Product Management and the Art of War

Alison Pyle
Product Coalition
Published in
5 min readOct 5, 2021

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A soldier viewed from the side aiming a keyboard like it was a gun
Photo by Halfingr on DeviantArt

I’m back from a long deployment in hostile territory (retail eCommerce) and I’d like to share some lessons with you from the battlefront.

Now, I don’t profess to be some sort of hero, but I have survived long enough to tell these tales…

Lesson #1 — Be with your team every day

What they don’t tell you is that Product Management is not glamorous. It’s not about polished strategies presented to rapt audiences in the boardroom.

Sure, at one point in the distant past, you may have carefully crafted a PowerPoint to convince the joint chiefs of staff to green-light your mission (get capital funding), but this is not the typical day.

Day-to-day you should be down in the trenches with your team, battling it out. In fact, if you are not neck-deep in mud most days, you are doing it all wrong. Never be concerned about getting your suit dirty.

In fact, please don’t wear a suit at all. Fatigues (jeans and a hoodie) are a far better option for this part of the operation.

Lesson #2 — Do whatever it takes to win

You are the captain of your team, but you are also the navigator, the sniper, and the bandleader. All the while setting up camp in a forward position (incepting the next epic).

Whatever needs to be done, it is your job to make sure that all jobs for the unit get done. This may mean making tough assignments, doubling up work detail, or easing up if someone is at a breaking point.

At times, when there is too much work to go around, then you will have to just do it yourself. Some nights this means you are running the mess hall or even cleaning the latrines (grooming JIRA).

Again, this is not glamorous work but it’s necessary for success. So roll up your sleeves, buckle your ego into the back seat, and get to work.

Lesson #3 — Build a team you have full confidence in

The team needs to be crystal-clear about the mission and be personally invested in it.

You are only as strong as your weakest link, so find out who is not carrying their weight (slow velocity) and ask yourself: are you willing to carry their pack (complete their story points) the last 5 miles in addition to your own? Ferret out any potential deserters from the beginning, anyone you can’t count on, and send them packing.

Don’t be in the heat of battle to be let down by your team, when your life is on the line. Make sure you are willing to die on the hill for each and every one of them, and they for you.

Lesson #4 — Be flexible

Your team, your preparation, and your strategy is your tactical advantage but it is not enough to win the war.

When you are in hand-to-hand combat on a daily basis with the deadly enemy (blockers), you need to stay flexible and constantly moving forward to get a better position.

The enemy is sneaky and their surprise ambushes will waylay you, distract you, slow you down, and even turn your team in the wrong direction entirely.

To counter attack, be nimble, be quick, and be prepared to pivot on a dime. Using this military tactical maneuver (agile development), the shortest distance between two points may actually be a zig-zag.

Remember: it’s harder to be shot down if you move in unanticipated ways.

Lesson #5 — Own the outcome

You are responsible for your unit, whether they succeed or fail. That’s a tough spot to be in but there is no other way except extreme ownership. This means you need to own all decisions, whether small or large, easy or tough, and especially when they seem impossible to make.

Sometimes the battlefield is filled with smoke and you’ve lost comms (lack of data). Sometimes you need clear direction from your chain of command but get conflicting messages (stakeholder confusion). Sometimes you’re not willing to retreat (reduce scope).

In the heat of the battle, you need to make the best decisions you can, relying on your training and your intuition.

However, this doesn’t mean that you make every decision alone. You are still part of a team. Effectively leading from the front, often means getting opinions from the back. But never forget: if the mission fails the blood is on your hands.

Lesson #6 — Leave no one behind

Hypothetical: You are running out of time to your target and you come across another captain stuck in the mud, do you seize upon their momentary weakness and steal their jeep (tank their project)?

Of course not, they are on your side and not a prisoner of war (that’s the trifecta of time, money, and resources). You lend a hand and help her back up.

[Author’s note: See what I did there? You thought the captain was a man, didn’t you?]

When there are many competing projects, it may seem that opposing teams have separate objectives, but you might not have seen the entire battle plan.

The general wants all the battalions to be successful, not just yours. Sometimes you need to sacrifice a bit of your forward momentum (velocity) to help others make it to safety (delivery).

Bottom line: Don’t sacrifice your brothers and sisters along the way to your goals. Tomorrow, you may be the one face down in the mud.

Lesson #7 — Win for the team

When you finally take the mountain (deliver a major code release) and the team is victorious, no one will begrudge the visibility you will have or the adulation you will receive.

Well, no one that has actually been to war. If they were an auxiliary unit on the sidelines (marketing, merchandising, sometimes even management), then they will never understand the sacrifices you made for your team. And the team for you.

It’s only when you have been shoulder-to-shoulder, dragging each other up the last precipice together, sharing the last sip of water from your canteen (the last red bull in the snack room) that you can truly understand what you have been fighting for all along: each other.

Make no mistake, this is war.

Product Management is having finite resources to take the hill with a diminishing window of opportunity. You are at war for capital. You are at war with deadlines.

You will win some, you will lose some, but you will have the tremendous honor to lead an extraordinary team.

If you are really lucky, you will get to plant a flag by putting something new in the world that wasn’t there before.

And after every sweet victory and every bitter defeat, you will look forward to getting back up to fight another day with a few good friends.

Now go kick some ass.

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Obsessed with product management, perplexing puzzles, and personal development when awake. Else: lucid dreaming.