Moving Up the Administrative Ranks: Ten Questions Every Aspiring Leader Should Ask

Higher education has no shortage of challenges—but it does have a shortage of strong leaders ready to tackle them. As Allison M. Vaillancourt argues in her Chronicle of Higher Education essay, “How to Move Up the Administrative Ranks,” the leadership pipeline is leaking badly

Presidents, provosts, and deans are stepping down at a faster rate, while search committees complain about the small pool of applicants. The stakes are high: colleges and universities are expected to solve near-impossible problems, from declining enrollment to cultural polarization, without raising tuition or causing controversy.

If you’ve ever thought about moving into administration, now might be the right time. But how can you tell if you’re prepared? Vaillancourt condenses years of consulting and higher education leadership experience into ten insightful questions that help faculty and staff consider if leadership is a suitable path.

1. Why do you want a leadership role?

Motivation matters. If you’re drawn by power, pay, or prestige alone, you’re unlikely to succeed. The best leaders are animated by service, problem-solving, and a desire to advance colleagues’ success.

2. Do you have the right competencies?

Effective leaders need strategic thinking, political savvy, communication skills, and personal resilience. Few people are strong in all areas, but a willingness to learn, adapt, and grow is essential.

3. Are you willing to be political?

Many recoil at the idea of campus politics, but as Vaillancourt notes, politics is how things get done in complex organizations. Navigating competing agendas with integrity—not avoiding them—is key.

4. Can you handle conflict?

Avoidance may keep the peace in the short term but erodes trust in the long term. Leaders must summon the courage to confront underperformance, deliver candid feedback, and make unpopular decisions when needed.

5. Will you put yourself out there?

Talent alone won’t land you an administrative role. Visibility matters: apply for stretch assignments, lead projects, join committees, publish thought pieces, and connect with professional networks. Self-promotion may feel uncomfortable, but it often separates those who move up from those who remain overlooked.

6. Do you have a brain trust?

Leadership can be isolating. A personal “board of advisers”—strategists, insiders, external peers, truth-tellers—provides perspective and accountability. These allies help leaders wrestle with dilemmas and anticipate challenges.

7. Can you take care of yourself while taking care of others?

Leadership is emotionally taxing. If you rely on constant validation, administration may prove draining. Resilient leaders protect their energy, establish boundaries, and find meaning in challenge rather than collapse under it.

8. Do you listen more than you talk?

Old leadership models prized the “expert with answers.” Today’s leaders excel by asking questions, practicing inquiry, and harnessing the wisdom of others. Listening, not lecturing, earns trust.

9. Are you prepared for critics?

The higher you rise, the more visible—and vulnerable—you become. Not everyone will root for your success. Leaders must expect resistance, avoid defensiveness, and use opposition as a source of learning rather than personal affront.

10. Will you know when it’s time to go?

Leadership positions rarely last forever. New presidents reshuffle teams; shifting strategies leave longtime administrators sidelined. Wise leaders prepare for transition, keep their CVs current, and exit with grace rather than bitterness.

What This Means for Higher Ed

The ten questions may not guarantee an easy path, but they do clarify the qualities today’s institutions urgently need. The era of the “heroic” president or dean has passed. Leaders who succeed now are humble, curious, courageous, and emotionally intelligent. They build coalitions, handle conflict, and stay resilient amid turbulence.

For aspiring leaders, the message is both sobering and inspiring. Sobering, because the work is relentlessly tough, often thankless, and nearly impossible to “balance” with personal life without intentional boundaries. Inspiring, because colleges and universities urgently need values-driven leaders—and because leadership is learned, not inherited. As Vaillancourt reminds us, the best leaders are built through observation, practice, and ongoing refinement, not through charisma alone.

If you find yourself nodding along to these questions—motivated by service, willing to learn, comfortable with conflict, open to politics—perhaps you’re more prepared than you think. Higher education doesn’t just need more leaders; it needs better ones. And if you’re willing to ask yourself the tough questions, commit to growth, and embrace the messiness of campus leadership, you might be exactly the kind of leader your institution is looking for.

Ultimately, climbing the administrative ladder isn't about ambition for its own sake. It’s about purpose: to enhance student success, support colleagues, and guide institutions through uncertainty with integrity. If that resonates with you, it might be time to step forward.