Why Leaders Avoid Tough Performance Conversations

And How to Actually Start Them

There are conversations that most leaders know they need to have. The knowing tends to come from instinct, from experience, from the quiet awareness that builds over time when you work closely with people.

Something in the organization feels off. Expectations are not being met. A behavior is showing up repeatedly. Or the dynamic on the team has shifted in a way that is hard to ignore.

And still, the conversation sits.

Not because it doesn’t matter. Not because the leader doesn’t care.

What is often underneath that delay is less about intent and more about fear. Fear of getting it wrong. Fear of how the other person will react. Fear of damaging a relationship that matters. Fear that raising the concern will make things more complicated, not less.

So the conversation waits. And the issue grows.

How Avoidance Shows Up

Avoidance is rarely deliberate.

It tends to show up quietly, through behaviors that are easy to justify in the moment:

• More time is spent gathering data, even when the pattern is already clear
• The conversation is pushed to a later moment, when there will be more time or more certainty
• Feedback is softened or redirected so that the issue is not fully named
• The symptoms are addressed, but the underlying issue is left untouched

The leader carries the concern longer than intended, and it starts to shape how they engage. Every decision made about that person, every interaction, gets filtered through an undisclosed concern. 

The individual continues without clear feedback, making it difficult to adjust their behavior and improve performance. Others on the team begin to form their own assumptions about what is acceptable.

This is not a question of intent. It is a gap in approach, and a missing skillset around what to do when the moment comes.

What Helps Leaders Start the Conversation

What stands out in practice is not that these conversations become easy. It is that they are approached with more structure and less pressure to get everything right.

A few shifts tend to make the difference:

• Creating a sounding board before the conversation
• Starting earlier, when something first feels off
• Opening with an observation or question, rather than a fully formed conclusion
• Letting the conversation unfold, instead of trying to resolve everything at once

One of the most practical pieces is how leaders prepare before they ever step into the conversation.

Shannon O’Connor Bock, president of A.J. O’Connor Associates, works with leaders on exactly this. Rather than reacting in the moment, her approach is to step back and work through the conversation in advance with someone outside, often a coach or trusted advisor. That process is not about scripting the exact words. It is about arriving at a more balanced and grounded point of view before walking in.

Typically, that includes a few things: clarifying what is actually being observed versus what might be interpreted, pressure testing whether the concern is fair and accurate, thinking through how the message might land from the other person’s perspective, and adjusting the tone so that it is direct without being overly sharp, and clear without being overly softened.

By the time the conversation happens, the thinking and intent have already been shaped. The leader brings a more considered perspective that can be communicated clearly, without carrying the same level of emotion into the room.

That preparation creates steadiness. It makes it easier to stay present in the conversation, to listen, and to adjust in real time based on how the other person responds.

What Happens Inside the Conversation

These conversations can feel like they need to carry a lot of weight.

There is often pressure to get it right, say everything that needs to be said, land it cleanly, and walk away with a clear resolution.

In practice, that expectation makes the conversation harder.

What tends to be more effective is a more deliberate, paced approach.

It often starts before the meeting itself. That means preparing ahead of time, and taking a momentary pause to center before walking in.

From there, the opening matters. Once in the room or on the phone, the goal is to name the issue in a way that is clear and measured, starting with the observation rather than a fully formed judgment or conclusion.

Once it is said, there is an instinct to keep talking, explaining, justifying, or softening the feedback.

Instead, it is important to create space for a reaction. Letting the other person process, respond, or even sit in discomfort for a moment. That space is what allows the conversation to become a dialogue, rather than a one-sided message.

It also changes the role of the leader in the room. This is less about delivering a verdict, and more about staying present, listening, and adjusting based on what comes back.

The close of the conversation matters too. Rather than trying to resolve everything on the spot, a strong close acknowledges what has been discussed and sets a clear expectation to return to it. The next step may be a follow-up conversation, a check-in, or a continuation of the discussion.

The goal is not to tie it up neatly in a single session. It is to create clarity, allow for reaction, and keep the conversation moving forward over time.

Why Timing Matters

Most of these conversations do not need to be heavy. They become heavy when they are delayed.

When a leader notices something and says nothing, the issue does not simply stay the same size. It compounds. What could have been a brief, grounded conversation about a specific behavior becomes something more layered, more charged, and harder to navigate. The concern has been carried for weeks or months. The leader has already formed impressions, made decisions, adjusted expectations, and all of it has happened without the other person knowing any of it.

That is not a fair position to put someone in.

Starting the conversation earlier is not about rushing to judgment. It is about giving the other person the information they need to respond, adjust, and have a real opportunity to change the outcome. Without that, the situation tends to move in one direction. Not because the person could not course correct, but because they never had the chance to try.

Starting earlier does not eliminate discomfort. It keeps the conversation grounded in what it actually is: a chance to share feedback and improve performance.

The Work Behind the Work

This part of leadership often goes unspoken.

Setting direction and driving results are recognized as markers of great leadership. Navigating the conversations that make those outcomes possible rarely gets the same attention. And yet it is often where the real work happens.

It is also a skill that develops with practice.

At A.J. O’Connor Associates, this is where much of our work with leaders begins. Creating space to think through how to approach these moments, building the confidence to start sooner, and strengthening the ability to handle what follows.

Because the difference is rarely whether the issue exists. It is whether it gets addressed in time.