Good leaders don’t shut down when employees push back—they do this instead

Twenty years ago, as the top digital and innovation executive for Citi’s credit card business, I led the team that spent months building what looked like a brilliant partnership. We’d found a startup with a disruptive payments platform—one that became the forerunner of what has become a new payment type used by millions of consumers today. The deal: strategic investment in exchange for access to the startup’s codebase as a sandbox for innovation pilots. No more waiting in the legacy systems queue. Just rapid prototyping with leading-edge developers.

We built the entire partnership in a silo of supporters, treating resistance as something to avoid until absolutely necessary. Then came final deal approval day. The senior executives heading risk management, compliance, legal, finance, regulatory affairs, and profit and loss (P&L) weighed in: “The regulators won’t like this.” “Have we gotten corporate approvals?” “What’s the ROI?” “We’ve never done this kind of deal.”

Deal torpedoed. Within a few years, that startup was acquired for close to $1 billion.

The loss wasn’t just financial. It was a failure to recognize that resistance contains intelligence about reality that plans built-in echo chambers inevitably miss. Colleagues felt blindsided—asked to bless a final deal rather than shape an evolving strategy. The resistance wasn’t about the idea. It was about being excluded from the journey.

I’ve spent the two decades since distinguishing the signal from the noise—and teaching leaders how to avoid the expensive mistakes we made.

Why We Keep Making the Same Mistake

Leaders faced with pushback default to a familiar playbook: build innovation in a protected silo, surround yourself with enthusiasts, keep resistors at arm’s length. The logic seems sound—protect the new thing from the “antibodies” of legacy thinking.

But here’s what we discovered the hard way: unfamiliarity, fear of the unknown, turf protection—these weren’t just emotional reactions. They were signals. Risk and compliance leaders felt threatened because no one had involved them early enough to anticipate possible regulatory concerns. P&L managers pushed back because the project diverted resources from their quarterly targets. The resistance contained intelligence about implementation realities that an enthusiast-only team couldn’t see.

When 70% of change initiatives fail despite massive investment, the problem isn’t that people don’t understand the plan. It’s that the plan doesn’t account for what people understand about reality.

Learning to Translate Resistance Into Intelligence

The shift starts with listening differently. When someone says, “We tried this before and it didn’t work,” leaders typically hear obstruction and respond: “This time is different—we have better technology.”

But what if you asked instead: “What specifically failed last time, and how does this approach account for those lessons?” Suddenly you’re mining history for intelligence about why elegant pilots don’t scale.

When a stakeholder says, “Our customers won’t understand this,” the dismissive response is “Of course they will—we have market research showing they favor this concept.” The intelligence-gathering response: “That’s an important observation. Where do you see the greatest failure points that we should account for?”

Or consider: “This conflicts with our other priorities.” Many leaders hear bureaucratic gatekeeping and respond by promising to “make the case” at prioritization meetings. But that’s still trying to convince. The intelligence approach: “We have a full load of urgent priorities, you’re right. Where do you see the biggest stress points this project might create?”

These aren’t just nicer ways of saying the same thing. They’re diagnostic questions that surface constraints the plan hasn’t addressed. When you ask, “Where do you see the biggest stress points?” instead of selling your solution, something shifts. You’re signaling genuine understanding, not persuasion. That act of listening—what former hostage negotiator Chris Voss calls “tactical empathy”—builds the trust that determines whether your initiative scales or stalls.

Why This Matters More Now

AI experimentation is amplifying every dysfunction in how organizations handle resistance. Consider a common pattern: A team builds an AI assistant for customer service reps. The tech enthusiasts love it at pilot stage—impressive accuracy, clean demo, excited exec sponsors.

But they never involved actual service reps. So, they didn’t discover until scale that the assistant couldn’t handle the 20% of calls requiring human judgment, created more work documenting exceptions than it saved, and made reps feel surveilled rather than supported. Adoption stalled. The pilot became another “AI experiment that didn’t work.”

The same dynamic plays out with creative teams resisting generative AI. The pattern sounds familiar: Our brand spends millions to sound like itself. The moment we start prompting a model trained on every competitor’s campaign, we’re paying to erase what makes us different.

Beneath the pushback is stewardship of hard-won brand equity, not necessarily technophobia. The intelligence-gathering response: “What if we approach AI as rough-draft only? How might we develop explicit guardrails for tone and references to preserve what makes us distinctive?”

From Stakeholder Management to Coalition Building

Traditional stakeholder management maps who supports and who resists, then tries to convert resistors through better communication. Coalition building does something different: it engages across the spectrum from the start to build trust—the foundation that determines whether change scales.

I’ve seen this work. When innovation leaders don’t own a P&L, they face scrutiny from business unit managers who question whether “the innovation people” truly care about quarterly targets. One way through: explicitly align early experiments to P&L managers’ top priorities—not to convince them your idea is right, but to demonstrate you’re invested in making them successful. Shared values become the bridge when you disagree on tactics.

The Questions That Change the Conversation

In my workshops with senior leaders across financial services and other sectors, I consistently hear the same story. As one CTO told me: “We built our gen AI strategy with only the innovation team. Now we’re stuck because compliance wasn’t engaged early.”

Here’s where to start:

“What do you see that we might be missing?” Assumes intelligence in the perspective, not obstruction.

“What would need to be true for this to work in your world?” Surfaces constraints before they become deal-killers.

“What shared outcomes matter most to both of us?” Finds the values bridge when tactics diverge.

The fundamental shift: from “How do I overcome resistance?” to “What intelligence am I missing if I don’t engage this perspective early?”

Twenty years later, companies are still building partnerships, AI pilots, and transformation initiatives in silos of supporters—the same mistake my Citi team made. Still treating resistance as friction to manage rather than intelligence to integrate: The billion-dollar missed opportunities keep piling up.

What changes when you treat resistance as the intelligence it actually contains? You build coalitions instead of echo chambers. You gain insights that improve your plan and trust that enables scale. And you stop repeating the expensive mistakes we learned from the hard way.