Leadership confidence doesn’t come from having all the answers or never making mistakes. It comes from knowing who you are as a leader and refusing to let anyone else rewrite that identity. I learned this the hard way — after a leadership experience that nearly convinced me I wasn’t cut out for management. I was told I was too nice. Too soft. That my relational approach to leadership wouldn’t work in the “real world.” And for years, I believed it. Until I realized the problem was never my leadership style. The problem was the environment I was trying to lead in.
If you’ve ever been made to feel like your humanity is a liability, like caring about your people makes you weak, like the only way to succeed as a leader is to become someone you don’t want to be — this is for you.
My First Leadership Role — And the Rules I Wasn’t Given
When I stepped into my first real leadership position, I thought I understood what management meant. I’d been a high performer. I’d studied leadership. I believed that if you showed up with integrity, invested in your team, and delivered results, success would follow.
I inherited a strong, likable team. I wanted to lead with trust first. Connection before control. I believed in giving people autonomy and having their backs when things got hard.
These weren’t naive ideals I’d picked up from a leadership podcast. They were values I’d developed over years of watching what worked and what didn’t. I’d seen fear-based management destroy teams. I’d seen micromanagement kill creativity. I knew the kind of leader I wanted to be.
What I didn’t know was that my leadership confidence would be systematically dismantled by someone who operated from an entirely different playbook.
When Leadership Models Collide
There are fundamentally different philosophies about how to lead people. Some leaders believe in compliance — getting people to do what you want through control, consequences, and constant oversight. Others believe in commitment — earning genuine buy-in through trust, development, and shared purpose.
Neither approach is automatically right or wrong. But when these models collide within the same organization, one of them usually loses.
I was leading with care. My manager was leading with control.
Every conversation became a correction. Every decision I made was questioned. The feedback never came with coaching — only criticism. The expectations shifted constantly, making it impossible to ever feel like I’d gotten it right.
My leadership confidence eroded one interaction at a time. I started second-guessing decisions I would have made confidently before. I stopped trusting my instincts. I began to wonder if everything I believed about leadership was wrong.
This is what happens when fear-based authority meets empathetic leadership. The empathetic leader starts to shrink. Not because their approach is flawed, but because it requires psychological safety to thrive — and psychological safety was nowhere to be found.
How Bad Leaders Rewrite Your Self-Concept
The most insidious thing about working under toxic management isn’t the obvious abuse. It’s the subtle reprogramming of how you see yourself.
“You’re too soft.” “This won’t work.” “You’re failing.”
When you hear these messages repeatedly from someone in authority, something happens in your brain. You start to believe them. Not because they’re true, but because the person saying them has power over your daily reality.
My leadership confidence didn’t disappear overnight. It was eroded through thousands of small moments. The raised eyebrow after I made a decision. The sighing before feedback. The implication is that real leaders don’t operate the way I operate.
I started questioning not just my choices, but my fundamental identity as a leader. Maybe I wasn’t cut out for this. Maybe being kind really did mean being weak. Maybe the only way to succeed was to become harder, colder, and more willing to treat people as resources rather than humans.
This is how bad leaders do their damage. They don’t just criticize your work. They rewrite your self-concept until you can’t remember who you were before them.
The Breaking Point
I broke.
Emotionally, physically, completely. I found myself unable to continue. I walked out, called HR, and took stress leave. For the first time in my career, I felt like a failure.
I honestly started to believe I wasn’t cut out for this — that being kind meant I was weak.
The breaking point matters because it’s where the real question emerges: Was I actually failing? Or was I trying to lead in an environment that was designed to make my approach fail?
It took distance to see clearly. It took leaving to understand that my leadership style wasn’t the problem. The environment was the problem. The mismatch was the problem. The complete absence of support or development was the problem.
But when you’re in it, you can’t see that. All you can see is your own perceived inadequacy.
Escaping Doesn’t Immediately Rewrite Beliefs
A LinkedIn message arrived the day after I decided I was done. A new opportunity. Better environment. A chance to start over.
I got the job. I should have felt relieved. I should have walked into my new role with renewed leadership confidence.
Instead, I carried every doubt with me.
I tried to be “harder.” More direct. Less relational. I attempted to fit the mold that had been prescribed to me — the mold that said real leaders don’t care too much, don’t get too close, don’t show too much humanity.
It didn’t work. Because it wasn’t me.
This is the trap so many leaders fall into after toxic experiences. You absorb the criticism as truth. You try to become what they said you should be. You lose yourself in the attempt to fit a model that was never yours.
Rebuilding leadership confidence isn’t just about getting into a better environment. It’s about unlearning the beliefs that got installed in the bad one.
The Long-Term Insight
It took years to fully understand what happened. Years to separate legitimate feedback from projection. Years to rebuild the leadership confidence that had been dismantled piece by piece.
Here’s what I finally learned:
Leadership is contextual. The approach that fails in one environment might thrive in another. The style that one manager criticizes might be exactly what another team needs. Your effectiveness as a leader depends enormously on the system you’re operating within.
Kindness without boundaries burns out. My instinct to care about people was never wrong. But caring without limits, without protecting my own energy, without being willing to have hard conversations — that was unsustainable. Empathetic leadership needs structure to survive.
Control without empathy destroys culture. I’d seen this before, and I saw it again. Leaders who manage through fear get compliance, not commitment. They get people who show up physically but check out emotionally. They get turnover, disengagement, and quiet quitting.
The leader who told me I was too soft created exactly the environment she claimed to be preventing. High performer burnout. Constant turnover. A team that feared rather than trusted.
The Leader I Chose to Become
Holy shit… I thought I was bad at leadership. But maybe I was just early. Maybe I was still becoming the kind of leader I was meant to be.
That realization changed everything.
I wasn’t bad at leading. I was unprotected, uncoached, and early in my development. I was trying to lead in a way that required psychological safety — in an environment that offered none.
My values were sharpened by contrast. I know exactly what kind of leader I refuse to become because I experienced what that leadership does to people. I know what I stand for because I was forced to decide.
The leadership confidence I have now isn’t naive. It’s not the untested idealism I walked in with during my first management role. It’s confidence forged through failure, through questioning, through nearly losing myself and having to rebuild.
I lead with humanity and accountability. With care and boundaries. With trust and clear expectations. Not because someone told me to, but because I’ve seen what the alternative creates.
I refuse to become what harmed me. And that refusal is the foundation of everything I do now.
What Empathetic Leadership Actually Requires
True leadership confidence — the kind that sustains you through difficult environments and challenging situations — comes from clarity about your values and how you’ll operate.
Empathetic leadership isn’t soft. It’s demanding in a different way. It requires:
The willingness to have hard conversations with compassion. To tell people difficult truths because you care about their growth, not because you want to control them.
The discipline to maintain boundaries while staying connected. To care deeply without losing yourself. To invest in people without making their problems your identity.
The courage to lead differently when everyone around you is leading through fear. To trust your approach even when it’s questioned. To stay human in systems that reward dehumanization.
This is leadership confidence that can’t be shaken by a single bad manager or a difficult environment. Because it’s rooted in something deeper than external validation.
If You’ve Been Told You’re Too Soft
If you’re reading this and recognizing your experience — if you’ve been in leadership positions where your humanity was treated as a liability — I want you to hear something clearly:
The people who told you that you’re too nice to lead were telling you about their limitations, not yours.
Your instinct to care about people isn’t a weakness. Your desire to lead with trust isn’t naivety. Your belief that there’s a better way to manage — that belief is valid.
You might need to develop boundaries. You might need to learn how to have difficult conversations. You might need to find environments that actually support relational leadership.
But you don’t need to become someone you’re not. You don’t need to abandon your values to succeed. You don’t need to let one bad experience rewrite your entire identity as a leader.
Leadership confidence can be rebuilt. Your approach can be refined without being abandoned. You can become the leader you’re meant to be — not the leader someone else tried to force you to be.
If you want to unpack your leadership style, process what happened in toxic environments, or rebuild your confidence as a leader — I’d love to talk.
Book Your Free 15-Minute Strategy Call → https://calendly.com/rosey-singh-eunioa/15-minute-catch-up
Because the world needs more leaders who give a damn. And you might be one of them.
Rosey has spent 15 years in HR and now runs Eunioa, a career concierge service helping professionals and leaders break through career plateaus, recover from toxic workplaces, and lead with both humanity and impact. Her “Sht They Forgot to Teach You” newsletter delivers the leadership and career advice you should have gotten years ago.*
