Circle the Wagons: The Three People Every Leader Needs Around Them

I was a huge fan of SportsCenter growing up. Everybody had their favorite anchor. Some were Stuart Scott people (“BOOYAH!”). Some preferred Dan Patrick and his dry brilliance. Others loved the left-field humor of Kenny Mayne.

But there was something different—almost electric—when the red light hit and Chris Berman anchored the highlights. And when it was NFL highlights? Whole different vibe.

He had that iconic line he’d throw out whenever the Buffalo Bills found themselves in trouble yet somehow regained their footing:

“Nobody circles the wagons like the Buffalo Bills.”

I can hear him grunting out those words right now…

It didn’t mean they were perfect.
It meant they were resilient.
It meant they knew how to tighten up when the pressure came.
It meant they never faced the fight alone.

And the older I get, the more I realize this:

Every leader faces pressure. Great leaders don’t face it alone.
They circle the wagons with the people who encourage them, the people who guide them, and the people who tell them the truth.

Great leaders don’t stay strong because they’re naturally strong.
Great leaders stay strong because they’re surrounded.

And every leader needs three kinds of people in their circle if they’re going to stay faithful, grounded, and resilient through the valleys and victories of leadership.

1. You Need People Who Encourage You

Every leader has moments when they question themselves.
Was that decision right?
Did I handle that conversation well?
Is anything I’m doing actually making a difference?

Encouragers aren’t hype machines. They’re truth-tellers of a different kind—the ones who remind you of what God is doing through you when you can’t see it yourself.

They point out fruit you’re too tired to notice.
They remind you of progress you’ve forgotten.
They speak life into the calling that’s been buried under criticism, comparison, or exhaustion.

Encouragers help you keep going when you want to give up.

If you don’t have people who consistently remind you of the good God is doing through you, leadership will feel heavier than it should.

2. You Need People Who Offer Wisdom and Perspective

Encouragement is necessary.
Wisdom is essential.

Every leader needs people who have walked longer roads, fought tougher battles, and lived through their own valleys—people who offer perspective instead of pressure.

These relationships take time to find, but they don’t have to be daily. They simply need to be present—regular voices that help you stay grounded.

Wisdom voices help you:

• Discern what God is doing

• Slow down when your pace is unsustainable

• Navigate conflict without destroying relationships

• See long-term impact when short-term emotions flare

• Avoid landmines you don’t even know are there

You don’t need an echo chamber.
You need a few seasoned voices who can shepherd you while you shepherd others.

These are the people who don’t just know leadership—they know you.
They steady you when circumstances shake you.

3. You Need Truth-Tellers Who Ask the Hard Questions

Encouragers lift you.
Wisdom voices steady you.
But truth-tellers keep you honest.

And honestly, these are probably the most important people to have in your life if you are going to serve over the long haul.

I don’t know where my heart would be if it weren’t for two men in my life who play this role for me.

Truth-tellers ask the questions no one else is willing to ask:

“How’s your soul really doing?”
“What are you avoiding right now?”
“Are you serving from overflow or depletion?”
“What fear is behind that decision?”
“What do you need to bring into the light today?”

These aren’t critics.
They aren’t cynics.
They aren’t nitpickers.

They’re people who care more about your heart than your performance.

And Scripture is clear that we need these people. Proverbs 27 paints the picture vividly:

“Faithful are the wounds of a friend…” (v. 6)
“As iron sharpens iron, so one person sharpens another.” (v. 17)

Sharpening is not passive activity.
It isn’t gentle or soft.
It creates friction, heat, and resistance.

Iron does not sharpen iron by polite distance.
It sharpens by contact.
By pressure.
By striking at angles that expose the dull edges.

Which means:

If you only surround yourself with people who praise you, you will never be sharpened.
If you avoid people who challenge you, you will eventually become dull.
And if you resist the friction of accountability, you will eventually lose the edge God called you to lead with.

Truth-tellers cultivate a space where authenticity becomes normal and accountability becomes welcomed—not resented. They provide the loving friction that sharpens a leader’s character, convictions, self-awareness, and obedience.

They refine you so you don’t drift.
They expose what pressure hides.
They help you become the kind of leader God can trust with more.

Truth-tellers often become the dividing line between leaders who finish the race and leaders who flame out along the way.

Leaders Don’t Fail Because They’re Weak—They Fail Because They’re Alone

Nobody “circles the wagons” naturally.
It takes humility.
It takes intentionality.
It takes vulnerability.
It takes time.

It takes inviting people close enough to see your strengths and your shadows.

But this is where resilient leadership is formed.

Encouragers lift you.
Wisdom voices steady you.
Truth-tellers refine you.

Together, they create a circle that isn’t just protection—it’s formation.

In a world where so many leaders fall, burn out, or spiritually drift, we don’t need more isolated heroes. We need more connected, grounded, accountable leaders who know how to circle the wagons with the right people.

Because no leader succeeds alone.
But many fall because they tried to.

Build your circle.
Protect your heart.
Invite the right voices.
And lead from a strength that isn’t yours alone.