When Solutions Become Problems: Three Stories of Leadership Evolution

Three conversations from my coaching practice have been circling in my mind lately, each one revealing something essential about how leaders navigate the space between aspiration and reality. While the details differ dramatically—a community college in the Midwest, a regional university in the South, and a private college in New England—the underlying questions feel universal: How do we know when our strategies are working? When do we find the courage to change course? And perhaps most importantly, how do we lead authentically when the stakes feel impossibly high?

The Marketing Mirage

The first conversation began with what seemed like a triumph. A college president had revolutionized their institution's visibility through an ambitious partnership with a national marketing firm. For nearly four years, the collaboration had delivered impressive results: sleek new branding, sophisticated digital campaigns, and a steady stream of prospective student inquiries that made admissions staff smile for the first time in years. But somewhere along the way, the partnership had evolved—or perhaps consumed. What started as targeted brand development had expanded into student retention consulting, academic program redesign, and even faculty development workshops.

"I keep asking myself," this president confided during our session, "at what point does a solution become the problem it was meant to solve?"

This question haunts me because it reveals something we rarely discuss openly in higher education: our tendency to seek external validation for internal challenges.

What struck me most wasn't the specifics of the marketing relationship, but the president's growing awareness that sustainable change requires internal ownership. "I realize now," they reflected, their voice carrying both regret and resolve, "that we've been renting our institutional identity instead of nurturing it."

The Reluctant Visionary

The second conversation unfolded with someone I'll call a hidden gem—though they would cringe at such a description. This academic affairs leader had spent over a decade quietly transforming their institution's approach to student support services. Their initiatives had improved graduation rates, reduced equity gaps, and earned national recognition from accreditation bodies. Yet when we began exploring their career aspirations, something fascinating emerged. Despite over a decade of increasingly successful leadership experience, they had convinced themselves that senior executive roles were somehow beyond their reach—not because they lacked qualifications, but because they had internalized a narrative about not being "presidential material."

"I keep thinking about all the committees I haven't chaired," they admitted, "instead of recognizing the students I've helped graduate."

This conversation reminded me of research on attribution bias, but it also revealed something more specific to higher education: how our sector's emphasis on traditional pathways can create blind spots about unconventional expertise.

The breakthrough coaching moment came when they began describing their vision for holistic student development. As they spoke about creating wraparound services for first-generation college students, about building bridges between academic learning and career preparation, I could hear their authentic leadership voice emerging. They weren't trying to become someone else; they were finally recognizing who they already were.

The Principled Strategist

The third conversation centered on perhaps the most complex leadership challenge: preparing for a presidency while honoring the full complexity of a human life. This leader had what search consultants call "an enviable background"—successful fundraising experience, innovative academic programming, strong community partnerships, and a clear vision for institutional transformation in the liberal arts. But unlike many aspiring presidents, this person refused to separate their professional ambitions from their personal convictions.

"I've watched too many leaders lose themselves in the pursuit of the next opportunity," they told me, their words carrying the weight of observed experience. "I want to lead from who I am, not who I think a president should be."

Much of the literature on presidential preparation treats personal considerations as obstacles to overcome rather than values to honor. But this leader was modeling something different: the possibility of preparing for senior leadership while maintaining clear boundaries about what they were and weren't willing to compromise.

Their approach reminded me of Parker Palmer's work on leading from within—the recognition that authentic leadership emerges from the intersection of personal integrity and professional competence. This leader possessed deep ambition for institutional change alongside an equally deep commitment to family and personal values.

The Courage to Reimagine

What connects these three stories is a shared willingness to question fundamental assumptions about how leadership development actually works.

In each case, the most transformative moments came not from learning new strategies or acquiring new skills, but from examining beliefs that had been operating below the level of conscious awareness.

These conversations remind me why I'm drawn to executive coaching in higher education. Our sector is filled with brilliant, dedicated people who often carry enormous responsibility for institutional success alongside their own professional development. The work requires creating sacred space for leaders to name what they're really experiencing, to examine their assumptions with gentle curiosity, and to imagine possibilities they might not have previously considered.

But these stories also point toward something larger than individual leadership development. They suggest that the future of higher education depends not just on better-trained administrators or more sophisticated strategic planning, but on leaders who can hold complexity without losing their authentic voice. The president is learning to build internal capacity rather than buying external solutions. The academic affairs leader is claiming their expertise and their right to shape institutional direction. The aspiring president is integrating personal values with professional ambition. Each represents a different facet of what I think of as sustainable leadership—leadership that can be maintained over time without burning out the leader or compromising the institution's soul.

As I reflect on these conversations, I'm struck by how each leader was practicing the kind of reflective courage that higher education desperately needs. They were willing to examine their assumptions with uncomfortable honesty, acknowledge what wasn't working despite significant investment, and imagine new possibilities that honored both institutional needs and personal integrity.

In a sector often paralyzed by tradition and risk aversion, this willingness to engage in honest self-reflection and strategic reimagining feels both rare and essential. The future of higher education depends not just on innovative programs or sustainable business models, but on leaders who can navigate complexity while remaining grounded in their own authentic vision of what's possible.

These three conversations give me hope that such leaders are emerging, one vulnerable conversation at a time. They remind me that the most profound changes in higher education don't always begin with strategic plans or board resolutions—sometimes they begin with a leader finding the courage to ask themselves who they really are, and who they want to become.