About the Author: Zachary Gleason works as a strategy and execution consultant to independent agencies.  As a part of this, he works with countless sales professionals and sales leaders in helping them take themselves and their teams to levels of sales strategy and performance.  

Leadership isn’t about being well-liked. It’s not about making people feel good or avoiding discomfort. It’s about driving results while helping people become the best versions of themselves. And that requires honesty—real, sometimes uncomfortable, unfiltered honesty. But honesty without empathy is cruelty. And empathy without honesty is negligence.

The best leaders master the balance between the two, ensuring that their teams not only hear the truth but also feel supported in rising to meet it. This balance is critical because, at some point, every leader faces a version of the same problem: a team member who isn’t improving, despite repeated feedback. The question isn’t whether the issue should be addressed—the question is how.

The Brutal Facts: A Case Study in Underperformance

Underperformance is a reality that plagues organizations everywhere. Consider Benedict, who has been in his role for a year and a half. He has received clear expectations, multiple rounds of feedback, and repeated guidance on improvement.

Yet, the same issues persist—missed deadlines, neglected processes, and a lack of accountability. His manager, Susan, has been patient but is reaching her limit. She’s pointed out the gaps, given explicit directives, and offered support. Benedict’s response? A casual, “My bad, sorry, I forgot.” So, what’s the right way to handle this?

The Leadership Process: A Tactical Approach to Honest Feedback

1. Set Clear Expectations—Again and Again

One of the biggest mistakes leaders make is assuming that stating expectations once is enough. If someone repeatedly falls short, revisit expectations explicitly. Make underperformance an impossibility, not an accident. Leaders must eliminate ambiguity. If the same questions need to be asked in every meeting, then so be it. Then, if performance isn’t improving, the issue isn’t a lack of reminders—it’s a lack of accountability.

2. Remove the Excuses

Leaders often default to giving underperformers the benefit of the doubt. But at some point, “he’s trying” isn’t enough. The real question is, “Is he actually improving?”

Effort without results is meaningless. Hope isn’t a strategy, and assuming someone will “get better with time” is just leadership procrastination. If performance isn’t trending upward, then something must change—either in expectations, management, or the team itself.

3. Turn Performance Management into a Process, Not an Event

Accountability doesn’t come from a single tough conversation, it’s a structured, ongoing process. Weekly check-ins, trackable progress, and objective measures eliminate excuses and create undeniable clarity. Leaders should treat performance management like a system. Instead of waiting for deadlines to be missed, the conversation should always be, “We are four weeks out—where are we?” If it’s not being tracked, it’s not being managed.

4. Recognize That Honesty is the Most Empathetic Thing You Can Do

One of the biggest disservices a leader can do to an employee is allowing them to believe they’re doing fine when they’re not. Avoiding hard conversations doesn’t protect someone—it sets them up for failure. The best leaders aren’t perfect, but they don’t let their own imperfections stop them from holding others accountable. Tough conversations may be uncomfortable, but letting dysfunction fester is far worse.

5. Accept That Not Everyone Will Elevate

Some people simply won’t improve, and that’s a reality leaders must accept. The critical mistake organizations make is allowing underperformers to drag down the standard for everyone else. High-performance cultures aren’t built on leniency. If mediocrity is tolerated, it becomes the norm. Leaders who refuse to make hard decisions about their teams ultimately limit the organization’s potential.

6. Leaders Don’t Have to Be Perfect to Hold High Expectations

Too many leaders hesitate to enforce standards because they fear their own flaws disqualify them from doing so. But leadership isn’t about being perfect—it’s about setting direction. Strong leaders recognize their gaps and hire to strengthen the team rather than using personal imperfection as an excuse to avoid accountability.

What matters isn’t flawless execution—it’s the willingness to push the team forward despite the discomfort.

The Bottom Line

If you want a high-performing team, you must be honest. And if you want that honesty to drive change, you must be empathetic. The balance between these two forces separates transformational leaders from those who merely maintain the status quo.

Yes, leadership is hard. Yes, uncomfortable conversations are inevitable. But the alternative—avoiding honesty, tolerating underperformance, and enabling mediocrity—is far worse. A leader’s job isn’t to keep people comfortable. It’s to make them better.