How to Quantify Your Ideas & Growth Bets

Most CEOs at your stage are making million-pound decisions based on optimism, political pressure, or whoever presented last. Not because they’re incompetent, because the tools to actually quantify strategic choices are either too academic or too simplistic.

Think about the last time you chose between investing in a new market segment versus doubling down on your core. Did you have a systematic way to compare them? Or did it come down to your gut feeling about which exec made the more compelling case?

The cost of getting this wrong is brutal. Back the wrong horse, and you’ve burned six months of runway and board patience. Say yes to everything, and you’ve got zombie projects draining resources. Say no to everything, and nothing changes, which is why they hired you in the first place.

What you’re about to hear is a system for putting actual numbers on strategic choices. Not financial projections, those are guesses dressed up in spreadsheets. This is about quantifying confidence, value, timing, and strategic fit before you commit scarce resources.

We’re drawing on one perspective today. Simon Hill has spent the last decade helping organisations measure innovation value through his Expected Value framework. Hill addresses the problem McGrath identifies from a different angle. Rather than asking “what assumptions do we need to test,” Hill’s framework asks “how do we quantify the expected value of different strategic choices to guide resource allocation decisions?”

Hill’s work emerged from watching hundreds of organisations struggle with the same challenge: teams had multiple growth initiatives in flight, all consuming resources, but no systematic way to compare their potential value. Executives made decisions based on politics, passion, or whichever initiative had the most recent success story. According to Hill, this leads to what he calls zombie projects, initiatives that stay alive because no one wants to kill them, not because they’re delivering value.

Simon Hill’s Expected Value framework provides a systematic methodology for quantifying strategic choices. The framework combines four variables into a single metric: 

Expected Value = Confidence × Predicted Value × Time Sensitivity × Strategic Fit.

Let’s unpack each component in the context of strategy decisions.

Confidence, in Hill’s framework, represents your conviction that you can actually deliver what the strategy requires. This isn’t general optimism, it’s a specific assessment across six dimensions. 

  1. Technical feasibility: can we actually build or deliver this? 

  2. User desirability: will customers actually want this? 

  3. Market viability: is there sustainable demand? 

  4. Operational delivery: can our organisation execute? 

  5. Implementation readiness: do we have the capabilities now? 

  6. Regulatory compliance: are there legal or compliance barriers?

Hill argues that confidence should be scored numerically, typically on a 0-1 scale. 

A new market entry where you have proven customer demand, existing operational capability, and low technical risk might score 0.7-0.8. 

A completely novel product requiring new capabilities in a market you don’t understand might score 0.2-0.3. 

The key is forcing yourself to assess each dimension separately rather than hand-waving “we can probably do this.”

According to Hill’s research, most organisations systematically overestimate confidence by 20-40%. 

Teams underweight the difficulty of operational execution and implementation readiness. Hill recommends using structured confidence assessments where you separately rate each dimension, then multiply them together. 

If technical feasibility is 0.9, user desirability is 0.7, market viability is 0.6, operational capability is 0.8, implementation readiness is 0.5, and regulatory risk is 0.9, your overall confidence is approximately 0.14, not the 0.7 that your gut might suggest.

Predicted Value in Hill’s framework represents the business impact if you succeed. This includes revenue growth, cost reduction, risk mitigation, and strategic positioning. Hill emphasises that this shouldn’t be pie-in-the-sky projections, it should be grounded in the unit economics McGrath described.

Hill provides a practical approach: estimate the value range across optimistic, realistic, and pessimistic scenarios, then use the realistic case for your Expected Value calculation. For a new market segment, realistic value might be “£5 million annual revenue within 18 months at 40% gross margin.” For a product line extension, it might be “£2 million incremental revenue protecting 20% of the existing customer base from churn.”

Time Sensitivity captures urgency and timing dynamics. Hill’s framework recognises that value decreases over time for many opportunities. A competitor gap that exists today might close in six months. A customer segment experiencing pain now might find alternative solutions. A regulatory change creating opportunity has a window.

Hill scores time sensitivity from 0-1, where 1.0 means “must act now or lose the opportunity entirely” and 0.5 means “timing is flexible.” If you’re seeing customers churn to a competitor and have a six-month window to respond before relationships solidify, time sensitivity is high (0.8-0.9). If you’re building long-term capability for markets that will develop over three years, time sensitivity is lower (0.3-0.5).

Strategic Fit assesses alignment with your core growth strategy and capabilities. Hill introduces the concept of Fit Quotient—measuring how well an initiative leverages your existing strengths, serves your target customers, and advances your strategic position.

According to Hill’s framework, strategic fit should be scored by evaluating whether the initiative: uses capabilities you already have (or can realistically build), serves customer segments you understand, strengthens your competitive position, aligns with where your organisation is heading. An initiative might score high on predicted value but low on strategic fit, suggesting it’s valuable but not for you.

Hill’s research shows that low strategic fit initiatives consume 3-5 times more resources than high fit initiatives because you’re building everything from scratch. Even when they succeed, they often become distractions that pull focus from core business.

The power of Hill’s framework emerges when you calculate the complete metric for competing initiatives. Consider two growth strategies:

Strategy A (New premium tier): Confidence 0.6, Predicted Value £8M, Time Sensitivity 0.7, Strategic Fit 0.9 = Expected Value of 3.02

Strategy B (Adjacent market): Confidence 0.3, Predicted Value £15M, Time Sensitivity 0.4, Strategic Fit 0.5 = Expected Value of 0.90

Even though Strategy B has nearly double the potential value, Strategy A has more than triple the expected value when you account for execution confidence, timing, and strategic fit. This is the calculation most CEOs make intuitively, Hill’s framework makes it explicit and comparable.

Hill emphasises that Expected Value isn’t about achieving mathematical precision, it’s about forcing structured thinking about resource allocation. The act of scoring each dimension reveals where you’re making optimistic assumptions, where you lack critical information, and which initiatives you’re backing based on hope rather than evidence.

According to Hill’s work with growth-stage companies, using Expected Value frameworks typically reveals that 30-40% of active initiatives have expected value below breakeven when honestly assessed. These are zombie projects consuming resources that should be redirected to higher-value opportunities. Hill introduces the concept of kill credits, rewarding leaders for stopping low-value initiatives early, freeing resources for better opportunities.

We’ve used this approach with customers when examining their ideas and strategic choices and it works well and it’s a great framework to include your Business OS.

Calculate the expected value for every significant growth initiative, rank them, then resource only the top initiatives until your capacity is exhausted. Everything else gets deprioritised or killed, regardless of political pressure or sunk costs.

The framework also provides common language for board and CFO conversations. Rather than arguing about whether Strategy A “feels” better than Strategy B, you’re discussing specific dimensions: where is our confidence low, what would increase it, what’s the predicted value based on unit economics, how does timing affect our options, does this leverage our strengths?

Hill’s research shows that organisations using structured expected value frameworks make resource allocation decisions 40-60% faster, reallocate resources from low to high value initiatives 2-3 times more frequently, and improve return on innovation investment by 25-35%.

And what we like about this is it gives us the quantification framework, a way to put numbers on confidence, value, timing, and fit. 

You’re facing multiple possible growth directions. New market segments, product extensions, geographic expansion, pricing changes, operational improvements. Your instinct is to test everything, but that’s impossible with constrained resources. You need to prioritise which assumptions to test.

Start by calculating rough Expected Value scores for your major strategic options. Don’t obsess over precision, use your best judgment on confidence (0-1), predicted value (pounds), time sensitivity (0-1), and strategic fit (0-1). Multiply them together. This takes two hours in a room with your leadership team, not two weeks of analysis.

The Expected Value scores reveal which opportunities deserve assumption testing resources. If Strategy A has Expected Value of 4.5 and Strategy B has Expected Value of 0.8, you now know where to invest your discovery budget. Test the critical assumptions in Strategy A using McGrath’s framework. Strategy B might be interesting, but it’s not where you place your bets right now.

Second, use Roger Martin’s choice cascade to ensure integration. Your “where to play” choices (quantified by Expected Value) must connect to your “how will we win” approach.

Third, when you take your strategy to the board, you’re no longer presenting optimistic projections. You’re presenting expected value analysis that quantifies confidence, identifies critical assumptions you’ll test, outlines checkpoint decisions, and explains why you’re saying no to attractive opportunities that don’t fit.

This is what strategic discipline looks like when resources are scarce and board patience is limited.

The practical next step: take your top three growth initiatives. For each one, score confidence (realistically across all six dimensions Hill identifies), predicted value (based on unit economics, not optimistic projections), time sensitivity (is the window closing?), and strategic fit (does it leverage your strengths?). Calculate Expected Value. Compare them.

Then ask: for your highest Expected Value initiative, what are the three assumptions that if wrong, make the entire strategy unviable? What’s the cheapest way to test those assumptions? What would you need to see to gain confidence before full commitment?

Glen Westlake
Project Principle

Glen has scaled and exited several companies. He helps customers develop their strategies, use OKRs, and execute their plans.

His deep understanding of sales processes and AI enablement makes him a great fit for customers with challenges in those areas.

  • Create value for customers and improve customer experience as a driver of competitive advantage and sales growth.
  • Increasing productivity of teams and individuals.
  • Evolve roles to leverage what are uniquely human advantages to create a happier, more engaged and more productive workforce.