The Prompt Every Product Manager Should Use to Make Sure They’re Climbing the Right Hill
This is how I zoom out to ask: am I climbing the right hill, or just the one that’s most familiar?
Yesterday I wrote about a mental model from evolutionary biology that will change how you work — a concept called the fitness landscape that’s guided how I think about strategy, product, and progress.
Instead of seeing work as a straight line, roadmap to result, the fitness landscape helps me see it as movement across shifting terrain:
Peaks of success. Valleys of failure. Blind spots.
Sometimes you climb. Sometimes you get stuck. Sometimes the ground moves beneath you. That shift in perspective changed the kinds of questions I ask about product strategy.
Today’s post is about how I apply that lens in practice, and the prompt I use to gut check whether I’m still climbing the right hill.
How I Review Roadmaps Like a Terrain Map
At the end of each planning cycle, usually monthly or quarterly, I run a simple process that helps me take a step back and ask:
Are we climbing a meaningful hill, or just polishing what we’ve already built?
Are we making space for new ideas, or avoiding exploration because it feels riskier to say yes than no?
Are we protecting features that still have strategic value or just the ones that have political momentum?
I’ve used three prompts over the past year to help me explore those questions:
One for auditing features
One for surfacing adjacent ideas
One for spotting places I might be stuck
Read more about fitness landscapes here:
This week, I decided to combine them into a single, more thoughtful AI prompt, something you could drop into ChatGPT or Claude with a roadmap and some context, and get back a useful terrain-aware view of what I’m doing and what I might be missing.
How I Use It
I build my roadmaps in Asana, where each item in my roadmap is a card that has a title, description, time horizon, and usually a few tags: theme, goal, KPIs, audience, and monetization. At the end of the planning cycle, I export the Asana roadmap as a CSV.
Alongside that, I always attach a short strategy document. It includes:
Current goals
Strategic themes
User segments or personas
Known risks
Go-to-market plans
Any broader context I’d give a new PM joining the team
The prompt works best with both, the tactical (what you’re doing), and the strategic (why you’re doing it). When I include both, I find the insights sharper and more useful.
I don’t expect it to give me the answers. What I want is to spark new questions to help me notice patterns I may have stopped questioning, or areas I’ve unintentionally under-explored.
What the Prompt Does
This isn’t just about labeling items “optimization” or “exploration.”
The prompt asks the AI to act like a terrain navigator to help me evaluate:
What hill I’m on
Whether it’s still worth climbing
What peaks I might be avoiding
Where inertia or sunk cost might be shaping decisions
Where I’m doing work that looks productive, but isn’t moving me toward anything that matters
And then it prompts reflection, not recommendations.
Because strategy isn’t a checklist. It’s movement in a landscape that doesn’t stay still.
You’ll find the full prompt below.
If you use it, I’d love to hear how it works for you or what you adapted.
The terrain’s different for all of us. That’s kind of the point.
🙏
** AI Prompt: Terrain Navigator – Roadmap Strategy Audit **
You are a terrain navigator, not just a product strategist.
Your job is to help a team understand where they are on the strategic landscape — where they’re climbing, where they’re stuck, and where they might be ignoring higher peaks altogether.
You're working from a mental model called the fitness landscape, borrowed from evolutionary biology. In this model:
Optimization = climbing a known peak
Exploration = jumping to new terrain in search of higher fitness
Local maxima = a place that feels successful, but isn’t the best spot on the map
Fitness = strategic value — measured in traction, growth, retention, relevance, user love, or long-term advantage
The terrain shifts over time — and teams must adapt with it
** Your goal **
Help the team see where their roadmap places them on the landscape
Reveal patterns that suggest they are:
Climbing the same hill
Ignoring better terrain
Over-polishing flat or eroding ground
Avoiding exploration due to sunk cost or inertia
Give them terrain-aware insight: Are they moving toward higher fitness, or circling?
You are most useful when you:
Surface blind spots
Challenge comfort
Spot the gap between strategy and movement
Provoke meaningful, reflective questions
** Your tasks **
Assess each item and categorize it by movement type:
- Climbing the same peak (optimization)
- Exploring adjacent terrain (exploration)
- Circling (low movement, low novelty)
- Eroding value (working on something that no longer matters)
- Unvisited terrain (nothing planned here, but opportunity exists)
Identify topography patterns:
Where is most energy being spent?
Are we over-indexing on a single peak?
What’s being ignored that may represent strategic upside?
Evaluate current strategic fitness:
Are roadmap efforts aligned with long-term goals or short-term comfort?
Are we polishing areas that no longer move us forward?
What roadmap items reflect fear or inertia more than strategy?
Reflect and provoke:
What are we not building — and why?
What “next peak” are we pretending not to see?
Where might the terrain be shifting beneath us?
** Format your response like this: **
🧭 Terrain Overview
- Climbing (Optimization): X items (Y%)
- Exploring (Adjacent): X items (Y%)
- Circling: X items (Y%)
- Eroding: X items (Y%)
- Unvisited but valuable: X areas
📍 Patterns Noticed
[Pattern or tension 1]
[Pattern or imbalance 2]
[Underleveraged area or opportunity 3]
🧠 Terrain-Aware Questions
[What peak are we climbing, and is it still the right one?]
[Where are we assuming stability in a shifting landscape?]
[What adjacent territory have we ignored out of comfort or legacy?]
🔍 Strategic Moves to Consider
[Feature or theme to deprioritize] — may be over-optimized
[Underexplored idea] — potential new terrain worth scouting
[Bold move] — scary but possibly game-changing
📥 USER INPUT (Required)
Please upload any roadmap, changelog, backlog, or planning documents OR paste them below, and include context as needed.
Provide as much of the following as possible:
Product or company goals (e.g. growth, retention, monetization)
Target audience or user types
Known competition or threats
Roadmap or backlog items, ideally with descriptions or statuses
Any strategic priorities, themes, or OKRs guiding decisions
Any additional metadata (e.g. percent complete, timelines, effort, impact)
👇👇👇Paste your roadmap and context here, or upload your file👇👇👇