The Joy of Making It Work: Leading Through Constant Change | Maureen Naughton

What do you hold onto when the technology, possibilities, and even the questions keep changing? Maureen Naughton, Chief Innovation & Information Officer at Lowenstein Sandler, has spent her career figuring out how organizations actually change. For Maureen, leading transformation no longer means having the next three years mapped out. It's about knowing what shouldn't change, building strong enough foundations to adapt around it, and staying curious enough to keep questioning what comes next. In this conversation, Gabrielle Kohlmeier and Maureen explore what it takes to turn the possibilities of AI into change that actually works. Maureen makes the case for transformation as evolution rather than revolution: start with the problems people actually have, meet them where they are, and use the “art of the possible” to create the energy that helps people move. That possibility still needs something solid underneath it. Maureen's premise for AI is simple: it should make us smarter, not dumber. The tools may change how work gets done, but they don't eliminate the need for human judgment, trust, relationships, ethics, quality or client value. In a world where Maureen now thinks in six-month plans instead of three-year plans, those constants become a foundation for navigating uncertainty rather than trying to eliminate it. Gabrielle and Maureen also get into the less glamorous work that makes transformation possible: data, process, governance, existing technology and operational design. Because moving faster doesn't always mean chasing the newest thing. Building the right foundation - across data, process and technology - makes it easier to identify where AI can actually add value and where to focus next. And underneath all of it is something Maureen genuinely enjoys: getting to figure out what doesn't exist yet. Change can be uncertain, vulnerable and difficult, and still create the energy to ask, How lucky are we that we get to build what comes next? Your Transformation Rep Let AI Coach Your Thinking Pick one decision, tension or problem you're genuinely thinking through. Instead of asking AI, “What should I do?” ask it to coach your thinking: “You get five questions. Ask me one at a time. Don't give me advice. Help me notice something that's missing, something that I'm assuming, and what matters most to me in this decision.” Answer the questions, then stop and ask yourself: Did I notice something I hadn't noticed before? The goal isn't to hand the decision over to AI. It's to use AI to create a little more space for your own judgment. Episode Highlights: Why transformation can be an evolution rather than a revolution How the “art of the possible” creates energy and momentum for change Why listening and vulnerability can strengthen leadership How to move AI skeptics by starting with problems that matter to them Why Maureen has shifted from three-year plans to six-month plans What remains constant when the tools and delivery mechanisms keep changing Why AI should strengthen human thinking rather than replace it The role of data, process, governance and existing technology in AI transformation What operational redesign means beyond simply adopting new tools Why strategy gives organizations a place to assess, learn and course-correct The joy of getting to create something that didn't exist before Ways to Connect with Gabrielle Subscribe to Technically Joyful on Apple Podcasts, Spotify, and YouTube: technicallyjoyful.com Newsletter: technicallyjoyful.com GK Strategic Advisory: gkstrategic.com LinkedIn: linkedin.com/in/gabrielle-kohlmeier