Most leadership teams don’t struggle to create strategy. They struggle to convert ambition into measurable outcomes – revenue growth, margin expansion, customer loyalty, cycle-time reduction, and resilience. The execution gap is rarely a single problem; it’s what happens when strategy is treated as a planning exercise rather than a delivery system.
A useful way to reframe the challenge: strategy becomes real one initiative at a time, and value is captured through the portfolio of initiatives, not a single “big bet.”
Don’t anchor on “70% fail” headlines – anchor on what’s measurable
You’ll often hear that “most” strategic initiatives fail. The academic literature is more cautious: widely quoted failure ranges (e.g., “50–90%”) are contested, with many estimates relying on weak or outdated evidence. The practical implication isn’t that failure isn’t common – it’s that leaders should instrument execution instead of debating a headline number.
One empirical anchor: in a large global survey of project professionals, the average project performance rate was ~73.8% (share of completed projects meeting business goals). That’s a baseline – and it leaves meaningful headroom.
The Initiative Engine: a pragmatic model for making strategy happen
High-performing organisations build an initiative engine with five disciplines:
1) Translate strategy into a portfolio (not a list of “chapter headings”)
Many “initiatives” are really slogans (“Win in X,” “Become digital,” “Fix cost”). The first upgrade is to force initiative specificity:
- Clear definition of success (what moves, by how much, by when)
- A quantified value hypothesis (P&L, cash, risk, customer, capacity)
- Named owners and decision rights
- Dependencies and constraints (talent, technology, suppliers, regulators)
Portfolio governance guidance from public-sector delivery bodies mirrors this logic: identify work components, prioritise using multi-criteria scoring (financial, achievability, attractiveness), then balance the portfolio across horizons, risk appetite, and organisational capacity to absorb change.
Output: a portfolio where every initiative has a business case and an execution design – not just a title.
2) Run the business and change the business – at the same time
Execution improves when leaders explicitly manage two different “modes”:
- Delivery initiatives: scaling known routines reliably (quality, cost, service levels)
- Development initiatives: discovering new solutions through testing and learning
Most organisations are optimised for delivery. The leadership challenge is creating protected conditions for development – without disrupting performance-critical operations.
Practical design choice: fund and govern these modes differently. Delivery gets operational KPIs and tight variance control; development gets learning milestones and speed-to-insight.
3) Design initiatives to “hit the first point of failure” early
The fastest way to waste capital is to scale an initiative before its assumptions are proven. High-performing teams design “micro-tests” (or pilot-like efforts) that are explicitly built to surface the first failure point – then learn whether it can be overcome and how to scale.
A strong development initiative typically includes:
- The single riskiest assumption (e.g., adoption, unit economics, regulatory feasibility)
- The minimum test that can falsify it
- Pre-agreed stop/iterate/scale rules
This is where many transformations break: organisations reward launches, not falsification. But disciplined learning is what prevents expensive momentum toward the wrong answer.
4) Build a learning system – not “lessons learned” slides
Learning doesn’t scale unless it’s codified and reusable. Leading organisations institutionalise communities of practice, shared playbooks, and internal “learning sites” that capture what worked, what failed, and why – so every new team doesn’t start from zero.
This matters because capability is a performance lever. In that same global survey, organisations offering multiple support “enablers” (e.g., mentoring, communities of practice) showed an ~8.3 percentage point increase in project performance versus those offering none.
Translation: execution maturity is not only governance – it’s organisational learning at scale.
5) Make portfolio health visible – and make “yellow/red” safe
If every initiative is green, it usually means the dashboard is lying – or people are afraid to tell the truth. The most effective portfolios use simple, executive-grade visibility: a single page showing initiative status (green/on track, yellow/at risk, red/off track), with rapid escalation and problem-solving.
But the tool is not the point; the culture is. Portfolios fail when:
- bad news is suppressed,
- risks are discovered late,
- and “governance” becomes performative reporting.
Leaders should reward early signalling (“we’re worried this goes off track unless…”) and treat red as a resource-allocation decision – not a reputational event.
Add a “pre-commitment check” before you approve the initiative
Execution problems are often lagging indicators. Research on large initiatives argues many failures are “baked in” at commitment – through optimism bias, social pressure, and ambiguous requirements – creating a commitment gap that later looks like an execution gap.
A lightweight pre-commitment checklist can prevent portfolio overload:
- Priority integrity: What will we stop to fund this properly?
- Readiness integrity: Do we have talent, data, technology, and change capacity?
- Assumption integrity: What must be true? How will we test it fast?
- Interdependency integrity: What else must move for this to work?
- Exit integrity: What is our stop-loss (time/capital/trigger)?
What “good” looks like in 90 days
If you want traction quickly, aim for these outcomes within a quarter:
- A cleaned portfolio: fewer initiatives, each resourced to win
- A common initiative blueprint: value hypothesis + first-failure test + metrics
- A single-page portfolio view: stoplight status + blockers + decisions required
- A learning cadence: monthly synthesis of what’s being learned and reused
- A leadership norm: yellow/red is welcomed, not punished
Done well, this shifts strategy from planning to production – and turns execution into a measurable, improvable system rather than a heroic effort.
