Nine Years Coaching Amazon Executives: Why Senior Leaders Plateau

The shift from running your team well to leading the enterprise is the hardest one most executives will ever face. Few get there.   

Pranav was in denial. 

We were three months into his coaching engagement, sitting together to debrief the stakeholder feedback I’d gathered from twelve of his colleagues. The feedback was consistent, and it wasn’tflattering. His peers described him as brilliant but territorial. His directs called him protective of his team but blind to the broader organization. His superiors said he wasn’t scaling. 

Pranav pushed back in the language I’ve heard from dozens of senior executives in his position. 

They slow me down. They don’t understand what my team does. Our goals aren’t really aligned. The system pits us against each other. 

He wasn’t wrong about any of it, exactly. He was just missing the point. 

The Pattern 

I’ve coached 47 executives at Amazon over the years, and I see a pattern there more clearly than I see it anywhere else. Not because Amazon is unusual, but because my sample size there is big enough for patterns to surface. I have no doubt the same pattern is at work at your company too. 

Here’s what I see: senior leaders operating from a narrow sphere. Their attention, their energy, and their sense of ownership rarely extend past the edge of their own org chart. They aren’tdefending that perimeter so much as they simply aren’t looking outside it. Anything beyond it is someone else’s job, someone else’s problem, someone else’s win. 

It shows up in ways large and small. Peer ideas get dismissed because they didn’t originate in-house. Partner teams get help only when a directive comes down from above. Weekly leadership meetings become reporting exercises rather than chances to shape the broader enterprise. And headcount becomes an obsession. Protecting it, growing it, reading every reorg as an existential threat. Junior executives notice all of this. They talk about it. 

The Real Ceiling Is an Identity Ceiling 

Most senior executives who plateau don’t have a skills problem. They have an identity problem. 

Their sense of themselves has fused with the size of their team. The empire has become the self. When they talk about their work, they use the word “my” often: my org, my people, my roadmap, my headcount. The broader enterprise is something happening nearby, not something they own a piece of. Asking what the enterprise actually needs, what the markets being served actually need, what sacrifice in their own org might unblock elsewhere, these questions aren’t ones they refuse to engage. They’re questions that haven’t even occurred to them. 

That’s the ceiling. And no amount of training on collaboration or strategic thinking gets past it, because the gap isn’t technical. It’s a sense of self that’s too small for the role. 

The Moment of Terror and Responsibility 

The shift, when it comes, doesn’t come from a framework. It comes from a mirror. 

The shift I mean is this: the move from running your own team well to operating as an owner of the enterprise. From playing your position to playing the whole field. 

In my coaching practice, the moment almost always emerges from the same process. I interview ten or twelve of the executive’s stakeholders, peers, directs, superiors, sometimes board members. I synthesize what I hear into a report that covers the full range of the executive’s leadership. Then we sit with the picture together. 

Most high-performing executives discover that their self-perception overlaps with how others see them by roughly 80%. It’s the remaining 20% that does the work. For executives like Pranav, the feedback that lands hardest is usually the same: not scaling, not collaborating, not seeing the bigger picture. 

The first response is almost always denial. Then anger. Then the rationalizations, many of them the same ones Pranav used, all of them partially true, none of them the point. 

If the executive has the honesty to keep looking, something changes. Not because I’ve framed it brilliantly, but because the picture, drawn by a dozen of their own stakeholders, is too coherent to explain away. Terror arrives first. Terror at seeing the larger sphere that’s been there all along, and at what operating from that sphere would actually ask of them, including the honest question of whether they can do it. Then responsibility. They can see, often for the first time, that their real sphere of agency extends far beyond their team. They can’t unsee it. 

Fewer than half of senior executives reach this moment. Fewer still press through it. The risk-reward calculation feels too dangerous. The reward for thinking bigger isn’t always visible or guaranteed. The system they work in rewards hitting this year’s stated goals with precision; the enterprise-level contribution that matters more in the long run is often unwritten and unspoken. Somost retreat. They find reasons the feedback was flawed, or reasons their situation is different, and they go back to the recipe they already know, the one they believe is what the system rewards them for. 

The ones who don’t retreat become the executives others will work for years later. 

The Long Game 

Let me tell you about one of them. I’ll call her Shreya. 

Shreya’s feedback looked a lot like Pranav’s. So did her first response. She went through the same grief, the same rationalizations, the same protective anger. Then, over weeks, something changed. Part of it was that the feedback was too consistent to dismiss. Part of it was that Shreya genuinely wanted her work to matter beyond her own org, and she began to see that the narrow posture was going to cap what she could contribute. And part of it, honestly, was that she wanted the VP promotion and she was smart enough to see that her current posture was the thing holding it up. 

Over the next 18 months, she did the work. She spent real time understanding what her peers were trying to accomplish, and looked for places her team could help them get there. In leadership meetings, she started speaking up for enterprise-level calls even when they didn’t directly benefit her org. She stopped reflexively protecting her team’s scope and headcount, and instead asked, more often than not, what the broader enterprise actually needed. She got promoted to VP. Two years in, she received the highest performance rating a VP at her level can receive. 

She isn’t fixed. Old habits still show up under stress. But she keeps working on it, and she treats the shift as a practice rather than a transformation. 

That’s the part of the story I want to be honest about. Reputations don’t change overnight. Even when an executive is genuinely changing their behavior, they often have years of reputation to outrun. The environment has to accumulate enough data points, over enough time, before the reputational balance shifts. 

Some executives can’t wait that long. They do the inner work, see the behavior change take hold, and then get discouraged when the external recognition doesn’t follow quickly enough. Patience runs out. They drift back to the old way because it at least feels like it’s getting them somewhere. 

Others never build the practice in the first place. They have the insight, they mean it sincerely in the moment, but they don’t do the weekly, sometimes daily, work of noticing their old habits and choosing differently. Without that repetition, the insight fades and the old behavior reasserts itself. 

The ones who break through are the ones who keep the practice going in the long middle, after the behavior has improved but before the reputation has caught up. They’re not necessarily the ones who did the most inner work most quickly. They’re the ones who stayed with it. 

Where Does Your Sphere End? 

The top of the pyramid is narrow not because there isn’t room. It’s narrow because few are willing to act as enterprise owners when the system around them is still rewarding this year’s numbers. The ones who reach it aren’t smarter than the ones who don’t. They’re more willing to pay the near-term cost, and more patient with how slowly the recognition follows. 

This week, ask yourself one question: what does your peer group need from you that you haven’t been willing to give? Then do one thing about it. Not a grand gesture. A single act of enterprise-mindedness in a place where your instinct would have been to focus on what is clearly yours. 

Then do it again next week. That’s how the shift actually takes hold.