Original Gangsters of Strategy Execution with Stuart Easton (Episode 6)
- Ben Chamberlain
- Jan 22
- 4 min read
The latest episode in the Original Gangsters of Strategy Execution series just dropped!
In this series on the Strategy eXecution Unlocked podcast, Ben Chamberlain sits down with the true pioneers who've shaped the strategy execution space—industry analysts, authors, founders of management consultancies and software companies, and of course seasoned practitioners.
In episode 6 of our OGs of Strategy Execution series on Strategy eXecution Unlocked, I had the privilege of hosting Stuart Easton, a true pioneer in strategic alignment and portfolio prioritization.
Stuart is the CEO and founder of TransparentChoice, the platform he built to help portfolio leaders rigorously score, prioritize, and select initiatives that deliver true strategic alignment and maximize business outcomes. He’s also a guest lecturer on project prioritization at the University of Oxford. With decades of global experience across industries and continents, Stuart has obsessively focused on the root cause of most strategy failures: poor alignment of investments and activities with what the organization actually wants to achieve.
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We dive deep into why misalignment is arguably the single biggest lever (and leak) in organizational performance—and how fixing it can transform profitability, speed, and value realization.
Some of the biggest takeaways from our conversation:
Strategy Execution defined: getting leadership aligned on what “strategy” actually means, translating it into a clear decision-making framework (distinct from performance measurement), then rigorously aligning investments, activities, and resources to deliver it—while continuously measuring results.
The massive power of alignment: McKinsey research shows companies that deliberately allocate capital to strategic goals (even just at the “what business are we in” level) are worth ~40% more over time than those that roll budgets forward year after year. Recent studies correlate 35–55% of profitability variation across firms directly to strategic alignment.
The silent killer stats: PMI data (2017) found ~20% of typical portfolio projects are so misaligned they should be stopped outright—not just waste, but actively pulling the organization backward. Overloading resources guarantees failure; stopping even a third of projects (any third) often unlocks dramatic throughput gains.
Why misalignment persists: executives often fail to clearly define and cascade strategy (no shared “North Star” or agreed trade-offs—revenue vs. ESG, growth vs. stability); decisions become politicized without transparent frameworks; people argue over “houses” (initiatives) instead of underlying goals; operational “run the business” spend dwarfs discretionary budgets but is rarely scrutinized for strategic drag.
The two-winged butterfly: true execution balances change/transformation with BAU/operational reality—resources are interdependent. Optimizing the operating fabric (Business/Enterprise Architecture, process/capability rationalization, legacy removal) can free 5–10% of ops budget, potentially doubling transformation investment and delivering 30–50% uplift in discretionary capacity for growth.
Root cause of persistent ~30% project failure rates: despite $5–7B spent annually on PPM tools, failure hasn’t budged in 15–20 years because most root causes trace back to misalignment and over-allocation—not execution technique alone. Fix alignment first (prioritize ruthlessly, don’t overload), then PPM tools deliver real ROI.
The executive ownership imperative: leaders must own clear strategy definition/communication and fund an enterprise function (Strategy Execution Office, Value Management Office, etc.) to orchestrate across SPM, architecture, execution, and change. This is a multi-year muscle-building journey—not optional plumbing, but core to running the business like a production line.
Stuart’s core insight lands like a hammer: Strategic alignment isn’t a nice-to-have annual exercise—it’s the highest-leverage process any organization has. Get it right and you stop going backwards, accelerate forward, plug value leaks, boost ROI on every dollar spent, and drive outsized profitability. Ignore it and you’re hemorrhaging value through every crack in the operating model.
If you’re frustrated by misaligned portfolios, wondering why great strategies stall, tired of 30%+ failure rates despite shiny PPM tools, or ready to treat strategic alignment as the profit engine it is, this episode is loaded with hard data, battle-tested insight, and urgent calls to action from someone who’s spent his career proving the numbers.
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Huge thanks to Stuart Easton for the passion, the stats, the analogies, and the clear roadmap to fixing what’s broken. The OGs series keeps delivering—more trailblazers on deck!
The Strategy eXecution Forum (StrategyXF) is an invite-only, no-fee professional community built by and for the practitioners who know firsthand how hard it is to close the persistent gap between strategy and results. We believe it takes a village to master strategy execution — which is why StrategyXF brings together senior leaders from across the enterprise: C-suite executives, Strategy & Operations leaders, Transformation Offices, Finance, HR, IT, PMO, Enterprise Risk, Change Management, Portfolio Management, Business Architecture, and more.
Together, members collaborate on real-world challenges, share battle-tested approaches, and shape the future of how organizations execute with discipline and impact. This isn't a passive network — it's a practitioner-led community where your experience adds real value, and where every discussion is designed to deliver practical ideas you can apply right away. If you're serious about elevating strategy execution as a mission-critical discipline, we invite you to apply to become a member and help us build something the profession has long needed.
