"You're hired!"...now what?
Suddenly, you’re not in Kansas anymore.
Or maybe you’ve been in your role a while, but the complexity and pressure haven’t let up.
You might notice it in how you’re operating:
- You feel like an imposter so you over-prepare and then hold yourself back
- You replay conversations late at night, worried you didn’t handle them right
- You hold onto projects you don’t need to, because delegating feels risky
- You struggle to shift the dynamic with former peers or new team
The pressure to prove yourself is intense.
The stakes are higher now.
 It adds up, and affects:
- The decisions you make (and how quickly you make them)
- The trust others place in your leadership
- Your ability to influence at higher levels
- Your trajectory from here
You’ve stepped into more power...and the rules changed.
This is where so many leaders stall, because no one taught them how to navigate this level.
The old leadership playbook wasn’t designed for you.
Most leaders try to solve this by copying the leadership model they’ve seen before.
The dominant executive voice. The performative confidence.Â
The behaviors that signal this is what a real leader looks like.
But if that model never felt like you, trying to inhabit it creates a different problem:Â
overcorrect into harshness and fake dominance to fit in…
or avoid your own power and lose authority.
That binary is false.
There's another way to lead.
The leaders I work with don’t fit the traditional leadership mold.
They’re self-aware and systems-aware. They might be neurodivergent, queer, women of color, or from working-class backgrounds. They’re often skeptical of the dominant power culture around them.
And now they’re being asked to run it.
This is where Misfit Leadership™ comes in.Â
Misfit Leadership is the lens I use to help you build a more intentional relationship with power, so you can lead boldly, authentically, and with integrity, instead of performing someone else’s version of “leader”.Â
In practice, that looks like:Â
✔️ Making decisions and moving on—without replaying them all night.
✔️ Navigating politics with your values intact.
✔️ Resetting the dynamic with your team or peers without overthinking it.
✔️ And walking into the room like you belong there. Because you do.
Private Executive Leadership Coaching
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A six-month, high-touch partnership rooted in my Misfit Leadership™ philosophy to help you step fully into your new role, lead with confidence, and operate in a way that actually fits you.Â
What’s included:
- Kickoff and goal-setting session (75 min)
- Ongoing coaching (2–4 sessions per month)
- CliftonStrengths or Enneagram assessment + session (60 min)
- Voice or email support between sessions
360 interviews are optional.
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HOW WE WORK TOGETHER
Our work creates the shifts required to lead at your new level. We focus on three areas:
Leadership Strategy
Clarifying what matters and working through high-stakes decisions, team issues, and organizational complexity.
Internal Patterns
Changing the habits and beliefs that affect how you engage with people, power, and your work itself.
Embodied Leadership
Building resilience and staying steady under pressure so you can think clearly and lead well.
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My approach builds the mental, emotional, and physical capacity senior leaders need for more effective decisions and bigger impact.
Schedule a call →
Hi! I’m Caitlin, and I'm a misfit, too.
I spent 20 years inside fast-growing startups and mission-driven orgs—operating in high-pressure environments, advising leaders, and shaping strategy at scale.
For most of that time, I felt like an outsider. Even when I had influence.
Working-class background in rooms of inherited privilege.
Ambitious and soulful inside profit-driven systems.
Questioning leadership norms in cultures that rewarded conformity.
I learned how to succeed inside worlds I didn’t fully belong to—without overriding my own instincts.
That experience shapes my work today.
The leaders I partner with often feel the same tension: stepping into power in environments that weren’t designed for them, and figuring out how to lead effectively in a way they respect.
That’s the work.
"I'm now approaching my work from a place of trust in myself and my team...
I can discern what’s truly urgent (and isn’t) without guilt, and I'm more confident in my ability to lead well without stepping into “superhero” or “victim” mode when things get hard.
Working with Caitlin made a tangible impact on our organization: delegation with my leadership team is easier and more effective, and we’re sharing responsibilities and operating with greater trust and grace.”
– Consuelo Tupper Hernà ndez, Executive Director, La Peña Cultural Center
Read the case study >>
You’ve earned your seat at the table.
Now it's time to lead like you belong there.
Let’s start with a conversation to see if it’s a fit.Â
