Episode 21 - The Power of Building Coalitions: Kathryn Wylde on Bringing Billionaires and Union Bosses Together
Defensiveness, not disagreement, is what kills change, according to Kathryn Wylde, former President and CEO of the Partnership for New York City. Kathryn spent five decades building coalitions between billionaires, union leaders, and government officials. Her central finding is both simple and underused: the leaders who get things done don't start by stating their position. They start by understanding what's driving the other side, quantifying the problem in terms they actually care about, and coming in with a specific ask instead of a grievance.
How do you get opposing sectors to actually work together?
The Edelman Trust Barometer's headline finding for 2026 is staggering: 70% of global respondents now say they are unwilling or hesitant to trust someone with different values, backgrounds, or information sources.
According to Kathryn Wylde – who’s been at the center of these kinds of conflicts for 50 years – the answer to this problem isn't about idealism. It's a structural issue. You need a forum explicitly designed to take people out of their sector identities and sit them down as stakeholders in a shared problem – not a political negotiation, not a press conference, not a debate. A room where the facts do the persuading. A radical concept for sure!
"Leaders from different sectors – from business, from labor, from government – have to have a forum where they can pool their resources, figure out how to tackle problems together. That's something we've gotten less good at over the years."
– Kathryn Wylde, former CEO, the Partnership for New York City
The proof of concept is New York City's 1975 fiscal bankruptcy, a moment when the city lost over a million residents, half its Fortune 500 companies, and ultimately its solvency. The bailout that followed wasn't a government rescue. David Rockefeller and Walter Wriston sat at the same table as union leaders, with the public sector unions agreeing to salary concessions and putting their pension funds on the line to keep the city solvent. Business, labor, and government, aligned not by ideology but by shared exposure to catastrophe. Nothing brings people together quite like the building being on fire. I guess the trick is learning to do it before the flames begin to spread.
The lesson Kathryn draws from that moment isn't that crisis is required; it's that the muscle of cross-sector collaboration atrophies when it isn't used, and the cities and organizations that maintain it don't have to wait for a crisis to deploy it.
How do you reframe a problem so people across sectors care?
In the early 2000s, New York's subway system was deteriorating and needed new financing. The idea of charging vehicles a fee to enter the central business district had worked in Stockholm. But in New York, political resistance against the policy was formidable. Nobody wanted to be the advocate for a tax.
Kathryn's move: commission an independent economic study to answer a question no one had asked. Not “should we have congestion pricing?” but “what does excess traffic actually cost, and who pays for it?” The original 2006 study put the annual cost to the region at $13 billion. By 2018, when the Partnership updated the research ahead of Governor Cuomo's congestion pricing push, that figure had risen to $20 billion – a 53% increase driven by more time stuck in traffic, higher wages, and rising operating costs.
"[By] coming in with facts that surprise them, you quantify the problem, and you quantify the benefits to them."
– Kathryn Wylde
The reframe transformed the advocacy landscape entirely. Employers who would have been resisters became champions, because the data showed them they were already paying, they just hadn't been told. That is the architecture of a durable coalition: find the version of the problem that makes the other side's self-interest visible to them.
The Amazon HQ2 story is the cautionary counterpoint. The what and the why were compelling – 25,000 high-quality jobs, a revitalized Long Island City – but the how was fatally flawed: a confidentiality agreement that kept the terms of a publicly subsidized deal secret, no process for community voices, no plan to address neighbors' legitimate concern that their kids wouldn't qualify for the jobs being imported. The result was predictable.
"Process matters. Good leaders, particularly on public-private deals, don't try and force their will. They try to make a case people will understand, and at the same time listen to what the concerns are."
– Kathryn Wylde
Why is defensiveness the biggest obstacle to effective leadership?
When leaders come in with anger, with outrage, or with a position they've already decided on, they trigger defensiveness in the other person. And defensiveness, as Kathryn puts it, is not just an obstacle, it's a full stop. Nothing moves. No amount of evidence, eloquence, or moral authority overcomes a person who feels attacked. Turns out, you can be completely right and completely stuck at the same time.
"When people are angry, they make other people defensive. There's no faster way to a roadblock for anything getting done than defensiveness. It's a restraining force. Things stop."
– Kathryn Wylde
The alternative isn't to suppress conviction or pretend disagreement doesn't exist. It's to lead with listening rather than positioning. The most effective leaders Kathryn has worked with – David Rockefeller being her primary example – were humble enough to understand that their resources and influence were only useful if the other people at the table trusted the process. Humility, in this frame, isn't a personality trait. It's a strategic discipline, and – ear muffs over your ego here – it’s effective.
"[The leaders I admire] don't start by pontificating their point of view. They start by gathering feedback from others, trying to find common denominator, areas of interest, agreement. And that's possible with almost anyone if you take the time."
– Kathryn Wylde
The same logic applies to every cross-functional negotiation, every difficult stakeholder conversation, every moment where a leader is tempted to lead with their conclusion rather than their curiosity. The goal isn't agreement. The goal is finding the shared problem underneath the competing positions. But that only becomes visible when someone stops talking long enough to listen.
What to do this week:
Before your next difficult stakeholder conversation, whether it's a resistant colleague, a skeptical board member, or a group pushing back on something you're trying to build, try Kathryn’s two-step prep:
Translate the problem into their currency: what does this issue actually cost them, and can you quantify it?
Come in with a specific ask rather than a general grievance. Pressure without a concrete request won’t take you far, but a concrete request gets you results.
Then, when you're in the room together, lead with a question instead of a position. Find out what's driving them before you explain what's driving you. To paraphrase Kathryn’s five decades of wisdom into one sentence: you can't find a common denominator if you don't know what the other person's numbers are.
Related Episodes
– How to Have the Hard Conversation You’ve Been Avoiding with Amy Gallo
– From Passive Tolerance to Active Inclusion with Rev. Mark Fowler
– Managing Yourself First with Margaret Andrews
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