When your boss leads by fear — and what you can do next
Over the past few weeks, I’ve been interviewing members of an Executive Leadership Team ahead of their offsite. The company is facing a pivotal transition as it navigates tradition, aggressive growth goals, and the quiet undercurrents shaping how decisions get made.
The conversations have revealed something I often see in founder-led or legacy-driven organizations:
A leader who isn’t ruling with anger … but with fear.
And that fear doesn’t stay contained at the top.
It trickles down, quietly determining outcomes, shrinking risk-taking, and keeping teams stuck in an exhausting defensive cycle — rather than playing to win.
This newsletter isn’t about demonizing one leader’s behavior.
It’s about understanding the system that forms around a leader who manages through fear — and what teams can do to shift that dynamic if they can recognize the opportunity.
When fear becomes the operating system
As I spoke with each member of the ELT, their descriptions of the majority owner and Chairman, Andrew, were strikingly consistent.
They didn't call him cruel.
They didn't call him volatile.
They called him afraid.
They described patterns of second-guessing, last-minute strategy reversals, and micromanagement — all rooted, in their view, in a deep fear of being wrong or appearing less capable than the legacy he had inherited.
And when a leader operates from fear, the organization learns to fear with them.
One executive put it bluntly: “His caution creates chaos. He's the biggest barrier to the company's success — and we’re all just playing not to lose.”
The effects were everywhere:
Leaders stopped challenging the chairman’s ideas because it became politically risky.
Decisions were made defensively, instead of strategically, in an effort not to upset the status quo.
The ELT, while aligned, kept getting pulled off course.
And talented individuals protected themselves instead of protecting the business.
The hard truth is one the team already knows:
He's not going to change.
But here’s the hopeful one:
They still have agency.
Their task now is learning to lead with him, not around him — and not in fear of him.
Self-Check: are you stuck in “Fear Response” mode?
When fear is present, our nervous systems adapt before our minds catch up.
Use the statements below to check in with yourself. Rate each one using this scale:
1 = never true • 2 = seldom true • 3 = sometimes true • 4 = often true • 5 = always true
I change or soften my perspective depending on who is in the room.
I hesitate to speak up, even when I know something is off or unclear.
I avoid pushing back because I’m worried about the consequences.
I spend emotional energy trying to predict how my leader will react.
I take on work that isn’t mine because it feels safer than saying no.
Add up your total score.
If you rated two or more items a 4 or 5, you’re probably deeper into reactive mode than you think.
If your total score is 18 or above, it’s time for a wake-up call: you’re operating in a fear-driven environment that’s affecting your confidence, judgment, and leadership presence.
This isn’t about blame.
It’s a signal — an indicator that something in the system needs to shift so you can operate with clarity, courage, and choice again.
A system problem, not a villain problem
Fear-based leadership often stems from insecurity.
When you understand this, you can stop personalizing the behavior and instead start coming together as a team to decide how you want to respond — as a collective.
I’ve seen this before.
At a wealth management firm I coached, a founder kept reaching back into operations long after handing over control.
He’d override decisions, revisit plans, and unintentionally undermine the new leadership.
It wasn’t because he lacked trust in the team, but because he feared becoming irrelevant.
The executive team eventually realized their stability couldn’t depend on him stepping back.
It depended on them stepping forward as one: aligned, consistent, and united.
That shift — not a change in the founder’s behavior — is what steadied the business.
So what does courage look like here?
Fear thrives when leaders retreat.
It withers when leaders step forward as a team.
For the ELT I’ve been working with, jumpstarting that process starts with three questions:
What do we enable by avoiding confrontation? If silence feels safer, ask: safer for whom? And at what cost?
What agreements would allow us to operate more effectively around the Chairman? Boundaries aren’t rebellion. They’re a form of stewardship.
How do we preserve our integrity and courage in a system that rewards compliance? Leadership isn’t the absence of fear — it’s moving anyway.
The next step is making these shifts — not hypothetically, but operationally.
Together, at our coming offsite, we’ll work on four core areas:
Purpose and grounding: Why this moment matters — acknowledging transitions, new leaders, and the need for renewed trust.
The current state: Naming how fear and caution show up day-to-day, and how it shapes the choices leaders make.
What’s most needed now: Shifting from protecting themselves to protecting the business.
From compliance → to commitment.FFrom silence → to constructive dissent.FFrom reacting → to responding.
Practical agreements: How they’ll communicate, make decisions, and hold each other accountable when the inevitable pressures resurface.
Because the real accelerator won’t be changing Andrew.
It will be in strengthening how they lead together.
If you’re navigating your own fear-based leader
Maybe it’s a founder who can’t let go.
Maybe it’s an executive who defaults to control whenever stakes rise.
Maybe it’s a boss whose insecurity becomes everyone else’s burden.
Here’s what I tell my clients:
Don’t take it personally — fear rarely is.
Don’t wait for them to become someone they’re not.
Focus on what strengthens your leadership presence.
Build alliances that create safety, clarity, and shared courage.
Fear-based leadership only thrives when others start leading from fear too.
The real courage lies in choosing a different way.