Strategy is compressing

Issue 240: New tooling changes where strategy is important

“Strategy” is one of those loaded words. I often hear people say, “I want to do more strategy,” especially when talking about career growth. But what does that even mean? “Strategist” feels like one of those titles we should retire—kind of like the “Ideas Guy” before it.

With technologies like AI and next-gen tooling, the pace of iteration has shifted from two-week sprints to multi-hour cycles. That changes everything. The good news? For people who think like me, the *performance theater* of strategy is getting squeezed out. Strategy is compressing—and that’s a good thing.

I’ve believed this since 2012, when I saw The Secret Truth of Executing Great Ideas by Frans Johansson, founder of The Medici Group. His talk focused on reducing iteration cycles and blending cross-functional perspectives. He also shared one of the most useful definitions of strategy I’ve ever heard:

“A strategy enables you to act.” —Frans Johansson

The idea is simple. Doing it in practice? Not so much.

Let’s look at why traditional strategy has historically been so bloated, how our tools are changing the process, and what a new, compressed strategic cycle looks like.

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Where strategy is getting compressed

A few core elements make strategy essential: prioritization, future casting, narrative alignment, and structured feedback. Strategy isn’t going away, but it is being reconfigured by modern tooling.

Front-loaded planning is becoming obsolete

A lot of strategic energy used to be spent on planning before anything could start. Because product development was expensive, companies leaned heavily on rituals like QBRs, roadmapping sessions, and long-term deck cycles. These things aren’t inherently bad—they help align teams and clarify impact, but they come at a cost.

Now, large language models and other research tools have radically lowered the barrier to accessing strategic inputs. What used to require weeks of synthesis and slide-making is now one query away.

Yes, judgment still matters. Knowing how to frame, analyze, and make sense of the data remains a uniquely human skill. But the cost of getting to the table with that information is no longer prohibitive. Strategy starts moving faster.

Strategy is embedded in the feedback loop

Traditionally, strategy lived upstream—something you nailed down before building. Now, it moves with the product. Living strategies evolve in real time, informed by what prototypes, user feedback, and data are telling us. Strategy is no longer fixed; it’s dynamic.

This is especially visible in design research. Historically, researchers relied on multiple concept testing rounds, often slowed down by the cost or complexity of creating viable prototypes. Many of those tests weren’t just about learning—they were also ways to avoid the expense of getting it wrong.

Now, with prototyping and research tools more accessible, the same person can ideate, build, and test within a single loop. Designers and researchers can co-produce faster, with less reliance on handoffs. Instead of designing around constraints, we’re testing around possibilities.

With cost and time-to-insight compressed, you can make dozens of strategic cuts without incurring heavy costs. It’s not about skipping rigor—it’s about embedding it into the cycle.

Insights arrive inside the build

We used to forecast first, build later. Now those things are happening nearly simultaneously. The act of learning is the product development cycle. Forecasting, testing, adjusting—they’re infused into the loop.

In many cases, the build is the test. A shipped prototype can tell you more than a hundred speculative slides ever could.

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Aspects of strategy that remain essential

A compressed strategy doesn’t mean the strategy itself is less important. What’s happening is that the noise of the bloated processes, the meetings-about-meetings, the performance masquerading as planning, is what’s getting squeezed out. What remains are the parts of the strategy that matter most. In some ways, they’ve become even more vital because clarity is the new constraint. When building becomes cheap and fast, judgment, intention, and alignment become the true competitive advantage.

One of those enduring elements is a clear mission, vision, and north star. These foundational elements can’t be automated or outsourced. They represent the human intent behind the work—why we’re doing something, what direction we’re headed, and how we’ll know if we’re on the right path. In a world where anyone can build anything, the point of view behind it becomes even more valuable. Without this, you’re just shipping noise. Tools can help you move fast, but only people can decide where to go and why it matters.

Organizational alignment is another aspect that never goes away—if anything, it becomes more essential as execution speeds up. I was once asked what size a team needs to be before alignment starts to matter. My answer: as soon as there’s more than one person involved. The moment your decisions impact someone else, you need a shared understanding of what matters and how choices are made. Alignment isn’t just a management function—it’s strategic glue. It allows teams to move quickly without veering off course or fragmenting across priorities.

And finally, brand and taste become the enduring differentiators in a world where the means of production are widely accessible. When tools make it easy for anyone to build polished, functional products, the experience layer—how something feels, how well it’s curated, how deeply it resonates—becomes your moat. The emotional quality of a product, the narrative it tells, the values it expresses—these are what make it memorable and defensible. Morgan Beller’s “AI is like water” metaphor captures this beautifully. Once a technology becomes ambient—everywhere, assumed, and invisible—the differentiating factor becomes how you channel it. Taste, story, positioning—those are human levers, and they’re what stand out when everything else becomes uniform.

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The shape of strategy

It’s scary how fast things are changing. Product Managers can now skip the design queue and prompt a janky prototype themselves. It might not be pretty, but it’s enough to bring discussion into a meeting. That used to take days—now it’s minutes.

We’ve gone from one shot at executing the strategy to one shot prompting our strategy.

Strategy isn’t disappearing. It’s getting closer to the build. It’s moving faster. And it requires more clarity than ever.

In this new world, everyone works on strategy—but only the ones who *also* execute will thrive.

The edge doesn’t come from having the plan. It comes from learning quickly, cutting through noise, and staying aligned while in motion. Strategy is compressing—and that’s the unlock.

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Hyperlinks + notes

• Thank you to the Perplexity Design team for putting on an original and fun event

• Revenge of the junior developer by Sourcegraph

• Llama 4 → You know you’re working in AI when a new model gets dropped on a Saturday