Leading Indicators of Strategy Failure: What to Watch Before It’s Too Late
About this webinar
Strategy can start losing value before delivery goes wrong. Ben Chamberlain and Stuart Easton distinguish portfolio structural risk, created by the mix of work the organization chooses to fund, from portfolio execution risk, which becomes visible through delays, overruns and failures.
What you’ll hear
- The best submitted projects can still produce the wrong portfolio. A bottom-up planning process can select the strongest proposals it receives and still miss work the strategy actually needs.
- Some value loss is hard to see. Ben describes this as opportunity cost: value the organization could have created but never sees. His evolving Strategy eXecution Forum indicators look for strategic misalignment, overlapping investment and business-as-usual activity or operating spend that escapes the same scrutiny as change.
- Years of improvement can still miss the real problem. Ben gives three reasons: executives can treat strategy execution as program management on steroids; functions can optimize their own areas while value is lost between them; and successive methods can start bottom-up, leaving the portfolio-level problem unresolved.
- Some execution problems start at portfolio level. Stuart argues that without clear priorities, work can't be sequenced, people get overloaded and projects collide. Better project management does not fix a portfolio that has taken on too much work at once.
- Build the case before the next crisis. Ben asks first whether the C-suite understands how much value is at risk. If not, he recommends building a coalition across the relevant functions. Stuart adds a head, heart and heartbreak case: prepare the logic and understand leaders’ pain before a visible failure forces action.
The central question is not only whether projects are being delivered well. It is whether the organization is funding the right mix of work in the first place.
Research in context
Budget-strategy alignment is not automatic. In a 2024 McKinsey Global Survey of 617 executives and managers, only about half said their companies effectively aligned budgets with corporate strategy, and 53% said their organizations fully funded identified priorities. The consequence: a strategy can be agreed while funding still supports a different set of commitments, creating structural risk before delivery begins.
Running the business versus changing it is also a live funding problem. In IBM's 2025 survey of 2,000 CEOs, 59% said their organization struggles to balance funding for existing operations and innovation when unexpected change occurs. The consequence: when conditions change, leadership may need to revisit how resources are divided between existing operations and new investment rather than treating that split as fixed.
How this connects to TransparentChoice
Shape demand before you rank it. TransparentChoice makes leadership priorities explicit and can use them upstream to shape which proposals are invited. Existing and proposed work can then be assessed together against funding, capacity and other constraints, so leaders compare feasible combinations rather than stop at a ranked list.
Put run and change in the same allocation picture. BAU or departmental work can be modeled as work items or as a separate portfolio drawing on shared funding and capacity. Leaders decide how resources are divided, then see what each allocation can support.
Learn more
Join the next live webinar
Turn the diagnosis into an executive case
Continue from the risk model into how PMO, Strategy, Finance, Architecture and Operations can turn upstream value leakage into a leadership case and coordinated action.
See how functional silos become one allocation problem
Explore how innovation, CapEx and transformation portfolios can be managed separately while drawing on the same shared resources, and why that fragmentation makes priorities harder to revisit.
Read the structural-risk argument in a planning context
See how individually sensible decisions in strategy, finance and delivery can combine into structural portfolio risk, and what leadership then has to decide.
Speakers
Stuart Easton is Founder & CEO of TransparentChoice. He works with leaders and portfolio teams on decisions about which investments and initiatives to fund, continue, change, defer or stop when priorities compete for limited funding and capacity. His work combines structured decision-making with practical portfolio choices.
