7 Lessons On Leading Through Change From a First-Time CEO

Most mornings this year started the same way: an early workout before the house woke up, the chaos of getting kids out the door, a quiet walk before I officially started my day. 

Coffee in hand, I’d run through the decisions waiting for me: Questions about where to take the business, how fast to move, and how much change people could absorb at once. 

Those walks became a moment to prepare myself to lead with both conviction and care before stepping into another day of leading a major transformation. 

After 20 years in this industry and more than a decade in executive leadership, I thought I understood change. I’d helped global brands navigate disruption, led through integrations and restructures. But stepping into the CEO seat at AnswerLab was different. This wasn’t about advising transformation; it was about owning it. 

Here are 7 core lessons I learned from leading through transformation as a first-time CEO.

1. Transformation is emotional 

I knew we needed to pivot. What I didn’t fully anticipate was how deeply that shift would affect the people who had built the business we were evolving. 

AnswerLab had deep roots and a strong sense of identity. My job was to guide it into a new era without losing what made it special. That meant learning where the heartbeat of the company was strongest, what needed to evolve, and what absolutely needed to be protected. It also meant making decisions that prioritized the long-term health of the business, even if they created short-term discomfort. 

I understood the transformation intellectually. What I didn’t anticipate was how exposed it would make me as a leader — how often I’d have to say, “I don’t know yet,” while still asking people to trust where we were headed. That tension defined my first year.

2. Transformation is non-linear 

Transformation is messy, but leading through it isn’t about slowing down; it’s about maintaining pace while becoming more intentional. 

To keep us moving forward without burning people out, we treated it more like an enterprise digital transformation than a traditional organizational change. We shifted to operating in sprints, revisiting priorities every two weeks and stepping back quarterly to assess what was working, what wasn’t, and where we needed to adapt. 

That rhythm allowed us to keep momentum while creating space to listen, learn, and course-correct. It taught me that transformation isn’t linear. It requires resilience, clarity, and a steady hand when things feel unsettled. 

3. Bringing people along is harder than being right 

One of the hardest lessons I learned was that being right about what needs to change doesn’t mean you’ve gotten how to change it right. There were moments when I underestimated the intention behind past decisions, even if they no longer served where we needed to go. 

That forced me to slow down in a different way—by asking better questions. By bringing in advisors. By taking the time to understand not just the strategy, but the emotional connection people had to it. 

There were moments when the most important thing I could do wasn’t explain the strategy, but acknowledge the uncertainty. Naming what I didn’t have fully figured out created space for others to contribute what they saw. Vulnerability didn’t slow us down — it sharpened us. 

And humility didn’t weaken my leadership. It strengthened it. 

4. Leadership sits at the intersection of clarity and connection 

A quarter into the year, we were building our annual plan, and the urgency was real. I took control to create clarity, but I didn’t explain why that was necessary at that moment. For a team used to building things together, it felt abrupt. 

Once I articulated my intention, everything shifted. People understood the need for speed. Trust deepened. Clarity builds connection faster than control or consensus ever could. 

That shift also required rethinking hierarchy—not by removing accountability, but unnecessary barriers to insight. When people felt safe challenging ideas, better thinking surfaced faster. The best signals often came from the people closest to the work. 

Great leaders know when to step in and when to step back. Connection and clarity aren’t opposites. They’re partners. 

5. Letting go doesn’t mean losing accountability 

As your scope of responsibility grows as CEO, so does what you have to let go of. Leading at this level required trusting my team, their teams, and the systems we were putting in place. 

That didn’t mean relinquishing accountability, but evolving how I defined control. I don’t need to hold every lever. I’ve learned to be more discerning about where my presence creates momentum and where it might unintentionally slow things down. 

Leadership at scale isn’t about holding tighter. It’s about trusting deeper. 

6. A curious culture leads to better ideas

If there’s one constant that carried me through this year, it was curiosity. Surrounding myself with people whose strengths outpace my own has been one of the most important decisions I’ve made as CEO. It sharpened the work and raised the bar for all of us. 

Curiosity isn’t passive. It’s the willingness to engage, challenge, and contribute, even when it feels uncomfortable. 

7. Leading doesn’t mean having all of the answers

Clarity doesn’t come from having all the answers, but from creating the conditions where the best answers can surface. My first year as CEO was a master class in courage, clarity, and connection. It deepened my belief that leadership isn’t about control, but trust; it isn’t about perfection, but presence. 

In a time of rapid change, empathy and understanding aren’t just strategic advantages; they allow progress to endure. 

Leadership isn’t about knowing every step of the road ahead. It’s about building a community willing to move forward with intention—one decision, one conversation, and one morning walk at a time.