Who Helps You Think Bigger, Better, and Differently?

by Claire L. Brady, EdD

Executive coaching has become increasingly common in higher ed, and I'm glad to see it. Presidents, vice presidents, deans, and other senior leaders are navigating enormous complexity, often with fewer resources, greater scrutiny, and little room to think out loud. Having someone outside your institution who can challenge your assumptions, help you work through difficult decisions, and support your growth can be enormously valuable.

But here's something I wish more leaders understood: Hiring an executive coach isn't simply about finding someone with an impressive résumé. It's about finding the right relationship for the work you need to do. I've spent nearly three decades in higher education leadership, and today I coach a small number of presidents and vice presidents. I've also worked with enough leaders to know that what one person finds energizing and productive, another might find frustrating or unhelpful.

So, before you sign a coaching agreement, here are a few things worth considering:

1. What do you actually need help with?

This seems obvious, but you'd be surprised how many leaders begin looking for a coach without being able to articulate what they want from the relationship. Are you navigating a transition into a new executive role? Struggling with a challenging supervisor or board relationship? Trying to strengthen your executive presence? Working through organizational change? Or do you simply need a confidential thought partner who understands the complexities of higher education leadership? Those are different needs, and they may call for different kinds of coaching.

You don't need a perfectly articulated development plan before your first conversation. A good coach can help you clarify your goals. But you should have some sense of what you hope will be different six months from now. Ask yourself: If this coaching relationship is successful, what will I be doing, thinking, or approaching differently?

2. What kind of coaching style works for you?

Some coaches are primarily skilled facilitators. They ask thoughtful questions, reflect what they're hearing, and help you arrive at your own conclusions. Others are more direct, offering observations, challenging assumptions, and drawing on their professional experiences. Neither approach is inherently better, but they can feel very different.

My own coaching style is conversational, candid, and strategic. I ask plenty of questions, but I'm also comfortable saying, "Have you considered another way of looking at this?" or sharing an example from my own leadership experience. I'm not particularly interested in spending an entire hour asking questions when a practical conversation could move us forward, but I am in the minority there as I approach coaching more as “in-house consulting..” Whereas, other leaders may prefer a more structured, reflective approach.

Ask a prospective coach: What does a typical session with you look like? How do you balance listening, questioning, challenging, and offering advice? And pay attention to how the conversation feels. Do you feel comfortable? Challenged? Heard? You should probably experience all three.

3. Do credentials matter? Yes. But so does experience.

There are excellent coaches who hold credentials through organizations such as the International Coaching Federation (ICF), and those credentials can demonstrate training, supervised practice, and adherence to professional standards. There are also outstanding executive coaches who don't hold formal coaching certifications but bring decades of leadership experience, strong facilitation skills, sound judgment, and a proven record of helping executives grow. And, of course, there are credentialed coaches who may not be particularly well suited to your needs.

I wouldn't dismiss certification, but I wouldn't treat it as the only indicator of quality, either. Ask about training, experience, coaching philosophy, confidentiality practices, and how they evaluate progress. Request references when appropriate. Most importantly, understand what you're purchasing. Are you seeking a coach who will primarily facilitate your own discovery, an experienced executive who can also serve as a strategic advisor, or some combination of the two? Those distinctions matter.

4. Should your coach have held your position?

Higher ed has no shortage of retired presidents, provosts, and vice presidents who have entered the coaching and consulting world. Many bring extraordinary institutional knowledge and hard-earned wisdom. But having successfully held a position doesn't automatically make someone an effective coach. Doing the job and helping someone else become better at the job require different skills.

A former president may offer invaluable insight into board relations, cabinet dynamics, fundraising, or institutional politics. But you should also consider whether their experience translates to your institution, your leadership challenges, and today's higher education environment.

And there's another possibility worth considering: Someone who hasn't held your exact position may bring precisely the perspective you need. Sometimes the greatest value comes from someone who understands the environment but isn't anchored to how they would have handled the job themselves. Ask whether a prospective coach is genuinely curious about your circumstances or primarily interested in telling you how they did things.

5. How do you prefer to communicate and work?

This is one of the most overlooked parts of selecting a coach. Do you want structured monthly sessions with defined goals and follow-up assignments? Or do you prefer a more flexible arrangement where you can bring whatever is most pressing that week? Would you benefit from written reflections or action items between sessions? Do you want someone available for a quick email or phone call when something unexpected happens? Do you prefer video meetings, phone conversations, or occasional in-person sessions?

Above all, be realistic about your own habits. If you're someone who processes ideas verbally, a coach who relies heavily on worksheets and written exercises might not be the best match. If you thrive on structure and accountability, an entirely conversational approach might leave you wanting more.

Also, discuss responsiveness and boundaries. Coaching relationships should have clear expectations about communication between sessions, availability, and what constitutes an urgent request. The right coaching arrangement should fit how you actually work, not how you wish you worked.

6. How much time are you willing to invest?

Executive coaching isn't something you can outsource. A coach can help you clarify priorities, examine assumptions, develop strategies, and hold yourself accountable. But the reflection, decisions, conversations, and behavioral changes are ultimately yours. Some coaching relationships involve two sessions per month. Others meet weekly or three times monthly, particularly during periods of significant transition or leadership development. Engagements may last three months, six months, a year, or longer. There's no universal formula.

What matters is having enough consistency to build trust, recognize patterns, and make meaningful progress. Before committing, ask yourself whether you're genuinely prepared to make room for coaching. Not just on your calendar, but in your thinking and behavior. If every session becomes another meeting you squeeze between emergencies, you may not get the return you're hoping for.

7. Can this person challenge you without making you defensive?

You should like your coach. You should trust your coach. But you don't necessarily need someone who agrees with you. In fact, I would argue that one of the most valuable things a coach can offer is a perspective you aren't already getting from your colleagues, cabinet, supervisor, or professional network.

One of the presidents I coach intentionally sought out someone with different political and social perspectives. He wasn't looking for someone to reinforce his worldview. He wanted someone who would help him examine decisions from angles he might otherwise overlook. I think there's something important in that choice.

The goal isn't to find someone who thinks exactly like you. It's to find someone who can challenge your thinking without turning every disagreement into a debate, and who understands that the decisions remain yours. A productive coaching relationship should be a place where you can be uncertain, frustrated, ambitious, imperfect, and occasionally completely wrong about something without feeling judged. That kind of trust takes time, but you can often sense its potential in an initial conversation.

A Final Thought: Interview Your Coach

I encourage leaders to talk with more than one prospective coach before making a commitment. Ask about their approach, experience, fees, time expectations, confidentiality, and what happens if the relationship isn't working. And don't be afraid to ask for an introductory conversation to assess the fit. A good coach should be evaluating that fit, too. I've had conversations with prospective clients where I've suggested that someone else might be better suited to their needs. That's not a failed business opportunity. It's good professional judgment. As for me, I intentionally keep my coaching practice small, working with no more than five executive clients at a time. That means I rarely take on new clients and I say no and refer to colleagues more often than I say yes.

But here's the good news. Through the Association for Higher Education Consulting and Coaching (AHECC), I have an incredible network of colleagues with diverse backgrounds, coaching approaches, certifications, and areas of expertise. Some are former senior executives. Others bring specialized experience in leadership development, organizational change, career transitions, and executive effectiveness. If you're considering an executive coach and aren't sure where to begin, I'm always happy to help connect you with someone who might be a great fit.

Because the goal shouldn't be to find the most impressive coach, the most recognizable name, or even the person with the most experience. It should be to find the person who helps you become the leader you're trying to be.

This image was created using ChatGPT