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The Year-End Questions That Actually Matter
The Year-End Questions That Actually Matter

December 13, 2025

Read Time - 4 minutes


”Experience is not what happens to you; it's what you do with what happens to you”

~ Aldous Huxley


I've ended more semesters than I can count the same way: worn out and making promises to myself about "next semester."

You know the promises. I'll set better boundaries. I'll delegate more. I'll finally address that personnel issue. I'll stop letting email run my day.

I meant every one of them—until the first week of January hit and I found myself right back in the same patterns.

It took me a few years to realize: The problem wasn't my effort. No one would have called me a slacker. The problem was that I never stopped to examine whether that effort was making me a better leader—or just a more exhausted one.

Studying music in school taught me something I didn't appreciate at the time: A person can work incredibly hard and not move an inch.

Some of my peers practiced endlessly and barely improved. Others practiced far less and made remarkable strides. I lived on both sides.

Eventually, I understood the difference wasn't talent or work ethic. It was about having a clear purpose in the work I was doing. When I had a clear goal—a sound I wanted, a skill I was chasing—my practice sessions had direction. When I didn't, I drifted.

I think leadership works exactly the same way.

Leadership Takeaway

Most academic leaders mistake activity for growth.

You handled crises. You attended meetings. You responded to emails. You put out fires. And at the end of the semester, you're tired enough to believe you accomplished something.

But if I asked you right now:

"What did you learn this semester that changed how you lead?"— could you answer?


Research shows that faculty and staff experience burnout at alarming rates—with studies showing that over 50% have considered leaving due to burnout, and 38% report feeling emotionally exhausted often or always. Yet most of us never pause to ask whether we're getting better at this job or just getting better at surviving it.

Experience isn't what happens to you. It's what you do with what happens to you. And if you don't build reflection into your leadership practice….sometimes, you're just accumulating scar tissue—not wisdom. That's why these five questions matter. They interrupt the autopilot. They force you to distinguish between the work that made you stronger and the work that just made you tired.

5 Questions to Reset Your Leadership for 2026

These five questions can give you a different angle on the year you just lived and the leader you're becoming. I like to do this at the end of every semester.

1. What did I hold onto this semester because it made me feel needed—not because I was the only one who could do it?

Higher ed leaders absorb endless tasks that quietly erode their bandwidth: the email that "only takes a minute," the scheduling question, the decision someone else could make. We often hold onto tasks because it feels faster, safer, or tied to our professional identity.

This question helps you:

Identify where you became the bottleneck

Clarify decision rights

Rebuild your time around work only you can (and should) do

I don't think of this as a delegation exercise, but more of an identity exercise.

Consider this: The hardest tasks to release aren't the ones that take the most time—they're the ones that make us feel needed. Pay attention to what you hold onto for identity reasons, not efficiency reasons.

2. If leading next semester felt 25% easier, what meeting, process, or expectation would I need to kill?

Not improve. Not optimize. Kill.

Leaders who make the work sustainable don't get there by doing everything better. They get there by doing less—and being ruthless about what they stop.

Imagine a lighter semester and pinpoint the hidden friction:

  • Meetings that drain more energy than they create

  • Communication loops that are redundant or irrelevant

  • Workflows that are outdated or complicated

This question invites you to build a leadership environment that works by design—one where you lead the week instead of being led by it.

3. Who on my team grew the most this year—and what conditions made that growth possible?

When someone gets stronger, it tells you something about the environment you created. Pay attention to it.

This question reveals:

  • What kind of feedback actually works

  • What kind of autonomy motivates people

  • Which supports matter most

  • The conditions that make people want to step up

Most leaders spend December thinking about problems. This question forces you to study what worked—so you can create more of it.

What to watch for: Growth often happens not because you gave someone everything they needed, but because you gave them just enough support to figure out the rest themselves. The conditions that produce growth usually include productive struggle—not comfort.

4. Which meeting do I dread most—and what would it take to change that?

You know the one. The meeting that makes you check email under the table. The one where nothing ever gets decided.

According to research from Michael Mankins at Bain & Company, executives spend nearly 23 hours per week in meetings—and consider more than half of that time poorly used. Academic leaders face similar patterns. Consider these angles:

Meetings you run:

  • Are they structured for decisions or updates?

  • Are the right people in the room?

  • Do they regularly produce outcomes?

Meetings you attend:

  • Do you need to be there?

  • Is your presence necessary or just expected?

  • Is the agenda aligned with your role?

Meetings you've inherited:

  • Has anyone questioned their purpose recently?

  • Do they still serve the institution's needs?

The goal isn't fewer meetings for the sake of it. It's rebuilding your calendar with purpose before the spring semester begins.

5. What goal did I circle around this year—naming it, discussing it, analyzing it—without actually giving it the ownership, budget, or timeline it needed?

Most leaders have a "ghost priority"—the initiative that would transform the unit if it actually moved.

Examining this surfaces:

The initiative you've been avoiding

The initiative that kept getting bumped for crises, emails, or last-minute needs

Where your leadership was shaped more by short-term pressure than long-term purpose

Talking about the goal isn't the same as committing to it.

Here's the tell: If you can describe the goal in detail but can't name who owns the next three steps and when they'll happen, you're still circling it.

Bottom Line

Music taught me that improvement isn't always a byproduct of effort alone. Those hours we spend working should be shaped by intention if we want to see growth.

And leadership is no different.

You can't become a better leader by accident.

You won't grow just because another semester passed. You won't improve just because you worked hard. And you definitely won't change your patterns by making vague promises to yourself over winter break.

Reflection is what separates leaders who get better from leaders who just get older.

If you move into January without making meaning of this semester, you'll carry the same patterns (for better or for worse) into your 2026.

So before the year ends, ask yourself these five questions. Not because reflection is easy, but because leading without it is exhausting.

And if you realize you can see the patterns but can't quite shift them on your own—that's exactly what coaching is designed for. You don't have to figure this out alone.

Try This Before Friday

Identify the one conversation or decision you've been avoiding all semester.

Finish this sentence: "If I had addressed this in September, fall would have been 25% easier because…"

Now do one small thing: Draft the email. Schedule the meeting. Set the boundary.

Not everything—just the thing that will keep January from repeating December.


So here's my question for you: What's the one thing you've been avoiding—and what small step will you take this week?

Reply and tell me. I read every single response.



That's it for today.

Until next Saturday!



Whenever you're ready, there are 3 ways I can help you:​

1.) Get the free guide: Your First 14 Days. A clear, practical playbook for new leaders navigating their first two weeks in higher ed leadership. 2.) Coaching for New Academic Leaders: A focused 1:1 coaching experience for higher ed professionals who want to lead with clarity, build smarter systems, and stay centered on what matters most. I work with a limited number of clients each quarter to provide highly personalized, strategic support. Send me a message.

3.) Professional Development Workshops: Interactive sessions for faculty, staff, and leadership teams that help reduce conflict, streamline decision-making, and shift culture with smart systems. Virtual and in-person options available. Sessions tailored to your campus needs.


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