3 Questions That Make You a Better Leader

Stop Journaling. Start Leading.

Author

Dan Watt
June 23, 2025 • Estimated Reading Time: 7 minutes

Most leaders don’t need more advice.

They need sharper questions.

Ask these three, and watch your confidence and leadership change.

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INSPIRATION STATION

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THE RUCKUS MAKER MONTHLY THEME: REFLECTION

The Ruckus Maker’s Journal: 3 Prompts for Confidence and Clarity

Most leaders I know don’t need more on their plate. They need sharper tools for thinking.

Reflection with intention helps cut through the noise.

I’m not talking about more writing, just sharper thinking.

Here’s three questions to get you started.

#1 Start with Strength

When you begin by focusing on what’s working, you create momentum.

Most leaders get stuck in problem-fixing mode.

But you don’t build confidence by fixing everything.

You build it by noticing what’s already working.

Ask yourself: What’s working that I want more of?

This is your chance to double down on the habits, relationships, and systems that are actually moving your school forward.

#2 Spot the Overcomplications

Leadership can be messy.

Maybe you’re running that weekly meeting out of habit, not purpose.

Maybe you’re overthinking a parent email instead of picking up the phone.

So, don’t make it harder than it needs to be.

Ask yourself: Where am I making things harder than they need to be?

Simplicity is a leadership skill, not a personality trait.

#3 Face What You Already Know

Most of us already know the answer to the thing we’re avoiding.

The decision you don’t want to make is often the one you need to face first.

Be courageous.

Ask yourself: What do I already know that I’ve been avoiding?

Leadership requires the guts to act on what’s true.

One More for the Ruckus Makers

If you want a bonus prompt, try this one: What would a Ruckus Maker do here?

You’re not in this work to play it safe.

You’re here to lead with creativity, courage, and clarity.

That’s what separates managers from real leaders.

Start asking better questions and watch your confidence grow.

Write less. Lead more.

❝

Don’t just follow the path. Question it.

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LEADERSHIP EDGE

  • Want to retain top talent? Ask these four questions

  • Summer’s For Weird Reads: Great leaders are great readers. Here’s a stack of summer classics, curated by Austin Kleon 

  • Leave Feeling Energized: as the school year winds to a close, pay attention and make good choices

  • Pure Joy. Just Listen. Jacob Collier improvises with the National Orchestra

MONDAY VIBES

WEEKLY CHALLENGE

The Bootstrap Buddy

This week’s challenge is inspired by Adam Grant’s book Hidden Potential. Try turning leadership challenges you might normally solve on your own into collaborative experiments.

Pair up with a colleague, share one challenge you’re facing, and help each other grow by asking one great question and offering one fresh idea.

Here are a few ideas to get you started:

  • What’s the real outcome you’re hoping for in this situation?

  • What’s making this feel stuck right now?

  • What have you already tried? What haven’t you tried? What worked, or didn’t?

  • If you could wave a magic wand, what would be different by next month?

  • Whose help or perspective might you be overlooking?

  • What part of this is fully in your control?

Leadership is better together.

And sometimes the right question unlocks the next step.

Try it with a teammate this week and achieve your next brilliant breakthrough.

Want help getting started? Just hit reply. Or join us here — we’re ready for you.

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