How To Be Strategic: 5 Secrets From History’s Greatest General

We don’t think about it much, but a surprising amount of life involves strategy. Career goals. Negotiating salary and major purchases. And the near-constant attempts at persuading others that we engage in every day.

So how do we get better at strategy?

Well, we could do a lot worse than studying Napoleon. Yeah, the hand-in-jacket guy. Most people hear the name and just think “short” and “French,” which is ironic because both of those things are wrong. He was average height for the time and he wasn’t even ethnically French. He was Italian, from Corsica.

By age 24 he was a brigadier general. He was running France by 30. And at 35 he became Emperor, literally taking the crown and putting it on his own head, right in front of the Pope. It’s pretty much history’s most memorable “you know what, I’ve got it” moment.

Incredibly, it took him just nineteen years to go from junior artillery officer to Emperor. (Meanwhile, it takes me two years to cancel a subscription.)

Historian Andrew Roberts says Napoleon’s record was just 7 losses out of 60 battles. Pretty impressive in almost any arena.

“Yeah, but he still lost in the end! Waterloo!”

Actually, that just proves my point. Napoleon had a set of principles about war. When he obeyed them, he kicked ass. When he didn’t, well… oops. So his maxims on strategy are actually demonstrated in both directions.

That said, your daily life isn’t the Battle of Austerlitz. The guy taking his sweet time at the self-checkout isn’t “disrupting your supply lines.” But the ideas underlying Napoleon’s maxims can help us more than we think in our minor everyday conflicts.

This time we’ll be looking at “The Military Maxims of Napoleon,” with a little help from “Napoleon: A Life” by Andrew Roberts.

Let’s get to it…

 

1) What If The Enemy Attacked Right Now?

Here’s Napoleon: “A general-in-chief should ask himself frequently in the day, What should I do if the enemy’s army appeared now in my front, or on my right, or on my left? If he have any difficulty in answering these questions he is ill posted, and should seek to remedy it.”

“Ill-posted” is an old military term meaning your forces aren’t in a position to effectively respond to a threat.

“Oh, he means I should have a plan.”

Nope. Planning is good, sure. But you can never predict the future. Being “well-posted” means that if reality looks at your plans and says “nope,” you still have options.

If my plan for dealing with a burglary is to grab my Louisville Slugger and call the cops, but my phone is in the basement and I don’t own a Louisville Slugger, I have a plan but I’m ill-posted.

For the record, fellow dead strategist Sun Tzu agrees: “The art of war teaches us to rely not on the likelihood of the enemy’s not coming, but on our own readiness to receive him; not on the chance of his not attacking, but rather on the fact that we have made our position unassailable.”

So routinely do a “Napoleon Check.” Ask yourself, “If the most likely problem happened right now, what would I do?”

If a good answer comes quickly, you’re probably fine. If your brain sputters, well, you’ve found an exposed flank.

• Computer dies right before the big meeting? I have a backup of the presentation on a thumb drive and in the cloud.
• Unexpected bill? I keep an emergency fund.
• Employer suddenly schedules a company-wide meeting called “Our Innovative New Chapter”? I have friends at other companies who would help me get in the door.

If a problem people in your situation commonly face requires information you lack, connections you never made, or cash you don’t have, you’re ill-posted.

(To learn more about handling conflict from history’s greatest strategist, click here.)

So you’re prepared. But how do you deal with the enemy’s preparations?

 

2) Never Do What The Enemy Wants

Here’s Napoleon: “It is an approved maxim in war, never to do what the enemy wishes you to do, for this reason alone, that he desires it… never to attack a position in front which you can gain by turning.”

Modern equivalent? Admiral Ackbar’s been yelling “IT’S A TRAP!” since 1983.

In a zero-sum situation, what’s good for them is bad for you. The fact that they offered it tells you all you need to know. If you approach the fight as is, you’re not merely fighting them; you’re fighting all the preparation that they put into speeding you to your demise.

Again, Sun Tzu agrees: “The clever combatant imposes his will on the enemy, but does not allow the enemy’s will to be imposed on him.”

Ask yourself, “Who benefits if I react in the most predictable way?” Because the most predictable response will be the one their setup is built to crush.

Military historian Liddell Hart looked at 280 campaigns from 30 wars and realized a direct approach was a wonderful way to turn soldiers into statistics. Doing the predictable thing that the other side prepared for was effective only 6 times out of 280.

So Napoleon says: change the game. Shift the point of attack or the timing. Refuse to play it their way. David didn’t accept the face-to-face sword fight Goliath probably expected. Instead, he introduced the giant to long-distance geology and we all know how that went.

Same move works off the battlefield. If the other side wants a screaming match, shift to calm logic and facts. If their negotiator wants to haggle, focus on overall deal value or an ongoing relationship.

“Gotcha. If they want me to do something, I’ll just do the exact opposite.”

No. Bad. Stop. You don’t want to do what they’ve prepared for, but if you do the opposite, they’re still in charge. Do what is unexpected but optimal for you. Otherwise, they just need to use reverse psychology:

Mom: Don’t eat those vegetables.

Child: YOU CAN’T TELL ME WHAT TO DO! (begins chewing asparagus)

Mom: Don’t clean your room either.

(To learn more about business strategy, click here.)

So you’re not doing what the enemy wants. Good. But what should you do? Well, try talking to a lot more janitors and secretaries…

 

3) Reconnaissance Means Local Human Knowledge

Here’s Napoleon: “To provide guides that may be depended upon. To interrogate the curé and postmaster. To establish rapidly a good understanding with the inhabitants…”

Why the heck does Napoleon want you to talk to the postmaster?

“The map is not the territory.” Yeah, it’s a cliché but that doesn’t mean it’s bad advice. Find the people closest to reality and get the details from them on how things actually work before making big decisions.

Trying to get the scoop on an area you’re unfamiliar with by looking at the public narrative is like thinking you can understand somebody’s marriage by looking at the wedding announcement. That frilly letter doesn’t tell you that the groom’s mom sees her future daughter-in-law as a pole dancer with a law degree, or that the best man is in love with both of them.

Does Sun Tzu agree? Of course Sun Tzu agrees: “…unless you can employ local scouts, you cannot turn the terrain to your advantage.”

Every organization has two maps. The formal, public map shows how stuff is supposed to function. The informal map is…

Linda. The receptionist. Or Gary in IT. The people who see how stuff really gets done and who is really in charge.

Ignore the mission statement. Find the Linda who has been there through five reorgs.

Don’t read the job description if you can talk to the HR assistant instead. They can tell you the magic words on a resume that get names on the “schedule interview” list.

Are you going to learn more from the apartment listing or from talking to the maintenance guy who knows which unit is right next to the noisy air-conditioning system?

(To learn more about strategy from Sun Tzu, click here.)

So you’ve got the info you need and you’ve avoided the enemy’s trap. Cool. But how do you set a trap of your own?

 

4) The Great Secret Of Offense Is Defense

Napoleon again: “…even in offensive warfare in the open field the great secret consists in defensive combats, and in obliging the enemy to attack.”

Choose the location and timing of the fight and then force them to come to you.

“But how do I do that?”

Threaten a spot they cannot afford to ignore so they have to leave their safe cubbyhole and come at you. In the expected way. That you have prepared for.

Of course, do not, under any circumstances, arrange a fair fight. As the old saying goes, “If you find yourself in a fair fight, you have not planned your mission properly.”

Yeah, yeah, you know… Sun Tzu agrees: “Whoever is first in the field and awaits the coming of the enemy will be fresh for the fight; whoever is second in the field and has to hasten to battle will arrive exhausted.”

Since you aren’t planning an invasion of the Whole Foods on 5th Street:

• Negotiating for a job? Walk in with another offer. If they do want you, now they gotta move.
• In a sales role? Build a reputation or an audience so leads come to you.
• Closing a deal? Be the first to send the term sheet and anchor ambitiously. You control the territory. Every change they want to make is an ask and an uphill climb.

(To learn the 9 secrets that will make you an expert negotiator, click here.)

So the battle is underway. But what if the enemy vastly outnumbers you? Don’t sweat it. That’s not the thing you should be counting anyway…

 

5) Strengthen Your Best Exit

Napoleon says: “When two armies are in order of battle, and one has to retire over a bridge, while the other has the circumference of the circle open, all the advantages are in favour of the latter.”

Does he mention how big the respective armies are? Nope. How skilled they are? Nah. Who has better cannons? Uh-uh.

He says better exits mean “all the advantages.”

Too often we’re impressed with big titles, money, head count, or market share. But we don’t spend enough time asking, “Who can walk away? Who can just wait?” A powerful person with no good options is not a powerful person.

And Sun Tzu isn’t just agreeing with this one; he’s hopping up and down. He’s twerking to the beat. You could make an argument that The Art of War is a book about exits. Again and again, Sunny is describing battlefields by how easy they are to leave. He even has names for them. Hemmed-in ground is when you can only escape by using “tortuous paths.”

And “desperate ground” is when there are no exits at all. You do not want to be there. (Interestingly, desperate ground is so dangerous you don’t want your enemy on it either. It only gives them a single option: fight as hard as possible. You just converted an easy victory into the third act of a John Wick movie.)

Going back to the 1960s, social scientists literally defined power in terms of alternatives. A related idea was later formalized into BATNA (“best alternative to a negotiated agreement”) by Fisher and Ury. Your BATNA is what you’re gonna do if the negotiation collapses. “Well, if I don’t get an offer, I’ll explore my options.” Does that sound like a BATNA? That sounds like what people mumble before moving back in with mom.

And the research supports its effectiveness. Got good options? You come out ahead. Bad options or no options? Ouch.

A solid BATNA tells you what the minimum deal worth accepting is. More importantly, it changes how you handle a negotiation. When you have backup, you feel more comfortable rejecting bad offers, pushing for more, and possibly walking away.

Always keep two things in mind: What’s my best alternative? And how can I strengthen it?

(To learn how to have emotionally intelligent arguments, click here.)

Alright, we’ve covered a lot. Let’s round it all up and learn the principle that ties all of Napoleon’s advice together…

 

Sum Up

Here’s how to be strategic…

• What If The Enemy Attacked Right Now?: If you’re not prepared for the most common problem people in your current situation face, you’re not prepared.
• Never Do What The Enemy Wants: Ask yourself, “If they had never made that move, would I still choose to respond in this way?” The obvious response is the one they’ve prepared for.
• Reconnaissance Means Local Human Knowledge: The formal map tells you where the bathroom is. Insiders tell you not to use it after Jeffrey.
• The Great Secret Of Offense Is Defense: Prepare a strategic location. Threaten something the enemy can’t ignore. Make them come to you. Counterattack.
• Strengthen Your Best Exit: The aisle seat on a flight lets me get up without asking permission. This is urinary strategic optionality. Window seat gets the view but lacks a good exit. Middle seat? That’s “desperate ground.”

So what ties all this together?

Refusing to be forced:

• Ask what you would do if the enemy attacked now and you’re not forced by surprise.
• Don’t fight on the enemy’s terms and you’re not forced by their preparations.
• Talk to the Lindas who know the territory and ignorance doesn’t force your hand.
• Make the other side attack on your terms and you’re not forced by uncertainty.
• Keep exits available and… you’re not forced at all.

Strategy is anti-reactivity. It’s about maximizing agency.

Learn a few lessons from Napoleon and conflict will go much easier for you.

But don’t overdo it. Shopping at Costco isn’t Russia in winter, though both involve supply problems and people vanishing into frozen expanses.

And if I start referring to the bathroom as a “defensible position,” please take away my Napoleon books.