The Workshop I Almost Ran
A few years back I built a training session I was proud of. Deep dive into system architecture, the kind of thing I'd talk about for three hours without a slide deck. I booked the room, blocked the calendar, told my team we'd spend an afternoon on it.
Two days before, one of my engineers asked if we might talk about something else instead: how to run a difficult conversation with a stakeholder who kept overriding her decisions. She'd been dreading a meeting all week. She didn't need architecture theory. She needed a script and a bit of courage.
I nearly said no. Not out loud, but in my head. I'd already written the slides. I liked the topic. It made me look sharp in front of the room.
I canceled the architecture session and we spent the afternoon role-playing her conversation instead. It was awkward and useful and nothing like what I'd planned to teach.
The afternoon taught me more about leadership than the architecture deck ever would have.
When Teaching Becomes Therapy
Here's the pattern I see in leaders everywhere, myself included: we pick training topics based on what we enjoy explaining, not what the team is stuck on. We run the workshop we're good at. We recommend the book we loved. We coach people toward the career path we wish someone had shown us.
None of it is malicious. It feels generous. We're sharing what we know.
But if the topic is chosen because it makes the leader feel competent and needed, rather than because it closes a gap the team has, the session isn't leadership development. It's the leader's own therapy, delivered to a captive audience.
The tell is simple: does the topic come from a conversation with your team, or from your own comfort zone?
The Numbers Back This Up
LinkedIn's 2025 Workplace Learning Report found only 15% of employees said their manager helped them build a career plan in the past six months. Down five points from the year before.
I don't think most of those managers stopped caring. I think they got busy, and busy managers default to whatever development topic is easiest to deliver: the one already sitting in their own head. Building a career plan with someone requires listening first. Running your favorite workshop requires nothing but a slide deck you already own.
Easy wins over useful, every time we let it.
It shows up on the receiving end too. eLearning Industry reports less than a third of employees, 29%, are satisfied with the learning and development opportunities offered to them for career progression. Not the training itself. The development chosen on their behalf. When leaders pick topics from their own comfort zone instead of a real conversation, the gap between what's offered and what's needed keeps widening, one well-intentioned workshop at a time.
Ego Dressed Up as Generosity
The uncomfortable part of this isn't the busyness. It's the ego hiding underneath it.
Teaching what you love feels like generosity because you're giving away something real. But look closer and half the time you're asking the room to admire what you know. You get to be the expert again. You get the nodding heads. You get to relive the version of yourself who first fell for the topic.
Your team walks out having learned something adjacent to useful, and you walk out having felt important. Everyone's satisfied enough nobody asks whether the hour was worth it.
I've done this more than once. I'd guess most leaders reading this have too.
It Isn't Only Training Sessions
Once I started noticing this pattern in myself, I saw it everywhere else too.
The book recommendation you hand a struggling manager. Was it chosen because it fixes the exact gap they're facing, or because it's the book which changed your own career and you've been waiting years for someone to hand it to?
The career advice you give a junior engineer who wants to move into architecture. Are you describing the path fitting their strengths, or the path you took, rebuilt as the only correct route because it worked for you?
The feedback you give in a performance review. Is it about the skill this person needs to grow, or the skill you happen to value most because it's the one you're strongest in?
I once spent a year pushing an engineer on my team toward public speaking. I loved presenting. I thought it was the fastest route to visibility and influence, and I said so, often. What she wanted was deeper ownership of a system nobody else understood well enough to touch. I was coaching her toward my own strengths instead of her goals, dressed up as mentorship.
She told me this, eventually, in a one-on-one I still remember for how uncomfortable it was. She was right. I'd mistaken my enthusiasm for her interest.
Stepping back from the training room, the same test applies everywhere a leader hands something down: a book, a skill, a piece of advice, a stretch assignment. Ask whether it answers a gap the other person named, or a story the leader wants to keep telling about themselves.
What I Do Differently Now
A few things changed for me after the canceled architecture session:
I ask before I plan. "What's the thing you wish someone had taught you this quarter?" is a five-minute conversation and it will wreck your carefully prepared curriculum in the best way.
I watch the one-on-ones, not the roadmap. Skill gaps showing up as hesitation, avoidance, or a repeated stumble in a 1:1 are almost always more urgent than the topic I'd pick for myself.
I let go of the topics I'm best at. If I'm the most qualified person in the building to teach something, it's often a sign I should find someone else to teach it, or find out whether the team needs it at all.
I treat "I don't know what they need yet" as an acceptable answer. Better to ask a second round of questions than to fill the gap with a topic chosen to flatter me.
None of this makes for a tidier training calendar. It makes for a team getting what it needs instead of what I most wanted to give.
The Real Job
Leadership development isn't a stage for the leader. It's a service for the people in the room. If a session, a book recommendation, or a piece of coaching says more about what you enjoy than about what your team is stuck on, it's worth asking who the hour was for.
What's the last thing you taught your team because you loved it, not because they needed it?