Humans, Tech, and Judgment: Humalogy in Exec Ed

• Uncertainty is a defining feature of organizational life. Leaders do not need training in how to find better answers but in how to make judgments based on partial and competing perspectives.
• While technology can support iterative learning, the study of humalogy suggests that if learners are to develop judgment, they will need to think of technology in human-centric terms.
• Managers must cross sectoral boundaries and engage in systems thinking in order to understand many of today’s leadership challenges, such as climate change and public health.

 
“Our doubts are traitors and make us lose the good we oft might win, by fearing to attempt.”

That quote, from William Shakespeare’s “Measure for Measure,” might easily be applied to the way business schools approach executive education in an era of technological and geopolitical disruption. While business schools have innovated the design, delivery, and content of their executive programs, many are reluctant to examine pedagogical assumptions about how executives learn.

Too often, executive learning remains centered on frameworks, cases, and analytical tools because educators assume that leaders need to make better analyses and gather more information. But leaders rarely encounter a single, coherent reality; instead, they navigate environments that are relational, contested, and only partially knowable. What they need from executive education programs is guidance on how to reflect, exercise judgment, and adapt in ambiguous environments.

As Shakespeare reminds us, unexamined assumptions can constrain action. Business schools need to challenge existing approaches to executive education by helping leaders understand how complexity arises from the multiple perspectives, relationships, technologies, and interpretations through which organizational realities are continually produced and experienced. Therefore, schools must provide educational experiences that do not simply transmit knowledge but lead to genuine cognitive transformation.

Executives Aren’t Typical Students

Unlike early-career learners, managers arrive with deep experience, established professional identities, and well-rehearsed patterns of decision-making. These shape not only what they learn but also how they interpret new knowledge. Jack Mezirow’s 1997 concept of transformative learning suggests that meaningful development occurs when individuals critically reassess and revise their existing “frames of reference.” This implies that executive education programs need to shift from simply delivering content to enabling managers to challenge the assumptions that shape their judgment.

As Henry Mintzberg argues in his book Managers Not MBAs, management is not a discipline mastered through analysis alone. Instead, it is a practice grounded in experience, context, and reflection. Treating executives as passive recipients of knowledge overlooks the deeper opportunity schools have: to reshape how leaders think and act in complex organizational settings.

In addition to providing managers with technical expertise, today’s business schools must prepare them to be what Ann Cunliffe calls philosopher leaders. Such individuals are able to question assumptions, engage in reflective dialogue, and embrace ambiguity rather than seeking premature certainty. From this perspective, uncertainty is not simply the consequence of insufficient information, but a defining feature of organizational life itself. Judgment therefore depends less on finding definitive answers than on acting thoughtfully from inevitably partial perspectives.

From Case Studies to Context

While case studies remain central to business education, their limitation is that they imply that organizational situations become understandable once sufficient information is assembled. But the reality is that uncertainty will always be present within an organization. Leaders do not need training in how to find definitive answers but in how to make judgments based on inevitably partial perspectives.

In his study “Stories of the Storytelling Organization: A Postmodern Analysis of Disney as ‘Tamara-Land,’” David Boje argues that organizational actors experience only partial versions of reality and that understanding emerges from fragmented, overlapping, and sometimes competing narratives. He draws on the theatrical production Tamara, in which audience members can follow only one character through multiple simultaneous performances.

His point is not only that managers lack information, but that organizations themselves contain multiple realities. What appears rational, urgent, or even visible to one actor may remain hidden from others—including managers—because they inevitably experience only fragments of the systems in which they participate. The challenge is not simply to obtain more information, but also to recognize that organizational life always exceeds what any individual can observe, understand, or represent. Therefore, effective leaders must be curious about what is missing from their current perspectives and aware of how their positions and relationships shape what they see.

Leaders do not need training in how to find definitive answers but in how to make judgments based on inevitably partial perspectives.

While leaders might receive regular reports that summarize organizational activity, this data simplifies complex human experiences into metrics and indicators. But organizational life contains far more activity than can ever be represented in formal reporting structures. Leaders must consider what information is captured, how that information is presented, what assumptions it contains, and what remains invisible because it is not measured or considered strategically relevant.

As Boje’s study makes clear, effective leadership depends on developing curiosity about what may be missing from the current perspective. This includes seeking out voices and experiences that sit beyond established reporting channels and recognizing forms of work that may remain invisible within conventional measures of performance.

Experiencing Multiple Perspectives

Executives aren’t the only ones who should learn how to engage with multiple viewpoints. Students throughout the business school can benefit from understanding that an organization is made up of many competing realities.

For instance, instructors can illustrate the idea to final-year undergraduates by asking these students how much they know about the university where they’ve studied for three years. It’s typical for students initially to say they’re familiar with 20 to 50 percent of university operations, assuming that familiarity with the campus equates to familiarity with the institution.

However, as discussions get underway, students begin to realize that every building contains numerous classrooms and offices they have never entered, and each one hosts multiple activities and interactions throughout the day. Then, they begin to consider less visible dimensions of university life, such as the meetings held, emails exchanged, research conducted, partnerships developed, and decisions made.

Finally, students debate where the university itself begins and ends. Does it consist solely of buildings and staff, or does it also encompass students, families, employers, community partners, and the wider social networks influenced by its activities? By the end of the exercise, many students conclude that they understand considerably less than 1 percent of the institution.

Similarly, executives can study how complex dynamics emerge in organizational settings. They come to realize that a merger, for example, is never experienced in a single way. Investors may focus on financial value, employees on identity and job security, customers on continuity of service, and regulators on market competition. Leadership therefore depends on exercising judgment across several legitimate, yet incomplete, realities.

Learning Through Relationships and Reflection

Executive education programs do more than help participants gain managerial capability. As Rakesh Khurana points out in the book From Higher Aims to Hired Hands, executive programs function as mechanisms of socialization, providing participants with valuable professional networks and influencing how leaders think and how they see themselves within broader professional communities. Therefore, effective executive education programs will include opportunities for peer engagement, mentorship, and cohort-based problem-solving as well as structured opportunities for reflection.

The human dimension is equally important when business schools consider how to integrate technology into executive education. The concept of humalogy emphasizes the need to achieve the right balance between human engagement and the application of technology. Research on blended learning suggests that technology can support iterative learning, but it cannot replace the human interaction, dialogue, and reflection through which managerial judgment develops. Effective program design must integrate digital tools with meaningful peer engagement, mentorship, and structured reflection.

Technology can support iterative learning, but it cannot replace the human interaction, dialogue, and reflection through which managerial judgment develops.

A second classroom example—this one from an executive MBA course—demonstrates that technology-related challenges should be used to develop judgment as well as technical understanding.

The assignment required learners to examine the ethical and organizational challenges of incorporating artificial intelligence and digital transformation into healthcare. Participants considered how leaders must balance opportunities for improved efficiency and innovation with questions of accountability, professional judgment, patient trust, and workforce adaptation.

The exercise showed participants that technological transformation requires leaders to navigate competing perspectives among clinicians, patients, administrators, regulators, and technology specialists. Executives moved beyond asking what AI can enable and began asking how technology should be integrated responsibly within complex human systems.

Two Critical Issues

While many executive education programs have evolved to reflect the fact that experienced managers learn differently from traditional students, two important challenges remain.

The first challenge is practical. While participant satisfaction and career progression are still common indicators of program success, schools are exploring ways to capture richer measures of impact.

For example, schools use action-learning projects to assess how participants apply learning to live organizational challenges. They rely on reflective activities to evaluate how executives’ assumptions, decision-making approaches, and leadership perspectives change over the course of the program. Schools also use feedback from organizational sponsors and participating firms to gauge the effectiveness of their programs.

Through such approaches, administrators acknowledge that the value of executive education lies in how well participants learn to exercise judgment and apply classroom learning in practice.

The second challenge is conceptual. While executive education traditionally has focused on improving organizational performance, many contemporary leadership challenges cannot be understood through the lens of a single organization. Executives will be grappling with climate transition, geopolitical uncertainty, and the impact of artificial intelligence. They will be working within increasingly complex digital ecosystems, and they will be making decisions that affect public health. These realities will require them to understand the interdependencies among economic, societal, and institutional actors.

Therefore, today’s leaders must engage in systems thinking, a point Peter Senge made 20 years ago in his book The Fifth Discipline. And they must be able to navigate across organizational, sectoral, and stakeholder boundaries, as Chris Ernst and Donna Chrobot-Mason emphasize in Boundary Spanning Leadership.

Many leadership challenges cannot be understood through the lens of a single organization. Executives must understand the interdependencies among economic, societal, and institutional actors.

This does not diminish the importance of organization-specific challenges; rather, it expands the context within which executives make those decisions. For example, sustainability transformation requires leaders to consider not only internal environmental, social, and governance (ESG) issues, but also the expectations of external regulators, investors, employees, customers, and supply-chain partners. Similarly, AI adoption requires judgment that extends beyond technological capability to questions of governance, ethics, workforce adaptation, and trust.

When systemic challenges are embedded into executive learning, participants can better connect broader societal and technological developments to their own organizational realities. Even more important, they can develop and strengthen the judgment they will need to lead responsibly.

Implications for Program Design

Addressing these challenges requires schools to rethink executive education. Rather than relying predominantly on abstracted cases, programs should incorporate learning within authentic organizational contexts. One way to achieve this is to have participants work collaboratively on unresolved strategic issues from their own organizations. Unlike retrospective cases, these problems evolve over time, requiring participants to reassess assumptions as new perspectives and information emerge.

A practical example from an EMBA classroom illustrates this approach. The learners examined a sustainability challenge within the food and beverage sector, where leaders articulated ESG ambitions that they could only implement with engagement from employees throughout the organization. Executives in the class worked together to identify the organizational conditions required to translate strategic commitments from company leaders into collective action.

Participants explored how leadership, culture, employee engagement, and change management shaped the implementation of ESG goals. They also considered the different perspectives of stakeholders within marketing, communications, human resources, finance, strategy, and research and development departments. The exercise made it clear that sustainability transformation is a complex organizational process requiring leaders to navigate competing priorities, interpretations, and interests.

The exercise highlighted three essential elements of executive education: reflection, which enables participants to question assumptions and strengthen managerial judgment; peer learning, which encourages meaningful human interaction that is enhanced but not replaced by digital technologies; and systems thinking, which equips leaders to navigate increasingly interconnected organizational, economic, and societal challenges.

From Knowledge to Judgment

Today’s executives do not primarily need more information; they need greater capacity to interpret complexity, challenge their assumptions, and act responsibly when certainty is unattainable.

Executive education should therefore aspire to create the conditions in which managers ask better questions, engage in deeper reflection, and form more considered judgments. It should help leaders develop the reflexive capacity to navigate organizational realities that are multiple, relational, and continually evolving.

In this sense, the enduring contribution of executive education is to cultivate thoughtful practitioner-philosophers capable of leading responsibly amid complexity, ambiguity, and competing interpretations of reality.