The Strategy-Execution Gap

Every year, boards approve ambitious IT strategies. Digital transformation. Cloud migration. AI integration. The presentations are polished, the business cases compelling, the budgets approved.

Then nothing happens.

Or rather, something happens — but it is not what was intended. Projects start and stop. Priorities shift. Teams work hard but move in different directions. And twelve months later, that brilliant strategy lives only in a forgotten PowerPoint deck.

This is the Strategy-Execution Gap — the silent killer of IT initiatives. And after 30 years in the field, leading turnarounds and building/maturing delivery- and project-organisations, I have seen the same pattern repeat across organizations of all sizes.

Why Up To 90% of Strategies Fail

Research consistently shows that between 60% and 90% of strategies fail to deliver their intended results. Harvard Business Review reports 67% failure rates. Kaplan and Norton, creators of the Balanced Scorecard, suggest up to 90% of strategies are never successfully executed.

I have over my 30 years in IT & Tech identified five core reasons why IT strategies, programs and projects often fail to deliver their full potential:

1. No operationalization plan — Strategy without a "how" is just a wish list. The board approves the vision, but nobody knows what to do Monday morning.
2. The middle management gap — They get the title but not the toolkit. Promoted to lead transformation, they have never actually done it before.
3. Framework confusion — SAFe, Scrum, PRINCE2, ITIL, DevOps... Paralysis by analysis. Teams spend more time debating methodology than delivering.
4. Governance as control, not enablement — Compliance processes that kill speed. Governance designed to prevent mistakes rather than enable success.
5. Missing The Translator — No one who speaks both languages fluently: boardroom strategy and developer reality. The gap widens because no one bridges it.

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The Fix: Start with "How"

At www.thehow360.com, it does not start with frameworks. It starts with questions:

• How will this strategy translate to weekly priorities?
• How do we maintain governance without killing speed?
• How do we build the bridge between vision and execution?
• How do we know if we are on track — really on track?

The answer is not another certification or methodology. It is building operational excellence that fits your context — pragmatic, framework-agnostic, and relentlessly keeping a focus on the drivers/enablers that generate results.

I call this approach The How ... because ‘how’ is the question that ultimately determines outcomes.

In this blog, I’ll share what actually works … and what doesn’t. I’ll explore why heavy frameworks often become barriers rather than enablers, and why execution discipline matters more than methodology branding.

You’ll find pragmatic insights, practical tools, and decision mechanisms you can apply immediately .. whether you’re an executive, sponsor, or emerging leader. The focus is simple: improving the probability of a successful outcome — in projects, programs, transformations, or when translating strategy into concrete execution plans.

The How takes a 360-degree view of delivery and operational excellence .. viewed through a governance lens. It clarifies where leadership attention truly belongs, which drivers actually move performance, and how to convert strategic intent into execution and measurable results.

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From Strategy to Reality

The gap between strategy and execution is not a technology problem. It is not a process problem. It is more often a translation problem.

And like any translation, it requires someone who speaks both languages fluently — someone who understands the boardroom concerns about risk and ROI, and the developer realities of technical debt and delivery cycles.

Someone who can take "digital transformation" and turn it into "here is what we do next week."

That is The How - 360.

That is the philosophy I carried with me when I started this blog. A pragmatic approach that bridges people, processes, methodologies and technology.

Thanks for joining the journey!
- Allan
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Next week: "The Governance That Enables (Instead of Killing) Innovation" — how to maintain control without losing speed.

References

Strategy Failure Research:

1. Harvard Business Review (2017). "Executives Fail to Execute Strategy Because They're Too Internally Focused."
2. Kaplan, R.S. & Norton, D.P. Balanced Scorecard Institute research on strategy execution.
3. ResearchGate Academic Study (2015). "Strategy Implementation: What is the failure rate?"
4. International Journal of Business (2020). Analysis of strategic failure rates across organizations.