Leading Transformations: Lessons from Three Major Shifts in My Career

Transformation is never easy, but it’s essential for growth. Throughout my career, I’ve had the opportunity to lead three major transformations that reshaped how teams and organizations operate. Each experience reinforced key leadership principles that I now carry forward into every change initiative. In this post, I’ll share the challenges, lessons, and outcomes from these three transformations—and I hope it inspires you to bring your own ideas to life.

1. Leading Two Companies to an Agile Product Operating Model

At two different companies of varying sizes, I led the shift from traditional operating models to an Agile product-led approach. While the contexts were different, the challenges were strikingly similar:

• Technologists were too far removed from the business, lacking a deep understanding of why certain initiatives mattered.

• Business areas didn’t fully grasp the technology available, leading to missed opportunities for efficiency and innovation.

• Cross-functional collaboration was limited, causing friction and inefficiencies.

Adopting an Agile product-led operating model addressed these concerns by aligning teams more closely with business objectives and fostering collaboration. The key steps in driving this transformation included:

1. Clarifying the challenges – Gaining leadership alignment by deep-diving into existing inefficiencies.

2. Pressure-testing the new model – Ensuring the Agile approach would resolve key pain points.

3. Assessing and upskilling talent – Identifying where to reskill or upskill employees to succeed in the new structure.

4. Educating stakeholders – Helping each area understand what the change meant for them and why it was beneficial.

5. Rolling out strategically – Implementing in phases to ensure smooth adoption.

6. Iterating and improving – Continuously gathering feedback and refining the process.

The results? Fewer struggling initiatives, increased employee engagement, and more frequent goal overachievement due to stronger collaboration between business and technology teams.

Lesson Learned: If I could go back, I would incorporate team-building exercises right from the start. Establishing strong relationships early on could have accelerated the transition.

2. Driving GenAI Adoption at My Current Company

My journey into GenAI adoption began with my own curiosity about emerging technologies. As I learned more, I saw the potential for GenAI to improve productivity and reshape how we deliver products to customers.

To make this transformation a reality, I:

• Educated the company through multiple forums, including email communications and an AI council with cross-functional representation.

• Engaged legal, compliance, and security teams from the start to address concerns proactively.

• Demonstrated real-world use cases to show the tangible benefits of GenAI adoption.

One of the biggest challenges was skepticism—especially around how GenAI works and concerns over customer and company data privacy. I tackled this through education and hands-on demos, showing exactly how use cases would function in a secure and responsible way.

We’re now in the process of launching three GenAI use cases, with the expected benefit of increasing productivity by 10-15%. I look forward to sharing the final results in a future update!

Common Themes in Leading Transformations

While these transformations were different in nature, they shared key leadership principles that helped drive success:

• Curiosity fuels innovation – Staying curious about new technologies and methodologies is key to spotting opportunities for improvement.

• Education is a powerful tool – Helping others understand the “why” behind a change makes adoption smoother.

• Make it personal – Framing change in terms of how it benefits each stakeholder makes it more relatable and compelling.

• Feedback is critical – Gathering input throughout the process ensures smoother adoption and continuous improvement.

• Lead by doing – Rolling up my sleeves and actively participating in execution helps build trust and momentum.

Call to Action & Invitation for Discussion

If you’ve had a transformation idea in the back of your mind, I hope these principles help you bring it to life. Change isn’t easy, but the right approach makes all the difference.

I’d love to hear from you! Tell me about a transformation you’ve led, or share a transformation idea where you could use some guidance. Let’s learn and grow together!