Original Gangsters of Strategy Execution with Ivan Lloyd (Episode 8)
- Ben Chamberlain
- Feb 5
- 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 8 of our OGs of Strategy Execution series on Strategy eXecution Unlocked, Ben Chamberlain had the privilege of hosting Ivan Lloyd, a highly respected expert and true pioneer in project, program, and portfolio management with over 30 years in the field.
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Ivan is the CEO and founder of Edison365, an innovative end-to-end strategy, innovation, project, and portfolio management platform built natively on the Microsoft ecosystem—designed to connect ideas to execution, align initiatives, manage benefits, and drive real business value. He previously founded and led CPS, a leading UK-based management consultancy specializing in governance frameworks, strategic initiative delivery, and tooling implementations for public and private sector organizations. With decades bridging consulting and software innovation (including long-standing advisory ties to Microsoft), Ivan brings unmatched perspective on what it takes to turn strategy into sustained outcomes.
We dive deep into why—despite massive investments in processes and tools over 30+ years—organizations still struggle to bridge strategy to execution, and what it will take to finally close the gap.
Some of the biggest takeaways from our conversation:
Strategy Execution core: defining clear objectives, then delivering on time with the right outcomes and benefits realized—yet few organizations have true accountability at the executive level or widespread understanding of the strategy across teams.
Persistent barriers haven't changed much: no single accountable executive for strategy delivery; poor communication (mid-levels and frontline often can't articulate the strategy); lack of dedicated enterprise structure (beyond siloed PMOs/VMOs/IPMOs); cultural resistance where people game alignment or hide work as "operational" to bypass governance.
The C-suite blind spot: executives react to revenue drops or cost spikes but often don't see suboptimal execution as core value leakage—transformation failure rates (~70%) and misaligned spend rarely surface clearly in dashboards; benefits realization loops are weak or nonexistent, so pain stays hidden in budgets as "operational expenditure."
Misalignment as the insidious killer: research shows ~31% of portfolios misaligned from the start + ~5% redundant; PMI stats highlight 20–48% of projects so misaligned they should be stopped outright—yet this "portfolio structural risk" goes unnoticed without strong strategic planning and architecture capabilities.
Executive responsibility starts at the bookends: clearly define, decompose, and cascade strategy as a North Star (why it matters, how everyone contributes); close the loop with rigorous benefits tracking and value realization reporting—without these, everything in between (alignment, prioritization, execution) falters.
The enterprise function imperative: a Strategy Execution Office (or VMO/equivalent) must go beyond traditional PMO operational focus—include cultural/marketing/sales-oriented people to "sell" the strategy internally, promote successes, drive adoption, and orchestrate across SPM, Business/Enterprise Architecture, project execution, and change management for a personalized, cohesive operating model.
Innovation as the forward engine: top-down strategy alone isn't enough—engage the whole business via structured idea capture, problem statements, and prioritization to fuel change; without organized innovation, organizations stagnate and get disrupted.
Human & change dimension dominates: frameworks and tools are enablers, but success hinges on culture—change management is chronically underfunded (e.g., $100k on systems, pennies on adoption); visibility from tools often resisted because it exposes issues people prefer hidden.
Looking ahead 3–5 years: AI will enhance insights and decision-making (as an accelerant, not a silver bullet); optimistically, more organizations will adopt consolidated views from strategy to value with dedicated accountability; rapid market changes will force the issue—now is the time for C-suite buy-in, enterprise-down approaches, and integrated disciplines to build the Strategy Execution muscle before bridges burn.
Ivan’s core insight rings true: Without executive ownership, clear communication, cultural buy-in, and a dedicated enterprise function that tells the story and closes value loops, even the best tools and processes fall short. Strategy Execution isn't just about projects—it's optimizing the entire operating fabric (innovation through to BAU) to deliver real, measurable business value in a fast-changing world.
If you’re puzzled by persistent transformation failures, frustrated by misaligned portfolios, wondering why benefits realization feels optional, or ready to advocate for that enterprise Strategy Execution capability, this episode packs decades of frontline wisdom and urgent realism from someone who’s built solutions and consulted globally on exactly these challenges.
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Huge thanks to Ivan Lloyd for the candid reflections, the full-circle insights, and the optimism amid the realism. The OGs series keeps raising the bar—more trailblazers coming soon!
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.
