After spending years working with product teams across countless organisations, I've noticed a persistent pattern: teams have become quite good at using strategic frameworks to generate options. They can run a Playing to Win session, map out Jobs to Be Done, plot initiatives on the Three Horizons - they'll walk out of a strategy workshop with flip charts full of possibilities.
But then they get stuck.
Faced with three or four seemingly viable strategic options, teams freeze. They delay. They ask for more data. They schedule another workshop. They do everything except the one thing that matters: make a choice.
The uncomfortable truth is that generating strategic options is the easy part. The hard part - the part that actually creates value - is choosing which option to pursue and then turning that choice into reality. Because strategy isn't about having options. It's about making choices and acting on them. I define strategy as a coherent set of choices about what we are going to do in order to achieve our vision. The keyword here is "choices". Without actual choices - without picking one path and saying no to others - you don't have a strategy. You have a wishlist.
The Analysis Paralysis Problem
I've written before about my favourite strategy tools for generating and evaluating strategic options. These frameworks and hundreds more are invaluable for understanding your market, identifying strategic opportunities, and crafting potential paths forward.
But here's what I've learned: most teams stop at option generation. They use the frameworks, they have great discussions, they create compelling possibilities... and then they can't pull the trigger. Why? Three main reasons:
- Hidden assumptions: Every strategic option is built on assumptions, but these remain implicit. Without surfacing and testing them, you're choosing blind.
- Unclear trade-offs: Each option requires giving something up, but teams haven't made these trade-offs explicit. They want the benefits of all options without the costs of any.
- No learning mechanisms: Teams treat strategy as a one-time decision rather than a hypothesis to test and refine. This makes every choice feel irreversibly high-stakes.
From Choices to Action: Three Essential Tools
So how do we bridge the strategy-execution gap? Over the years, I've found three tools that consistently help teams turn strategic intent into strategic impact.
1. Assumption Mapping: Making the Invisible Visible
David J. Bland's work on assumption mapping addresses a fundamental challenge: every strategic choice is built on a mountain of assumptions, but these assumptions usually remain implicit. When assumptions stay hidden, you can spend months executing a strategy only to discover that a core assumption that underpinned the whole idea was wrong.
Assumption mapping forces you to:
- List every assumption underlying your strategy - about users, markets, technology, competitors, and your own capabilities
- Map them on two axes: importance (how critical to success) and evidence (how much proof you have)
- Prioritise ruthlessly: High-importance, low-evidence assumptions become your focus
Don't forget the less obvious assumptions that can sink strategies:
- Organisational readiness: Do we have the skills, culture, and bandwidth to execute this?
- Competitive dynamics: Will competitors respond? How quickly can they copy us?
- Market timing: Is the market ready for this? Are we too early or too late?
The visual nature of assumption mapping immediately reveals where your strategic risks lie. I've seen leadership teams go quiet when they first see their assumptions mapped - suddenly realising how much of their strategy rests on things they've never validated.
But mapping assumptions is just the first step. What matters is what you do next.
2. The Riskiest Assumption Test (RAT): Start with What Could Kill You
Here's where most teams go wrong: they test the easy assumptions first. It feels productive - you're learning! - but it's a form of procrastination. The real power comes from identifying and testing your Riskiest Assumption first.
Your RAT is the assumption that, if proven wrong, would invalidate your entire strategic direction. It sits at the top right corner of your assumption map - at the intersection of "critical to success" and "we have no evidence this is true." These are the assumptions that make you uncomfortable to voice aloud because if they're wrong, you need to fundamentally rethink everything.
Let me give you some examples:
- Before building an enterprise version: "Enterprise customers will pay 10x our current price for these additional features"
- Before entering a new market: "We can acquire customers in this segment for less than $X CAC"
- Before building a platform: "Third-party developers will invest time building on our platform"
The beauty of the RAT approach is its efficiency. Why spend six months executing a strategy based on ten assumptions when you could spend two days invalidating the one assumption that matters most?
Finding your RAT requires brutal honesty. Look for assumptions that:
- Would require a complete pivot if proven false
- Stakeholders get defensive about when questioned
- You justify with phrases like "obviously" or "everyone knows"
Once you've identified your RAT, design the simplest possible test. This isn't about statistical significance - it's about getting directional evidence quickly. And here's where my friend Nate Walkingshaw's wisdom comes in: "The customer breaks the tie." Don't test your assumptions in a conference room. Get out of the building. Talk to real customers. Run smoke tests with actual users. Buy David’s book and run one of the dozens of tests he outlines. The best assumption tests involve the people who will ultimately determine your success or failure - your customers. They should be co-creators in your strategy, not just recipients of it.
3. Scenario Planning: Building Resilience into Your Strategy
Even after testing your riskiest assumption, strategic execution happens in an uncertain world. This is where scenario planning becomes essential - not to predict the future, but to ensure your strategy can survive multiple possible futures.
For any major strategic initiative, develop at least three scenarios:
- Base case: Your assumptions prove roughly correct
- Optimistic case: Adoption is faster, competition is weaker, or capabilities are stronger than expected
- Pessimistic case: Key assumptions prove wrong, competition intensifies, or external factors shift
For each scenario, ask:
- What early signals would tell us that this scenario is unfolding?
- What would we need to do differently?
- Does our strategy still make sense?
The goal isn't to have a plan for every possibility - it's to build adaptive capacity into your execution. When teams think through multiple scenarios, they make better decisions in the moment because they've already considered the possibilities.
The Decision Stack: The Connective Tissue Between Strategy and Action
Throughout this process, the Decision Stack serves as the connective tissue between strategy and execution. It works by layering decisions from most foundational to most tactical:
- Mission/Vision - Why do we exist and where are we going?
- Strategy - How will we achieve our vision?
- Objectives - What specific outcomes are we targeting?
- Opportunities - What problems or needs could we address?
- Principles - What constraints and guidelines shape how we work?
The Decision Stack enables two critical movements:
Moving up the stack by asking "Why?" When someone questions a specific initiative or feature, you can trace it back: this addresses this opportunity, which serves this objective, which advances this strategy, which moves us toward this vision. This creates clarity and alignment.
Moving down the stack by asking "How?" When you have a strategic choice, you can trace forward: given this strategy, what objectives must we hit? What opportunities should we pursue? What principles guide our execution? This turns abstract strategy into concrete action.
What makes the Decision Stack particularly powerful for execution is how it reveals disconnects. If you can't trace a project back up to your strategy, why are you doing it? If you can't trace your strategy down to specific opportunities, how will you execute it?
Making the Call
All these tools help you analyse and de-risk strategic execution, but they don't execute for you. At some point, you need to make decisions and move forward. Here's how to do it well:
Create Decision Criteria Upfront
Before you analyse options, establish what will drive your decisions. I recommend three to five criteria, weighted by importance:
- Strategic fit (via the Decision Stack)
- Coherence (via the Playing to Win Cascade or Kernel)
- Risk-adjusted return
- Time to learning/validation
- Reversibility of the decision
- Resource requirements vs. availability
Setting these criteria before you analyse options prevents you from retrofitting justifications for predetermined choices.
Synthesise Conflicting Signals
Different tools might point in different directions. Your RAT might validate market demand while scenario planning reveals competitive threats. This isn't a bug - it's a feature. These tensions reveal real trade-offs.
Document explicitly:
- What does each analysis tell us?
- Where do they conflict?
- What are we choosing to optimise for?
Time-box the Decision Process
Perfect information doesn't exist. Set a deadline and work backwards. Analysis expands to fill available time - don't let it.
But here's a crucial nuance: not all decisions deserve the same time investment. Jeff Bezos's distinction between Type 1 and Type 2 decisions is invaluable here. Type 1 decisions are one-way doors - once you walk through, you can't go back. Type 2 decisions are reversible - you can walk back through the door if needed.
Most teams treat all strategic decisions as Type 1, which can lead to paralysis. In reality, many strategic choices are more reversible than we think. For Type 2 decisions, move fast and test. You can always adjust or reverse these decisions. For true Type 1 decisions - those that lock in major resources or close off future options - take the time to do thorough analysis. But be honest about which type you're facing.
The Role of Leadership Judgment
When data is ambiguous - and it usually is - leaders must:
- Make the call based on pattern recognition and experience - strategy is an intuitive leap just like any other hypothesis
- Consider factors frameworks can't capture (market/investor sentiment, timing, momentum, team morale, etc.)
- Take responsibility while giving credit for analysis
- Communicate the "why" clearly
Remember: not deciding is a decision - usually the worst one.
Build a Culture of Decisive Learning
The best strategic executors aren't those who are always right - they're those who:
- Make clear decisions and learn quickly
- Change course based on evidence without ego
- Create psychological safety for smart risks
- Value learning speed over analysis perfection
Document and Communicate the Decision
Once you've made the call, document:
- What we decided and what it means
- Why we decided - the key factors
- What we're betting on - critical assumptions
- How we'll know if we're wrong - trigger points for reconsideration
- What we're explicitly not doing - the trade-offs
This is where the Principles layer of the Decision Stack shines. Principles are "even/over" statements that make trade-offs explicit: "We prioritise conversion even over profit optimisation." When you find yourself making the same trade-off repeatedly, codify it as a principle. This makes future decisions faster and more consistent.
But making the choice is only the beginning. Once you've chosen your strategic direction and begun executing, the next challenge is ensuring your entire organisation understands and aligns with that choice. As I've written in my posts about creating strategic clarity and crossing the chasm in your organisation, even the best strategies fail when teams don't understand how their work connects to the bigger picture. The Decision Stack becomes essential here - it's the mental model that creates a line of sight from individual actions up to company vision and the best way to consistently communicate the why and how of your strategy to your wider organisation.
The Courage to Choose
Here's the bottom line: strategy frameworks and tools are essential, but they're not sufficient. Turning strategy into action ultimately requires courage - the courage to test your scariest assumptions, to make decisions with incomplete information, to admit when you're wrong, and to keep moving forward.
The tools I've shared - assumption mapping, RAT, scenario planning, and the Decision Stack - help you move from strategic intent to strategic impact. But they're tools, not crutches. They reduce uncertainty and increase confidence, but they don't eliminate the need for judgment and action.
Because in the end, strategy isn't what you write in a document or decide in a meeting room. Strategy is what you do, day after day, choice after choice. It's the accumulated impact of thousands of decisions, all pulling in the same direction.
The companies that win don't just make better strategic choices - they build better execution muscles. They build cultures that test assumptions faster, adapt quicker, and maintain coherence even as they learn and evolve.
Remember: a mediocre strategy brilliantly executed beats a brilliant strategy poorly executed every time. The question isn't whether you have the perfect strategy - you don't. The question is whether you can turn the strategy you have into action that moves you forward.
Use these tools. Test your assumptions. Plan for multiple futures. But most importantly, act. Because strategy without action is just an expensive conversation.
How do you bridge the gap between strategy and execution in your organisation? What tools have you found most helpful for turning strategic choices into reality? I'd love to hear about your experiences.
If you're struggling with putting strategy into action, check out my hands-on workshops or reach out if you want to work with me as an advisor or coach!