Why Leaders Shouldn’t Stop Learning

There’s a peculiar irony at the heart of corporate life. The moment professionals reach the upper echelons of leadership, the scaffolding of support that helped them climb suddenly disappears. Mid-level managers enjoy structured onboarding, regular one-to-ones, skip-level meetings, and formal mentorship. Junior members of staff enjoy a never-ending slew of self-betterment opportunities. Senior leaders, by contrast, often transition into new roles and are met by silence [1]. They’re expected to set vision, guide others, and deliver results immediately, all whilst navigating unfamiliar terrain without a safety net.

Writing in Harvard Business Review, executive coach Marlo Lyons, who has observed this pattern repeatedly, argues that this invisible drop-off represents one of the least-recognised risks in organisations today [2]. The assumption underlying this abandonment is seductive in its simplicity. We are to believe that these individuals have “arrived”. They are masters of their craft who no longer require handholding. Yet this mastery is a myth. The belief that executives inherently “know what they’re doing” simply because they’ve reached the top fundamentally misunderstands the nature of leadership development [3].

The consequences extend far beyond individual executives. When senior leaders lack adequate support, the effects ripple through entire organisations. Decision quality suffers. Cultural stability erodes. Performance declines. And the very people entrusted to set the course for everyone else may find themselves questioning the capabilities that brought them to senior positions, either making poor decisions or hesitating to make them at all.

The Economics of Neglect

The leadership development industry represents a multi-billion-pound global enterprise, yet it harbours what Senior Forbes Contributor Mark Murphy calls the “dirty secret” that most leadership programmes are evaluated by the people who design and deliver them, not by the employees who are supposed to benefit [4]. This fundamental flaw in evaluation methodology helps explain why leadership training continues to disappoint despite massive corporate investment.

Murphy’s research, involving surveys of over 150,000 employees, managers, and executives across hundreds of organisations, reveals a shocking disconnect. Whilst training departments celebrate completion rates and executives praise programme design, the people actually led by these “developed” leaders tell a dramatically different story [5].

Consider the findings from a study of 21,008 employees evaluating their leaders across seven critical competencies. Only 29% say their leader’s vision aligns with organisational goals. Despite countless hours spent in strategic leadership training, more than two-thirds of employees see their leaders as misaligned with organisational direction [6]. Only 20% report that their leader always shares the challenges the organisation faces, despite transparency being a core component of virtually every leadership programme [7]. And merely 27% say their leader always encourages and recognises suggestions for improvement, even though creative leadership and employee engagement have become ubiquitous buzzwords in professional development [8].

The business impact proves even more damning. Employees who believe their leaders demonstrate strong leadership are dramatically more engaged and productive. Those whose leaders share organisational challenges are ten times more likely to recommend their company as a great employer. Employees whose leaders encourage suggestions for improvement are twelve times more likely to recommend their organisation [9]. The return on investment potential is enormous, if leadership development actually produced effective leaders.

Why Support Evaporates at the Top

Several interlocking factors explain why organisations cease investing in talent development precisely when the stakes are highest. Beyond the mastery myth, there’s the matter of programme prioritisation. Companies direct resources towards directors and vice presidents, where leadership pipelines are built and turnover is higher [10]. This makes intuitive sense from a resource allocation perspective, but it ignores the exponentially greater impact (both positive and negative) that senior leaders wield.

Then there’s what Lyons identifies as “the stoicism culture” [11]. Admitting uncertainty at senior levels is perceived as weakness, particularly when executives were hired to “figure it out” on their own. This creates a vicious cycle in which senior leaders don’t ask for development or support because they believe they should already have the answers, which reinforces organisational assumptions that such support is unnecessary [12].

This stoicism and resistance can lead to isolation and anxiety at the top. SVPs, EVPs, and C-level leaders may begin questioning the very capabilities that elevated them to these positions. Some respond by reverting to old habits such as getting into the weeds on execution instead of strategy, because that’s where it feels safe and how they rose through the ranks [13].

Writing in Forbes, Professor of Leadership at Henley Business School Benjamin Laker frames the problem more broadly: “The higher someone climbs, the less likely they are to be formally supported in thinking critically, creatively or ethically” [14]. This isn’t merely short-sighted. It’s genuinely risky. The most senior people in firms hold decision rights over the biggest levers, be it strategic priorities, organisational culture, financial bets, technology adoption, or workforce policies. When their thinking becomes stale or reactive, the consequences echo far beyond the boardroom.

A Dearth of Thinking

Much of what’s celebrated in business relies on what psychologists call System 1 thinking. It’s fast, intuitive, and efficient. But when complexity enters the picture, instinct isn’t enough. The messy, high-stakes challenges that now define leadership, such as climate change, geopolitical tension, workforce transformation, or AI ethics, cannot be solved on autopilot [15].

As Daniel Kahneman observed in Thinking Fast and Slow, “Thinking is to humans as swimming is to cats. We can do it, but we’d rather not” [16]. Deep, reflective thought is cognitively expensive, and most of us avoid it. That becomes problematic when leaders are tasked with navigating uncertainty, interpreting ambiguous data, and making decisions affecting hundreds or thousands of lives.

The World Economic Forum lists analytical and creative thinking as the top skills needed in the global workforce [17]. Yet in many leadership pipelines, these skills are underdeveloped and under-supported [18]. The danger is compounded by artificial intelligence tools that, whilst streamlining tasks, also discourage hard thinking. When tools generate plausible answers before leaders finish formulating their questions, the temptation to skip the difficult parts such as wrestling with ambiguity, weighing nuance, or facing doubt becomes stronger [19].

The risk isn’t that AI provides bad answers. It’s that it delivers “good enough” ones that sound right, feel familiar, and allow us to move on. But effective leadership isn’t about sounding right. It’s about being right, at the right time, for the right reasons [20].

Five strategies

Addressing this paradox requires deliberate intervention. Lyons proposes five strategies to close the gap between senior leaders’ needs and the support organisations provide [21].

First, normalise executive onboarding every time. One successful senior executive Lyons onboarded received personalised training covering company and product history, the history of the team they were hired to lead, and company-culture nuances. Within two weeks, she had gained deep knowledge that accelerated her ability to make an impact [22]. Not every company can create personalised onboarding for every senior leader, but they do need executive onboarding that’s more comprehensive than what’s provided to all new hires. This should include specialised sessions focusing on expectations, company-specific leadership styles, and culture dynamics, scheduled meet-and-greets with cross-functional stakeholders, and daily touchpoints during the first two weeks to answer questions so mistakes are minimal and confidence can build quickly.

Second, build confidential peer-coaching opportunities. Every senior leader needs a safe space to test ideas without fear of judgement. Coaching that pairs leaders with peers from different functions can create that outlet. Rotating peer-coaching partners quarterly for the first year can broaden perspectives and relationships. Small senior leadership group forums where executives workshop challenges can reframe vulnerability as a strength and collaboration as the norm, reducing isolation whilst normalising learning [23].

Third, facilitate reflection early and often. Executives benefit from structured reflection time, particularly in their first six months. Sessions where leaders examine what’s going well, what’s unclear, and where adjustments are needed, facilitated by neutral internal or external facilitators, reduce performance pressure and create space for vulnerability. Positioning reflection as an investment in accelerating impact provides executives time and permission to adjust before small issues escalate [24].

Fourth, introduce focused 360-degree assessments at key intervals. Feedback doesn’t end at the director or vice president level. In fact, it’s even more critical at the top, where blind spots carry organisational consequences. Lyons has witnessed senior executives hesitate to give direct feedback to a new peer, choosing instead to discuss concerns privately and hoping the individual will “figure it out” [25]. The results are predictable. It ends in misunderstandings, misinterpretations, and eventual failure . Running a 360 assessment to capture early impressions can shape direct feedback and help a leader pivot quickly. Conducting another at six months evaluates growth and alignment. This practice reinforces a culture of continuous learning, even at the highest levels [26].

Fifth, formalise upstream mentorship and coaching. Senior leaders need trusted guides, sometimes a board member, other times an external executive coach. Pairing new executives with mentors who understand the unique stakes of senior leadership provides essential guidance and perspective. External coaches bring not only impartiality but also insight about navigating company culture. Connecting new leaders with board sponsors can accelerate their understanding of the organisation’s higher-level risk and governance approach, grounding them in the strategic, financial, and reputational considerations that drive board-level priorities [27].

Learning leaders

There’s a tendency in both business and policy to cut the ladder after the climb, assuming that those who’ve reached the top no longer need support for their continued ascent. The evidence suggests otherwise. Leadership is a practice that deteriorates without deliberate effort. Smart firms won’t wait to be told this. They’ll invest in learning not because it’s mandated, but because it’s mission-critical. Because once thinking stops, leadership does too.