Key Takeaway:The end of the year isn’t about performance reviews or goal setting alone. It’s about reflection. The leaders who grow next year are the ones willing to ask questions that feel uncomfortable today.

Leaders don’t fail because they don’t care. They struggle because they don’t slow down long enough to ask the right questions.

As the year winds down, most leaders are doing one of two things. They’re sprinting to the finish line, trying to close loops, hit numbers, and survive the calendar. Or they’re already looking ahead. Planning. Resetting. Thinking about next year. Very few are doing the one thing their team actually needs right now. Pausing to ask better questions.

Not the safe ones. Not the checkbox ones. The real ones.

What Teams Wish You’d Ask (But Rarely Do)

Over years of coaching Leaders, running assessments, and sitting in honest conversations, I’ve noticed a pattern.

Teams don’t want grand speeches at year-end.

They want to feel seen, heard, and taken seriously.

Here are a few questions your team likely wishes you’d ask. And mean.

1. “Where did I make your job harder this year?”

   • This question requires humility.

   • It also requires restraint. No defending. No explaining. Just listening.

   • Most leaders unintentionally create friction through unclear priorities, shifting direction, or last-minute urgency. Asking this surfaces where your leadership system broke down, not where people failed.

2. “What did we say mattered… but didn’t act like it?”

   • Values only exist if they show up in decisions.

   • This question exposes gaps between intention and behavior. It helps teams name the quiet disconnects that slowly erode trust.

   • If your calendar, rewards, or attention didn’t match your stated priorities, your team already knows. They’re just waiting to see if you do.

3. “Where did you stop speaking up?”

   • Silence is data.

   • When people disengage, it’s rarely because they don’t care. It’s because they learned their voice didn’t matter, or that it wasn’t safe to use.

   • This question opens the door to psychological safety. It also challenges leaders to examine how dissent, feedback, and mistakes were handled this year.

4. “What decision should I stop owning?”

   • Leadership isn’t about making every call. It’s about building decision capacity in others.

   • If everything funnels back to you, your team is constrained. This question invites delegation at the right level and signals trust.

   • Over time, strong leaders move decisions away from themselves, not toward.(Reach out to me about my Decision Tree to help you with this.)

5. “What do you need from me next year that you didn’t get this year?”

   • This is the bridge question.

   • It connects reflection to action. It tells your team that this isn’t just a conversation. It’s a commitment.

   • Clarity, consistency, availability, feedback, boundaries. The answers here often surprise leaders. And they’re almost always practical.

Why Most Leaders Avoid These Questions

They might seem risky, and since they invite feedback you can’t always control, they can challenge your self-image. They might slow things down when you feel safer. But if you avoid them, the truth doesn’t disappear; it just goes underground. And unspoken issues don’t just vanish.They compound.

How to Run a Simple Year-End Leadership Debrief

You don’t need a retreat or a long survey to do this well.

Here’s a simple approach:

• Choose 3–5 questions. Fewer is better.

• Set the expectation that this is about learning, not evaluation.

• Listen without correcting or explaining.

• Capture themes, not quotes. Take Notes!!

• Close the loop by sharing what you heard and what you’ll do differently.

Reflection without action feels performative.

Action without reflection is usually misaligned.

You need both.

A Final Thought

Leadership isn’t proven by how confidently you speak at year-end. It's proven by what you’re willing to ask.And what you’re willing to change.If you didn’t ask these questions this year, that doesn’t make you a bad Leader. It makes you human. What matters is whether you’ll ask them next year. To ensure you do, put it on your calendar now.

Become a Great Leader

Great Leaders ask these questions throughout the year. In group settings and 1 on 1s. Make them part of your normal feedback loop.

If you're ready to build a team culture grounded in clarity, accountability, and trust—or you'd like access to my curated leadership resources—Book an Introduction Call: 👉Jeff Hill 15min Introduction

P.S. You can also take my Leadership Self-Assessment to help you focus here. Do you need the free 2026 Monthly Calendar to help you plan you Leadership focus? Download it here: Free Template