Why Busy People Aren't Making Progress

A few months ago, I sat in on a leadership offsite where a president told her team, "We need to be more strategic this year." Heads nodded. Someone wrote it on a whiteboard. The meeting moved on to a 45-minute debate about which project management tool to standardize on.

Nobody in that room was lazy or coasting. Every calendar was double-booked. Six months later, the "strategic" priority hadn't moved an inch.

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The Real System Running Your Org

There's a second organization operating inside your first one. It doesn't appear on the org chart. It wasn't designed. It has no official authority. And yet it shapes which decisions actually stick, which ideas survive contact with the culture, and who really has power.

It’s a shadow system.

Every organization has one. It's the set of unwritten rules, informal networks, and unspoken agreements that run parallel to everything you've intentionally designed.

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Boards That Govern, Leaders That Lead

Consider two people who both care deeply about the same organization. The first is an executive director, several years into a role at a nonprofit they have loved since their earliest days on staff. The burnout is quiet, but it is real. The second is a board member. They said yes because they believed in the cause. They show up, mostly, though life is busy and the expectations were never entirely clear.

Neither of them alone is failing. The partnership is.

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Beyond the Office: Rethinking Proximity in Modern Work

I keep having versions of the same conversation with leaders and managers.

Sometimes it’s a remote team that feels like onboarding has become impossible. Sometimes it’s a hybrid team that’s technically “back,” but still spending most of the day on video calls. Sometimes it’s a co-located team where everyone sits in the same building and still struggles to coordinate across functions, or understand what other people are actually doing.

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The Mindset Myth: Why Your Resolution is Already Toast

It's early February, and if you're like 80% of Americans, that shiny New Year's resolution you made three weeks ago is gathering dust somewhere between "I'll start Monday" and "Maybe next year." Perhaps you resolved to be more positive, adopt a growth mindset, or finally become that unflappable leader who sees every setback as an opportunity. Noble goals, all of them.

Here's the uncomfortable truth: mindset work isn't a resolution. It's a renovation.

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Reflecting on Dowling Street's Most Important Evening

As we recently celebrated Dowling Street's 12th anniversary, I found myself thinking back to an evening two years ago that crystallized what this work is really about.

On March 21, 2024, we gathered in New York City to mark our 10th anniversary. But this wasn't a typical milestone celebration. It was a chance to honor our firm's most important work to date, and to hear from a man whose story embodies the very principles we've built our practice around.

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The Velocity Trap: Why Moving Fast Is Making You Slower

Every leader I know is sprinting. Racing to adopt AI. Rushing to transform. Scrambling to stay ahead. And yet, when you look at the actual results, most of them are running in circles. MIT's recent study reported that 95% of generative AI pilots are failing to deliver measurable value. Nearly all organizations are seeing zero return on their AI initiatives. 

That's not an AI problem. That's a velocity problem. 

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Organizational Scar Tissue: Building Trust After Disruption

Between the ages of fifteen and eighteen, I had three knee surgeries to repair a torn ACL. I know scar tissue well: the dull ache, the resistance, the slow work required to move through it. One post-op appointment stands out. After months of work, my doctor told me scar tissue was building up again. Unless I increased my range of motion, I would need another surgery to remove it.

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Why Your Organization Needs to Be Antifragile

It's 2024, and suddenly everyone's talking about the WNBA like it's an overnight success. Caitlin Clark! Angel Reese! Sold-out arenas! But here's what the "overnight success" narrative completely misses: the WNBA spent years getting knocked down, dusting themselves off, and figuring out how to use each setback as fuel for what came next. And that's exactly what your organization needs to learn to do.

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