There are some parallels between a strategy exercise and product creation.
One of them is optimism.
Pick a product PRD and it beautifully defines how the feature should work, what are the specifications, how the customer journey would look like and the metrics the product intends to move.
When you roll out the product, it often doesn’t work the way it should.
You find new edge cases, unfamiliar customer behavior you didn’t plan for or the customer simply didn’t appreciate the experience and keeps dropping off, and many other things. You get the point.
You started with optimism, you ended up with an unhappy path of your product.
You must be a Product Manager living under a cave, if you haven’t heard of an unhappy path before.
Good Product Managers have an advanced product sense, and they are good at predicting the unknowns i.e the unhappy paths the product could take and they plan for it in many ways: i) Handling unknown errors ii) Planning deviating paths of customer journey and much more.
Strategy creation process suffers a similar fate.
You start with optimism…err.. I mean you start by answering the 5 big questions:
Future Vision – "Where to be in next X years"
Opportunity Focus – "Right markets"
Target Customers – "Serve who? in those markets"
Competitive Edge – "Why us? vs. others to serve them"
Action Plan – "What we’ll do to get there"
This is Strategy Foundation work as I call it. You’re setting the foundation for the year(s) to come and when in doubt you can align the organization on above 5 aspects and clarify this is why we do what we do.
And then few months of execution happen… reality hits.
Your strategy was just a ‘happy path’ strategy, and you ended up with more questions to answer than you started with.
Maybe your execution was much slower.
Maybe you had too many distractions and could not properly focus on your strategy execution.
Maybe you were not staffed well.
or simply you were doing everything you can, but you were not moving closer to the goal.
More organizations often end up in the ‘unhappy path’ of their strategy and react to it with:
Let us do a strategy review
Strategy is right, execution is the problem
Let us prioritize better, we have too many things!
While you could argue with some degree of confidence some of above reactions make sense, but I have learnt with a higher degree of confidence that one should plan for unhappy path of strategy early in the strategy creation process, and not as a reaction.
I call this Operational Discipline. (or ‘The Unhappy Path’ of Strategy)
It has 5 aspects to it:
Risk Management – "Which risks lie ahead, how do we mitigate them"
Decision Triggers – "Pivot points where we will revisit strategy"
Focus Discipline – "Which of the distractions we will actively avoid"
Required Support – "What is needed to make shit happen"
Progress Metrics – "How do we know we’re progressing well"
In-fact, when asked in a Product Strategy Survey we did recently on Productify: Which out of the 5 happy path aspects and 5 unhappy paths aspects are covered well in product strategy?, it was obvious that companies rarely do well on addressing unhappy path in the strategy creation process:
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So let us address the elephant in the room.
Let us look at how you can actively address 5 ‘unhappy path’ aspects of product strategy and make sure you include it in your strategy document along with the other 5 ‘happy path aspects’:
Identifying Risks with your strategy and Mitigation measures
If you’ve ever built a product, you know that what kills momentum isn’t always what’s in your plan—it’s what you didn’t see coming. Same goes with Strategy as well.
That’s the real risk.
Risks in strategic execution doesn’t wear a name tag. It shows up as an overestimated market, a technical “should be doable” that turns into months of refactoring, or a competitor you ignored suddenly launching your idea, better and faster.
Good product teams get ahead of this. They do something I call an “assumption slam” during strategy process —they surface all the hopeful beliefs baked into their strategy: that customers want this, that we can build it in time, that our edge will hold. Then they stress-test each one: How critical is this? How sure are we? What can we do to avoid the counter-result?
This gives you a map of strategic landmines before you start walking. You’re not avoiding risk—you’re designing around it.
Creating Dynamic Strategy Review Cycles with Clear Pivot Criteria
No strategy survives first contact with reality.
The product doesn’t grow the way you expected. Competitors zig when you thought they’d zag. That beautiful 3-year vision? It’s aging fast after 3 months.
What you want is structured reconsideration: weekly tactical nudges, monthly strategy checkpoints, and quarterly “should we pivot?” moments. And you need clear triggers—not just gut feels.
Think: Did customer adoption stall? Has a new tech changed our moat?
Always doubt your strategy, until you see results.
3. Focus: Combat Scope Expansion and Creep
Strategy process should actively call out “We will not do X and we will not let Y derail our plans to a large extent”
X and Ys are your distractions and out of strategy scope topics.
Scope creep in strategy doesn’t happen because teams are reckless. It happens because opportunities are shiny, and there’s always someone asking: “What if we just add this one thing?”
If you haven’t lived through this, just wait.
What saves you is a focus framework. At the start, you define your scope like a product vision: this is who we’re building for, this is the problem, this is how we’ll win. Then you stack every new idea against it.
The product roadmap isn’t a feature dump—it’s a hard, deliberate curation of what not to build.
If you don’t choose your focus, someone else will. Probably a stakeholder with a pet feature or the loudest voice.
4. Support Infrastructure to make shit happen
You can’t execute a strategy with ‘I have a good feeling about this bet’.
The best vision in the world will crash if your team structure, tools, and skills aren’t up to the task. And you won’t know it’s broken until things start moving slowly… or not at all.
You should ask: “What do we need to win here?” and then go build/ or ask for the support system around that. This includes not just people, but autonomy, collaboration rhythms, and culture.
Think of support infrastructure as your product engine. If the engine’s not tuned, don’t blame the driver.
5. Measuring Progress of your Strategy
Have you ever had this feeling:
The dashboard looks green, the goals are on track—but everyone in the room knows something’s off. Why? Because the metrics are wrong or lagging or just vanity.
Or worse, they’re not telling the story you need to hear.
Metrics are only useful if they map to strategy. You need a stack that covers the full journey—acquisition, activation, engagement, retention, monetization—and you need to split them into leading vs. lagging indicators.
A good measurement framework doesn’t just ask “Are users signing up?” It asks: “Are they finding value?” “Are they sticking around?” “Is it monetizing?” It’s built to catch drop-offs early and explain why they’re happening—not just what’s happening.
Good strategy measurement isn’t about reporting—it’s about revealing. The moment you start treating metrics as a conversation, not a scoreboard, you start seeing real progress.
So to summarize.
Here’s what you should have in your strategy document always:
