Strategic Context: How to Keep Your Product Strategy Pointed at Reality
Converting Market Signals Into Winning Product Decisions
In my last post, "Mastering the Art of Ruthless Focus in Product Strategy”, I wrote about the power of ruthless focus, committing to fewer things and doing them exceptionally well. But here's the catch: focus only helps if you're focused on the right thing.
If your strategic context is outdated or wrong, no amount of sharp execution will save you. You’ll just get to failure faster.
This post is about the other half of product strategy: building and continuously updating your view of the market, your customers, and the shifting ground you’re competing on. That view is your strategic context. And it's what separates companies that adapt from those that stall.
Strategic Context vs. Product Sense
It’s worth clearing up a common confusion: Strategic Context isn’t the same thing as Product Sense. They’re tightly connected and reinforce one another, but operate at different levels.
Product sense is personal. It’s the intuition great product leaders develop through direct experience, an internal compass for what customers want and what feels right.
Strategic context is shared. It’s the external map: a collective understanding of your market, competitors, customer segments, and broader trends. It’s documented, deliberate, and distributed across the leadership team.
Strategic context enhances product sense: When product managers understand the broader market, customer segments, and competitive landscape, they make sharper, more relevant product decisions.
Product sense informs strategic context: Insightful product managers often surface patterns, shifts, or customer truths that hadn’t yet been codified into the company’s broader strategic view.
Product sense helps you notice what others miss. Strategic context helps you align those insights with where the business is headed. The best teams build a feedback loop between the two, turning instinct into strategy, and strategy into sharper instinct.
Why Strategic Context Is Your Real Moat
Strategy isn't a one-time plan. It's an ongoing interpretation of reality. When companies stop actively revisiting that reality, they don't just fall behind—they start optimizing a map that no longer matches the terrain.
Your strategic context is how you stay oriented. It tells you:
Who you're really building for, and who you're not
What problems are actually urgent to your customers right now
Where your differentiation is growing, or eroding
What bets competitors are placing, and which ones are working
And crucially, it helps you catch signals early enough to shift before the market forces your hand. If you're not already doing this systematically, don’t worry. This post gives you the framework and cadence to build that muscle.
Ask Yourself These 3 Questions First
Could everyone in the company consistently and confidently name the top three customer problems you solve?
Have you made explicit decisions about which segments you do not serve well?
Do you update your market understanding on a regular cadence, and share those insights beyond the product team?
If the answer to any of these is "no," your strategy is likely grounded more in old assumptions than current truth.
From Gut Feel to Ground Truth: Systems That Keep Your Strategy Honest
These practices help high-performing teams build and maintain a living view of their market.
1. Market Mapping
Tracks
Competitive landscape and customer value perception
Why
Most teams do a competitive analysis once and never touch it again. The best teams build a living market map that evolves as conditions change.
How
Hold quarterly market mapping sessions with product, sales, and exec leaders
Map competitors on the dimensions customers actually care about (speed, support, integrations, etc.)
Track shifts in perception and performance over time
2. Customer Insight Infrastructure
Tracks
Customer priorities, decision drivers, and pain point hierarchy
Why
Strategic context without fresh customer input is just confident guessing.
How
Run ongoing Jobs-to-be-Done switch interviews to understand why customers change tools
Use Customer Problem Stack Ranking (CPSR) to see where your product sits in the hierarchy of customer pain
Capture and centralize signals from support, sales, churn interviews, and usage data
3. Market Sensing
Tracks
Emerging trends, weak signals, and early market shifts
Why
The best teams notice weak signals before they become loud ones.
How
Assign internal "market sensors": people who track competitors, customers, or tech trends
Run monthly pattern recognition sessions where teams share what they’re seeing
Build a lightweight leading indicators dashboard (new competitors, trend inflections, etc.)
4. Red Teaming Your Strategy
Tracks
Strategic blind spots and unchallenged assumptions
Why
Every strategy has blind spots. The longer you look at your own, the less you see them.
How
Run regular pre-mortems: "If this strategy failed, what happened?”
Assign a rotating team to challenge your assumptions with outside-in perspectives
Invite non-obvious voices (sales reps, customer success, analysts) to poke holes
5. Cadence: Make It a Habit
Strategic context isn't something you do once a year. Here's how to make it part of your operating rhythm:
Monthly: market sensing session
Quarterly: Deep-dive strategy reviews, assumption updates, context dissemination
Annually: Reset foundational beliefs based on structural shifts
Making Strategic Context Actionable
A great market map doesn't help if nobody looks at it when making roadmap decisions. Here's how to embed strategic context into your workflows:
1. Connect It to Decisions
Require strategic context checks in product reviews
Include context alignment in roadmap prioritization docs
2. Communicate It Well
Share aha moments and resonating clips from interviews as they happen.
Send a monthly "What's Changing" digest to the whole company
Share market shifts and key learnings in the company, All Hands
Use “"context card" to summarize key insights during planning
3. Build a Shared Repository
Create a simple, timestamped wiki for customer, market, and tech context
Note confidence levels “High conviction” vs “Emerging signal”)
Track how insights evolve over time
Your Strategic Context Starter Plan
One of the most powerful uses of strategic context is to surface and derisk your highest-risk assumptions early, before they become expensive missteps. Inspired by the work of David J. Bland and others in the lean experimentation community, this means mapping your assumptions and testing them deliberately, not treating them as facts.
Start by identifying which beliefs underpin your current strategy. Then ask: what would need to be true for this to work? What are we least sure about? What could kill the strategy if we're wrong? Prioritize your riskiest assumptions and find fast, lightweight ways to test them.
Now, here's how to get started in the next 30 days:
Week 1
Run a 1-hour workshop: “What do we believe about our market today?"
Inventory existing insights (research, interviews, sales intel, churn data)
Identify the biggest gaps and most questionable assumptions
Week 2–4
Run 5–10 customer switch interviews (for reference: watch Bob Moesta and Chris Spiek teach you the theory behind switch interviews, skip ahead to 18:40 to see an example if you don't want the theory)
Assign market sensing owners for competition and customer segments
Stand up a simple market wiki and start logging changes
End of Month
Share the top 5 updated assumptions with the exec team
Add a strategic context section to the next roadmap review
Schedule your first quarterly strategy deep dive
Final Thought: Strategy Is a Living System
The companies that thrive regardless of the market's twists and turns aren't just focused. They're focused on the right thing and stress-test their assumptions constantly.
They don't treat beliefs about customers or markets as facts. They map them, rank their risk, and deliberately try to break them before reality does.
That discipline of derisking your riskiest assumptions early keeps strategy grounded in truth, not optimism.
Strategic context isn’t a one-and-done document. It's a system for learning, adjusting, and staying aligned with a reality that doesn't sit still.
In my next post, I'll dive into Finding Big Bets, including practical exercises to identify which objectives matter most and how to test them before you commit. It's where strategy meets execution, and where risk becomes insight.
Until then, check your assumptions and make sure your strategy is still pointed at reality.
Well said and I agree. This was clear, helpful, and actionable.