You Can't Coach Yourself From the Field

December 20 2025

Read Time - 4 minutes

"The eye cannot see itself."

~ Bulgarian proverb

I was in my third year of collegiate teaching when I finally asked Sam Pilafian to help me become a better teacher. Sam was a world-renowned musician who had performed with everyone from the New York Philharmonic to Pink Floyd. But despite that resume, he was best known as a teacher's teacher—someone who made other educators better at their craft.

Up to that point, I'd received positive student evaluations. My colleagues seemed to respect my work. I had developed what I thought were effective teaching strategies through trial and error, reading pedagogy books, and modeling the teaching styles that had been effective with me when I was a student.

I was doing fine.

But I also knew I had blind spots—aspects of teaching I wished came more naturally. So, I contacted Sam and asked if he would work with me over the course of a semester. He observed my teaching regularly, took notes, and we met consistently to debrief—me asking questions, bringing up issues I was dealing with, and him coaching me on what he observed and helping me develop as an educator.

What I learned I couldn't have done on my own.

He pointed out patterns I had no idea existed: how I was rushing through material instead of creating space for real learning to happen. How I would jump in too quickly with the "right" answer, inadvertently shutting down student exploration. How my body language when students struggled was discouraging the very risk-taking I said I valued. How I was leading my classroom the way I'd been taught to lead, not necessarily the way my students actually needed to learn. He helped me see the entire arc of a semester, not just individual class sessions—how to build momentum and engagement over the long term, not just deliver content week after week.

The improvements I implemented didn't happen in one observation or one conversation. It happened because Sam was there consistently, helping me identify blind spots, asking questions that shifted my perspective, holding me accountable to becoming the teacher I wanted to be.

None of this was visible to me when I was the one teaching. I was too busy managing the lesson, tracking time, monitoring comprehension. I couldn't simultaneously teach and observe my own teaching with any objectivity.

This is the paradox every academic leader needs to understand: You cannot coach yourself from the field.

That semester of ongoing coaching transformed how I showed up in the classroom because I finally had someone who could see what I couldn't see from inside the performance—and who stayed with me long enough for real change to take root.

Leadership Takeaway: Why Being "In It" Limits Your View

So often in leadership we find ourselves analyzing problems in isolation, making decisions without processing them with anyone, carrying the weight of every personnel issue and budget crisis without burdening anyone else. We have colleagues, sure. But often they're not people we can really confide in. Certainly not someone who can see our blind spots or help us navigate the messy contradictions of campus leadership.

So we end up second-guessing ourselves, making avoidable mistakes, carrying it all alone because we're coaching ourselves from the field—which we simply cannot do effectively.

I have certainly been there. But I'd learned something from Sam: I could find a leadership coach.

Not because I was failing. Or lost. But because I wanted to accelerate my learning curve—with someone who could see what I couldn't.

Think about your journey as a researcher. You had advisors, right? Mentors who guided your dissertation, reviewed your manuscripts, helped you think through methodology. They could see things you couldn't because they had perspective you lacked.

Now you're a department chair, director, a dean, a program manager, an associate provost. You're making decisions about personnel, budgets, strategic priorities, and institutional culture. You're navigating conflict, managing up and down, trying to balance competing demands while maintaining your integrity…and sanity. And somehow, we've convinced ourselves that this is the arena where we should just figure it out alone.

But can we? After contentious faculty meetings, you replay the conversation in your head—but you can only see it from your own perspective. When you craft a difficult email to a problematic colleague, you read it through your own lens, unable to catch where your frustration might be leaking through. When you're trying to build a healthier culture in your department, you assess your leadership based on your intentions, not necessarily your impact.

An external perspective can help you see the gap between the two.

What Coaching Actually Looks Like

Example 1: A chair had been managing around a problematic faculty hire for two years. Every decision was shaped by working around this person's dysfunction. "How do I get them to be more collegial?" they kept asking. A good coach reframes the question: "What's the cost of continuing to manage around this person instead of addressing it directly?"

That single reframe created a new perspective. The issue wasn't how to change the faculty member—it was about having the accountability conversation they'd been avoiding.

A coach doesn't just tell you to have the hard conversation—they equip you to have it well. The chair learned how to frame clear expectations, document patterns objectively, and create accountability structures that didn't depend on personality change.

Within weeks, they had the conversation. The faculty member's behavior didn't transform overnight, but the dynamic did. The chair stopped managing around dysfunction and started managing performance. More importantly, they'd gained a skill they could use with every future personnel challenge.

Example 2: A program director was drowning. They ran every meeting, solved every problem, mediated every conflict. Their faculty had learned to wait for them to rescue everyone. A coach asks: "What would happen if you stopped doing that?"

They couldn't see their own over-functioning because it felt like good leadership—being responsive, helpful, indispensable. A coach helped them see another angle: they were preventing their team's growth and burning themselves out.

Recognition is only the first step. A coach gives you the framework to actually change the pattern. The director learned how to identify which faculty were ready to step up, how to set them up for success, and how to coach without rescuing. They discovered the difference between supporting their team and doing the work for them. Faculty stepped up. The director reclaimed hours each week and gained something more valuable than time: the ability to develop leaders.

That's what good coaching provides: frameworks and skills to actually solve problems, accountability without judgment, and someone who won't let you hide from yourself.

The Bottom Line

Here's what I know after years of being coached and coaching academic leaders: A good coach accelerates your learning curve, helps you avoid preventable mistakes, and serves as a thought partner in your leadership journey.

Leadership in higher ed is isolating. You need a confidential space to process what you can't share with your team, your dean, or your faculty. You need someone who can spot the patterns you can't see, ask the questions you don't know to ask, and hold you accountable to your own priorities without judgment.

A new semester will be upon us soon. So, here's the single most important thing you could do to lead it differently: Find a coach.

There are lots of great coaches out there who work with academic leaders. I've benefited enormously from having coaches throughout my leadership journey, and I now have the privilege of coaching others through the same challenges.

If you're not sure where to start, look for someone who understands higher education—the unique dynamics of faculty culture, institutional politics, and the impossible balancing act you're managing. The right coach isn't necessarily the most credentialed one; it's the one who can see what you can't and who you trust enough to be honest with.

That kind of coaching relationship is worth finding.

For this next week, I wish you a restful break and time with people who matter most.

Until next Saturday,

P.S. If you're interested in coaching for spring semester, I have two options:

• 1-on-1 coaching — 2 spots for personalized support tailored to your specific challenges

• Group Cohort: "Sustainable Campus Leadership" — 8 academic leaders meeting biweekly to tackle burnout together, reclaim time, and build sustainable leadership systems (starts late January)

Want to talk it through? ​Schedule 15-minutes here​ or just reply to this email.