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Every year, PMOs watch the same ritual unfold. Strategic planning season arrives. The whiteboards fill up, the Post-its multiply, coffee flows.
After weeks of debate, the strategy emerges - polished, ambitious, and ready to roar. There’s a leadership briefing (maybe over pizza), and a flurry of kick-off meetings. And then slowly everyone reverts to their old priorities. The racing car stalls.
Sound familiar?
Here’s the hard truth: “Less than one-third of respondents … say their companies’ transformations have been successful at both improving organizational performance and sustaining those improvements over time.” (McKinsey)
That’s the cost of misalignment, and it's exactly where you, the PMO, can make the difference.
Why Strategies Fail Without Execution
- Leadership loses interest after the initial sign-off
- Too many projects chasing too few resources
- Budgets approved without capacity planning
- “Business as usual” drowns out strategic initiatives
- PMO is judged on process, not outcomes
The strategy looks good on paper - but it slowly collapses under real-world constraints.
The Alignment Challenge: CSO, CFO, PMO
Put simply, strategic execution is a collaboration challenge, which can only be solved by knitting together the key owners of elements of it...
- The CSO - The Planner: Defines strategy and OKRs, but often ignores constraints.
- The CFO - The Funder: Allocates budgets, but rarely accounts for people capacity.
- The PMO - The Enabler: Does their best to deliver the portfolio, but inherits an overloaded plan.
Without collaboration, each role optimizes for their own silo. The result? Too many projects, not enough focus.
How Collaboration Unlocks Executive Engagement
For strategy to stick, the CSO, CFO, and PMO must align around one process. Their roles are different, but complementary:
- CSO → Clarity: What matters most
- CFO → Discipline: What we can afford
- PMO → Reality: What we can deliver
When these voices converge, executives get one joined-up narrative, agreeing on:
- What we’re doing
- What it costs
- What it delivers
- How it fits together
This unified story makes it far easier for leaders to commit - and role-models the collaboration the rest of the organization needs to see. It also reduces administrative burden with a joined-up demand management funnel for new work.
Five Principles for Successful Strategic Planning
Every organization is different, but successful planning generally builds around these 5 principles:
- Create a shared Demand Management process: Finance, Strategy and PMO. Work out the minimum level of admin needed for it to succeed.
- Build a golden thread around benefits: Connecting funding, resourcing, delivery and reporting. Use it to focus updates on outcomes that leadership care about.
- Recognize the cost of dysfunction to build the business case: Work out what poor alignment has cost. Use this to set goals and overcome objections to change.
- Go beyond complex spreadsheets with fit-for-purpose tooling: Focus your energy on getting people to collaborate. Use a bespoke solution with data collection, reporting, AI and collaboration built in.
- Improve & iterate: Rather than searching for a "perfect-on-paper" process. Success will come through developing buy-in over time, not endless tweaks to a big slilde deck.
What This Looks Like in Practice
At TransparentChoice we help clients deliver this change with expert tooling and a network of specialist delivery partners. For example:
- Working with the PMO: US trade association learned to say “no” to pet projects at annual planning, saving millions, and driving focus.
- Working with the CSO: UK non-profit turned a five-year strategy into a phased, capacity-driven roadmap that gave their executive a choice of realistic scenarios.
- Working with the CFO: Global life sciences’ annual prioritization moved from spreadsheets to live collaboration, enabling 100+ colleagues to build plans in parallel.
The outcome? Fewer projects, clearer priorities, stronger execution. All with no spreadsheet headaches for the teams collaborating on the process.
Your Next Step as a PMO
If you’re ready to stop firefighting and drive strategic alignment:
- Explore our free Ultimate Guide to Strategic Planning.
- See how software enables better Strategic Planning. Is this meets your use case let's connect.
- Build your business case with our expert help. We've done this before, and can help put this into terms that the CFO and CSO will support.
- Connect with our partner network to find expert support. They'll help you customize this approach to your sector, your maturity, your stakeholders.
TransparentChoice helps PMOs like yours turn strategy into results. Don’t let your race car stay engine-less - it’s time to fuel execution!