About Me
Hi. I’m Meagan O’Leary
I’ve spent my career helping organizations solve complex problems.
- Sometimes that meant leading global strategy.
- Sometimes it meant building operating systems.
- Sometimes it meant helping teams understand one another well enough to move forward together.
What I’ve learned is surprisingly simple:
People rarely disagree because they lack intelligence.
They disagree because they’re standing in different places looking at the same problem.
These observations eventually became the foundation for the Beach Ball Paradox
How I Help Leaders
People often ask me to help when organizations need to:
- Create clarity
- Solve complex or complicated problems
- Scale execution
- Navigate AI
- Build high-performing teams and systems
- Turn strategy into measurable impact
I enjoy bringing people together around a shared understanding so they can move forward with clarity and confidence.
My Journey
My career has taken an unexpected path.
I began in public accounting, where I learned the discipline of financial stewardship and data-driven decision making.
Owning a restaurant taught me what it feels like to serve customers directly and make decisions where every dollar—and every experience—matters.
Eight years at T-Mobile deepened my understanding of finance, enterprise operations, and large-scale transformation.
For more than two decades at Microsoft, I’ve had the privilege of leading global strategy, customer success, digital transformation, AI initiatives, and operational excellence across some of the company’s most complex organizations.
Each chapter has shaped the leader I am today.
Beyond Work
I’m endlessly curious about people, performance, health, and what helps meaningful change actually stick.
I’ve completed certification programs in health coaching and Primal Health Coaching, studying how nutrition, movement, sleep, stress, and everyday habits influence how we feel and function. My own health journey, including facing cancer twice, made that learning deeply personal.
Health coaching reinforced something I’ve seen throughout my leadership career: information alone rarely changes behavior. Lasting change begins by understanding the whole person, including their circumstances, motivations, obstacles, and perspective.
I enjoy traveling, writing, spending time with my family, and continuing to explore ideas that challenge how we think, lead, and live.
Looking Ahead
Technology is changing how we work.
AI is changing how we make decisions.
But leadership has always been about people.
My goal is to help leaders combine perspective, technology, and thoughtful execution to build organizations that are more connected, more adaptive, and more human.
Because in the end, I believe the best leaders don’t just help people work harder.
They help people see more completely.
And when that happens…
Perspective changes everything.
Want to Learn More?
I am currently consulting and advising with amazing leaders. If you want to engage with me or learn how I work …