New CEO Challenges: Why Experience Alone Won't Save Your Strategy

By Erin Sedor | Black Fox Strategy

Being a CEO is tough stuff. That’s not a complaint. It’s a baseline reality that gets glossed over in most leadership conversations. We celebrate the title, the authority, the corner office—and then quietly wonder why so many leaders who look ready on paper end up stuck within the first eighteen months.

Experience matters. Of course it does. But experience is not intelligence. Not the kind that matters when you walk into a new organization, a new industry, a new set of relationships and power dynamics that have their own history, their own wounds, their own unwritten rules. Experience tells you what worked before. Intelligence—the organizational kind—tells you what’s happening right now.

And that distinction is where most leaders get tripped up.

The Comfort of Familiar Answers

There’s a gravitational pull toward applying what worked in the last role to the challenges in the current one. It makes sense. You earned your seat at this table because of the results you’ve delivered. So, when you see a performance gap, a culture problem, or a team that’s clearly not firing on all cylinders, your instinct is to reach for the playbook that got you here.

The problem is that tried-and-true approaches fail—routinely—when applied to new environments without the necessary organizational, performance, and cultural intelligence. That’s not a knock on your competence. It’s a recognition that no two organizations are alike, and what looks like the same problem on the surface rarely has the same root cause underneath.

A CEO who successfully restructured a sales organization at her last company may walk into a new one and see similar symptoms—missed targets, low morale, finger-pointing between departments. Same movie, right? Not even close. At the last company, the issue may have been structural. At this one, it could be a trust deficit at the leadership level that’s been quietly poisoning performance for years. The symptoms are identical. The cause is completely different. And the fix that worked before? It might make this one worse.

I call this the experience trap. And seasoned leaders fall into it precisely because they’re seasoned.

The Messy Reality of Root Cause

Getting to the root of a problem is never as easy as we want it to be. Every organization is a living system—a web of interconnected processes, people, relationships, histories, and unspoken agreements that form a mesh far more complex than any org chart will ever reveal.

There’s the strategy itself and how it was built. There’s how it gets communicated—or doesn’t. There are the relationships between senior leaders and whether they actually trust each other enough to have the conversations that matter. There’s the culture: what gets rewarded, what gets punished, what gets quietly tolerated. There are systems and processes designed for a version of the organization that no longer exists. There are environmental drivers—market shifts, regulatory changes, community expectations—that interact with all of the above in ways that aren’t always visible until something breaks.

These things don’t exist in isolation. They interact. They amplify. They mask each other. A team that looks disengaged may actually be exhausted from navigating a leadership team that can’t agree on priorities. A strategic initiative that keeps stalling may not be poorly designed—it may be colliding with an unexamined cultural norm that punishes the kind of risk-taking the initiative requires.

New CEO Challenges

I’ve seen organizations invest millions in a new CRM system to fix a “sales problem” that was actually a leadership alignment problem. I’ve watched boards replace a CEO because revenue was flat, only to discover that the flatness was driven by a culture so risk-averse that no one at the operational level would make a decision without three layers of approval. The revenue problem was real. The diagnosis was wrong. And the replacement CEO walked into the same invisible headwinds that took down her predecessor.

You can’t see any of this if you’re only looking at the surface. And you definitely can’t see it if you’ve already decided what the problem is before you’ve done the work to find out.

Here’s a truth that makes a lot of leaders uncomfortable: organizations behave more like ecosystems than engines. You can’t just replace a part and expect the whole thing to run better. Every change you make sends ripples through the system—some predictable, some not. Every new leader, every restructure, every strategic pivot shifts the dynamics of the entire network.

This is a core principle of complexity science, and it applies directly to the way we need to think about strategic performance. In quantum physics, we call it entanglement—the idea that elements within a system are so fundamentally interconnected that a change in one immediately affects the others, regardless of distance or apparent separation. Organizations work the same way. A decision at the executive level doesn’t just cascade down through hierarchy. It moves laterally, diagonally, backward through relationships and informal networks in ways that no top-down communication plan can fully anticipate.

Yet we keep treating organizations like machines. We diagnose problems in silos. We build strategies in silos. We measure performance in silos. And then we’re surprised when silos are exactly what we get.

According to McKinsey, 45% of executives report that their strategic planning processes fail to track execution of strategic initiatives. That’s not a planning problem. That’s a systems-level awareness problem. They’re building plans without a clear picture of what’s actually driving—or undermining—performance from the inside out.

The Danger of Assumptions

The most common failure in organizational diagnosis is also the most human one: assuming we already know where the core problems are. It’s a thing – it’s called the Einstellung effect — you see the problem through the lens of solutions you already know, which blocks you from seeing it accurately. This is the process at play that I refer to as the experience trap and it is at the top of the list for new CEO challenges.

We do it because speed feels strategic. We do it because the pressure to deliver results is relentless. We do it because sitting with uncertainty—especially when the board, the funders, or the market is watching—feels like a luxury we can’t afford.

But it’s not a luxury. It’s the work.

When we skip the diagnostic and go straight to the prescription, we’re gambling. Sometimes we get lucky. More often, we solve the wrong problem—or solve the right problem in a way that creates two new ones. That’s how organizations end up in perpetual transformation mode: cycling from one initiative to the next, burning out their people, spending their capital, and never quite landing anywhere that feels like solid ground.

It’s a transformation treadmill. You keep running, the scenery keeps changing, but you never actually get anywhere. And the people watching—your team, your board, your stakeholders—start losing faith. Not in the strategy. In you. Because what they see is motion without progress. Activity without outcomes. And that erosion of confidence becomes its own strategic risk, compounding everything else that’s already going sideways.

Consider: 61% of executives report that they were not prepared for the strategic challenges they faced upon being appointed to senior leadership roles. Not because they lacked intelligence or drive. Because the complexity of what they walked into exceeded what their experience alone could decode. The patterns they relied on didn’t map to the new terrain.

This is not a failure of leadership. It’s a failure of approach. And it’s fixable—if you’re willing to look at the whole picture before you start trying to change it.

Feel like your lost in a maze? Information is your way out.

Holistic Assessment Is Not a Nice-to-Have

When I say holistic, I don’t mean abstract or philosophical. I mean practical. I mean looking at the operational core—the business model, the systems, the culture, the learning capacity—and understanding how those things actually connect to each other, where the gaps are, and where hidden opportunities are being missed.

I mean assessing business discipline—not just whether you have a strategy, but whether the structural design of that strategy actually supports performance, and whether leadership is articulating vision in a way that people can follow and believe in.

And I mean looking at the deeper layer: the cohesion of purpose across the organization, the decisiveness of strategic decision-making, the capacity to navigate uncertainty and adapt in real time. These are the attributes that separate organizations that thrive from organizations that survive—barely—one planning cycle at a time.

Taking these things together, in context, in relationship to each other, is the only way to get an accurate picture of what’s really happening. Anything less is a snapshot—and snapshots lie. They freeze a moment and strip away the motion, the tension, the direction things are heading. A snapshot of quarterly revenue tells you nothing about whether the team generating that revenue is held together by duct tape and exhaustion or by genuine alignment and shared commitment. A snapshot of employee engagement scores tells you nothing about whether the questions being asked are the right ones, or whether people feel safe enough to answer honestly.

Organizations are dynamic. The assessment that informs your strategy needs to be equally dynamic—capturing not just where things are, but how they got there and where they’re headed.

The best thing you can do for yourself right now, today, is recognize that understanding the totality of your organization is absolutely critical to the next strategic moves you want to make. Not just last quarter’s financial, not just your employee turnover rates, not just your efficiency metrics. Before you make a move in the market, you better know what your organization is capable of so you’re not walking yourself blindly through a maze.

A Different Kind of Diagnostic

This is exactly why I built the ESQI 360.

The ESQI 360—Essential Strategy and Quantum Intelligence 360—is a performance intelligence model anchored by the Purpose, Growth, Evolution, and Equilibrium foundation of Essential Strategy. It was designed to do what most assessments don’t: identify what is and what is not driving strategic performance from the inside out. It draws on my deep expertise in enterprise risk, resilience planning, and strategy design to give you a holistic view that’s calibrated to the stage of growth you’re in right now—not where you were last year, and not where a generic benchmark says you should be.

The model works across three integrated levels. At the Operational Core, we look at business model and systems, culture and learning, and the interlocks—where the dots connect, where we have gaps, and where hidden opportunities are sitting in plain sight. At the Business Discipline level, we assess the structural design of strategy, how well your systems support actual results, and whether leadership is articulating vision in a way that lands with the people who have to execute it. At the Quantum Intelligence level, we measure for the cohesion of purpose across the organization, focused on six key attributes: aspiration and alignment, intelligence and decisiveness, navigation and adaptation.

These aren’t abstract measurements. They’re the difference between a leadership team that can sense a problem forming and course-correct, and one that doesn’t know there’s a fire until the building is already burning.

Every organization is unique. The mesh of relationships, systems, influences, and drivers that define yours is unlike anyone else’s. Any assessment worth its salt has to honor that complexity rather than flatten it into a standardized template. The ESQI 360 does exactly that. It meets you where you are, reveals what your experience alone can’t see, and provides the intelligence foundation upon which real strategy—the living, adaptive kind—can be built.

Experience Is the Starting Point, Not the Answer

None of this is an argument against experience. Your track record, your instincts, your hard-won wisdom—these are assets. Significant ones. But assets without intelligence are just resources waiting to be misallocated.

The best leaders I work with are the ones who know how much they don’t know. They’re the ones willing to sit with the complexity long enough to see the real picture, rather than the one their experience has primed them to expect. They’re the ones who understand that getting it right the first time isn’t about having all the answers—it’s about asking the right questions and building the organizational awareness to act on what you find.

That kind of intelligence doesn’t come from another leadership book or a weekend retreat. It comes from doing the diagnostic work that most organizations skip because it feels slow, because it’s uncomfortable, or because someone in the room thinks they already know the answer. It comes from recognizing that the complexity of your organization is not an obstacle to strategy—it is the strategy terrain you must learn to read.

Being a CEO is tough stuff. That much is true. But tough doesn’t have to mean blind. And with the right intelligence, it doesn’t have to mean alone.

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Erin Sedor is an executive advisor and strategic performance consultant with 30+ years helping leaders build the organizational intelligence that drives strategy from the inside out. She is the creator of Essential Strategy, the ESQI 360, and the Quantum Intelligence framework for conscious, adaptive leadership.