Three Ways to Lead Learning

Over the past 25 years executives have become fervent advocates of learning, calling it an imperative, career insurance, and the only source of competitive advantage. That enthusiasm is warranted: Today the development of new skills, knowledge, and mindsets is critical to most businesses’ key strategic efforts—from navigating global crises and unprecedented industry change, addressing the rise of generative AI, and driving innovation, to attracting and retaining talent, building inclusive workplaces, and making a positive difference in society.

Indeed, more and more business leaders are moved to make a bold promise: that their company is not just a machine to deliver profit but also a community devoted to social impact and its members’ well-being. Learning is key to fulfilling that promise, especially in an age when talent flocks to organizations that offer to upskill employees and support their development. A commitment to learning is critical to making organizations both more efficient and more humane.

The growing importance of learning has heralded the arrival of a new breed of senior leaders—people I call leaders of learning. They may be chief learning officers, heads of learning and development, heads of talent and organizational development, and in some companies, chief human resources or chief people officers. They advocate for and organize learning, developing learning strategies and implementing learning initiatives for the enterprise and its employees.

But many of their efforts are going awry. Academic studies reveal mixed evidence on whether such initiatives produce lasting individual or organizational change. Despite their public commitment to learning, in private many executives I meet express skepticism about the quality and effectiveness of it in their workplace. “How do I know this has any impact on my company’s transformation?” I often hear. And there’s skepticism from employees as well: “My boss doesn’t actually care about my learning, just about results” is a common complaint.

Throughout my career I’ve taught, coached, and collaborated closely with leaders of learning. I’ve watched their excitement turn to frustration as their efforts were met with ambivalence and resistance or failed to deliver after raising much hope. To find out why so many are stymied—and what can be done about it—I teamed up with Annie Peshkam, a learning researcher and coach, to interview leaders of learning at 69 multinational firms across industries and continents.

One of our key findings is that companies begin to stifle learning when executives assume that there’s a single right way to do it that will serve all the organization’s needs. That’s simply not the case. We found that there are three distinct ways to lead learning—as a custodian, a challenger, or a connector—all of which can be successful in the right context. The methods used by leaders with the three approaches don’t vary much; they all involve a combination of formal workshops, on-the-job learning, cases, speakers, 360-degree feedback, and so on. But how and why leaders deploy them differs dramatically. And we found that too often the intent of learning was unclear in organizations, resulting in a mismatch between the learning approach and current company needs. That caused friction and frustration and derailed efforts to improve learning.

Understanding the three approaches and the differing goals they serve can help executives select, develop, partner with, and be better leaders of learning for their companies.

Custodians

Custodians see learning as instrumental to executing an organization’s strategy and strengthening its culture. In their view learning is a tool to help employees perform their roles better (and get better roles). While learning helps employees succeed and advance, the ultimate beneficiary is the organization, and any learning that doesn’t provide a concrete advantage to the company is probably useless.

Custodians embrace this view because they see themselves primarily as stewards of the business. For them, alignment with senior leadership is a top priority; they create value by bringing others on board with the top team’s agenda. Indeed, many custodians we spoke to were business leaders in other areas before they came to learning, and most noted how much they had in common with their C-suite peers.

Instrumental learning gets people to converge toward a norm, be it a cultural framework or a competency framework. Employees are assessed against a clear model and then get assignments meant to fill any gaps identified and build cultural cohesion. (A major concern of a custodian is thus picking the right people for the right learning at the right time.)

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. Learning experiences are explicitly connected to the company’s strategy and culture, since custodians disdain initiatives that are “too academic,” or too distant from immediate application in the company. In the right contexts programs designed like this help participants strengthen their skills and rise up the ranks and help the company grow.

A classic example of the custodian approach is Apple University. Aware that the company was growing fast and that he would soon let go of its reins, Steve Jobs hired Joel Podolny, then the dean of the Yale School of Management, to develop a bespoke curriculum to socialize employees in Apple’s unique ways of making decisions, communicating, and building products—and teach them the fundamental principles of simplicity, usefulness, and intuitiveness that Jobs held dear.

The custodians we spoke with were most successful and most satisfied in companies where there was a pressing need for alignment—for example, following the launch of a new strategy or after a period of fast growth that had strained coordination across the firm. In such circumstances custodians can bring much-needed standardization and strengthen the common culture through their approach to learning. But we have seen custodians suddenly be fired, too—for example, when a new CEO determines that the company’s learning approach is too rigid, stifling innovation or overlooking talent whose views might benefit the organization.

Challengers

When CEOs want a learning leader who is less concerned with upholding standards and more focused on developing innovative capabilities, they often turn to a challenger. In contrast to custodians, challengers embrace a humanistic belief that employees have an intrinsic right to grow and forge their own paths and that the organization must honor that right. While the organization benefits from learning because it helps employees raise the quality of their work, challengers believe that the ultimate beneficiary must be the individuals themselves, or learning will become oppressive.

Challengers often consider learning to be a moral duty of the organization rather than a financial one. “I believe that education is the way to help people grow personally and live a better life,” one told us.

Challengers tend to claim they have an “outsider” perspective that differs from the organization’s mainstream thinking. They see themselves as valuable specialists who bring unique expertise to the C-suite—often with learning-focused résumés. These leaders love telling stories of their peers’ skepticism; friction with other senior leaders seems only to affirm their view that most executives are champions of the status quo who need redeeming rather than pleasing. That reflects challengers’ perception that learning is valuable in helping people defy norms and break habits that hold the company back. While instrumental learning fosters convergence and alignment, humanistic learning encourages divergence from a norm.

There are strong benefits to the challenger approach. The first is engagement: A number of challengers we spoke to reported proudly that employees they worked with had turned down higher-paid jobs offered by other companies, because they were afraid they would be made to conform and would lose the freedom they enjoyed. The second is innovation: Liberated, energized people are more likely to come up with new ways to do things. They can adapt global policies to local cultures. They do not wait for instructions to seize an opportunity or respond to a market turn. Most important, they are the restless, tinkering, internal champions of change that Clay Christensen believed were necessary in established companies, lest disruptive innovation from nimbler firms find them unprepared. It’s perhaps ironic that while challengers report caring less about retention than custodians do, by making employees feel their skills are more portable, they improve it.

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. When challengers program speakers, often they’re luminaries outside the company’s industry (artists, philosophers, other inspiring thinkers). When challengers offer classes, they favor workshops that help people reflect on the company’s culture and their own habits, work, and interpersonal styles. Challengers frequently support talented employees who wish to pursue courses and programs outside the company’s official offerings—be they cooking classes or spiritual retreats. Accountability comes from frank conversations about what those employees will do differently at work as a result of what they’ve learned.

If military training is the obvious application of a boot camp, training for an architect or an artist would be an appropriate one for a playground. More and more companies are realizing that playgrounds are valuable for leadership development, too. 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. In the right contexts, playgrounds foster new ideas, the questioning of norms, and changes in perspectives and relationships, allowing for not only innovative leaps in thinking but also holistic personal growth. Boot camps are best for acquiring new skills; playgrounds for developing new selves.

Laszlo Bock’s Work Rules!, which is based on his experience as the head of people operations at Google, can be read as a challenger manifesto. The title of a central chapter, “Let the Inmates Run the Asylum,” captures challengers’ view of organizations and their intent in them. The learning initiatives Bock describes throughout the book are all based on one principle: The more freedom leaders provide and the more attention they put on the growth and aspirations of each individual, the more attractive a company becomes to talent and the more likely that talent is to have new ideas and turn them into breakthrough products.

Bock’s approach worked wonders for Google at a time when the company was set on building an innovation engine and competed fiercely for talent. But those are not the only circumstances in which it works. Challengers are most successful and satisfied in companies that are hungry for change. Those could be firms in which strong traditions or a stretch of success has made people cautious or complacent. In such circumstances challengers have the most impact and experience the fewest clashes with their executive teams. The most successful challengers are often protégés of CEOs or CHROs who want “something different” and value professional expertise.

It’s worth noting that while many CEOs are uneasy being champions of this approach themselves, they do want it to be represented on their teams, so they hire challengers but don’t give them enough support. That kind of ideological tokenism is a recipe for failure. And like custodians, challengers can fall out of favor when their work is no longer seen as constructively questioning the status quo but, rather, as a costly subversion.

Connectors

Learning leaders in the third group, connectors, strive to integrate the business-minded approach of custodians with the person-focused approach of challengers. Working through the two conflicting sets of principles, connectors tend to cast themselves as bridges between established leaders at the company’s core and emerging leaders at its periphery. Their aim is to turn the company into a community that is both effective and made up of individuals who act and grow authentically. Perhaps unsurprisingly, connectors are also some of the most seasoned leaders, who have experience with both instrumental and humanistic approaches.

While our research wasn’t based on a random sample, connectors do seem to be rarer than custodians or challengers. Connectors say their integrated approach requires striking a tricky balance but believe that focusing solely on results is dated and can stifle creativity, and that focusing solely on empowerment is inefficient and can strain coordination.

Like custodians, connectors favor initiatives that are anchored in a strategic imperative for the company. However, they pay particular attention to those that require the collaboration of different groups, because they prioritize building employees’ mutual connections rather than their connection to the organization.

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, specifically to allow them to learn about and from one another—and they see such exchanges as potentially more valuable than the educational content itself. I call this a “town hall” approach. Connectors value high-quality facilitation of conversations among executives—for example, about solving a thorny innovation problem—for two reasons. First, they believe that’s how the organization can best figure out how to overcome hurdles. Second, even if an idea that springs from such discussions doesn’t get implemented, the relationships built while working on it might endure and serve people and the company well in the future.

When the CEO of the global energy specialist Schneider Electric set the company on a path toward digital transformation, its head of talent, inclusion, and culture, Tina Mylon, championed a seven-year learning initiative called Transforming Schneider Leadership, or TSL (which I played a part in designing and delivering). It was built on the core principle that transformation should be the business not of individual leaders but of a leadership community. TSL provided a space for Schneider’s executives to think and relate in new ways, through an intensive experiential workshop that took a playground approach, while also helping them develop the skills for implementing a digital strategy, through a digital boot camp at which people acquired and practiced using specific innovation tools. Since the program began, the company has tripled in value and grown into a provider of innovative and sustainable energy-management solutions. The organization is prized for its diversity and has improved retention and increased internal promotions. There’s no way of knowing how much of that success is directly attributable to TSL, but Mylon has in that time reported seeing the company’s extended pool of leaders grow “more diverse, skilled, and impactful, and more connected to each other,” something that has served the company well in its cross-unit innovation and culture efforts.

Connectors are most successful and satisfied in companies where inclusion is a top priority—companies where community building is necessary to sustain a healthy leadership pipeline or to integrate the values and views of different groups. These are organizations where the viability of the business and the vitality of the community are understood to go hand in hand—which would be most companies, when you think about it.

In my experience, custodians frequently are assumed to be the best fit for business, and as noted, challengers are often hired as tokens of innovative thinking but given little support. It seems to me that both those patterns stem from the fact that most businesses focus excessively on alignment and as a result wrestle with innovation, inclusion, and sustainability. With their integrative approach, connectors help companies overcome those problems.

But connectors aren’t perfect. Their work is criticized as being inefficient, and it surely takes time. They also often mentioned that it was a struggle to hold instrumental and humanistic views of learning simultaneously. And in circumstances where community building isn’t a priority, connectors can appear unfocused. When introduced to the three types, some executives have even told me that they do not believe connectors really exist—that they’re just custodians or challengers without enough discipline or enough courage to state their convictions. Perhaps those executives are simply skeptical that a company might truly honor both instrumental and humanistic principles, doing well and doing good. Connectors view that skepticism as unfounded and work to overcome it.

Finding the Best Fit

Understanding the three ways to lead learning can help you shift the conversation away from the methods and costs of educational initiatives and toward their values and aims. It can also help you grasp why the learning leaders you work with might be struggling: Custodians and challengers can become embattled when people disagree with their preferred approach, and connectors often internalize the tension between the different views of learning.

Awareness of the various approaches can help learning leaders make the case for their initiatives, to the benefit of the firm.

When a learning leader I worked with, whom I’ll call Mark, took the role of director of corporate learning and development at a large global firm, he was given a bold challenge: Increase internal hires to 75% of all appointments for top roles by better preparing existing talent for leadership. Through Mark’s connector lens, the problem was evident: The current talent-management process was disjointed. While some business groups and regions had knowledge about how to develop leaders, the organization lacked a common framework that established which skills the company’s leaders needed and how they should acquire them, and aspiring leaders were mostly isolated in their individual divisions.

Mark proposed engaging all the company’s learning-and-development professionals and leaders to create that framework together and proposed a suite of collaborative global programs as a vehicle for building relationships across leadership generations. The senior management team resisted. Surely this was a competence problem; how would connecting people spur leadership? “It was the worst meeting of my whole career,” Mark recalls.

But a friend helped him see the meeting as a reflection of the very challenge he was working to address: He needed to help senior executives let go of their custodian strategy, in which they were the gatekeepers for all learning and development, and collaborate to develop talent. Mark recast his strategy in this way, and a few months later it received a green light. And in time it has delivered. During Mark’s tenure, leadership development has come to span all regions and business groups—and the percentage of senior leadership roles filled by internal candidates has reached the company’s target. In a recent round of top management appointments, 100% were internal candidates, saving the company money and raising its profile as a workplace where talent is given opportunities to develop and lead.

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Whether you’re hiring a new learning leader or trying to understand the dynamics of the one your company has in place now, ask yourself: What is your organization trying to accomplish? Does your team (or division or organization) need to execute on a clear vision, or does it need to forge a broader one? Is the learning required to make progress more instrumental or more humanistic? What is needed to promote the right combination of those approaches for your organization? Answering those questions might help you find the learning leadership that can bring that vision to life.