Leadership development

The Conversation No One Is Really Having With Their Manager Anymore

By Jamie Slingerland, MCC · Co-Founder, Catalyst Coach Academy

Why real, developmental conversations between managers and employees are disappearing – and how coaching rebuilds the capacity to have them.

The Conversation We’re All Missing More and More

Think about the last time someone at work asked how you were really doing — and meant it. Not as a greeting. Not as a warm-up before the “real” agenda. A genuine question, asked by someone who stayed present for a genuine answer.

For most people below the very top levels of leadership, that kind of conversation is becoming rare. And the gap it leaves — between what people need from their manager and what they actually get — is one of the most underestimated drivers of the drop in engagement, increased turnover, and leadership failures we read about in nearly every workplace study from the last five years.

What has replaced that conversation is not silence. It’s performance management. Metrics. Check-ins that are really just status updates. One-on-ones where the agenda is the work, not the person doing it.

Leaders today are busier than ever — managing more people, in more complexity, with less time and less organizational support than a decade ago. The intention to have real conversations is often genuine. The follow-through isn’t happening.

Why It Still Isn’t Happening

When I talk with leaders about this in coaching sessions, something very consistent shows up. Most of them know these conversations aren’t happening. They feel the gap. They can name people on their team they haven’t had a real exchange with in months — not task-focused, but a genuine conversation about where that person is, what they’re wrestling with, what they actually need.

When I ask what gets in the way, the answers almost always come down to three things.

• Time. Real conversations feel like they take more time than a status update. So they’re continually postponed.
• Skill. Asking how someone is really doing — and staying present for the real answer — is not a natural competency for most leaders. Most were developed for outcomes and decision-making, not for the depth of listening real developmental conversations require.
• Psychological safety. This is the least discussed, and perhaps the most important. Many leaders don’t know what to do if someone actually tells them the truth. What if they hear that someone is overloaded? What if that person is considering leaving? What if they reveal something the leader doesn’t know how to hold? The fear of opening a door they don’t know how to walk through keeps many leaders from opening it at all.

Why Telling Managers “Have Better Conversations” Doesn’t Work

The advice is everywhere: have more one-on-ones, ask better questions, be more present. Leaders have heard it. Most of them genuinely want to do it. And yet the conversations still aren’t happening with the quality or frequency that’s needed.

The reason is that leading an authentic, developmental conversation is a skill — a deep one. It’s not a communication technique you can pick up in a workshop. It’s a capacity you build through practice, feedback, and an honest look at what you’re actually doing when you’re supposedly listening to someone.

Here’s what I mean. Most leaders who think they’re asking how someone is doing are really just waiting for the answer that will burden them the least. They’re hoping to hear “good, all good,” so they can move on to the “real” agenda. Their listening is confirmatory, not genuinely curious. And people feel that. They sense the contours of what their manager truly has space for, and they give them exactly that answer.

Coaching training develops something different. The capacity to ask a question and actually mean it. To stay in the discomfort of not knowing the answer in advance. To follow the thread of what someone is really saying instead of steering the conversation toward the conclusion you already had in mind. To hold silence without filling it. To receive hard information without immediately managing it.

These are not “soft” skills. They are highly demanding capabilities that most leaders have never had the chance to develop — because most leadership development programs don’t touch them at all.

A Moment I Come Back to Often

A few years ago, I was coaching a senior leader in a company going through major restructuring. On paper, his team was delivering. The numbers looked fine. Retention was holding.

I asked him when he had last had a real conversation with each of his direct reports. Not a check-in. A real one.

He thought about it for a long moment. Then he named one person he hadn’t had that kind of exchange with for almost eight months.

We spent the next thirty minutes on that one relationship. Not on strategy. Not on what to say. On what was actually happening inside him when he thought about opening that conversation — what he was afraid of hearing, what he assumed he wouldn’t be able to handle, what it would mean about him as a leader if that person wasn’t doing as well as the numbers suggested.

What emerged wasn’t complicated. He was afraid that this person was considering leaving and didn’t know how to have that conversation without making promises he couldn’t keep or losing someone he deeply valued. So he avoided it — unconsciously, but effectively.

Two weeks later, he had the conversation. The person wasn’t leaving. They were struggling with something he could actually help with. The relationship shifted in a way neither of them had expected.

Nothing about that outcome required technique. It required a leader who had looked at what was keeping him from showing up in that conversation — and who had enough clarity to walk through that door anyway.

That’s what coaching develops. Not a script. A capacity.

What the Research Is Actually Saying

This isn’t a “soft” argument. According to Gallup, managers account for at least 70 percent of the variance in employee engagement scores. The most consistent predictor of whether someone stays in a role is the quality of their relationship with their direct manager — not compensation, not alignment with the mission, not career development programs. It’s their manager.^¹

And yet most organizations invest in manager development in ways that create only surface-level improvements — the kind that show up in training evaluations and disappear from behavior within ninety days. A feedback workshop. A seminar on difficult conversations. A module on psychological safety.

None of these are bad. But none of them build the underlying capacity that makes the difference in the critical moment — when a manager is sitting across from someone who is struggling, and the question is whether they have the presence, skill, and willingness to truly be in that conversation instead of just managing it.

ICF-accredited coaching training develops that capacity in a way traditional leadership development can’t. Not because it’s more inspirational or better designed — though I believe it often is. But because it requires real practice. Real coaching conversations with real feedback from certified coaches who pay attention to what is actually happening, not just to what the leader intended to do.

That’s what changes behavior. Not information. Practice under observation. Feedback from someone who has done this work at a high level and can see what you’re missing.

A Question Worth Sitting With

If you’re a leader reading this: is there someone on your team who — if you’re honest with yourself — has gone too long without having a real conversation with you? Not a task update. Not a performance review. A genuine exchange where you authentically wanted to know how they were doing and were fully present for the answer.

If that person exists — the question isn’t what to say. You probably already know what to ask.

The question is: what is keeping you from having that conversation.

That question, taken seriously and honestly with yourself, is where real leadership development begins.

A Call to Action: If You Want Your Managers to Truly Have These Conversations

At Catalyst Coach Academy, we train managers and leaders in ICF-accredited coaching skills — not as a communication add-on, but as a fundamental capacity that changes how they lead people and conversations at work.

Our Level 1 program is designed for people doing real work in real organizations who want to show up differently in the conversations that matter most — the ones that shape engagement, retention, and the courage to tell the truth.

If you’re considering whether coaching training is the right investment for your leaders, we’d be glad to talk about what it could look like in your context — without pressure, and with the same quality of listening we teach managers.

About the Author

Jamie Slingerland, MCC, is a leadership coach, ICF Mentor Coach, and co-founder of Catalyst Coach Academy. For over 20 years, he has worked with leaders facing significant change and has completed more than 6,500 hours of coaching with executives and teams across a wide range of industries.

¹ Gallup, State of the American Manager, gallup.com