The world went digital. Business got more sophisticated. And a lot of the people running companies didn’t notice.
I’m talking about the VPs, the senior directors, the executives who are still running a playbook from 20 or 30 years ago like nothing changed. The game has substantially changed over the past two decades, and the old playbook just doesn’t apply anymore. But you’d never know it watching how some of these people operate.
Why the old playbook used to win
Here’s the thing, that playbook worked. For a long time.
Business back then was simpler. Less competition in most markets, less sophistication in markets, and you could succeed without being an expert in marketing or anything else. A personality type that was rough, persistent, and arrogant could win in sales, because they had a tangible lever. The lever was conversations, contacts, and communication. They could always pick up the phone and talk to someone, or do something to the same effect.
That’s a real advantage in a simpler world. More effort, more output. You push a little harder, you make a few more calls, you close a few more deals. The math was straightforward, and the people who were loud and persistent enough usually got there.
Why it doesn’t win now
Now we have technology. We understand human psychology at a deeper level. We know that buying isn’t a single transaction, it’s a journey, and we’ve created campaigns and strategies to help people navigate it at every step. From learning your product exists, to understanding how it could help them, to deciding to buy, to falling in love with it and recommending it to everyone in their world.
On top of that, there are more competitors now and the markets themselves are more sophisticated. The room is more crowded and the customer is sharper. So it takes thought. It takes planning. It takes being strategic about how you play the game. It’s a completely different thing than business was 20 or 30 years ago, and that’s the part the old guard keeps missing. You can’t just do more anymore. You have to be more deliberate about how you do it. It’s not what you do, it’s how you do it.
What game are we playing?
Before any of this matters, you have to answer one question. What game are we playing?
Every company is trying to accomplish something. If you can’t say what that something is in a clear sentence, nothing downstream of it is going to work. So here’s how I think about it. If business is a sport, then the goal of the game is to win. That sounds obvious, but watch how people actually operate and most of them have lost the plot. You cannot win by being reactive and non-strategic. That’s not playing the game, that’s running around the field hoping the ball finds you.
So how do you win? You use the data available to you to paint a picture of your customers and their world. Who they are, what they want, what they’re dealing with. Then you craft strategies that support and assist those people, built from what the data actually shows you. Data tells a story. Your job is to read it and act on it.
And this is where the people delegating come in. If you’re a VP or an exec handing out work, your first job is to explain the game. What are we trying to accomplish, and what does winning look like? If you can’t articulate that, your team isn’t executing a strategy, they’re just guessing in your direction. You can’t delegate your way out of not having a destination.
What the old playbook looks like in practice
So what happens when someone runs the old playbook in today’s world?
No coherent plan. Pure reaction. Every new idea becomes a quick, last-minute, drop-everything project, and those almost never work. It’s spray and pray. High-priority fire drills built on whatever crossed their desk that morning, busy work that never moves the needle, and a team underneath them quietly burning out chasing things that were never going to matter.
And it’s hurting these businesses. The wild part is the people doing it are usually the most convinced they’re right.
“If you fail to plan, you are planning to fail!”
Benjamin Franklin
Two ships
There’s a line from Earl Nightingale’s The Strangest Secret that captures this better than I can.
“Think of a ship with the complete voyage mapped out and planned. The captain and crew know exactly where the ship is going and how long it will take and it has a definite goal. And 9,999 times out of 10,000, it will get there.
Now let’s take another ship and just like the first and only let’s not put a crew on it, or a captain at the helm. Let’s give it no aiming point, no goal, and no destination. We just start the engines and let it go. I think you’ll agree that if it gets out of the harbor at all, it will either sink or wind up on some deserted beach and a derelict. It can’t go anyplace because it has no destination and no guidance.”
Earl Nightingale – The Strangest Secret
That’s the whole thing right there. So let me give you two companies.
The first company is reactive. They run the old ideas and the old strategies from 20 years ago, and they’re heavily sales-driven in their leadership appraoch. They may have done really well back then. But now they’re scatterbrained. They spray and pray. They spin up high-priority projects for the whole team based on something random, and they’re convinced that if they just apply this one short-term tactic, the whole thing turns around. It won’t. That’s the ship with the engines running and nobody at the helm.
The second company is strategic. They did the research on who their customers actually are. Demographics, psychographics, as much data as they can get to understand what their customers are looking at and how they think. They’ve reviewed their market and what their competitors are doing, the offers, the packages, the policies on refunds and promotions, all of it. They understand the customer journey intimately, and they align their campaigns to the avatars they’ve defined, with the constraints understood at a deeper level. There’s no flipping a magic switch and printing money. They know that, and they plan around it.
The second company is just less pie in the sky. Less hope, more data. One ship has a destination. The other one is drifting until it sinks or runs aground.
Shiny Object Syndrome
In my experience, a leader without a real strategy falls straight into shiny object syndrome. They’re always surfacing spontaneous ideas and pet projects for the team to drop everything and chase, convinced that this one is the silver bullet that finally grows revenue overnight. Flip a switch, money pours in. It never works that way, but without a plan to anchor them, every new idea looks like the one that’s going to change everything.
Modern Marketing Leadership Commandments
Since the textbook isn’t getting picked up, here’s the short version.
- Pick a destination before you start the engines. No goal, no aiming point, and you end up exactly where that second ship ends up. A campaign without a destination isn’t strategy, it’s motion.
- Know your customer & their world better than they know themselves. Demographics, psychographics, what’s actually going through their head when they decide. If you can’t describe who you’re selling to, you’re guessing.
- Study the people you’re up against. Their offers, their pricing, their policies, their promotions. You’re not selling in a vacuum, and pretending you are is how you lose.
- A tactic is not a strategy. that single idea that got you fired up last night is not a plan, no matter how good it felt in the moment.
- Strategy first, execution second, in that order. Drop-everything, last-minute tactics feel like progress. They’re busy work with a deadline.
- There’s no magic switch. Nobody flips a setting and prints an extra million dollars. Anyone who tells you otherwise is selling you something.
- It’s not what you do, it’s how you do it. Everyone has the same tools now. The edge is in the thinking, not the tool.
- Stay a learner or get out of the way. The game keeps moving. If you stopped learning two decades ago, you’re not leading the team, you’re slowing it down.
- Ego is not a strategy. Being the loudest person in the room used to move business forward. Now it just moves it backward.
- Doing more isn’t doing better. You can’t out-hustle a bad plan. More effort pointed the wrong way just gets you to the wrong place faster.
Leaving Corporate
I’ve always been a learner. I’m wired to need to know more, understand more, get sharper. So when I was in corporate, I was genuinely hopeful that I’d get taken under an executive’s wing, learn the strategy, and come out better for it.
I was disappointed. A lot of the people holding those roles simply didn’t have the strategic skills I was hoping to learn from. I’d report to people who were loudly opinionated on things that didn’t matter. One time my boss, a VP, said “I don’t like pop-ups, so we’re not going to use them.” That was the strategy.
That’s when I stopped expecting the title to come with the skill.
The point
Business evolved. The game changed. And more isn’t a strategy.
Strategy is knowing your market, your customer, your competitors, and your positioning, and then doing the work to act on it. The companies that get this are mapping the voyage. The ones that don’t are running the engines and hoping.
Remember, business is like a game, and the goal is to win. You don’t win by reacting to whatever lands in front of you that day. You win by being smart about your strategy and sticking to the plan all the way through the season. The teams that play it that way are the ones lifting the trophy. The reactive ones never make it that far.
It’s not what you do. It’s how you do it.