thinking: “Isn’t this just treating people like replaceable parts, sacrificing human dignity at the altar of corporate profits?” Absolutely not. This is about understanding the profound impact that a healthy company has on everyone involved—including their families and personal lives.

The Cost of Avoiding Difficult Leadership Conversations

Everyone remembers William Hung’s American Idol audition in 2004. His painfully off-key performance revealed a deeper truth: his parents, friends, and teachers all knew he couldn’t sing, yet no one told him. It shouldn’t have taken Simon Cowell on national television to let him know (nor the myriad others who’ve followed in his footsteps).

As a result, society was openly auditorily assaulted in every elevator, grocery store, and shopping mall we entered for months on end. The inability of the people who supposedly loved that guy to express it via the truth caused what may be irreversible damage to psyches everywhere, not to mention the long-term impact on music history.

Silly as the example may be (though spot on), it demonstrates the truth that when leaders shy away from tough discussions, it doesn’t just affect those directly involved—it impacts the entire team.

  • High performers become demotivated when they see underperformance going unaddressed.
  • Trust erodes as teams notice leaders avoiding problems.
  • Innovation stalls when feedback isn’t shared openly.

By confronting challenges head-on, however, leaders foster an environment where excellence is the standard, and everyone sees that their contributions matter.

The Power of Truth-Telling: Making Difficult Leadership Conversations Work for You

Jeff Bezos said it this way, “Any high-performing organization has to have mechanisms and a culture that supports truth-telling. Truths often don’t want to be heard. Important truths can be uncomfortable, awkward, exhausting, challenging.”

I’ll admit, I’m writing this because I struggle with a desire to have all of the people like me. All of them. Confronting others with hard news feels big and painful and anti- the thing I want, so I don’t want to do it. In fact, there are times I wish I could hire someone whose sole job it is to tell everyone what I see but want to avoid addressing myself. It’s tempting to delegate the discomfort, but leadership demands that we step into it—personally. Sucks, right?

But it’s not about being ruthless or unemotional; it’s about understanding that avoiding these conversations is ultimately unkind, not to mention that they can sink your business. By not addressing the issues, we deny others the opportunity to grow and improve, we risk the health of the organization and, by extension, we place everyone’s livelihoods in jeopardy.

Leadership isn’t about enjoying a position of power and ignoring the accompanying challenges. It’s about making tough decisions, having hard conversations, and not tolerating the things that negatively impact the organization – even when it feels like “the worst.” It’s really hard, but by avoiding these conversations, you risk far greater harm—to your organization, your team, and yourself.

So leaders, let’s acknowledge the discomfort and choose to engage in difficult leadership conversations anyway, so that we can become the leaders our organizations need and they can grow and prosper in health in the days to come.

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