by JW | May 18, 2026 | Briefing
Each of us pays rent on yesterday’s decisions. This weekend, I rented a 15-foot U-Haul to help my mother clear out the last of her condominium before replacing the flooring. We loaded it with furniture, boxes that hadn’t been opened in decades, and the...
by JW | May 4, 2026 | Briefing
Over the past couple of weeks, I’ve been noticing a pattern in conversations with leaders I’m working with. Things aren’t necessarily broken, but they’re taking far more effort than expected—more time, more energy, more attention than anyone planned for going in. Most...
by JW | Apr 20, 2026 | Briefing
You can’t force a wave to form. You can only recognize it—and move at the right moment. I learned that the hard way as a kid in Hawaii. The same is true in strategy. Leaders spend a great deal of time refining strategic design and improving execution. When a strategy...
by JW | Apr 6, 2026 | Briefing
The instinct to simplify is almost always wrong. Over the past several weeks, I’ve noticed a recurring pattern in conversations about organizational design and management systems. At some point—often immediately after a system is introduced—the same request emerges:...
by JW | Mar 16, 2026 | Briefing
Friday night a Kona storm rolled across Maui and knocked out the power. For nearly twenty hours the lights were out. The street outside our condo flooded, and for a while it was impossible to drive anywhere—even if we wanted to. Inside, however, everything was...
by JW | Mar 2, 2026 | Briefing
As we enter March, I’m noticing an unsettling pattern across several leadership teams I’m working with: in many cases, key contributors are already showing early signs of burnout — and we are only two months into the year. For senior leaders, this is more than a...
