Weekly Posts and Insights
Lead Within: The Art of Changing Systems Without Losing People
Most leaders eventually face the same tension: Do I spend my energy attacking the system from the outside, or changing it from the inside? This week’s Brief is about that difficult middle space, the space between idealism and pragmatism. The strongest leaders do not confuse patience with passivity, nor conviction with chaos. They learn the system they are in, understand its pressure points, and steadily move people toward a better future without losing the trust of those still living in the present one.
Accountability Makes People Uncomfortable
HB Weekly Leadership Brief
Week of March 9, 2026
Every organization eventually reaches a moment where the systems are in place, the plans are written, and the resources have been invested — yet progress still stalls. At that point, the issue is rarely about strategy. It is leadership.
Lead at the Right Altitude (Stop proving. Start scaling.)
What am I still doing because it makes me feel valuable, but actually limits our growth and my effectiveness as a leader?
Most executives don’t struggle with effort. We struggle with identity. For many of us, our early career success came from outworking others, doing it ourselves, being detail obsessed and fixing what others couldn’t (or didn’t want to). Gold Star! That’s how we got here. But that same identity becomes dangerous at scale.
Leading in a Loud World
A week or so ago, my wife sent me an Instagram clip featuring Sharon McMahon, #1 New York Times bestselling author, civics educator, and creator of The Preamble newsletter, in conversation with Dylan Michael White of @dadchats. As parents, coaches, friends, neighbors, and leaders, I think many of us are carrying a similar quiet belief: I’m not doing enough right now. We’re not present enough. Not mindful enough. Not showing up the way we think we should. And what we’re missing is context.
A Privilege to Lead
Leadership is a privilege, but it can also be a drain. Not because it’s wrong or misaligned, but because leadership requires presence, judgment, emotional regulation, and decision-making long after others have clocked out. Over time, even meaningful leadership can leave us running on fumes. That doesn’t mean you’re failing; it means you’re human. One of the quiet responsibilities of leadership is knowing when it’s time to refuel.
Tough Minds, Tender Hearts: Why High Standards Require High Support
If the expectation is excellence, then the work required to get there usually involves risk: trying a new approach, initiating hard conversations, innovating, confronting conflict, stretching beyond comfort, and showing up daily with discipline. That’s not a small ask. So a reasonable person will quietly assess one thing before committing to that level of effort: Do I believe my leadership (manager, boss, board, etc.) has my back?
Trust and Credibility and Why They Still Matter
When we talk about what makes communities and organizations truly successful, the first place we should look isn’t strategy documents, technology stacks, or growth plans. It’s our people — and more specifically, how we lead them. Organizations that thrive don’t do so because they’re well-funded, have better technology, or are lucky; they do so because they have the right leaders in the right positions, leaders who are able to capitalize on talents, communicate a clear and compelling vision, rally support — and build trust. This was true yesterday. It’s true today. It will be true tomorrow.
Leading Beyond the Grind: Lessons in Learning Before Earning, Health, Hustle, & 20-Hour Work Week I Direct Application with Matt Harrington
In this interview episode of Direct Application we talk to Bennett Maxwell — entrepreneur, founder of Dirty Dough, now with Craveworthy Brands! Bennett’s journey is one of grit, reinvention, and radical transparency. He grew up knocking doors in Utah, dropped out of a pre-med track to chase communication and sales, built and sold companies in multiple industries, scaled Dirty Dough to more than 450 franchises sold, helped ignite a national “cookie war,” and then completely rebuilt his physical and mental health — losing 120+ pounds along the way.
Empowering People Too Early (And Why It Backfires)
A practical leadership guide to the IEE Continuum—Include, Engage, Empower—and why empowering employees too early leads to failure and frustration. Learn how to develop supervisors, managers, and rising leaders through intentional modeling, coaching, and earned autonomy. Includes real-world scenarios for applying the IEE model to performance conversations, meetings, and cross-department projects.
Team Meetings Are Your Playing Field I Direct Application with Matt Harrington
High-performing teams win or lose in their meetings. In Episode 20, Matt Harrington explains why team meetings are the true playing field of organizational performance and shares three practical strategies—structure, shared accountability, and role rotation—to transform meetings into high-impact collaboration.