Learning for a Living

The event was running over, the car was waiting, but the keynote speaker did not seem to mind. He was enjoying fielding questions from a large auditorium packed to the rafters with executives, aspiring entrepreneurs, and management students. “Get ready for an age in which we are all in tech,” he had told them, “whether you work in the tech industry or not.” The moderator called for one last question. “What’s the best way to get ready?” a woman asked. “Be great at learning,” he said without hesitation. “The moment you stop learning is the moment you begin to die.”

Calls for learning have long been common at corporate retreats, professional conferences, and similar gatherings. But with the furious pace of change that technology has brought to business and society, they have become more urgent.1 Leaders in every sector seem to agree: Learning is an imperative, not a cliché. Without it, careers derail and companies fail. Talented people flock to employers that promise to invest in their development whether they will stay at the company or not.2 And companies spend heavily on it. By one estimate, in 2018, corporate outlays on learning and development initiatives topped $200 billion.3

Despite the lofty statements and steep investments, however, learning at work remains complicated. People are ambivalent about it, if not outright resistant. We want to learn, but we worry that we might not like what we learn. Or that learning will cost us too much. Or that we will have to give up cherished ideas.4 There is often some shame involved in learning something new as an adult, a mentor told me at the start of my career. What if, in the process, we’re found lacking? What if we simply cannot pick up the knowledge and skills we need? I have spent two decades studying adult learning, helping companies design and deploy learning initiatives, and teaching and coaching thousands of high potentials and executives all over the world. And I have found that mentor’s words to be wise: Nothing truly novel, nothing that matters, is ever learned with ease.

Furthermore, most organizations are not as hospitable to learning as their rhetoric suggests.5 In my work, I hear the same complaints over and over again:

“My manager does not care about learning.”

“Pressure to perform trumps our need to learn.”

“We are told to celebrate failure as a learning opportunity, but I never feel that I can afford to fail.”

Even though we want to learn and companies need us to, it’s hard, and we get little space for it. Part of the problem, I have found, is that we often think of learning as something that happens at work or alongside it. We seldom acknowledge that learning is work — work that, paradoxically, gets harder in successful careers and organizations, where shame is most unwelcome.

So how can employers make space for learning, and how can we as individuals tackle the work of learning, especially the sort of learning that transforms careers and organizations? Both endeavors require understanding that learning is plural. There is more than one kind, and each kind needs its own space and challenges us in different ways.

Learning Is Plural

Andrew and Sandra (names have been changed) were getting into trouble for not learning fast enough. He was a talented product manager who, after yet another performance review in which he had been told that he should learn to delegate if he aspired to move up the ranks, had come to resent his company for not helping him prepare for senior leadership. She was a respected executive who was running afoul of her boss, the company’s CEO, for not pushing a digital overhaul of her division fast enough. Despite their history of strong performance, both were saddled with a perception that they were not agile enough (management-speak for “stuck in their ways”). They both read widely, attended courses, and sought advice. But none of those efforts seemed to get them unstuck.

When I met Andrew, it did not take him long to admit that he did not really want to change. He wanted a hack. He took pride in being a problem-solver and had long been rewarded for it. As a result, when he passed a problem to his team, he felt embarrassingly useless. No wonder he could not learn to delegate. It threatened the habit — the virtue, as he saw it — of self-reliance that had been prized in all his roles thus far.

Learning threatened Sandra in a different way. Her accomplishments had taken her to the top of her company’s largest division, where she was responsible for a significant portion of the organization’s profits. Pressure to keep the ship steady came from the same boss who urged her to “rock the boat,” from her colleagues, and from the thousands of people whose livelihood depended on her division’s results. Trying something too new felt reckless in her role.

Stories like Andrew’s and Sandra’s are common. The pull of habits and the push of expectations are familiar to anyone who works hard to earn others’ trust. It is not just pride or fear that keeps us stuck. It is also the shame that comes with being exposed and letting others down. The more valuable our identities and commitments are, the less space we feel we have to question them. On the contrary, we shore them up, developing ways to keep potential shame at bay, such as focusing on performance and the organization’s demands.

Managers could be forgiven for concluding (like Andrew’s and Sandra’s bosses did) that we are not learning much when we proceed this way. But they would be wrong.

We are all, in fact, learning every day. Most of that learning, however, is incremental, improvements that build on what we already know and do. We expand our knowledge and refine our skills in ways that strengthen our identities and commitments. Hardly a day went by that Andrew and Sandra did not solve a new problem: A process got fixed, a region got reorganized. Each time, their bosses pointed them to another problem to solve, or they spotted one themselves. The process sharpened their competence, broadened their expertise, and got them attention. Each day they got better — and a little more stuck.

Learning that broadens our expertise is valuable, but it is not enough. Incremental learning does not alter the way we see others, the world, and ourselves. Therefore, we do not just miss opportunities to accelerate that learning. We often miss learning of another kind altogether, the kind that scholars call transformative because it changes our perspectives and relationships, laying the foundations for personal growth and innovative leaps.6 Both kinds of learning are necessary, of course. Incremental learning helps us deliver, while transformative learning helps us develop. When we make space for the former and avoid the latter, however, frustration ensues, change stalls, and investments go to waste.

Making Space

The kind of space we need for learning, and the way to make the most of that space, depends on what kind of learning we are after. For incremental learning, we need a more focused, less distracting, safer replica of our workplace — a boot camp of sorts, where we can practice the best possible way of doing things, get feedback, and try again.7 If we are after transformative learning, what we need is a familiar yet open frame — a playground of sorts that magnifies our habits and the culture that breeds them so that we can examine both, and imagine and try new ways of being.8

A boot camp must replicate workplace constraints to help us master ways of navigating them more efficiently. Whether it’s a course on, say, reaping insights from data analytics or a training session on giving respectful feedback, the space supports practice and improvement. A playground must remove most constraints to promote experimentation. Providing some distance from day-to-day reality allows us to get real in a deeper sense. A boot camp amplifies and exploits the shame of learning, helping us learn how not to be found wanting. A playground exposes and challenges that shame, helping us realize that if we were less anxious, it might be easier to claim what we want and discover how to get it.

That’s what Andrew and Sandra needed but didn’t have. Both were insightful. Andrew understood the classic trap of talent: What got him noticed as a future leader got in the way of becoming one.9 Sandra feared the curse of successful executives, which is being seen as a monument to the past that stands in the way of the future.10 What they did not get was that to make the leap forward, they did not need to master a new way to act but rather a new way to learn. They both put emphasis on trying to find out what they needed to do better. They had plenty of resources for that. What they did not have was a space where they might be different without risking too much.

That’s often a problem in organizations. Even when they make space for learning, as in executive education programs and management retreats, they favor incremental learning. Boot camps cater to the performance mindset and focus on conformity at the office. Furthermore, the kind of learning they support works well for a broad range of skills but not for learning to lead or ignite change. To help people shift to a new way of being at work, we need more open spaces such as leadership development workshops or strategy retreats where we are purposefully disoriented — spaces where we are freed up to question the status quo within and around us and invited to try out different directions.

Most organizations promise to help their members learn, but only those that provide both kinds of spaces truly keep that promise. We value and often remain loyal to them even after we leave, because they offer “identity work spaces” where we can learn to fit in and become who we aspire to be, as well as learn what it takes to deliver and what we need to develop.11 In such spaces, there is focus on a broad vision and freedom to bring the vision to life in our own way. But even when organizations recognize that learning is plural and provide spaces for incremental and transformative learning, efficiency and change are not guaranteed. Ultimately, learning is practice. We need to do the work to make the most of the spaces we are given — the work of learning from experts and experience.

Doing the Work

I have never met a manager who told me that people learn to succeed, lead, or change by reading articles like this. You learn from others whose expertise you lack and from personal experience, they say. I can’t argue with that. But most people also admit that while we have expert mentors and plenty of experience at work, we do not always have so much learning, and change remains hard. That will continue to be the case until we discover how to make the most of the experts and experiences in our learning spaces.

Transformation might well happen at a boot camp, and we might get “fit” on a playground. But any overlap in benefits is incidental. The spaces are fundamentally different, and so are the types of work they require:

Incremental learning through deliberate practice. In a boot camp, where incremental learning prevails, we align our habits with established norms, conform to the ideals laid out by experts and organizational authorities, and thus reinforce the existing power structure. In this whole endeavor, the experts are central. They set out conceptual models, serve as role models, guide us in drills, and correct us.

First, as learners, we study the past and the lessons drawn from it through academic research or corporate benchmarking. Then we bring in the future — the aspirations our leaders have outlined in our career plans or in corporate strategy. That mixture of past and future defines the ideals we will strive for. We then consider the present to define the gaps in skills we need to fill with deliberate practice.

Boot camps allow us to examine our experience, to judge what we lack and learn how to act differently. In these spaces, however, we seldom inquire why we had an experience, where the ideals come from, what makes them ideal, what they afford us, and what they cost us. For the purpose of incremental learning, those lines of inquiry are impractical and inappropriately subversive.

Transformative learning through reflective engagement. In playgrounds, where transformative learning prevails, the work involved is reflective engagement.12 There, we are not just allowed but actually expected to subvert the power structure. We put experts to the side and our experience front and center.

Playgrounds often provide a clear frame for exploration but leave it broad enough that there is not one single way to fill it. The frame outlines what could be without prescribing what should be. It may be as simple as a call for innovation or inclusion that lacks detail on what kind of innovation to pursue or who to include. Such calls may seem abstract through the lens of incremental learning, because they offer little guidance about what to do, but they are liberating seen through the lens of transformative learning, because they leave room to define what to do.

The ability to learn from experience in the present — from moments, not models — is just what is needed when the past has become a hindrance and the future is unclear. Experts still play a role in transformative learning, but a supporting one; they encourage our engagement and gently guide our reflection. The work is easier said than done: We pay attention, have a conversation, and then let interpretations inform experimentation.

Since this way of working with experience is less familiar than the deliberate practice outlined above, let us break it down with the help of a group of executives from a tech company that I shall call Star.

Transformative Learning in Action

I met the Star executives in a formal learning space, a workshop designed to support a companywide strategic shift. The transformational intent of the workshop was clear to everyone — leaders must change before their company can — and consistent with the new direction the organization was taking. Overtly, there was a great deal of support for change. And yet, most of the executives involved agreed that the company was not changing as fast as they had hoped. They felt the clock ticking and wanted to discuss what they should do differently. They had little appetite to do what was needed most: slow down and understand why they acted the way they did before experimenting their way toward lasting change.

That became clear as participants, divided into groups, engaged in a simple exercise. Each group had to build a contraption to retrieve an object from a bounded enclave. They all had competence in excess and plenty of resources. The only pressure came from competing with teams of their peers. It is easy to dismiss such exercises as unrelated to the complex real world. I find that to be a flimsy defense against noticing, voicing, interpreting, and coming to terms with what is real about those activities — the way people think, feel, and act while working together. There is nothing more real, and consequential, than that in the world of work.

Notice the experience. The work of transformative learning begins with the simplest but most radical of steps. Pay attention to your experience in the present — the hum within, the buzz around. Notice where your attention flows. What is easy to see and do? What are you missing or leaving out? Try to set aside the past and the future; pause the what-if train of thought. Use your brainpower to notice what is in as much detail as you can.

As one of the Star teams approached the assigned task, executives took note of the large amount of material available and conceptualized two different contraptions, both of which would work. Resources were distributed within the group, and two prototypes were built. The team decided to test the simplest one, which won the competition. What happened next was fascinating. No one stopped to celebrate. They put the object back in the enclave and set off to retrieve it with their second, more complex contraption. The atmosphere was full of activity and stilted at the same time. People were tired, but they kept going until we made time to talk.

Voice it. Share your experience and inquire about the experience of others. Start from what you see around you, but don’t neglect what you sense within. Keep noticing as you discuss, with an ear to the variety of experiences in the same moment and place. Are there any patterns in who is seeing and sensing what? Keep judgment at bay. It is easier, and more fruitful, to learn from patterns of experience if you can approach them with an open, curious mind.

Once they started sharing what they had noticed, most of the group members seemed to agree: After realizing that they had two viable ideas, they had felt obligated to prototype both. And once the prototypes were built, they both had to be tested, even though the contest had been decided. More than one person admitted mixed feelings about it. They were proud of being creative, but it was also exhausting, let alone unnecessary, to do all that work twice. There was no trophy for a “second win.” One executive said that it had seemed inefficient, but he chose not to mention it at the time. Someone else asked, Why did they feel compelled to keep going? That question moved the work toward interpretation.

Interpret it. Ask yourself why you and others are having those experiences. Continue to resist judgment about what should or could have happened or what you need to do next. Focus on the meaning of your experience. Look at the data and linger on the why. Try to come up with interpretations that challenge the usual excuses: “We were short of resources; we did not have time; that is just the way we are.” How did you help sustain the status quo?

When they began wondering why they had kept working and ignored their own doubts, the first interpretation the Star executives landed on was “pride.” That felt plausible but incomplete. It could not just be pride, reasoned one participant, because their creativity had been on full display and their execution was successful the first time around. Why keep going? “Some of us would have been embarrassed otherwise,” a proponent of the second prototype said. It became clear that not wanting to shame others or to be shamed had been a major driver for the group, one that had kept them going even when it was not necessary.

Own it. Once you put aside interpretations that focus on external factors, you can begin to learn a lot about yourself and the people around you. Here you can bring past and future, your relationships and culture, into the conversation at last. How do your history and aspirations explain what is happening? What do the events unfolding say about your relationships with others involved and about the culture you share? Try to make links between those levels. Looking at experience as an expression of personal, relational, and cultural habits will yield insights about sources of resistance to, and avenues for, change.

To be without ideas, or to have ideas that wouldn’t work, would be as embarrassing in the exercise as it was in their daily jobs, several Star executives admitted. They were the senior leaders of a successful tech company, after all. And since they did not want to be caught in that shameful place themselves, they also avoided putting others into it. Passing on an idea was spoken of as “killing it.” Seen that way, product choices became existential threats.

People throughout the company felt and acted similarly in their day-to-day jobs. They took great pride in their creativity, hard work, and concern for one another. Their company’s culture valued “caring, indefatigable doers.” Fitting that profile reassured people that they were bright and useful. It also cost them a great deal of effort. And it made the imperative to stop what they were doing and change feel like a condemnation of their competence rather than an opportunity.

If upon reading this you are wondering whether Star is a pseudonym for your company, let me tell you a secret: I have witnessed the same pattern in many organizations. I have seen it in teams at established companies and at startups, with young high potentials and C-suite executives, with groups of men and women alike. “We wanted to give everyone a chance to shine,” managers usually tell me at first, when I challenge their obvious overwork. But what they set up, really, is not a level playing field for contributors; it’s a thick layer of busyness that disguises the organization’s deficits, because the thought of overcoming those weaknesses through learning induces shame. Seen that way, overwork is not the cause of our struggle to learn but a consequence — a defense mechanism.

Experiment. There is freedom that comes with transformative learning. If you can notice, voice, interpret, and own your experience, you can also begin to imagine how to change it. Once you have one or more plausible hypotheses out in the open, it is time to test them to confirm them, to dissuade yourself of their truth, or to refine them. All of that can be done through little experiments aimed at eliciting new experiences and drawing further conclusions.

At Star, executives looked for small ways to prevent overwork without inducing shame and ways to find and offer affirmation without using project approvals and successes as proxies for it. For example, one executive told me months after the workshop, “I keep asking myself and others, ‘Are we doing this because it is really necessary or because it would be embarrassing not to do it?’” Using this question as a prompt for reflection helped him distinguish between those activities driven by a sense of obligation and those that truly advanced his business unit’s strategic goals. He had also begun publicly praising people who stopped doing things that did not make sense or, more precisely, that made sense only from the perspective of the old culture. “We can give up the overwork without giving up pride,” he kept repeating. The employees in his unit were grateful for the new mantra.

The Brave Learner

I often meet people who say they want to learn from experience and really mean it, but they find that it is hard to muddle through without clear parameters. They want to be told what to focus on, assess their progress (and be assessed), and have a plan for putting what they’ll learn to immediate use. That response is understandable, and it’s compatible with incremental learning, which fosters alignment at work. Incremental learning makes us fit the mold. But transformative learning makes us misfits. It invites responsible subversion. That takes courage. It takes courage to own our complicity in the status quo, and it takes courage not to remain captive to it. Just as shame impedes learning and hampers leadership, having the courage to learn gives us the courage to lead.

Transformative learning does not transcend incremental learning, however. It lays the foundations for it. Transformative learning sets us free to envision and create a new future. Incremental learning makes us stronger as we pursue it. We might not be able to do both at the same time, but we are better off doing both over time.

Once we begin to master both ways of working with experience — deliberate practice and reflective engagement — they produce less shame and more courage. People who regularly make room for both types of learning, especially under pressure, eventually no longer need to be offered formal learning spaces. They make every space a learning space.

Doing that work on an ongoing basis develops attention, curiosity, and imagination — virtues that enhance one’s current leadership and one’s future expertise. And once we are brave enough to care for our own learning, we usually begin to care for others’ too, becoming the leaders that every organization needs and every employee deserves.