When you think of a “great leader,” what image comes to mind?
For many of us, it’s someone who’s bold, charismatic, confident, and always has the answers. But as Craig Denison—founder of The 90 Day Leader—shared in our conversation, that image is not only misleading, it’s one of the biggest things holding new leaders back.
This episode is a must-read for new and aspiring managers who want to lead authentically, grow their confidence, and stop trying to fit into someone else’s mold of leadership.
Breaking the “perfect leader” myth
Craig shared that, early in his career, he believed great leaders were “uber-confident, dripping with charisma, and smarter than everyone else.”
The problem? He wasn’t any of those things.
“I tried to act like that archetype and failed miserably,” he said. “People can sniff out when you’re not genuine. And that version of a leader—the one who has to be the smartest person in the room—isn’t a great leader anyway.”
The truth: leadership isn’t about being perfect—it’s about empowering others.
Once Craig stopped trying to perform and started leading from his authentic strengths, everything changed. His anxiety dropped, his meetings got better, and he realized that good leadership is more about asking great questions and helping others thrive than it is about knowing all the answers.
Why so many managers feel lost
According to Craig, 82% of managers are “accidental leaders.” They were great at their job, so they got promoted—but with little or no training. Suddenly, they’re managing people with a completely different skill set than what got them promoted.
“Doing your job well isn’t the same as leading others doing the job,” Craig explained.
And most companies don’t bridge that gap.
That’s why Craig created The 90 Day Leader—a jumpstart program to help new managers develop the tools and confidence to lead effectively, faster.
The tools every new manager needs
Craig shared a few of the frameworks from his program that help new leaders shift from survival mode to success:
1. Working Genius
Created by Patrick Lencioni and The Table Group, Working Genius identifies the stages of work where you naturally thrive—and the ones that drain you.
Craig uses it to help leaders:
- Understand what energizes and depletes them
- Identify where their team has gaps
- Turn chaotic meetings into productive collaboration by naming what kind of conversation they’re having (“Are we ideating, discerning, or getting stuff done?”)
Desiree—also a certified Working Genius facilitator—added, “It’s one of the best tools for building both self-awareness and empathy. Once you know how you’re wired, it’s easier to understand how others work too.”
2. The Leadership Ladder
This simple but powerful visual helps leaders find the balance between micromanaging and abandoning their people.
The lowest rung: an employee who needs clear, step-by-step direction.
The highest: someone who’s independent and simply needs regular check-ins.
Using this tool in one-on-ones allows managers and employees to discuss where they are on the ladder—and what progress looks like.
Craig encourages leaders to print it out, talk it through, and use it as a living roadmap.
“The goal is to help each person climb the ladder at their own pace,” he said. “That’s how you build trust and confidence on both sides.”
Rethinking “burden” vs. “privilege”
Many individual contributors resist leadership because they see it as a burden—long hours, endless stress, constant pressure.
Craig’s response: “It’s both a privilege and a stretch.”
He compared it to parenting: “You never feel ready. They just send you home with a kid, and you grow as you go. Leadership is the same way—it stretches your capacity, and that growth benefits every part of your life.”
Still, he acknowledged that leadership isn’t for everyone. “If you don’t want to go through the stretching and growth process, that’s okay. But don’t opt out just because you’ve only seen bad examples. There are better ways to lead.”
The most important trait of all: humility
When asked to sum up his leadership philosophy, Craig didn’t hesitate:
“The single biggest thing that brings peace and effectiveness is humility. The moment leadership becomes about you—your image, your ego—it gets hard fast.”
When you choose humility:
You make faster progress because you’re not protecting your pride
You stop chasing perfection
You create space for others to shine
