I posted this article on my LinkedIn profile recently. I used to think moving into management meant giving up the part of my career I loved most, building cool things. Over time, I realized leadership is just another form of building. And surprisingly, AI has become one of the tools that’s helped me make that transition. Here’s what I learned…

Smarter SMART with AI, and Finding Joy in Helping Others Build

One of the greatest privileges of my career has been occupying a unique space within technology organizations: being trusted enough by CIOs, CTOs, COOs, directors and executive leadership to help shape modernization strategy, while still remaining close enough to the work to personally build and deliver solutions.

There’s something deeply satisfying about taking an idea from a whiteboard discussion to a proof of concept, evolving it into a minimum viable product, and ultimately deploying it into production where people rely on it every day. Watching an idea become a real solution has always felt like a win.

Over the past decade, I’ve been fortunate to help lead and deliver several initiatives that began as executive conversations and ultimately became enterprise solutions. These include modernizing the California Department of Education’s DataQuest reporting platform, modernizing data platforms for the San Diego County Employees Retirement Association and the California Department of Managed Health Care, and developing a legal document search platform for the DMHC. Each started with a vision presented to executive leadership, and I had the opportunity to help execute that vision from concept through production.

For many years I hesitated to pursue higher leadership positions because I knew it would mean fewer opportunities to build software and more time spent in meetings, planning sessions, budgets, and personnel management. I’ve always loved learning new technologies and creating systems that solve real problems. As my responsibilities grew, I had to accept that my role would gradually shift from being the primary builder to enabling others to build.

That transition changed my perspective on management.

Performance evaluations, for example, can easily become a compliance exercise. This is especially true in unionized environments where ratings often have little direct impact on compensation. (But that is a spiel for another day). Rather than viewing them as another administrative requirement, I wanted them to become meaningful conversations grounded in measurable accomplishments and focused on future growth. I also wanted employee goals to truly be SMART: specific, measurable, achievable, relevant, and time-bound.

The challenge was measurement.

Over the past year, one of my team’s modernization efforts has been implementing a contemporary project management platform, documentation repository, and source code management environment. While this created a wealth of operational data, transforming that information into meaningful insights remained difficult.

This is where AI, specifically ChatGPT Codex, became an unexpected leadership tool. Using Codex, I quickly developed reports that summarized project contributions, technical accomplishments, documentation, and development activity. Those reports provided objective evidence that helped me write more thoughtful performance evaluations and establish meaningful SMART goals for each team member.

Out of curiosity, I even experimented with having AI draft entire evaluations. Technically, it worked remarkably well. It populated our PDF evaluation forms correctly. But something was missing. It didn’t sound like me. Technology can summarize accomplishments, identify patterns, and save hours of administrative work. What it can’t replace is the human understanding of a person’s growth, character, resilience, and potential.

In the end, AI didn’t replace my judgment, it amplified it. By reducing the time spent gathering evidence, it allowed me to spend more time on the part that actually matters: recognizing achievements, providing meaningful feedback, and helping people grow.

Looking back, I realize that my definition of “building” has changed.

Earlier in my career, the greatest satisfaction came from delivering production systems. Today, I still enjoy creating solutions, but I find equal satisfaction in helping shape strategy, equipping my team with better tools, and watching them deliver outstanding work.

Perhaps that’s one of the more rewarding transitions in leadership: realizing that success is no longer measured only by what you build yourself, but by what you enable others to build.