Episode Overview
Your latest team probably isn’t broken—it’s just been handed impossible expectations. Barninder Khurana, CTO of CoverWhale, knows this intimately. After a decade-plus navigating the insurance tech space as CIO of GeoVera and leading digital transformation at ProSight, he’s discovered that most organizational change initiatives fail not because teams lack skill, but because leaders treat transformation like a separate function instead of building it into the team’s DNA.
In this episode, Barninder shares his counterintuitive approach to leading through uncertainty: upskilling your existing team beats hiring specialists every time. Your people already understand your culture, your technology, and your constraints—teach them the new skills rather than bringing in outsiders who’ll spend months learning what your team already knows. He draws parallels between failed “Chief Digital Officers” and today’s siloed “AI teams,” warning that specialized groups without organizational integration create more problems than they solve.
You’ll hear why Barninder writes lists of life goals (and actually follows them), how he approaches parenting with ADHD as a research project, and why his dog sits next to his wife in LEGO form but probably nowhere else. Most importantly, you’ll understand why the future of AI adoption isn’t about building something revolutionary—it’s about composing specific solutions for specific problems, and why your existing team is better positioned to do that than any outside hire.
Guest Bio
Barninder Khurana is CTO of CoverWhale, where he helps insurance organizations move faster, work smarter, and grow profitably. With over a decade of leadership across the MGA and carrier space—including roles as CIO of GeoVera and leading digital transformation at ProSight—Barninder brings a pragmatic perspective on building high-performing teams through rapid change. When he’s not leading technology transformation, you’ll find him on his motorcycle (unless there’s ice on the ground), reading voraciously, or researching everything from ADHD parenting strategies to the next item on the life goals list he wrote at 21. Connect with him on LinkedIn.
Timestamps & Key Moments
00:00 - 04:14 | Who Barninder Is Beyond Work Father of three boys, motorcycle rider, perpetual learner. His growth mindset extends beyond work—when his youngest was diagnosed with ADHD, he and his wife researched extensively, consulted doctors, and interviewed other parents. Before having kids, they interviewed couples whose children they admired to build mental models for parenting.
04:15 - 07:20 | Building High-Efficiency Teams The best teams have unity of thought before execution alignment. Leaders must know when to lead from the front, from behind, or get out of the way entirely. Empowerment means understanding what motivates each team member rather than defaulting to “just replace people.”
07:21 - 10:45 | The Ladder as Escape Route Not everyone will fit your approach, even with effort. The ladder represents recognizing when someone’s emotional baggage or resistance prevents progress—and knowing when to create an exit path rather than forcing alignment.
10:46 - 14:30 | Navigating Restructures and Mergers Barninder’s real-world experience: acquisition eliminated his entire team, he retained one person while rebuilding from scratch. The key to leading through restructures is building trust early, understanding your new peers, and knowing when to make difficult decisions about fit.
14:31 - 18:05 | Worst Team Experiences Toxic environments where people won’t help each other because “that’s not my job.” Barninder learned the hard way: no amount of process can fix fundamental trust issues. You either fix the culture or accept you’re managing dysfunction, not building a team.
18:06 - 21:04 | AI as Composition, Not Revolution The future isn’t one AI solving everything—it’s composing specialized solutions for specific problems. Generic models lack the precision needed for trust. The next wave: specialized AI for legal teams, medical diagnosis, contract analysis. Then comes composition: combining solutions to solve your unique operational challenges.
21:05 - 24:24 | Why Upskilling Beats Hiring Specialists Controversial take: Creating separate “AI teams” or “digital transformation officers” fails because they operate outside organizational DNA. Your existing team already knows your company, culture, and technology—upskill them rather than hiring specialists who’ll need months to understand context. This approach is more cost-efficient and builds lasting capability.
24:25 - 25:37 | Reflection on LEGO Serious Play First-time experience with LSP. Barninder found translating thoughts into visual brick representation harder than expected—but valuable for expressing complex ideas differently than verbal communication allows.
Notable Notes
“Unity of thought comes before execution alignment.” Most leaders jump straight to “how” before ensuring everyone agrees on “why” and “where.” Get alignment on the goal first—then diverse approaches to execution become strengths rather than sources of conflict.
The innovation culture paradox: You can’t bolt innovation onto an organization through specialist hires. Building innovation into your team’s DNA means empowering people who already understand your business to solve problems with new tools, rather than hiring external experts who’ll battle existing culture.
The digital transformation lesson: Remember when companies hired Chief Digital Officers and dedicated transformation teams? They failed because existing teams said “that’s your job, not mine.” AI adoption is following the same pattern—separate AI teams building parallel data stores that won’t sync with core systems. Learn from history: integrate new capabilities into existing teams rather than creating organizational silos.
Growth as identity: Barninder’s approach to growth—reading, learning, evolving as parent/professional/person—extends beyond self-improvement platitudes. He researches parenting strategies like a technical problem, interviews role models before major life decisions, and maintains a life goals list from age 21 that he’s still actively working through.
The emotional baggage reality: Even with excellent leadership and clear vision, some people carry baggage that prevents them from moving forward. The ladder in Barninder’s model represents recognizing this reality—sometimes the most compassionate leadership decision is creating an exit path rather than forcing someone to stay in a role that isn’t working.
