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How to build defensible roadmaps that stop executive whiplash and give your team strategic breathing room

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If you’re a Product Owner, Product Manager, or Customer Journey lead, you’ve probably lived this nightmare:

You’ve got a solid roadmap for the next 9 months. Your backlog is prioritized. Your team knows what they’re building and why. Then an executive returns from a conference, reads an analyst report, or has a conversation with a customer, and suddenly you’ve got a new “top priority” that blows up everything you’d planned.

Your team groans. You scramble to justify why this new thing should wait (or shouldn’t happen at all). The executive pushes back: “But we need to do this.” You don’t have a compelling counter-argument because you haven’t looked that far ahead. So you rebuild the roadmap, again, and watch team morale take another hit.

The problem isn’t bad executives. The problem is strategic blindness beyond your current planning horizon.

Product teams who can only see 9-12 months ahead are vulnerable to every shiny object, competitive panic, and strategic pivot that comes along. They’re playing defense because they haven’t done the work to play offense.

This is the workshop framework I developed to fix that. It’s designed to be run every 6 months with product teams, takes about half a day, and produces something more valuable than another roadmap: a defensible strategic position.

The Problem This Solves

Before we get to the framework, let’s be clear about what we’re solving for:

Symptom 1: Roadmap Whiplash Your team builds for Q1-Q3, then in Q2 someone throws in a Q4 priority that invalidates half your assumptions.

Symptom 2: Reactive Strategy Every new requirement feels equally urgent because you haven’t mapped out what’s coming or why it matters.

Symptom 3: Lost Team Autonomy Your team wants to own their roadmap but can’t defend it against executive-level course corrections because they lack strategic framing.

Symptom 4: Guesswork Masquerading as Planning You know you need to think further ahead, but “horizon scanning” sounds like expensive consultancy theatre rather than practical product work.

More

For a long time growing up, I don’t ever recall being ‘well off’. My parents worked, and gave what little they had to myself and my sibling. I went through the state education system, took loans for university and entered the world of work. I spent decades struggling financially. The kind of struggle where every decision comes with a calculation, where “enough” felt like a distant fantasy rather than an achievable state. Then something shifted. Through partnership, shared resources, and finally earning a stable income, I found myself in a place I’d never been before: financially secure.

You’d think that would be the happy ending. In many ways, it is. But reaching this vantage point has revealed something deeply unsettling about human nature and our collective future.

The Problem With “Enough”

When Elon Musk talks about “sustainable abundance” as humanity’s goal, I understand the appeal. Who wouldn’t want a world where everyone has what they need? But having lived on both sides of the scarcity divide, I’ve come to see a fundamental problem: humans don’t seem wired to accept “enough.”

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