#236 | Creating AI Systems With Kesha Williams

AI, Careers

July 14, 2026

AI is everywhere right now, and if you’re anything like me, you’ve probably wondered where to even begin. It seems like there’s a new tool, update, or headline every single day, making it feel impossible to keep up. When people ask me where to start with AI, my answer is almost always the same: don’t try to learn everything. Start with one problem you want to solve.

That’s exactly why I was so excited to sit down with AI expert and software engineer Kesha Williams. With more than 25 years of experience building software and AI solutions, Kesha has a refreshingly practical approach. Instead of chasing every shiny new tool, she focuses on creating systems that save time, reduce repetitive work, and give people more space to focus on what they do best.

Think Beyond Prompts

For many people, AI starts and ends with asking ChatGPT a question. And there’s nothing wrong with that; it’s a great first step. But Kesha challenges us to think a little bigger. Rather than treating AI like a search engine, think of it as a teammate that can help complete entire workflows. Whether it’s researching a topic, organizing information, preparing for meetings, or generating first drafts, AI becomes much more useful when it handles repeatable processes instead of isolated tasks. The easiest way to get there is to look at your own day. What do you do over and over again? Which tasks happen every week? What work follows the same pattern each time? Those are usually the best places to start. You don’t need a complicated setup to see results. Even automating one repetitive task can free up more time than you might expect.

The Best AI Still Needs a Human

One of my favorite parts of our conversation was Kesha’s reminder that AI shouldn’t be left completely on its own. As impressive as these tools have become, they can still make mistakes, misunderstand context, or confidently give you incorrect information. That’s why she encourages building guardrails into every workflow and keeping humans involved when decisions really matter. We swapped a few stories about AI agents behaving in unexpected ways, including one that spent more money than instructed, which made for some entertaining examples, but they also reinforced an important point. AI works best when it has clear boundaries and someone reviewing the final output. Think of it as an incredibly capable intern, not someone you’re handing the keys to without supervision.

The Future Belongs to People Who Work Well With AI

One of the biggest takeaways from our conversation had nothing to do with technology; it had everything to do with people. Kesha believes we’re moving toward a future where everyone has their own AI assistant helping with research, scheduling, writing, and countless everyday tasks. But that doesn’t make human skills less important. If anything, it makes them even more valuable. As AI becomes better at handling routine work, the qualities that set us apart become communication, curiosity, relationship-building, critical thinking, and emotional intelligence. Those are the skills that create trust, build teams, and strengthen relationships, things AI simply can’t replace. So yes, keep learning the technology. But don’t forget to keep investing in the skills that make you uniquely human.

The big takeaway from our conversation with Kesha is this: you don’t have to become an AI expert overnight. Pick one repetitive task that slows you down and experiment with ways AI can help. Once you’ve built confidence there, move on to the next opportunity. AI isn’t about replacing your work; it’s about creating more time for the work that matters most. And when you combine smart technology with good judgment, creativity, and strong relationships, that’s where the real magic happens.