Strategic entropy doesn’t arrive with a bang. It creeps in, disguised as velocity. One AI feature here. Another there. Suddenly your roadmap is cluttered with “quick wins” that feel innovative but don’t connect to anything coherent.
The team is shipping. The board is nodding. But something’s off.
That “something” is system drift. Because GenAI doesn’t just disrupt workflows — it destabilises the foundations those workflows rest on. The roadmap you drew six months ago was built for a world that no longer exists.
GenAI moves fast. But your strategy? It’s unravelling faster.
Roadmaps Don’t Survive GenAI
Traditional roadmaps thrive on predictability. They assume a stable pace of delivery, linear sequencing, and well-scoped bets.
GenAI obliterates that. Not because the tools are complex, but because their behaviour is emergent. LLMs aren’t features — they’re systems-within-systems. Their output is probabilistic, making their impact hard to predefine. Every AI addition has ripple effects the roadmap can’t account for.
This mismatch creates a dangerous illusion: the more we ship, the more progress we assume. But in the GenAI era, velocity without recalibration creates entropy.
You’re adding functionality — but subtracting strategic clarity.
And the longer you chase execution without reflection, the further you drift from your north star.
The Strategic Drift Pattern
Drift doesn’t announce itself. It accumulates.
You’ll spot it in your rituals before your retros:
- Teams launching AI-powered tools that no one really uses — but look good in demos.
- PMs running fast on “AI ideas” that never ladder up to the core product strategy.
- Technical debt expanding not from code, but from misaligned capability.
Internally, the drift creates silos: an “AI group” shipping at breakneck pace, disconnected from design systems, user journeys, or commercial logic. Externally, your narrative starts to fragment. Are you a search platform? A knowledge assistant? A productivity tool with smart features? No one knows — not even your leadership team.
This is strategic entropy in motion. Not failure. But unexamined acceleration.
From Prediction to Positioning
So what now?
Stop predicting. Start positioning.
Old strategy models asked: What should we build this quarter?
New strategy models ask: What scenarios should we be ready for next quarter — and what capabilities position us to adapt?
This shift from planning to positioning doesn’t mean abandoning direction. It means changing altitude:
- You design for adaptability, not precision.
- You build systems that learn — not just features that work.
- You use tools like value loops and model maturity curves to sense when it’s time to pivot, pause, or double down.
One product team I worked with scrapped their AI roadmap entirely. Instead, they defined three future states of their market — and built strategic guardrails around how to respond to each. The output? Fewer features. Better timing. Clearer vision.
Because strategy, in the GenAI era, isn’t about predicting what will happen. It’s about ensuring you’re positioned to respond when it does.
Conclusion
Strategic entropy isn’t a tech problem. It’s a clarity problem.
GenAI will continue to change faster than your process can keep up. That’s not a reason to panic. It’s a reason to rethink what strategy actually means.
If you’re still writing fixed roadmaps, you’re not leading. You’re lagging.
Start positioning instead. Anchor your system. Sense the drift. And build in a way that can bend without breaking.
