Cowboys, Shepherds, and Leaders: Cool or Cruel?

by Jeff Holland

Short-term team leaders. Want cowboys or shepherds? Learn more about hippie-styled shepherding.

Growing up in Texas, I saw a lot of cows. Range cattle out west. Dairy cows to the east. And cattle ranches all around.

When it came to sheep and goats, I didn’t see many.

Cowboys seemed cool. They got to drive the cattle. Horses. Whips. Spurs. And Stetson Hats.

Shepherds seemed like a relic from a bygone era. No real cool factor.

Then I went to Africa. A place with few cows. But sheep and goats? Everywhere!

Where there are sheep, there are shepherds. I saw two main types.

The Teddy Roosevelts: “Speak softly and carry a big stick.” With this motto, shepherds leverage intimidation to make things happen.

They’re like cowboys but on foot. Not quite cool. Kinda’ cruel.

The hippie shepherds: A peace and love type who went out and stayed with the sheep all day. They loved being in the fields with their sheep, the sheep knew their voice, and their presence kept predators at bay.

Watching the shepherds taught me about different kinds of leaders. Teddy Roosevelt-styled and hippie-styled. Those who use a stick. Those who build a relationship.

What kind of leader are you trying to be?

How to Shepherd like a Hippie

  • Focus on relationship instead of control.
  • Walk ahead of the flock as an example and to provide protection.
    • Know your purpose, but don’t miss the special moments.
      • Help move your flock to be part of what God has designed for them.
      • Model flexibility. Some of God’s best teachable moments come spontaneously.
    • Keep your eyes peeled not only for dangers but for good things to lead the flock towards.
    • Don’t walk behind simply waiting to whack them when they’re wrong. Praise them for what they do right!
  • Rest and work among the flock.
    • Serve them well and tend to their needs.
    • Be part of their lives and know them by name.
    • The flock should know your voice.
      • When you call for them, they come. They trust you.
      • Even when you are not near, they know your expectations.
  • Lead the flock to safety.
    • While on the journey, provide a “sheep pen,” an emotionally safe place where the flock can gather.
      • They need time to relax, regain their strength, and prepare for their next events.
      • Show that you are interested in what they experienced.
      • Encourage the flock to care for one another and share their concerns.
    • When the team is eventually back home, make sure they remain healthy.
      • Check on them occasionally.
      • If they have “scattered,” help them to find ways to reconnect and take care of one another.
      • Entrust your flock to the other shepherds (families, church leaders, and others).

Hippie-styled shepherding. It may not be cowboy-cool. But it’s certainly something to aspire to.


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