Top Leadership Reflection Questions for a Better 2026

Why High Performing Leaders Avoid Reflection

If you’re anything like most of the leaders I coach, you’re always moving.
Meeting to meeting. Project to project. Goal to goal.
It’s the great trap of ambitious people. You’re praised for producing, so you keep producing.

And reflection becomes something you’ll “get to when things slow down.”
Which of course, never happens.

But here’s the truth:
Reflection is how the 5% grow faster than everyone else.
It’s how you stop repeating old patterns. It’s how you make bigger leaps. It’s how you work less, perform better, and feel human again.

I avoided reflection for years. I loved planners, goals, and strategy sessions, but I was building new years on top of old habits. Every January felt like a reset I hadn’t earned.

Once I finally slowed down long enough to look back, everything changed. Reflection helped me go from overwhelmed middle manager to calm, confident C-suite executive before 40. And now it’s the reason my clients get extraordinary results while designing lives they actually love.

Why Reflection Matters More Than You Think

Most people do a quick mental recap at the end of the year. A light “wow, that was a year.”

Not good enough.

To truly level up, you need two layers:

1. The After-Action Review
What worked?
What didn’t?
What do I want to do differently?

2. The WHY
Why did that work?
Why did that drain me?
Why did I avoid that?
Why did I spend so much time on low-value work?
What part of me was I trying to protect?

If you understand the why, you can change anything.
If you ignore it, you’ll rebuild 2026 on top of the same autopilot patterns you were trying to escape.

The 6 Reflection Questions Every Leader Should Ask

You don’t need a notebook yet. Let these questions sit with you. Your brain already knows the truth.

1. What are you genuinely proud of this year?
Not the polished performance-review answer. The real one.

2. What drained you more than it should have?

3. Where did you avoid something important?

4. What did you overcomplicate?

5. What do you wish you had done sooner?

6. What surprised you about yourself this year?

These are the exact questions I take my clients through inside the PH+ Lab and during our end-of-year Reflection Workshop. When leaders answer honestly, the next year becomes a completely different experience: calmer, lighter, more strategic, and more fun.

Designing an Epic Life Requires Intention

We spend hours building business strategies.
We map out X to Y by When.
We create project plans, contingencies, heat maps, pivot points, and resourcing plans.

Yet we almost never pause to design our actual life.

Inside Epic 2026, we flip that script.
You slow down long enough to design a year you would be proud of if it were your last.
A year filled with intentionally crafted memories, adventures, and joy.
A year that makes you say, “Damn, I really lived.”

Want to Do This With Me Live? Join the Free Reflection Workshop.

For the first time in months, I’m hosting a free two-part workshop to help you close the year clean and step into 2026 with intention.

Part 1: December 10 at 12 PM CT
We’ll walk through your After-Action Review and deeper WHYs.
You’ll understand exactly what helped you succeed and exactly what held you back.

Part 2: December 17 at 12 PM CT
We identify who you need to become and what needs to change so 2026 unfolds differently.
Before you set goals, you’ll know the patterns, choices, and behaviors that will actually get you there.

It’s rare that I teach a workshop like this for free.
Come join me and experience the up-level that happens just by being in a room full of 5%ers.

Register at shaylaking.com/reflection-workshop

And if this episode added value, leave a five-star review so we can reach even more leaders ready to rise into the 5% Club.

your coach, cheerleader, and accountability partner, Shayla

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