The Leadership Development Paradox:  Why We Keep Investing in Leaders and Seeing So Little Change < Chrysalis

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The Leadership Development Paradox:  
Why We Keep Investing in Leaders and Seeing So Little Change

Posted on 27th February 2026 by Sheila Vasan Singla

There is something quietly disconcerting about the way organisations speak about leadership development. 

Never before have we invested so much in building leaders. Across industries and geographies, organisations have constructed elaborate academies, curated multi-month journeys, executive immersions, digital pathways, competency frameworks, assessment centres, and coaching ecosystems. We speak fluently about empathy, resilience, psychological safety, adaptive leadership, inclusion, strategic thinking, and systems awareness. The vocabulary of leadership has matured. The infrastructure has scaled. The budgets have grown.  

And yet, when pressure mounts and decisions carry real consequence, behaviour inside organisations often looks remarkably familiar. Leaders still avoid difficult conversations. Silos reappear when deadlines tighten. Short-term metrics crowd out long-term thinking. Hierarchy resurfaces when ambiguity makes people uncomfortable. 

The machinery of development is active and well-intentioned. The behavioural outcomes are uneven and often fragile. This gap between investment and impact cannot be dismissed as accidental. It cannot be explained away by poor facilitation or lack of enthusiasm. It reflects something deeper. It reflects the quiet assumptions upon which most leadership development architectures are built. 

Until we surface and interrogate those assumptions, leadership development will continue to be one of the most generously funded and least systemically integrated efforts inside organisations. 

The Content Assumption 

If we give leaders better frameworks, they will become better leaders. 

The content assumption: people offering support

The dominant model of leadership development has long been content-driven. We identify leadership capabilities that matter, curate research-backed frameworks, translate them into digestible models, and design immersive learning experiences that communicate these ideas compellingly. 

There is an implicit belief that understanding precedes transformation. If leaders grasp the concept of psychological safety, they will foster it. If they internalise a coaching framework, they will coach. If they study systems thinking, they will naturally think systemically. 

Consider the example of a global financial services organisation that launched a year-long inclusive leadership academy. The design was rigorous and grounded in research. Leaders engaged in reflection exercises, simulations, and facilitated dialogue about bias and belonging. Feedback scores were exceptionally high. Participants left feeling intellectually enriched and emotionally stirred. 

Six months later, however, engagement data revealed a sobering reality. Team members still hesitated to challenge authority. Cross-functional collaboration remained inconsistent. Senior leaders continued to dominate decision forums under pressure. When performance targets were at risk, speed and control once again trumped dialogue and shared ownership. 

The content had been powerful. The behaviour had been temporary. 

This pattern aligns with decades of research on transfer of training, which shows that while leadership programs can improve knowledge and even short-term behavioural expression, long-term transfer depends heavily on reinforcement mechanisms, managerial support, and contextual alignment. Insight alters cognition. It does not automatically rewire behaviour under stress. 

The mistake is subtle but consequential. We overestimate the power of explanation and underestimate the power of environment. 

The Individual Assumption 

If we transform the leader, the organisation will transform itself. 

The individual assumption: people trying to climb individually

A second assumption sits beneath many high-potential and executive development efforts: that organisations change when individuals change. This belief is attractive because it personalises responsibility and simplifies complexity. Identify strong leaders, elevate their capability, and the ripple effect will follow. 

Yet organisations are not passive backdrops. They are dynamic systems composed of incentives, reporting structures, informal hierarchies, performance metrics, governance rhythms, and cultural norms that have evolved over time. These systems exert gravitational pull. 

In a large manufacturing company, a cohort of senior managers completed a development journey centred on empowerment and distributed decision-making. Participants left committed to delegating authority and creating space for frontline innovation. However, performance dashboards continued to track error-free execution, quarterly cost efficiency, and centralised approval compliance. When one manager experimented with granting greater autonomy and a production error occurred, senior leadership responded with scrutiny rather than curiosity. 

The message was not explicitly stated, but it was unmistakable: autonomy is welcome as long as it does not disrupt predictability. Within months, most leaders reverted to familiar patterns of tight oversight and centralised decision-making. 

The individuals had shifted their mindset. The system had not shifted its incentives. 

Research in organisational behaviour consistently demonstrates that structural alignment is one of the strongest predictors of sustained behavioural change. When systems reward yesterday’s behaviour, tomorrow’s leadership cannot take root. Leadership development that ignores systemic reinforcement is asking individuals to swim upstream indefinitely. 

The Measurement Assumption 

If participants rate it highly, it must be working. 

In many organisations, leadership development is evaluated through engagement scores, attendance metrics, and satisfaction surveys. These metrics are accessible, visible, and easy to compare across programs. But they reveal very little about behavioural durability. 

A global technology company once celebrated a flagship leadership summit that received extraordinary feedback ratings. Participants described the experience as “life-changing” and “deeply transformational.” The event generated energy, social media visibility, and executive endorsement. 

Twelve months later, however, internal data told a different story. Cross-functional friction persisted. Strategic initiatives stalled due to decision delays. Employee attrition among high performers had not declined. The summit had created emotional resonance, but it had not been followed by structural reinforcement, managerial accountability, or measurable behavioural commitments. 

The organisation had measured inspiration, not integration. 

When learning is measured primarily through participant reaction, organisations optimise for experience design. When it is measured through participation rates, they optimise for scale. When it is measured through completion data, they optimise for compliance. 

Very few organisations consistently measure how leaders decide differently under pressure, how team climate shifts over time, or how capability influences strategic execution. 

Measurement shapes behaviour. If we measure satisfaction, we will produce satisfaction. If we measure decision quality and cultural shifts, we will begin to design for those outcomes instead. 

The Awareness Assumption 

If leaders understand what good leadership looks like, they will practise it. 

The awareness assumption: person making notes and planning

There is a profound difference between knowing and becoming. 

In a professional services firm, managers attended an intensive coaching skills program. They practised questioning techniques, feedback loops, and developmental dialogue in carefully designed simulations. During the program, their performance was impressive. They demonstrated empathy, curiosity, and structured coaching behaviours. 

However, during year-end performance cycles, many reverted to directive conversations focused on ratings and billable targets. Time pressure, client urgency, and performance anxiety compressed space for dialogue. 

This was not hypocrisy. It was habit under stress. Behavioural science tells us that under cognitive load or emotional strain, individuals default to familiar patterns that feel efficient and safe. Without repeated rehearsal in real contexts, supported by feedback and reinforcement, new behaviours remain intellectually accessible but practically fragile. 

Leadership development often excels at explanation. It struggles with repetition. 

Awareness builds vocabulary. Practice builds reflex. And reflex, not intention, governs behaviour in moments that matter most. 

The L&D Ownership Assumption 

Leadership development belongs to the Learning function. 

Leadership development is frequently positioned as a specialised function within the broader organisational architecture. L&D designs programs, secures faculty, manages logistics, and reports metrics. The business participates as a stakeholder. 

But leadership behaviour is shaped daily by executive modelling, performance management systems, compensation structures, succession planning criteria, and informal cultural signals. 

In one organisation, the learning team designed a leadership pathway emphasising enterprise thinking and cross-functional collaboration. Meanwhile, senior executives publicly endorsed collaboration but privately rewarded leaders who maximised their own business unit’s performance, even when doing so created friction elsewhere. 

The content advocated collaboration. The system rewarded competition. 

In such environments, leadership development becomes linguistically aligned but behaviourally misaligned. Leaders adopt the language of enterprise thinking while acting in ways that protect local optimisation. 

Leadership development cannot be outsourced to a department. It must be co-owned by the system that shapes behaviour. 

The Deeper Paradox 

The deeper paradox: person looking at detailed plan

The paradox is not that leadership development fails because it lacks sophistication. It fails because it underestimates context. 

Organisations invest in upgrading leaders while preserving incentives that reinforce legacy behaviour. They introduce new frameworks without redesigning governance rhythms. They seek transformation without recalibrating accountability structures. 

Leadership is not a set of competencies to be acquired. It is a pattern of decisions enacted repeatedly under uncertainty. Patterns do not shift because they are described. They shift because the conditions that sustain them are redesigned. 

Until organisations accept this, leadership development will continue to oscillate between enthusiasm and frustration. 

From Programs to Behavioural Architecture 

If leadership development is to move beyond inspiration and into impact, it must transition from programmatic thinking to architectural thinking. 

Architectural thinking recognises that behaviour emerges from systems. It integrates capability design with structural reinforcement. It aligns metrics, incentives, modelling, and feedback. 

This means selecting a small number of strategic capabilities that matter disproportionately for future success and embedding them into: 

• Executive modelling 
• Performance evaluation criteria 
• Promotion decisions 
• Governance forums 
• Incentive structures 
• Managerial rituals 

It means designing for rehearsal rather than exposure, for iteration rather than information. It means measuring not how leaders feel at the end of a session, but how they decide six months later when confronted with competing priorities. 

Most importantly, it means acknowledging that leadership development is not about delivering content to individuals. It is about reshaping organisational behaviour. 

A More Demanding Definition of Leadership Development 

A More Demanding Definition of Leadership Development: Jenga blocks hanging in balance

Perhaps the most uncomfortable truth is this: leadership development is not a learning intervention. It is a strategic transformation lever. If it is treated as optional enrichment, it will produce optional change. If it is embedded into the operating fabric of the organisation, it will produce durable capability. 

The organisations that will succeed in the coming decade will not be those that host the most inspiring leadership summits. They will be those that redesign their behavioural architecture so that desired leadership behaviours are easier to enact than legacy ones. 

They will understand that sustainable leadership is not born in classrooms. It is built in context. And when leadership development becomes architecture rather than activity, its impact stops being episodic. It becomes systemic. 

ABOUT AUTHOR

Sheila Vasan Singla

Founder and Managing Director

Sheila is the Founder & Managing Director of Chrysalis. She is a pioneer in Human Performance Improvement in India who has been passionate about driving business impact through Results Based Learning™.

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