Resources
It Doesn't Have to Be This Way
Unstuck Monthly | August 2025
What if your worst boss was your origin story
When Leaders Leave Scars
Last month, I was working with a client I’ll call Natasha when she shared something that made me very sad.
“I was just trying to be collaborative,” she said, describing a moment from many years ago when she worked at a global firm. “I thought my boss would appreciate me sharing our presentation deck with the design team before the client pitch. You know, getting everyone aligned?”
What happened next changed how Natasha approaches similar professional decisions.
Her boss erupted. Not just frustrated but truly enraged. He yelled at her in front of the entire team, told her she had “fundamentally misunderstood her role,” and made her feel like she’d committed some unforgivable professional sin. The worst part: he never explained what she’d actually done wrong.
“I kept asking myself, what was I supposed to do differently?” Natasha told me. “I still don't know. That uncertainty has followed me ever since.”
The Invisible Aftermath
Natasha’s story happened years ago, but its effects ripple through her career today. She second-guesses decisions that should be straightforward. She asks for permission when she should take initiative. She’s developed analysis paralysis because she’s terrified of triggering another explosive reaction.
The cruel irony? Natasha is exceptionally talented. Her colleagues consistently praise her strategic thinking and collaborative approach. But that one leader’s dysfunction sparked a cycle of self-doubt that’s been hard to shake.
Natasha’s boss was a confidence-killing leader. Bad leadership like his rewires how people approach their professional lives.
It Doesn't Have to Be This Way
Since Natasha shared her story, I’ve been reflecting on my own experiences with dysfunctional leaders. How many of us carry invisible scars from leaders who should have known better?
More importantly, how many of us might be unconsciously perpetuating these dysfunctional cycles with our own teams?
Natasha’s boss probably thought he was just “maintaining standards” or “being clear about expectations.” Assuming best intentions, he likely had no idea he was fundamentally undermining someone’s professional confidence and altering the course of their career.
To judge a confidence-killing leader, impact matters more than intent.
The most insidious part of dysfunctional leadership is how it normalizes itself. We tell ourselves “that’s just how business works,” or “they were under pressure,” or “I should have known better.” We adapt to dysfunction instead of recognizing it for what it is.
The Origin Story Reframe
From as far back as my high school days, I remember seeing dysfunctional leaders—some of the adults in my life and fellow student leaders—and thinking that we, collectively, could do better. I felt called to leadership, not just for myself but to stand beside other good leaders, so we could harness the collective strength needed to end those cycles.
For those of us who have taken up the mantle to do things better, I’m sure we’ve all had a moment when we’ve said, “I never want anyone on my team to feel the way I felt.”
This is the beginning of what I call an origin story reframe. The same experience that created self-limiting patterns can become the foundation for exceptional leadership capabilities. For Natasha, that included an acute awareness of power dynamics, her instinct to over-communicate rather than under-communicate, and her natural inclination toward collaboration. These are leadership superpowers waiting to be fully embraced.
Breaking the Cycle
The leaders who leave a positive lasting impact are often the ones who experienced dysfunction and decided, “It doesn't have to be this way.”
Future teams deserve leaders who commit to nurture the psychological safety they once missed, and who continually strive for better, more effective ways to get results.
Natasha’s boss probably never realized the lasting impact of his explosion so many years ago. But Natasha has the opportunity to ensure that her own leadership approach creates a completely different legacy….And so do you.
Thank you for sticking with me!
Until next time,
Alex
P.S. If Natasha’s story resonates with you, I’d love to hear about it. Reply and let me know what leadership experience shaped how you show up today. And if you know someone who needs the reminder that tough experiences can build strong leaders, please share this with them.
Self-reflection questions
What leadership moment shaped how you show up professionally?
How might that experience be driving your current leadership approach?
In what ways are you overcompensating that might be limiting your effectiveness?
What do you want to ensure never happens to the people you lead?
Ready to create your professional future on your own terms?
I partner with ambitious leaders who are ready to strengthen their inner capacity for exceptional leadership. Let’s explore how your own story can become the foundation for transformational leadership—book a call today.
Great conversations start with shared insights. My coaching practice, like this newsletter, thrives on connections. If you know someone who's navigating their own leadership and professional sticking points, I'd love for you to share this with them.
