Why ‘Add 5%’ Isn’t a Strategy—And What to Do Instead
The greater danger for most of us lies not in setting our aim too high and falling short; but in setting our aim too low, and achieving our mark — Michelangelo
I left Amazon at the end of 2005. Over the past two decades, I’ve had the opportunity to help leaders navigate high-stakes situations, where uncertainty and possibility clashed, where risk-aversion and ambition battled, and where complacency, hubris and Short-termism typically won over innovation, experimentation and thinking big.
These stories and the framework for managing these situations are the essence of my books — The Amazon Way, Think Like Amazon and Big Bet Leadership.
At the incredible Imagine AI Live conference this year, I shared stories, frameworks, and tools for how senior leaders can drive bold moves in the age of AI. The central message? We need to rethink how we lead transformation.
Why?
Because if there is anything history has shown us, really great business operators and traditional management systems, including Agile and Lean management, do not get at the hard topics or address the tendencies, pressures or biases leaders face during high-stakes, high-ambition, high-uncertainty strategies — what I call “big bets”.
Let me walk you through some of the most important ideas from that conversation—stories, systems, and mindsets designed to raise your ambition and build your organization’s capacity for bold change.
1. The Bezos Moment That Changed How I Lead
In January 2003, shortly after launching the Amazon Marketplace, I was in an S-Team meeting when Jeff Bezos asked me:
“John, how many merchants have we launched this year?”
I started to explain that we had just opened the apparel category and didn’t have new merchants lined up yet. He cut me off and said,
“The answer to that question starts with a number.”
I paused and said, “Six.” - and attempted to explain that there weren’t any merchants to launch — something beyond my responsibilities.
And then the reaction!
That moment wasn't about metrics—it was about mindset. Jeff was reinforcing something foundational:
Don’t hide behind your job title. Think like an owner. Drive the business. Don’t let process, policies, org structures or politeness slow you down.
That interaction catalyzed how Amazon was crystallizing its leadership principles. We were shifting from being a first-party retailer to a platform company.
That mindset—and the systems behind it—have influenced everything I’ve done since.
2. Why Most Leaders Struggle with Transformation
Most senior leaders are rewarded through their careers for being great operators:
Identify the issue
Make a plan
Execute
Deliver results
But transformation isn’t an extension of operations—it’s a different game. The rules are different. The timelines are different. The rewards and risks are asymmetric. And yet, we often use the same language for both, which leads to confusion and frustration.
That’s why I authored Big Bet Leadership—to create a distinct playbook for transformational leadership. One that gives executives the tools, frameworks, and mental models for navigating high-risk, high-reward strategic moves.
3. AI: Be an Active Skeptic
At Imagine AI Live, I emphasized a principle we close the book with:
Be an active skeptic.
“Active” means you engage deeply. You explore bold use cases, test new customer experiences, rethink your operating model. “Skeptic” means you validate, test, and avoid hype-driven decisions.
AI can absolutely create new competitive moats—but only if it’s tied to your business value chain — a fresh, advantaged and real business value chain.
Leaders should ask:
How could AI create a better experience for our customers?
How could it dramatically reduce cost or cycle time?
Where are the new value propositions or business models?
Start early, before the pressure hits. The best time to experiment is when you have tailwinds—not when you’re reacting to churn or margin erosion.
[Watch my conversation with Chris Madden at the Imagine AI Live Conference]
4. The Power of Engineered Prompts and Custom LMs
Most people use tools like ChatGPT to speed up simple tasks. That’s useful, but it’s not transformational.
What’s transformational is when you use highly engineered prompts, guided by frameworks, to address complex, strategic problems. These are the types of “wicked problems” I help leadership teams navigate:
How do we grow in a flat market?
What’s our AI strategy?
Where do we invest when the path is uncertain?
We use tools like ChatGPT projects, NotebookLM, and custom distilled frameworks to create specialized LLMs that support these challenges. The outputs are not just fast—they’re high-quality, directional, and actionable.
5. Case Study: Moving Past “Add 5%” Thinking
Recently, I worked with a mid-market company in agriculture—real-world, salt-of-the-earth business. Their “strategic” plan was essentially last year’s plan with a 5% growth target.
That’s not a strategy. That’s a low-ambition “do the same; be the same” gimme plan. A board member called me because that is what he sensed.
My approach was this — I needed to increase their ambition first, and then figure out the ways to do it. I challenged the board and CEO — Don’t we owe it to our young employees who are betting their future on us, to grow the business and create more future opportunities and resilience in the business? Shouldn’t “stewardship” — the principle of creating future opportunities for others, be a driving force?
That triggered them. That started the mindset shift to increased ambition.
We dug into customer behavior, unit economics, adjacent market activity, and unmet needs. Together, we built a portfolio of strategic concepts:
Some were “moves of no regret”—clear improvements to implement now.
Others were big bets that needed experimentation: new pricing models, product features, channel partnerships. It even included a degree of “channel disruption”, concepts to shake up the cozy status quo.
By breaking these into testable components, we capped downside risk while unlocking bold, new possibilities.
And because the process involved senior leadership directly—not outsourced to a consulting team —the organization developed the muscles and mindsets to repeat the process going forward.
6. What Makes the Big Bet System Different?
Most consulting models focus on analysis, not leadership. They don’t challenge the internal culture—the short-termism, bureaucracy, or complacency that erodes strategic intent.
But bold moves require addressing both the strategy and the decision-making system. This includes:
Uncovering leadership biases: loss aversion, overconfidence, fear of ambiguity
Creating mechanisms to think clearly under uncertainty
Aligning cross-functional teams to experiment fast, at low cost
Building repeatable systems to evaluate and scale winning bets
In short: it’s not just the idea. It’s how the idea is selected, tested, and owned by your team. It’s about understanding how our human tendencies and organizational biases and incentive systems compromise great decision making when there is “calculated risk” involved.
7. What the Typical AI Conversation Gets Wrong
I left Imagine AI Live inspired. Unlike some events where AI is just a parade of AI gimmicks, this one focused on business value.
But here’s what leaders must remember: AI is not a strategy in itself. It’s a tool. Your strategy starts with the customer. It ends with measurable value and competitive advantage.
Start by asking:
Where’s the friction?
Where’s the opportunity to change cost curves?
Where are the under-served or over-priced segments?
What needs to change along with AI — because the technology will not solve these issues.
Then work backwards—with ambition, clarity, and a portfolio of options.
Ready to Raise the Ambition?
I work with leadership teams through keynotes, workshops, and advisory partnerships to help them:
Define and prioritize bold strategic opportunities
Build an internal system for experimentation and decision-making
Integrate AI into strategy in a way that’s grounded, safe, and value-focused
Avoid the common traps that keep organizations stuck.
Let’s talk if you're ready to make moves that matter.
Read about the Big Bet System. Connect with me here or on LinkedIn
Here’s to bold thinking and big bets!
Onward,
John
Author of The Amazon Way, Think Like Amazon, and Big Bet Leadership
Advisor | Keynote Speaker | Early Amazon Executive|
See John in Action — HERE