Why Every Founder Should Master the 5 Cascading Strategy Questions

When it comes to business strategy, clarity is everything. Without it, we risk getting lost in a tangle of buzzwords, unfocused ambitions, and half-baked initiatives. But when we’re truly clear about what we’re trying to achieve, and how we’ll get there, everything changes: decision-making sharpens, teams align, and execution accelerates. 

At Aditure, one of the most useful tools we’ve found for creating that kind of clarity is the Five Cascading Questions framework, developed by Roger Martin and A.G. Lafley in Playing to Win. It’s a deceptively simple approach that helps turn high-level ambition into grounded, actionable strategy. You can read more about it directly on Roger Martin’s site here: rogerlmartin.com. 

The Five Questions That Make Strategy Tangible 

Here are the five cascading questions: 

1. What is our winning aspiration?

   Why do we exist? What impact do we want to have? 

2. Where will we play?

   In which markets, segments, geographies, or customer groups will we compete? 

3. How will we win?

   What’s our unique value proposition? How will we create and capture value better than others?

4. What capabilities must be in place?

   What must we be especially good at to win in our chosen space? 

5. What management systems are required? 

   How will we track performance, make decisions, and stay aligned? 

This framework has been instrumental in our recent work with a diverse range of clients: 

• An AI company in the manufacturing sector - Helped leadership re-evaluate their current business model and develop viable new strategic options in response to significant operational and market challenges. 

• A 20+ year-old technology business - Guiding the development of new revenue streams by leveraging their world-class technical assets and reputation. 

• An early-stage start-up - Co-developing their first strategic blueprint during incubation - turning early hypotheses into a clear vision and executable roadmap. 

• A medical technology company - Partnered with leadership to shape a commercialisation roadmap and unlock sustainable growth.

Why It Works 

What makes this approach so powerful is its structured simplicity. It’s intuitive enough to use in workshops with startup founders, yet robust enough to guide the strategic direction of complex, established businesses.  

It forces teams to make deliberate choices, rather than vague commitments, and connects big-picture vision to day-to-day execution. 

Martin is known for championing integrative thinking—the ability to hold opposing ideas in tension and find creative solutions. This mindset is embedded in the Five Questions: it encourages leaders to wrestle with trade-offs and make intentional choices rather than defaulting to vague ambition or reactive planning.

As Roger Martin puts it: “Strategy is about making specific choices to win in the marketplace. It’s about deliberately choosing to do some things and not others.” 

As business advisors, we find ourselves returning to these five questions again and again—not just with clients, but in our own strategic thinking. They help structure conversations, test assumptions, and align teams. More importantly, they’re an exceptional tool for communication. Founders and executives who can clearly articulate their answers to these five questions are far better equipped to rally investors, partners, and employees around a common cause. 

Strategy That Drives Execution 

In our experience, the real value of strategy comes not from elegant decks or abstract visions, but from focused execution. The 5 Questions framework bridges that gap. It enables better resource allocation, more efficient operations, and a stronger sense of purpose across the organization. 

If you're a founder or executive trying to drive strategic change, we highly recommend starting with these five questions. Answer them honestly. Revisit them often. And don’t be surprised if your path forward becomes a whole lot clearer. 

PS: If you'd like to learn more about how we use this framework to support growing businesses—from seed stage to scale-up—drop us a message or connect via aditure.com. We’re always up for a strategic coffee. ☕