Embrace the Dark side of Leadership to Unlock Unwavering Loyalty

When I was sixteen, I worked at a deli chain.  Two of my managers stand out in my mind now.  First, there is the one who sometimes comped me a free cup of chili on my lunch break – Dave.  Then there’s Jeff, who fired me.  I think of these two when I get asked, “Is there anything to admire in a wicked leader?”

Where Dave was ingratiating and charming, Jeff was tough, he had high standards.  He was always stepping out from behind the counter to tidy up the empty Sweet’N Low packets from the iced tea bar. I couldn’t confirm whether Dave did that. Probably.  But the main memory he left you with was that he understood your struggles.  Dave  used effective nicknames. When I tried to pay for chili, he’d get quiet and say “I got you Big Al,” then wave me off with a sort of winking gesture.  Contrast Jeff.  Sure, he would pat you on the shoulder and say “good job” now and then – very audibly. But if you showed up late more than once, you would probably get fired – which is more or less what happened to me.  (In fairness, looking back, I would have fired myself too).

I have often wondered, which of these managers was actually better?

The answer can be found in a certain quality of the Spartan admiral Lysander.

Historians typically portray Lysander as a cynical, Machiavellian iceman. As commander of the Spartan ships, Lysander defeated Athens in a major sea battle, and thereby ended the long Peloponnesian war with a smash Spartan victory.  After the battle of Aegospotami (404 B.C.), he executed almost all of the captured Athenians.

Lysander once remarked, “You can cheat children with dice, and men with oaths.” Consider what he did at Miletus. He tricked the populists into letting their guard down; he even told them he was their pal. Then he slaughtered them.

Lysander has many haters, but I think they make the mistake of looking at him too objectively.

While Lysander could be stone-cold in the face of his enemies, his troops, allies, contractors – in short, everyone playing on his team – all loved him.  You get hints that he could pull you aside, get real quiet, and make you feel like you were the only other person in the room.  Wherever it was thought some allied city might defect from Spartan hegemony, Lysander would forcibly install an oligarchic dictatorship, a “dekarchy” of ten men, who were fanatically loyal to him.  Often, they were not great guys.  But Lysander picked them for their ruthlessness, and for his personal trust in them. In many cases, these oligarchs were more attached to Lysander than to Sparta.

Contrast Lysander with the guy Sparta installed as his replacement: Callicratidas.  Callicratidas was a good, honest Spartan.  A good soldier.  Straightforward.  Lysander was a fox, Callicratidas was a lion.

When he succeeded Lysander as admiral, during the war, Callicratidas didn’t want to sweet-talk some Persian prince into sending gold to the Spartan war chest.   He didn’t want to chum up and backslap with corrupt merchants.  Callicratidas wanted everything to be “above board.”

Callicratidas was a reliable manager – like trusty, tidy, Jeff.  No free stuff for employees, no practical jokes in the back kitchen.  Whoever Jeff’s boss was, they probably thought he was a straight shooter.  The Spartans definitely thought Callicratidas was.  Callicratidas was going to make sure the war operation was run on solid Spartan principles – no favoritism or flattery giving Sparta a bad name.

When Callicratidas first arrived at the fleet, the Spartans and their allies admired Callicratidas’ virtue, “as they would the beauty of a hero’s statue.” 

But they still missed Lysander.

The sailors agreed, Callicratidas was among “the justest and noblest of men,” and his manner of leadership “had a certain Doric [= Spartanoid] simplicity and sincerity.”

Still, they missed Lysander.

Why?  Lysander was their partisan, their bandit captain.  If forced to, he would rather lie, cheat and steal for his men than see them lose.  He was more obsessed with advancing their interests than they were themselves.

And for that reason, the partisanship went the other direction too.  Lysander’s loyalists were strong and effective, his sailors and captains fought hard to win his favor.  He wasn’t just being nice, it was a leadership strategy.  Favors pressure us to respond in kind.  I didn’t stick around long enough for Dave to call in his favors… but if he had ever asked me to do something against Deli rules – say, something upper management would frown upon – I wouldn’t have hesitated.

Callicratidas was, objectively, a good man.  Lysander was, subjectively, the best team captain.  He was also the better naval commander – Callicratidas bravely went down with his ships in a major sea battle that he lost to the Athenians.  Lysander won the war (see above).

I still don’t know which one was the better deli manager.  But if you want to command your team’s loyalty like Lysander, then you need to be a partisan for your people.  Dave had this effect, the beginnings (at least) of what I call the Lysander Effect.  The Lysander Effect isn’t about giving people free stuff and being nice and easy on them – Lysander was terrifying too, and he could be a strict disciplinarian.  Breeding loyalty in no way conflicts with competence.  Best would be to combine the favoritism of a Dave with the diligence of a Jeff.

But to harness the Lysander Effect, you must focus on taking your people’s side in everything, even when it’s unreasonable.  Not as a flatterer, but as a partisan – a pirate boss, even.   If you can combine this sometimes devious favoritism with a worthy mission, as Lysander did (that’s another story), you may be surprised at the lengths your team will go to be your partisans.

Callicratidas appears alongside Lysander in Episode 1 of 3 of the Cost of Glory Podcast retelling of the The Life of Lysander.