I spend most of my days as the principal of my healthcare executive search firm on the phone with seasoned industry leaders. These are individuals who’ve climbed to the highest ranks of household-name payers, providers, and healthcare technology organizations. Too often, what I hear are stories of deeply dysfunctional corporate cultures; places where those hired to drive transformation are quickly marginalized.
The theme is disturbingly consistent: “They hired me to lead Transformation/Integration X, but it became clear within weeks that the organization had no appetite for what real change required.”
So our conversations shift. We start trying to map out whether any viable path forward exists. We ask hard questions about what would need to change - and whether that’s likely to happen. Many calls end the same way: “I’m going to give it my best shot, but keep an eye out for me if something better fits.”
Let me be clear: these are not easily discouraged people. They didn’t reach the top by folding when things got hard. They understand the barriers to change. But too often, the honest conclusion is this: the culture itself is too toxic or resistant to allow transformation to succeed.
Why is this so common in healthcare? And more importantly, can anything be done about it?
To be fair, I won’t name names. But the executives I speak with come from every corner of the industry: Fortune 500 payers with skyrocketing valuations, dominant regional Blues plans, health tech unicorns, and flagship health systems. These are respected, successful organizations. On the outside, at least.
Inside? Many of these leaders were brought in to drive transformation in areas like Value-Based Care, Digital Health, Population Health, and care model integration. But what they find is a set of structural and cultural landmines that all but guarantee failure.
Here are the most common organizational roadblocks they encounter:
Untouchables -- These are underperforming individuals or entire power centers that leadership refuses to confront. It might be a politically savvy executive who’s failed upward and lacks core leadership ability. Or someone who was once effective but now clings to the past. It could also be a function or business unit that sees innovation as an existential threat. These individuals and entities act in self-preservation, not in service of the organization’s future. They block progress, hoard information, and operate with the unspoken support of others at the top.
Untouchables thrive in not-for-profit settings that prize consensus over performance. “Don’t rock the boat” becomes the unspoken mantra, even when the boat is sinking.
The Detached CEO -- These CEOs have a grand vision for transformation, but little connection to the reality on the ground. They speak the language of innovation. They see themselves as disruptors. But they’re blind to the actual mechanics and culture of their organizations. The result? Lofty goals with no traction. Transformation in theory only.
The In-the-Weeds CEO -- On the other end of the spectrum, some CEOs are buried in minutiae. They micromanage. They overstep. Their teams feel undermined and paralyzed. Innovation dies in a culture of fear and overcorrection.
Broken Governance -- Some Boards are simply not equipped to do their job. I’ve heard stories of disengaged, outdated Boards with little understanding of the challenges at hand. In other cases, the CEO has created a bottleneck, only letting the Board see what they want seen. Either way, when Boards are ineffective, oversight suffers and accountability disappears.
Institutional Resistance -- Culture is inertia. The longer an organization has operated in a particular way, the harder it is to change. Without full alignment and sponsorship from the Board and C-Suite, any transformation effort will collapse under the weight of its own resistance.
So what can be done?
At a minimum, we must start being honest about how prevalent and destructive these issues are. Too many executives step into roles thinking they’re about to lead meaningful transformation—only to find themselves boxed in by politics, dysfunction, and a culture that isn’t ready or willing.
If this paper helps just one executive spot the warning signs before taking a doomed role, it will have been worth writing. Better yet, maybe some organizations will begin to confront their cultural blind spots before hiring someone they can’t support.
As always, I welcome your feedback. Did I miss a major source of dysfunction? Am I overstating the case?
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