Today the development of new skills, knowledge, and mindsets is critical to most organizations’ key strategic efforts. This has given rise to a new breed of senior leaders—leaders of learning—who advocate for and organize learning initiatives for departments and their employees. But the evidence on whether their programs are actually effective is mixed, and both managers and employees remain skeptical about them.

While most leaders know they need to champion learning, they often assume that there’s a single right way to do it that will serve all of their organization’s needs. But that’s simply not the case. There are, in fact, three distinct ways to lead learning in any organization—as a custodian, a challenger, or a connector—all of which can be successful in the right context.

Custodians see learning as instrumental to executing an organization’s strategy and strengthening its culture. They believe that learning must serve the needs of the organization first and foremost. They can also bring alignment and strengthen culture in periods of flux—for example, following the launch of a new strategy or after a period of fast growth.

Custodians prefer centrally developed boot-camp-type learning that facilitates the deliberate acquisition and practice of new skills. Courses replicate the actual workplace, offer employees timely feedback on their practice attempts, and allow them to try again. The goal is for people to efficiently gain facility with new or difficult skills.

Challengers think individuals have an intrinsic right to grow and that learning must support their development. They often consider learning to be a moral duty of the organization rather than a financial one. Challengers shine when the organization is stuck and needs to innovate.

If conformity stifles companies and silences employees, as challengers see it, then the boot camp typical of organizational learning often makes it worse. Humanistic learning, in contrast, is best pursued in a “playground,” where it’s self-guided and more personalized. Employees choose what to learn and when on the basis of their interests, strengths, and personal goals; there is less emphasis on models, assessments, filling skill gaps, and the best practices of experts. A playground inherently allows people to acquire a larger variety of skills and viewpoints than they would at a boot camp—and develop the kind of agility and autonomy that’s required to lead.

Connectors integrate both approaches and emphasize bringing people together to learn from one another. Connectors can help in siloed organizations that need to boost collaboration. Like custodians, connectors favor initiatives that are anchored in a strategic imperative for the company, paying particular attention to those that require the collaboration of different groups.

Like challengers, connectors usually incorporate personalized learning opportunities into their courses and workshops. They encourage employees to see tackling a corporate challenge as a vehicle for their own personal and professional growth. Yet connectors place a unique emphasis on using learning experiences to bring people together to learn about and from one another.

Understanding these three approaches and the differing goals they serve can help you select, develop, partner with, and be a better “leader of learning” for your area.

 

References:
Harvard Business Review (2025, January-February) Gianpiero Petriglieri: Three Ways to Lead Learning. Which one is best for your organization?