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Are You Secretly a Bad Boss?
The identity shift required to go from individual to leader.
Howie Chan
September 21, 2025
Dear Legend,
You already know this.
But I’m going to say it anyway:
Having the title does not make you a great leader.
Most leaders get promoted because they are great “doers.”
(And the irony? The better you are at the “doing,” the worse your first leadership attempt probably was.)
Let me prove it to you.
A few weeks ago, I had Mita Mallick (Me-tah) on my podcast and she shares some horrific stories about bad bosses (including her own bad behavior.)
(Mita is a former corporate executive turned bestselling author, workplace inclusion expert, and leadership truth-teller. She’s led teams at top global companies, advised Fortune 500 CEOs, and her work has been featured in Harvard Business Review, The New York Times, and Fast Company. Her latest book, The Devil Emails at Midnight, is a must-read playbook on what great leaders can learn from bad bosses—based on 20+ years of experience navigating, surviving, and transforming corporate culture from the inside out.)
When Mita was first promoted into leadership, she did what every high performer does:
She tried to do everyone else’s job.
Micromanaged her team.
Hovered.
Second-guessed.
Rewrote their work.
Stressed out.
And then stressed them out.
“Nobody taught me that leadership meant I had to stop doing. I was trying to do Howie’s job instead of teaching Howie how to do it.”
Sound familiar?
You’ve been there.
We all have.
And maybe no one told you what I’m about to tell you next. But you’re ready to hear it now.
❤️ Heartset: You’re Not a Bad Person. You Just Haven’t Shifted Yet.
We fall into bad leadership habits because we were never taught how to transition. I was never trained to transition! Not in terms of mindset anyway.
We go from individual contributor to “boss” and just assume more hours, more control, and more stress are signs that we’re doing it right.
Wrong.
“We still promote based on factory-line thinking… You’re great at widgets? Congrats, now you’re in charge of 12 widget-makers. But coaching isn’t the same as producing. And we don’t train for that.”
We reward performers with promotions and then leave them to drown.
No wonder you feel like a fraud.
🧠 Mindset: Leadership Isn’t About You Anymore.
You used to ask:
“How did I do?”
“Did I hit my numbers?”
“Did I crush that deck?”
Now you have to ask:
“How did they do?”
“What’s blocking them?”
“How can I make them better than me?”
Here’s the line in the sand:
“If you are still measuring your value by how much you personally output, you’re not leading. You’re managing tasks in a costume.”
🧰 Skillset: The 3 Levels of the Leader Identity Shift
Level 1: From Execution to Coaching
Old belief: “No one can do it like me.”
New belief: “My job is to make others better than me.”
🧠 Tactic: Use the 70% Rule
If your team member can do the task at least 70% as well as you, delegate it and don’t take it back. Then, schedule a coaching moment after the task is done, not during. Ask:
“What worked for you?”
“What would you do differently next time?”
“Where do you want more support?”
This creates learning, not dependence.
Level 2: From Identity in Output to Identity in Outcomes
Old belief: “I’m valuable because I do great work.”
New belief: “I’m valuable because my team thrives.”
🧠 Tactic: Shadow Share & Step Out
Once per week, choose one high-visibility task (deck, presentation, report) and:
Let a team member lead it
Be present but silent
Let them have the win (even if it’s imperfect)
Then share their work in a public channel or meeting, giving them full credit.
This rewires your status from “star player” to “talent builder.”
Level 3: From Hoarding to Multiplying Talent
Old belief: “If I lose them, I lose value.”
New belief: “If they grow, I become a magnet for talent.”
🧠 Tactic: Build a Career Map Together
In your next 1:1, ask this:
“What’s a role you want in the next 12–18 months, inside or outside this company?”
“What’s one skill we can start developing to get you closer?”
Start tracking that skill in your check-ins.
When they grow into it? Celebrate and if needed, let them go.
Nothing builds a leadership legacy faster than being known for helping people rise.
I’ve had SOOOO many people leave under my leadership in my past role (and it’s not because they hated me… I promise!)
Don’t miss👇🏽
The Legend Effect Podcast
In this episode, we unpack why good people become bad bosses and how to stop it before it happens.
Mita Mallick reveals the 3 triggers that lead to toxic leadership and breaks down frameworks like the 5Ds of allyship, the anti-hustle leadership model, and journaling for self-awareness.
And yes, there are stories. Including the wild one about a boss who threw a Chanel shoe at a team member’s head. (You can’t make this stuff up.)
You were promoted because you were great.
But you’ll only be remembered if you make others great.
That’s the true shift: from “Look what I built” to “Look who I built.”
And if you get it right?
They’ll be telling your stories long after you’re gone. (In a good way.)
I will see you next Sunday!
Make your mark, live your legend 🤘🏽
Howie Chan
Creator of Legend Letters
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