**Annie Lyons**

Operations Leader | Change Maker | Collaboration Champion | Lover of Ambiguity

With over a decade of transformation management, Annie Lyons is a dynamic force in the industry. She has successfully led transformational projects for leading health insurers and Fortune 500 retail organizations. Her unique ability to embrace ambiguity and drive exceptional results has catapulted both clients and colleagues to new heights.

During this journey, Annie had the unique opportunity to go deep within the insurance industry while spending six years in management consulting. This combination has given her a unique perspective of both what success looks like from the outside-in and how success works from the inside-out.

When she’s not looking for the next thing to make her uncomfortable, Annie enjoys seeking insights on trends shaping the retail and insurance industries (with a strong belief these industries should be learning from each other) and mentoring the next generation of leaders. An avid believer in the growth mindset, Annie is forever in pursuit of that next humbling moment.

Annie’s colleagues often say, “Annie makes ambiguity look easy.” Her secret? A relentless curiosity and a commitment to harnessing uncertainty to drive meaningful results.

The Leader’s Guide to Doing Hard Things (and Why It’s the Only Way to Grow) with Annie Lyons

“I want to help people do really hard things.”

This simple yet profound statement is the core of Annie Lyons’ leadership philosophy. A seasoned operations leader, change-maker, and transformation expert, Annie has built a career on navigating ambiguity and leading teams through uncharted territory. In this episode of Fixin’ Your Crown, Boo, host JD Johnson sits down with Annie to discuss why embracing the “hard things” is the secret to unlocking growth, innovation, and resilience.

In this conversation, Annie and JD explore:

* The Myth of the All-Knowing Leader: Annie busts the myth that leaders need to have all the answers. Instead, she advocates for leading with curiosity and the courage to say, “I don’t know, but let’s figure it out together.”

* Learning in Public: Why the most effective leaders are those who are willing to learn, stumble, and hone their craft in front of their teams. Annie shares how this vulnerability builds trust and gives permission for others to take risks.

* Operationalizing Empathy: Annie breaks down how empathy isn’t just a feeling—it’s a strategic business tool. She discusses the importance of understanding individual motivations (”What’s in it for me?”) to align personal goals with organizational missions.

* Navigating Ambiguity: From her eclectic journey through five different colleges to leading massive digital transformations, Annie shares her personal strategies for thriving in uncertain environments and helping teams find clarity in the chaos.

* The “Village” of Leadership: Why leadership is never a solo act. Annie and JD discuss the critical role of mentors, “personal boards of directors,” and support systems in sustaining a long and impactful career.

Why Listen? If you’ve ever felt unprepared for a new challenge or overwhelmed by the pressure to be perfect, this episode is your permission slip to be human. Annie’s insights offer a practical, compassionate roadmap for leading with authenticity, resilience, and a growth mindset.

Tune in to discover how doing the hard things can be the most rewarding part of your leadership journey.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jsquaredelevateconsulting.substack.com