The Hardest Lesson I Learned About Leadership This Year
The hardest lesson I learned about leadership this year didn’t come from a book, a conference, or a podcast.
It came during an incredibly uncomfortable conversation with my core team.
We were on a call when they told me they didn’t feel like they knew where we were going - what my vision was for Alpine.
At first, I’ll be honest… I was defensive. Really defensive. I thought, What do you mean you don’t know where we’re going? I’m working all the time. I’m constantly building, fixing, and strategizing. How could that not be enough?
But after I sat with it for awhile (a really long while) I realized: I was working on the wrong things.
I had been so busy in the business that I wasn’t leading the business. I was solving immediate problems instead of painting the bigger picture. I wasn’t delegating well. I was working on what was urgent and not what was important.
My team didn’t need me to work harder - they needed me to lead better.
That realization wasn’t easy to swallow but it did help me (and Alpine) grow.
The Leadership Mirror
A few weeks later, our team took the CliftonStrengths assessment together. When I got my results, I felt an unexpected wave of disappointment. None of my top strengths were in the “relationship building” category - the area I value most. As an Enneagram 9, I lead with peace, empathy, and connection. I care deeply about people, and I always want to build harmony. Seeing my results feel so different from who I thought I should be as a CEO left me questioning whether I was the right person to lead at all. Should I be a leader or running a company?
I wrestled with that for a while. If you haven’t noticed, 2025 was a lot of wrestling.
Later, I had a sales call with a potential real estate client - a big one. At this point I was still second-guessing myself. I didn’t feel like I “fit the mold” of CEO. But the client chose Alpine.
Here’s what she told me afterward:
“What stood out most to me was how clear, grounded, and easy our conversation felt. You listen when feedback comes, you see it as collaboration rather than criticism, and you focus on solutions instead of policies or excuses. It’s obvious that you care about providing good service and about building relationships where clients want to stay long-term.”
That feedback meant so much to me because it created a “lightbulb” moment for me - that is leadership.
I may not lead through charisma or hard-charging dominance like I’d like to. I lead through clarity, calm, and genuine connection.
That’s not less than leadership. That’s just a different kind of strength.
Leadership, Redefined
This year taught me that leadership isn’t about being who you think you should be - it’s about becoming more of who you already are.
I used to think my value was in how much I could juggle or how polished I could appear. But my team doesn’t need perfection; they need presence. They need vision and direction, not a CEO buried in task lists.
When I started leading from my actual strengths - groundedness, listening, collaboration, empathy - Alpine became stronger too.
The hardest lesson I learned about leadership this year was also the most freeing: I don’t have to fit someone else’s version of what a leader looks like to be an effective one.
The Takeaway
Leadership isn’t a personality type - it’s a posture.
It’s not about being the loudest or most commanding person in the room. It’s about being the one who creates clarity, builds trust, and keeps people aligned on the vision.
Your leadership might not look like anyone else’s, and that’s the point. The way you show up - steady, empathetic, intentional - might be exactly what your team or clients need most.
As it turns out, the thing I doubted most about myself was the very thing people valued most in me.
