Leadership Study: Gideon and his Fleecy Moments

Gideon in action

During this retreat, I promised myself I’d finally sit down and do a proper character study of someone in the Bible. Gideon has been on my “must-look-deeper” list for a while, so I decided: okay, it’s your turn.

Gideon actually intersects with my own story in a pretty personal way. When I was deciding whether to respond to the King of Bhutan’s invitation to work in his kingdom back in 2013, I had what I’d call a “Gideon’s fleece” moment.

I knew Bhutan’s population was more than 99% Buddhist. I also knew that if my faith was going to be a problem, I wanted to find out before I uprooted my life. So I prayed: if the King of Bhutan were to ask about my religion, I would answer truthfully and entrust the outcome to God. That was my fleece.

True enough, during the audience, that question came up very quickly—right after the customary, “How was your flight up here?” I remember thinking, slightly dryly, that this might be the shortest HR interview in history.

So I told him: “I am a Christian.”

He replied, “Good, we need the diversity.”

I took that as my sign. It felt like God’s quiet way of saying, “It’s alright to be yourself here—Christian and all.”


There’s a lot to glean from Gideon’s story, but here are three things that struck me this time round.

1. People are stupid when they come together.

Blunt, yes. But look at Gideon’s story and tell me it’s not at least a little accurate.

Time and again, people stand in the way of what Gideon is trying to do. On at least three occasions, the collective opinion of the people is a snare to him:

  • “We want you as king!”
  • “You must die for breaking down Baal’s altar!”
  • “Why should we give bread to your troops—never mind that you’ve just won a great victory?”

In one situation, though, the stupidity of the masses actually works in his favour. That’s how, with just 300 men, Gideon manages to rout an army “as countless as locusts, with camels as numerous as the sands of the sea.”

Psychologists talk about the C factor (collective intelligence) versus the G factor (individual intelligence). The research isn’t kind to groups. Collective IQ often struggles to match what individuals can do, and in many cases, groups produce poorer outcomes on most tasks. That’s one reason why leaders often do it alone rather than delegate.

There are a few conditions under which the collective can outperform individuals:

  • High social sensitivity (empathy and awareness)
  • Equal turn-taking in communication
  • True group diversity

If you’ve interacted with any normal human being for any length of time, you’ll know how rare all three are in the same room. Empathy in groups is hard. Equal turn-taking is hard. Diversity that isn’t just cosmetic but actually shapes decisions? Also hard. And in some places (Singapore comes to mind), the majority race often dominates the worldview, and everyone else has to adjust.

So when the Bible talks about mobs, crowds, “the people”—I now read those scenes with a knowing sigh. Gideon’s story is very much a case study in how crowds can be both powerful and, frankly, a bit daft.


2. Gideon is overly cautious—and God takes that into account.

Gideon is not your stereotypical fearless leader. He’s more like that person who asks, “Are you sure?” eight times before agreeing to anything.

The fleece incident is the classic example:

  • “Lord, make the fleece wet and everything else dry.”
  • God does.
  • “Okay thanks, but now can you make the fleece dry and everything else wet?”
  • God obliges (probably with a patient sigh).

And that’s just one episode. God had to constantly encourage this timid commander-in-chief.

At one point, God told him:

“If you are afraid to attack the camp, go down to the camp with your servant Purah and listen to what they are saying. Afterwards, you will be encouraged to attack the camp.”

In other words: “I know you’re scared. So here’s a baby step. Also, take a friend, because I know you won’t go alone.”

There’s no peer-reviewed study I can cite on “How God Assigns Momentous Tasks to Silly Humans,” but Gideon’s story suggests this much: God knows exactly what we are like—our fears, cautiousness, self-sabotaging tendencies—and still calls us. He doesn’t ignore those traits; He works with them.

Whether we listen at all, and how we respond, is on us. Which brings me to my third point.


3. Gideon is a fool.

There’s a Hokkien phrase: kiang tio ho, mai ge kiang—be smart, but don’t pretend to be smarter than you are.

Gideon is the walking, talking embodiment of what happens when you ignore that advice.

Somehow, he flips from being a cautious, timid man into a reckless, unethical, “my way or the highway” kind of leader.

A few lowlights:

  • He decimated two towns for refusing to supply his army. To be fair, those towns were basically acting just as cautiously as he once did. Maybe he hated that trait in himself and projected it onto them.
  • He forced his young boy to kill two captured enemy commanders. When the boy could not do it (possibly because he was, well, timid and also a child), Gideon killed them in front of him. Again, perhaps he despised the timidity he recognised in his son. But you don’t need a degree in psychology to guess that the boy was probably traumatised as a result.

What’s crucial here is that God did not tell Gideon to do any of this. The instructions to raze those towns or execute those commanders that way? That’s all Gideon.

His ge kiang-ness became the downfall of the very people he was called to rescue. He imposed a tax, used the gold to make an ephod, and that ephod became an idol—yes, the same sort of idolatry he tore down at the beginning of his story.

After all the battles, all the victories, all the miracles, the people ended up right where they started: ensnared in idolatry.


So, what do I do with Gideon?

On one hand, he’s relatable: cautious, fearful, needing repeated reassurance, wanting signs. On the other, he’s a warning: that the same person who started out dependent on God can, after a few successes, slide into pride and harmful self-reliance.

Gideon’s story comforts me—my timidity and hesitation aren’t disqualifiers. God can, and does, work with that.

But it also sobers me. The journey doesn’t end with “being called” or even “being used by God.” The real test seems to be: who are you after the victories God achieves through you? Do you now want to become God? Do you let transient power, capricious affirmation, and fleeting success get to your head?

Gideon showed that being used by God doesn’t automatically make one wise. Or kind. Or safe. For ourselves and for others, we still need to watch that little ge kiang voice in us—because it might just outlast the fleece and the miracles.

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