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Somewhere between $84 trillion and $124 trillion will move from the baby boomer generation to heirs and to charity over the next two decades, depending on which research firm is counting. A meaningful share of it is headed toward philanthropy, and it's arriving into vehicles built to receive it: donor-advised fund assets grew 30 percent in a single year to $326 billion, and combined DAF and foundation assets are projected to reach $2 trillion by 2026.
Read MoreA 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.
Read MoreEvery transformation announcement follows the same arc. There is a compelling rationale, a strategic framework, and a call to action. Leaders communicate the vision. Managers cascade the message. And then, quietly, the organization does what it has learned to do: it waits.
Not out of laziness. Not out of resistance. Out of experience.
Read MoreThere'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.
Read MoreConsider 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.
Read MoreIn a village in Rajasthan, India, a 14-year-old girl named Nisha Vaishnav was at football practice when a family arrived to evaluate her as a potential bride. She refused the proposal. When her father later questioned why she kept going to practice, she told him: "There is no lover. I am going to play football. That is my love."
Read MoreI 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.
Read MoreIt'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.
Read MoreAs 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.
Read MoreEvery 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.
Read MoreBetween 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.
Read MoreTwo concerns tend to dominate our conversations with leaders: skepticism that AI is not all that powerful and the hype is overblown, or fear that AI is dangerous and perhaps best avoided altogether. However, these perspectives are distractions, slowing leaders down, narrowing imagination, and prevent experimenting with what is possible.
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