Why Most Leadership Training Fails and What Really Drives Strategy Execution Success
- 19 minutes ago
- 5 min read
A former top-tier HR evaluator, Naeema Siddiqui, specializes in transforming brilliant but "invisible" managers into commanding executives. She is a leadership strategist and the author of Respect At First Sight: Body Language Secrets for Leaders.
Organizations don’t lose momentum because they lack vision. They lose it after the strategy is announced. The offsite ends. Slides are shared. Leaders feel aligned. And then, quietly, execution slows.
Decisions stall. Priorities blur. Accountability softens. Weeks later, senior leaders are asking the same question they’ve asked before: Why does so much leadership investment produce so little sustained change? After years of advising organizations across sectors, I’ve reached a conclusion many are uncomfortable naming:
Leadership training doesn’t fail because leaders lack capability or intent. It fails because strategy execution lives in the middle, and the middle is rarely designed to execute.
The gap no one likes to name
Most organizations obsess over two layers:
Senior leadership, where strategy and direction are set
Frontline teams, where work is delivered
What sits between them is treated as a conduit, rather than a system.
Middle managers are expected to:
Translate strategy into operational decisions
Align teams under pressure
Make trade-offs with limited authority
Deliver outcomes amid constant change
Yet many operate without:
Clear decision rights
Explicit ownership for execution
Consistent operating rhythms
A shared definition of what “good execution” actually looks like
So, they compensate. They buffer. They firefight.
Over time, execution weakens, not because managers don’t care, but because the organization asks them to perform without design.
Research consistently supports this reality. Middle managers are often described as the heart of the organization, yet overloaded with administration, ambiguity, and competing priorities. When this layer falters, execution suffers, even when strategy is sound.
Why strategy breaks down after it’s announced
Strategy rarely fails on paper. It fails in translation.
Leadership development often focuses on insight and inspiration but neglects reinforcement once people return to real work. Strategy and execution drift apart not due to weak vision, but due to weak integration into daily decisions.
The data is sobering:
Up to 70% of large-scale change initiatives fail, largely due to execution breakdowns, not flawed strategy
Organizations that build effective middle-management capability see meaningful gains in performance, productivity, and engagement
Those that neglect this layer experience compounding inefficiencies, rework, and escalation
The earliest warning signs are subtle:
Meetings become updates instead of decisions
Priorities shift weekly
Accountability diffuses
Escalation replaces ownership
By the time leaders notice, execution has already slowed, and leadership bandwidth is already being consumed.
The real cost leaders underestimate
Execution failure rarely shows up as a single crisis. It appears as friction.
Decisions that should take days take weeks
Senior leaders are pulled into issues they shouldn’t own
Teams wait for clarity instead of acting
Strategy must be revisited, not because it was wrong, but because it never fully landed
The hidden cost isn’t just time. It’s lost momentum, diluted accountability, and leadership energy spent compensating for system gaps.
A real case: Microsoft made middle managers the lever, not the problem
Microsoft’s transformation under Satya Nadella is often cited for its cultural shift. What’s less discussed is how operational that shift actually was. The transformation wasn’t driven by vision alone. It was driven by changing how managers behaved every day.
Microsoft introduced clear expectations for managers through a deceptively simple framework: Model, Coach, Care, embedded into leadership systems, not treated as a slogan.
This was not soft language. It was an execution mechanism.
Model the standards, priorities, and behaviors
Coach to build capability, unblock teams, and accelerate learning
Care to sustain trust, performance, and retention under pressure
Leaders explicitly linked this framework to building a growth mindset and aligning the organization to new strategic choices. The success of the transformation required changing how decisions were made, how risk was handled, and how managers showed up, not merely announcing a new direction.
The emotional truth of the case is simple: When pressure rises, people don’t need more slogans. They need managers who create clarity, remove friction, and stay present.
That is the middle-manager gap, solved by making managers the standard-bearers of execution.
How to close the middle-manager execution gap
Over time, I’ve seen execution improve consistently when organizations make three deliberate shifts.
1. Redefine the middle-manager role
Middle managers must stop being treated as “in-between.” Their role must be explicitly designed as:
Translators of strategy into operational decisions
Owners of execution rhythm and follow-through
Developers of people through continuous coaching
Removers of blockers, not absorbers of friction
When the role is clarified and simplified, managers regain the capacity to lead execution instead of managing volume.
2. Connect strategy to daily decisions
Strategy becomes actionable only when managers know:
What success looks like in operational terms
Which decisions they own
Which priorities matter, and which don’t
This clarity shortens decision cycles, reduces escalation, and prevents hesitation. Execution improves not when managers are more motivated, but when they are more certain.
3. Treat leadership development as an operating system
One-off programs don’t change behavior. Execution improves when leadership development:
Reinforces execution habits weekly
Embeds coaching into real work
Measures execution health, not just engagement
Middle managers are the determining factor in whether training sticks. When they reinforce behaviors consistently, learning translates into performance.
The Zanovah Principle
Strategy does not fail because leaders lack vision. It fails when the middle is not designed to execute.
At Zanovah Middle East, we help organizations diagnose where execution breaks, rebuild the middle-manager operating system, and turn managers into multipliers, not points of friction.
Organizations that redesign the middle regain speed, clarity, and leadership bandwidth, without changing strategy.
If this perspective resonates, a short diagnostic often brings immediate clarity, and shows exactly where to intervene first.
Follow me on LinkedIn for more info!
Naeema Siddiqui, Founder & CEO, Zanovah Middle East
For seven years, Naeema Siddiqui sat in the executive "evaluator’s chair" at top-tier firms, witnessing firsthand why brilliant technical experts often fail to command the boardroom. She diagnosed this systemic issue as the "David Syndrome," a costly disconnect between strategic brilliance and executive presence.
She provides high-impact toolkits for professionals ready to master the unspoken rules of power and reclaim their influence. Naeema is also the author of the critically acclaimed book, Respect At First Sight: Body Language Secrets for Leaders.
References:
Harvard Business Review – Why Leadership Training Fails – and What to Do About It
Harvard Business Review – When Strategy and Execution Fall Out of Sync
Harvard Business School (Working Knowledge) — The “Secret Ingredient” for Effective Training: Middle Managers
Harvard Business Review (Podcast) –Microsoft: A Case Study in Strategy Transformation
Harvard Business Publishing – Culture Transformation at Microsoft
McKinsey & Company – Middle managers are the heart of your company
McKinsey & Company – Activating middle managers through capability building
Deloitte Insights – Is there still value in the role of managers?
