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The Harder Play
Unstuck Monthly | February 2026
Leading well when the culture above you doesn't — that takes a specific kind of nerve.
A few weeks ago I was with a group of mid-level managers — a client's leadership development program I've been running over the last few years. We were deep in a conversation about servant leadership: what it asks of you, what it gives back, why it works.
Someone stopped the conversation cold.
"This all makes sense," she said, "but my leadership doesn't operate this way. So what's the point?"
The room got quiet. Because she was right. And everyone in that room had felt exactly that.
The Trap in the Middle
Leaders at all levels, but especially mid-level managers, live in a structural trap. They're accountable upward to leaders who may not model what they're trying to build, and accountable downward to a team that needs clarity, psychological safety, and direction. We're often creating these conditions without support from above, filling a vacuum and hoping we get it roughly right.
In that environment, servant leadership gets dismissed fast. It reads as soft. When the culture above is coercive or purely results-driven, empathy gets treated as a luxury — something for healthy organizations, not for the chaos most managers actually inhabit.
Here's what that view misses: servant leadership isn't a posture of deference. Robert Greenleaf's original model centers on foresight — the ability to see around corners and anticipate what your team needs before they ask. It demands clarity of vision, deliberate community-building, and growing the people around you toward something worth reaching. That's a strategic act, not a soft one.
The Reframe: Protection and Bravery
Practicing servant leadership under bad leadership isn't naivety. It's a deliberate act of protection and an act of bravery in chaotic times.
In January, I wrote about nerve: the small acts of courage that compound into something transformational. At the team level, this looks like choosing to play bold when the culture above coerces us to be small. That defiant act of leadership refuses to let our people get lost in the swell. That takes nerve.
You don't need permission from above to prove the model works. The team you build, the results they deliver, the trust they extend to you — that's the argument. And this isn't selfless sacrifice. Leading well inside a broken system advances you. The evidence travels.
What This Actually Looks Like
Three moves for the manager caught in the middle:
Create the clarity your leadership won't. When structures, priorities, or expectations aren't flowing from above, build them at your level. Your team needs to know what success looks like, especially when senior leadership is vague, shifting, or absent. Don't wait for permission to give your people a north star. That's foresight in practice.
Communicate like someone who's steering. Your team can handle the truth about constraints, competing pressures, and organizational friction. What they can't handle is the feeling that no one is steering. Transparency names what's real. Candor says the thing that needs saying even when it's uncomfortable. That combination builds the kind of trust that holds when things get hard.
Lead from the front when the moment calls for it. Servant leadership and authority live in the same body. Sometimes someone needs to be in charge to make the call, hold the outcome, set the boundary. The managers who do this well aren't contradicting their servant leadership posture. They're drawing on the trust they built through the first two beats. Because you've already shown your team you're playing for them, they trust your judgment when you shift gears. They follow your lead in harder moments because they've seen what you're about in the easier ones.
Back to That Room
The room full of mid-level leaders never fully resolved the question. But something shifted — from 'what's the point' to 'this is the point.' If you can't control what's above you, you can control what you build below. That's the choice. And the leaders who make it stop waiting for the culture above them to change before they build something worth being part of.
Thank you for getting unstuck with me!
Until next time,
Alex
P.S. What's one small experiment you could try this week? Reply and tell me—I'd love to hear what you're working on.
Alex helped me break some old patterns as I settled into a new role. I consistently left sessions with specific ideas and experiments I could implement to move toward new ways of showing up. —Global Marketing & Communications Leader
Self-reflection questions:
Where are you filling a vacuum that leadership above you left empty?
What would your team say about the micro-culture you've built?
What decision or actions have you been waiting for permission to make?
Ready to lead boldly in the space you actually occupy?
I work with ambitious leaders who want to build something worth being part of — even when the culture above them doesn't make it easy. If you're ready to lead with more clarity, candor, and nerve, let's talk.
Great conversations start with shared insights. If you know a leader who's been silently doing the harder play, I'd love for you to share this with them.
