The CEO Complacency Trap: How Success Can Stall Growth

Is the phone buzzing in your pocket an iPhone? Chances are, it is. Apple controls 21% of the smartphone market. But when Andre van Hall hears the buzz of that sleek device, a different rectangular fixture of American life comes to mind: the Sears catalog.

While he admires Sears for having the courage to challenge the success of their catalog, he notes that they did so without adding the kind of innovation that would have propelled them forward.

“If Sears had hung on for another 10 years, they could have digitized their catalog and beat Amazon to the punch,” says van Hall, author and 2025 Vistage Speaker of the Year.

What caused the once-great retail star to fade? The same force that van Hall and other leadership experts warn may eventually catch up with Apple and companies like it: complacency.

Success has a way of rewiring a leader’s brain, turning bold innovators into timid guardians of the status quo. Eventually, those laurels you’re resting on dry out. Only 1 in 10 S&P 500 companies maintained above-GDP growth to keep a coveted spot on the list for more than 30 years, largely because leaders tightened their apertures and stopped pursuing — or even imagining — new growth opportunities.

“Success teaches leaders the wrong lessons. What worked in the past becomes almost like religion,” says Ian MacDougall, Founder and Principal Associate of Corporate LifeCycles, Inc. and 2024 Vistage Speaker Lifetime Achievement Award winner. “They become prisoners of their past success, and they’re immobilized to deal with what’s happening around them.”

According to MacDougall, the effect success has on a leader’s thinking can erode growth gradually — and then all at once. He and van Hall explain why success changes leadership behavior, and what to do about it.

How Success Rewires CEO Decision-Making

Van Hall was a successful hospitality industry CEO when a highly specific and unusual confluence of circumstances caused blood flow to stop to his optic nerve, rendering him blind. In a show of solidarity, his executive team sent a note to the board declaring their willingness to “pick up the slack” so van Hall could keep his job. The offer enraged him.

“What do you mean I can’t do it?” he recalls thinking. “Get lost. I’m Andre.”

Van Hall experienced an extreme version of what researchers describe as a blurring of the line between a leader’s sense of self and the organization they lead. It’s treacherous territory for leaders whose methods achieve extraordinary success in one set of conditions — only to become constraints when conditions change.

Van Hall says past wins build a “confirmation bias” that prioritizes instinct over inquiry — a posture that filters down. Teams begin to hold back rigorous challenges to leadership’s decision-making because they sense it isn’t welcome.

“One of the biggest shames of life is to have your eyesight but not see the blind spots that are holding you back,” he says. “Curiosity and humility are the tools to eliminate your blind spots.”

The problem isn’t just psychological; it’s structural. MacDougall points to a key inflection point in every company’s lifecycle: the moment when professional managers begin to replace entrepreneurial founders at the top. Entrepreneurs have a youthful “mental age,” the disparity between what they have and what they strive for is still wide. But as organizations mature, the CEO may become quite satisfied with the status quo. Or the entrepreneurial CEO leaves, and the role goes to executives optimized for protecting margins and meeting quarterly targets rather than chasing the next horizon.

“Look at who’s being promoted to the CEO role in big companies,” MacDougall says. “That is a huge tell in terms of how the company is going to be managed.”

The Subtle Signs You’re Already in the Success Trap

Has your success landed you in a complacency trap? With year-over-year growth, you might confidently answer no. But look a closer at this checklist culled from business experts, including MacDougall and van Hall and ask yourself whether that nice warm pot you’re in is getting warmer by the quarter:

• Do leadership meetings feel smoother but lack real debate?
• Do strategic decisions face less pushback than in the early years?
• Has the innovation pipeline begun to slow?
• Have external inputs — advisors, peers, market signals — decreased?
• Have you become insulated from dissent?

Of all these warning signs, MacDougall points to innovation as the most revealing diagnostic.

“Innovation — and I don’t just mean a cosmetic upgrade — real innovation is the ultimate test of whether there’s complacency,” he says. “In the last 12 months, what new products did you introduce? What new market segments did you target? Or did you focus a lot on cost-cutting and getting more money to the bottom line? That’s stagnation.”

MacDougall uses Apple as a case study. The company’s annual iPhone updates incrementally improve a product already in most pockets — a development he calls cosmetic rather than innovative.

“At some point,” MacDougall says, “somebody at Apple should have asked: What are we? Who is Apple?”

Why Teams Stop Challenging Successful CEOs

MacDougall describes the lifecycle of a company in 3 stages: growing, aging, and dying. At the transition between growing and aging, a company is in its prime — internally aligned, laser-focused on customers, and successful by any measure. Unlike people, companies can stay in the prime of their lives for years, provided they retain the entrepreneurial spirit that earned their early wins.

“The most dangerous time for a company is late prime,” he says, “This is when a company doesn’t realize it’s in trouble. If you have 20 consecutive quarters of sales growth, nobody wants to rock the boat. But that is when organizations grow on residual momentum.”

Another word for this is inertia. It often emerges from a self-protective fear among teams who perceive a power distance between themselves and the CEO. Rather than raise uncomfortable questions, they prioritize stability. Information flow trickles. Corrective feedback stops reaching the top.

Van Hall experienced this dynamic firsthand and admits he contributed to it. His reaction to his team’s letter (“Get lost. I’m Andre.”) was not the humility of a leader open to input. It was the pride of a leader who had come to see himself as synonymous with his company’s success. That conflation, he argues, is one of the most common and most dangerous traps in leadership.

“As CEOs, if we want to create a culture where our team is comfortable coming to us with hard truths,” van Hall says, “we have to model that humility ourselves.”

The Plateau Pattern: Where Complacency Leads

Jeff Bezos once famously predicted his company’s eventual demise. He made that statement in direct response to an Amazon staffer’s question about how the retailer could avoid Sears’ fate. At the time, Sears had just begun to exhibit the classic plateau pattern: growth flattening, market trends ignored, and teams shifting from strategic thinking to operational execution. Bezos argued that while death comes for most companies, fighting complacency would do much to delay the inevitable.

A 2023 McKinsey digital strategy survey found that top performers were 63% more likely to allocate resources to new product development or entering new markets, and 44% more likely to pursue opportunities outside their current industry. The data confirms what van Hall and MacDougall observe in the field: a willingness to look beyond the existing playbook is what separates companies that sustain momentum from those that quietly coast to a stop.

Mark Cohen, a former Sears executive, spent a decade warning that cost-cutting and the absence of a growth north star would sink the retailer: “Sears Roebuck lost its forward momentum. You’ve got to be able to be profitable without the benefit of endless, ongoing, and mindless cost-cutting.”

Reintroducing Productive Tension

If success narrows thinking and stalls growth, the antidote is reintroducing challenge and discomfort — not by blowing up what works, but by deliberately designing a culture where challenge is expected.

Van Hall did exactly this as general manager of a large hotel chain, structuring the organization so that anyone, at any level, could be an innovator. One housekeeper noticed that sheets could be folded together in the laundry, 2 per packet, thus transforming bed-making into a single-motion endeavor instead of two. That small process change, multiplied across nearly 2,000 beds in a sold-out hotel, saved 2,000 minutes of labor per day.

“That won’t happen if you don’t create a culture where it’s okay to speak up,” van Hall says.

He also draws a sharp distinction between judging an employee’s idea and assessing it. Judging is fast and instinctive (“We tried that before,” “We can’t afford it,” “Not right now.”) Assessing requires critical thinking: pausing to ask why the employee sees what they see, what problem they’re pointing to, and what might be possible.

MacDougall approaches the same problem from the organizational level. He recommends leaders start by asking themselves the most discomfiting question of all: “What is our company?” Once that question is genuinely wrestled with, decentralizing operations frees the CEO to focus on vision and strategy while empowering the rest of the team to drive toward it.

“Decentralizing equates to more entrepreneurship,” he says. “In many aging companies, there are entrepreneurial people who can’t get their ideas to the right table. So guess what they do? They leave.”

CEOs Must Stay Sharp After Success

Winning feels great. But the morning after the most profitable Sunday in your company’s history is still Monday. Getting comfortable is not an option if you want to keep growing.

This is where peer advisory groups like Vistage become a strategic advantage. MacDougall credits the organization with normalizing frank conversations about stalled innovation and risk-averse leadership.

“The first thing I advise a company that’s aging is to bring leadership together and get them dissatisfied with the status quo,” he says. “If that doesn’t happen, nothing’s going to change.”

By creating structured environments for honest feedback and outside perspective, Vistage challenges CEOs to question their assumptions and continue growing long after initial wins.

“That is what I think the role of the Vistage group is: to put the CEO in the kind of uncomfortable position that gets them out of the day-to-day operations,” van Hall says. “This awakens their curiosity and gives them the opportunity to do the analysis: How am I growing?”

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