Coaching is having a moment. Everyone's talking about it, investing in it, building it into performance reviews like it's the organizational equivalent of kale smoothies. And yet? Most people still feel stuck.
Here's what I see constantly in my work: coaching conversations are happening, but real development often isn't. Employees (and leaders) walk out of sessions feeling motivated and clear, then walk right back into the same systems, pressures, and habits that created the problem in the first place. It's like going to therapy, having a breakthrough, and then immediately texting your ex.
It's not that coaching doesn't work. It's that we've built a development ecosystem that's advice-heavy and practice-light. We're all insight, no reps.
The Insight Trap (Or: Why Knowing Better ≠ Doing Better)
Most coaching today lives in conversation. We reflect. We ask powerful questions. We surface insight. And those moments? They're gold. They create awareness, perspective, relief — sometimes even breakthroughs that feel like the leadership equivalent of finding money in your coat pocket.
But here's the thing: insight alone doesn't change behavior.
You don't become a better communicator by knowing you should listen more. You don't lead through conflict by understanding the theory. You get better by practicing — in safe, relevant, real-world conditions — until the new behavior becomes muscle memory. Otherwise, you're just collecting leadership wisdom like Pinterest boards: beautiful, inspiring, and completely unused.
Without that practice:
Old habits reassert themselves the second pressure hits (hello, fight-or-flight mode)
Confidence erodes when situations feel unfamiliar
Growth stays theoretical instead of embodied (a.k.a. "I know I should, but...")
This is especially true for leaders navigating complexity, conflict, and constant change. Insight is the starting point, not the finish line. It's the trailer, not the movie.
How Humans Actually Learn (Spoiler: Not by Osmosis)
The most effective development environments mirror how we're wired to grow:
We reflect.
We try.
We miss.
We adjust.
We repeat.
Reinforcement doesn't mean drilling people or over-structuring growth like some kind of corporate boot camp. It means giving leaders the chance to practice new behaviors intentionally before they're tested in high-stakes moments. That's where coaching becomes sustainable — not because the conversations stop, but because they're supported by systems that turn insight into action.
You know, like how you don't learn to ride a bike by reading about it.
Where AI Fits (and Where It Absolutely Doesn't)
Let me be clear: AI should not replace coaching, judgment, or human connection. It can't understand nuance or emotional context the way a human coach can. It doesn't hold space for vulnerability. It doesn't ask the question that shifts everything. And it definitely can't read the room when someone's about to cry or rage-quit. Simply put: AI lacks Emotional Intelligence.
What it can do — when used thoughtfully — is:
Surface patterns that are hard to see manually (because humans have blind spots the size of Texas)
Reduce subjectivity in performance feedback (goodbye, "cultural fit" as code for "I just vibe with this person")
Create consistent, repeatable practice environments (like a flight simulator, but for difficult conversations)
Extend learning beyond one-on-one conversations (because not everyone has access to a coach 24/7)
When used well, technology supports awareness and reinforcement. When used poorly, it overwhelms, distances, or dehumanizes. The distinction matters. A lot. Like, "this could make or break your culture" a lot.
What to Look for in Tools (If You're Going to Use Them)
Not all technology supports human-centered leadership. Some of it just... surveils people with extra steps. Before adopting tools, ask:
✅ Does this reinforce learning, or just measure it? (Dashboards ≠ development)
✅ Does it reduce judgment and subjectivity, or increase it? (Looking at you, "culture fit" algorithms)
✅ Does it help people practice safely, or perform for a score? (We're building leaders, not training circus animals)
✅ Does it align with our values, not just our metrics? (Because what gets measured gets managed, and what gets managed can get... weird)
The right tools should make coaching more effective, not more complicated. If your tech stack requires a PhD to navigate, you've lost the plot.
Why I Work with SymTrain (And No, They Didn't Pay Me to Say This)
I'm intentional about the tools I align with, because they reflect how I believe leadership development should work. One tool that's become central to my training and coaching strategy is SymTrain — because it directly addresses the biggest gap I see in organizations: the disconnect between coaching conversations and real behavioral change.
What stands out to me isn't just the technology. It's the philosophy behind it:
🎯 Training and coaching should be human-centered, not punitive (no one learns when they're terrified)
🎯 Data should support development, not replace judgment (numbers tell you what, not why)
🎯 Practice should be embedded into the flow of work, not bolted on (because "mandatory training modules" are where motivation goes to die)
SymTrain's AI-powered simulations create realistic, low-risk environments where leaders and teams can:
Practice difficult conversations (without the actual difficult consequences)
Reinforce new behaviors (through repetition, not shame)
Build confidence through practice (not trial by fire, or worse, trial by Slack thread)
Their approach treats technology as a support system for leaders — making it easy to build, manage, and deploy customized AI simulation training programs at scale. Leaders get to practice, reflect, and improve before they're in high-stakes, live situations. You know, like how pilots train in simulators before flying actual planes full of actual people.
The result? Organizations can scale coaching without losing empathy. Teams move faster to proficiency. Friction and burnout decrease. Confidence builds through repetition, not trial by fire (or trial by "let's see what happens in this all-hands meeting").
If you're exploring how to bring coaching, learning, and performance closer together in a way that feels supportive (not surveillance-y), you can learn more about SymTrain's approach here.
Coaching That Lasts (Not Just Coaching That Feels Good)
The future of leadership development isn't human or AI. It's human and intentional systems working together. Like peanut butter and jelly.
Coaching works when people feel seen, supported, and challenged — and when they're given the opportunity to practice who they're becoming, not just talk about it. That's where real growth happens. Not in the insight. In the repetitions.
Because here's the truth: you can't workshop your way to transformation. You have to do the thing. Repeatedly. Until it stops feeling awkward and starts feeling like you.
Want to go deeper into these ideas?
Watch my full Coach's Corner conversation with Dan McCann, CEO & Founder at SymTrain, where we explore modern coaching, AI, and human-centered leadership in practice.