In this edition:
1 REMINDER
How to INTRODUCE it in your team
How to DEVELOP it
How to use RELATIONSHIPS to harness it
Something just for you COACH
WHY this matters
Leadership is lonely. The weight of all that falls on you is, well, the weight of everything. The success of your team or business rises and falls on leadership. Sorry, it’s on you. Sometimes, that pressure, it can begin to break us. But here’s what’s beautiful about that…. that’s your choice. You get to choose if it breaks you OR shapes you. The leader you’ve been built into came from roots that are deeply entrenched in values and firm foundation. Lean into those roots when the winds start howling. When the ground beneath you begins to wash away, cling to those roots. Be the tree that would not fall, no matter how broken.
- Coach Castillo
No matter what - Stay Anchored
Intro
Before you ever led a team…
Before you held a title…
Before people looked to you for answers…
Someone was pouring into you.
Someone showed you how to treat people.
How to handle adversity.
How to respond when things didn’t go your way.
How to stand up. How to stay steady. How to care.
You didn’t just learn from them —
you were formed by them.
That’s your origin.
And when leadership gets heavy, complicated, or loud…
the most powerful move you can make isn’t forward —
it’s inward.
Back to your roots.
Back to who shaped you.
Back to who you are.
“I forgot how good it feels to be rooted. And to be rooted is not the same thing at all as being tied down. To be rooted is to say, here I am nourished and here will I grow, for I have found a place where every sunrise shows me how to be more than what I was yesterday, and I need not wander to feel the wonder of my blessing. And when you are rooted, defending that space ceases to be an obligation or a duty and becomes more of a desire.”
― Kevin Hearne, Shattered
According to a Gallup poll: Only about 20% of employees strongly trust their organization’s leadership. But when leaders consistently demonstrate key trustworthy behaviors, 95% of employees fully trust them. Employees who trust leadership are 61% more likely to stay with the organization
Develop
When things get hard in leadership, most people reach for tactics:
“How do I fix this?”
“What system do we need?”
“What should I say?”
But great leaders know something deeper:
Leadership doesn’t break down from lack of strategy first.
It breaks down when we drift from identity.
Your origin holds your:
• Values
• Convictions
• Why
• Moral compass
• Definition of success
The leaders who shaped you helped build those things. And when pressure hits, you don’t need a new personality — you need to return to the one that was built in you.
Take Action:
Take five minutes this week and write down the names of the people who shaped your character early in life. Next to each name, write the trait they modeled that still lives in you today.
“To be rooted is perhaps the most important and least recognized need of the human soul.” - Simone Weil
72% of people say purpose should matter more than profit
That means modern athletes, students, and employees are actively looking for leaders who stand for something.
Relationships
We Lead from What Was Poured Into Us
You don’t lead from nowhere.
You lead from inheritance.
The patience you show? Someone showed it to you.
The grit you carry? Someone modeled it.
The mercy you extend? Someone gave it first.
That means something powerful:
“The way you lead today is someone else’s future origin story.”
Co-workers. Employees. Athletes. Students. Staff. Family.
They are learning what leadership looks like by watching you.
So when you lean into your roots —
you give them roots.
When you lead from identity instead of emotion —
you give them steadiness.
When you remember who shaped you —
you become someone who shapes others.
Take Action:
Tell one person this week how they impacted your leadership journey. Then intentionally model one of their traits for someone you lead.
“As you become more rooted inside -- as you drink from this silent stream of life that runs beneath the surface of everything -- as you live from that depth of your own being more and more, then you’ll be able to rise taller and stronger in this world; more than you may have ever thought possible.” — Derek Rydall
Leadership research now confirms what coaching has always known:
Leaders with emotional intelligence (self-awareness, empathy, integrity):
build stronger trust
improve motivation
increase commitment
improve overall organizational performance
Just For You Coach
I love to ask questions. They usually turn into more questions! My favorite questions to ask myself and others are the really hard ones. The ones that cut into us, exposing where we need to grow and learn. But sometimes, they can also direct us to return. To who we hope to be, to who we were built to be, to why we ever wanted to lead in the first place. Back to our roots is always a good place to return to when leadership gets hard and doubt creeps in. You were not made to be beaten.
• Who are the three people who most shaped your character?
• What trait from them shows up in your leadership today?
• Where have you drifted from your roots under pressure?
• What practice helps you return to who you truly are?
• Who is currently learning leadership by watching you?
Are you shaping them? Showing them? Or leading them astray?
“You have walked through fire, survived floods and have triumphed over demons- remember this the next time you doubt your own power.” — Jung Pueblo
The research is clear: leadership effectiveness isn’t first about strategy — it’s about formation. The leaders who know who they are create trust, and trust is what actually drives engagement, retention, and performance.
Why This Matters
Leadership pressure has a way of pulling us toward performance and away from purpose.
But when leaders forget their origins, they start:
Reacting instead of responding
Chasing results instead of building people
Leading from stress instead of conviction
Returning to your roots doesn’t make you soft.
It makes you anchored.
Anchored leaders create stability.
Stability creates trust.
Trust creates impact that lasts beyond seasons and scoreboards.
Your origin is not your past.
It is your foundation.
My mom is in the hospital. So much of who I am is found in her. On my 5 hour drive down I stopped at a coffee shop in the community where I started my coaching journey 23 years ago. I ran into a young man whom I coached in my first year as a high school football coach. He’s now a father, husband, and impressive man of character and faith. He always had that in him even as a kid. He recently lost both his father and mother and explained to me how he felt all alone at first. That is, until he started to instead feel gratitude for the person they helped him become. Knowing their faith, he’s at peace with their passing. And in him I saw the mindset God wanted me to see. Not worry for my mom’s health, but gratitude for her life. A few hours later I was hugging my mom. Even as a 90 year old, partially blind, cancer survivor, her faith and strength remain unshaken. As her body is failing her, she still returns to what has shaped her to deal with this new storm. Faith, hope, love. And I saw the greatest of these in action, in theory and in medicine. As my wife and kids hugged her, held her, and spent time with her, we were all overflowing with it. And as it filled the room on Valentine’s Day, hope and faith bloomed as a result of their roots, in her — Love. I’m struggling lately. I’ve thought things I shouldn’t have. New winds awakening old demons. But on Valentine’s Day, I returned to my roots. Deep in southeast Arkansas. Where faith and BBQ are food for the soul. I got a good old fashioned dose of reminders of who I am and how I was built. I am the tree that would not fall. And, so are you.
Do you know a coach or friend who’d enjoy this newsletter? Pass it along! Send me an email at [email protected] and I’ll send you a highly effective teammate connection assessment tool!
Coach Castillo’s Challenge of The Week: Sit down and write a letter, not an email, a letter. Write it to the person who helped build your foundation. If they’ve passed, write it anyway. Tell them all about who you are, not what titles you have. Explain to them why you’re grateful for them. Send it to them, or their spouse, or their kids. If that’s not feasible, send it to someone you love that needs a reminder of who they are. We all need to return to our roots from time to time. Have a blessed week.
Lead, Live, Play Beautiful
Have A Blessed Week,
