Always Play Offense AND Defense, Part II
Sometimes I am surprised by an article flopping.
Other times, one of the pieces gets a big reaction.. and I completely expect it. Not because I am a genius talent writer.. but because of what I am writing about.
We all want to build a better life for ourselves.
We all understand that working systematically outperforms bursts of effort or disconnected energy / attention. When I write a piece that helps people understand pieces of wealth systems, or frameworks to build + grow them, you all resonate with it.
“Always Play Offense AND Defense” was one of those I bet this one resonates posts and I was right. It was one of our most shared posts on social media. Thanks to the great feedback we’re going to put together a series to give tactical advice, talk about leveraging teams and more.
Check out Part I if you haven’t already:
In the last piece, we talked about philosophy.
We drew a line in the sand between the business brawler, the reckless, chin-out haymaker-thrower…and the business boxer, the master technician of the sweet science. We established the core principle that guides the technician: every single move you make must be both offensive and defensive. It must advance your position while simultaneously protecting you from a knockout blow.
Philosophy is the easy part. It’s inspiring. It’s the ‘what’ and the ‘why.’
But a philosophy that doesn’t change how you act is just a pretty sentence. It’s a ghost in the machine, a framed poster on the wall of a failing business. The hardest thing for any leader to do is to bridge the canyon between knowing a thing and doing a thing. It’s the difference between watching a fight on TV and stepping through the ropes.
So, welcome to the training camp.
This is where we take that philosophy and beat it into your muscle memory. This isn’t a lecture; it’s a series of drills. This is the playbook that turns abstract ideas into concrete actions. This is the ‘how.’
The One Question That Changes Everything
For years, I’ve worked to distill this entire mindset into a tool, something sharp and practical that I could use in the heat of the moment.
It’s a question I ask myself in the boardroom, in the middle of the night when staring at the ceiling, in every high-stakes negotiation and every single job interview. It has become the engine of the whole system.
I call it the Dual-Purpose Question, or DPQ for short:
“How does this move us forward, and how does it protect our flank?”
Simple, right?
Deceptively so.
Most leaders, the brawlers, live and die by the first half of that question. They are addicts, hooked on the adrenaline of forward momentum, of “crushing it” of growth at all costs. The second half of the question, the defensive half, feels like a drag. It’s the parent asking if you’ve done your homework. It’s the brakes on a race car.
But a master technician knows the brakes aren’t there to make you go slow. They’re there to let you go fast safely. The second half of that sentence is where discipline is forged and empires are protected.
Let’s break it down into the two critical tests that every decision, big or small, must pass before you greenlight it.
The Offensive Test: This is the language of momentum. It’s the fun part. Does this action create a new, tangible opportunity? Does it allow us to capture new ground, accelerate our core mission, or put a competitor on their back foot? This is the question of upside. It’s the crisp, point-scoring jab. It’s the move that puts you ahead on the scorecards.
The Defensive Test: This is the language of paranoia. It’s the hard part everyone skips. What is the ‘graceful failure’ mode here? If this decision blows up in our face (and we must assume it might) what is our fallback position? Does this action make our organization more fragile or more resilient? This is the question of downside. It’s the subtle shift in footwork that keeps you balanced and ready for a vicious counter-punch.
It’s what keeps you off the canvas.
A move isn’t a good move until it passes both tests. If you can’t clearly articulate the answer to the defensive question, you’re not making a calculated risk. You are, in the plainest terms, gambling with your company’s future.
Drills from the Corner: Putting the DPQ to Work
Let’s get out of the abstract and into the ring.
Here’s how the DPQ plays out in the trenches, with the gut-wrenching decisions you have to make every single day.
The Drill: Hiring (The Character Play)
The Brawler’s Move: You find a candidate with a golden resume. A certified killer from a top competitor who can triple your sales. You see the upside, get blinded by it, and hire them on the spot. All offense.
The DPQ in Action:
Offense: “This candidate has the skills and network to land the three enterprise accounts we’ve been chasing for a year.”
(Clear pass.)
Defense: Here, the questions get harder. “What is their character? Have we done the real homework…not the curated references they served up, but the quiet, back-channel calls to people who worked for them? Are they a team player, or a toxic superstar who will leave a trail of bodies and poison our culture? What happens if they fail? Will they blame others, or will they own it? How will they act under pressure?” A bad hire isn’t just an underperformer; they are a slow-acting poison that can rot your company from the inside out. A great hire is an asset and a fortress.
You have to check for both.
The Drill: Product Development (The Kill Switch)
The Brawler’s Move: Your team has a brilliant, game-changing idea for a new feature. You get excited. You pull out all the stops, hard-code it deep into the core product, and launch it with a massive, expensive marketing splash. All offense.
The DPQ in Action:
Offense: “This new feature will delight our power users and create a new, defensible selling point against our primary competitor.”
(Clear pass.)
Defense: “But how are we building it? Is it woven so deeply into our codebase that a single bug could create a cascade failure and take down the entire platform? Or are we building it as a separate, containerized module? Can we deploy it behind a feature flag and roll it out to 1% of our users first? If it’s a disaster—if it’s buggy, if users hate it, if it has unforeseen legal implications—can we hit a kill switch and have it disappear in seconds, with no collateral damage?” Building in a graceful exit isn’t pessimism; it’s professional-grade engineering. It is the ultimate defense.
The Drill: Negotiations (The Escape Hatch)
The Brawler’s Move: A huge, prestigious company wants to partner with you. You’re so flattered by their attention and the potential of the deal that you sign the first contract they put in front of you, locking in the terms for five years. All offense.
The DPQ in Action:
Offense: “This partnership gives us access to a distribution channel that would take us a decade to build ourselves. The reputational halo alone is worth it.”
(You see where where this is going.)
Defense: “But where are the escape hatches? What are the termination clauses? Are we locked in, even if they fail to perform their side of the bargain? What happens if they get acquired by our biggest competitor next year? Have we built in a 90-day, no-fault exit clause? Who owns the customer data? Who owns the IP we co-develop?” A bad contract is a cage. Never, ever enter a room you can't walk out of. In any deal, your best defense is always optionality.
The Drill: Financial Planning (The War Chest)
The Brawler’s Move: You just raised a big round of funding. You pour every single dollar into growth—hiring, marketing, expansion—to show your investors a steep upward curve. The burn rate is terrifying, but the growth looks amazing. All offense.
The DPQ in Action:
Offense: “Deploying this capital aggressively will allow us to capture market share and solidify our position as the industry leader.”
Defense: “But what happens when the market turns? What if a new competitor emerges, or a recession hits, and our revenue projections are suddenly cut in half? Have we maintained a ‘war chest’ aka a significant cash reserve that isn’t earmarked for operations? Can we survive for 18-months with zero new revenue?” Cash isn’t just for spending. It’s a defensive weapon. It allows you to survive a downturn your competitors can’t. It allows you to acquire a weakened rival for pennies on the dollar.
It is the ultimate shock absorber.
You can buy time with cash.
From a Playbook to a Culture
You might be thinking this all sounds good, but it also sounds exhausting. And you’re right.
At first, it is. It requires a deliberate, conscious, and sometimes contrarian effort to constantly ask the defensive question when everyone else is shouting about the glorious offensive upside.
But the goal isn’t for you, the leader, to be the only paranoid one in the room. The goal is to build a culture where everyone is asking the DPQ. The goal is to create an organization that has this philosophy in its bones. A place where your head of product pushes back on a launch because the defensive plan is weak. Where your head of sales is willing to walk away from a big, messy deal because the contractual terms would leave the company exposed.
You get there by rewarding it.
Our entire business culture is built to celebrate the home run. The massive product launch, the record-breaking sales quarter, the splashy press release. The offensive wins. To build an offensive-defensive mindset, you have to start celebrating the defensive saves with just as much fanfare. The lawsuit that was avoided because your legal team built an ironclad terms of service. The PR crisis that never happened because a junior engineer spotted a potential data privacy flaw before launch. The server crash that was prevented because of a smart, redundant architecture that cost money but saved the company.
Offensive wins might get you on the cover of a magazine for a month.
A deep, instinctual, company-wide defensive mindset is what lets you build an empire that lasts for decades.
Now, stop reading.
It’s time to run the drills.
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