The PMO Value Leak: Find it, show it, fix it
About this webinar
Strategy execution problems do not begin only when projects slip. In this panel discussion, host Stuart Easton is joined by Ben Chamberlain, Fadi Bayoud and Rebecca Reynolds to look further upstream at where value can leak as strategic intent moves into governance, investment choices and delivery.
Ben Chamberlain on the operating problem: Strategy execution is an enterprise operating problem, not a larger version of project management. Strategy, finance, operations, business architecture, transformation, PMO and other functions can each optimise their own part of the system while the organisation as a whole remains fragmented.
Financial information matters too. Understanding where money is going, and whether both operational and discretionary spend support strategic direction, is part of understanding how strategy is actually being executed.
Ben also introduces the distinction between portfolio structural risk and execution risk. Some value can be lost before individual projects begin to fail, because investments are misaligned or duplicated.
Rebecca Reynolds on leadership blind spots: One of the biggest is executives who are not aligned with each other on what the strategy means. Governance, resources, capabilities and organisational capacity then have to be part of the same conversation. Ambition alone is not enough if the organisation cannot support what leadership is asking it to do.
Fadi Bayoud on translation: Strategy has to be translated into practical decisions. That requires a shared understanding of what the strategy means, governance that turns it into action, and feedback that keeps strategic intent connected to changing conditions.
Stuart’s executive test: Rather than giving a CEO more project detail, ask: “Is it more or less likely to succeed this week than last week?” His point is to show whether things are trending in the right direction, rather than burying leadership in the detail of why or how.
Rebecca’s addition: Leaders also want to know whether something can be done. Is there a lever, such as a governance, authority or resource issue, that they need to switch, what is being asked of them, and what would it buy?
From diagnosis to action: Ben’s closing advice, echoed by Rebecca, gives the discussion a practical sequence. He argues that the enterprise function matters more than its name, whether that is an enterprise PMO, a strategy execution office or a transformation office.
- Find leading indicators of value loss.
- Show the resulting value at risk in language leaders care about.
- Connect colleagues across strategy, finance, architecture, transformation and delivery.
- Act by taking one aligned case into the leadership conversation.
What you’ll hear
- Why strategy execution is broader than project delivery and depends on decisions across multiple functions.
- Why investment allocation, operational spend and capacity for change belong in the strategy conversation.
- How PMOs can move from detailed status reporting towards information about value, risk, blockers and the leadership action required.
- Why strategic ambition has to be tested against resources, capabilities and organisational capacity before commitments become an execution problem.
- How PMO, strategy, finance, operations, architecture and transformation teams can work together rather than optimise their parts of the system separately.
Research in context
In PMI’s 2025 survey of 300 senior executives across regions and industries, a disconnect between planning and execution was the most-cited barrier to reinvention, selected by 35%.
The panel takes that recognition one step further: where does value leak as strategy moves into governance, investment choices, capacity and delivery?
How this connects to TransparentChoice
A recurring question in this discussion is what happens when strategic ambition meets finite funding and capacity. At that point, the problem is no longer only whether individual projects are being delivered well. Leadership has to decide which commitments the organisation can actually support.
TransparentChoice supports that decision layer by making leadership priorities explicit, considering existing and proposed work alongside funding, capacity and other constraints, and comparing feasible portfolio choices.
Where leaders hold different views about relative priorities, their judgements can be captured separately so the differences are visible before the group decides. When priorities, assumptions or constraints change, the choices can be recomputed to show what stays, what gives way and whether the earlier decision still holds.
TransparentChoice starts from the direction and governance leadership already has and supports the allocation decision that follows. Leadership makes the final call.
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Speakers
Rebecca Reynolds is a reinvention expert, systems innovator, and author with over 30 years of experience guiding leaders and organizations through large-scale transformation. She has developed and applied innovative models for advancing change capability across government, non-profits, and communities. Her new book, Thresholds of Change: The Way Through Transformational Times, distills her proven approach to navigating disruption with clarity and confidence.
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.