When you recall some of the most intense learning experiences of your working life, they are often associated with some big project or assignment that was at the edge of your comfort zone. Challenges are exciting – the work is new, you learn quickly and deeply, and the reward for success is great. But challenges also carry a lot of risk.

When you support other people’s development, you often decide to put them in a position where their skills will be challenged. You assign them to tough projects, or to projects that are outside of their experience. Or you give them assignments that will require particular skills that need to be honed. To advance knowledge and skill, the assignment should be hard, but not so hard that learners are left floundering.  Giving someone a “stretch” assignment is a great developmental move – but it should come with built-in supports.

Giving challenging assignments is a form of experiential learning. And assignments don’t necessarily need to be deeply challenging to provide opportunity for learning. Actually doing the work, applying knowledge in context, and engaging in practice are important elements of anyone’s learning and development. Challenging work creates more learning opportunities, but it also goes to the edge of an optimal learning zone. To “challenge” well, it’s important to understand the learning process here.

The nature of learning from experience

In facilitating professional and leader development courses, I have often reminded people that there is a huge difference between having 10 years of experience and having one year of experience repeated 10 times. That difference is demarcated by learning. But how exactly, do people learn from their experiences?

David Kolb’s seminal conceptualization of the process of learning from experience is still relevant, albeit a bit oversimplified. Kolb’s theory proposed that experiential learning is generated from a cycle of experiencing, reflecting, sense-making (thinking), and applying (acting). As people have experiences, they turn those over in their minds, reflecting on what happened, why, how it connects to other experiences, and more. Based in that reflection, they abstract lessons, articulating principles for action in the future. Then, they experiment to see if the lessons they have garnered are indeed playing out in other contexts.

Other theorists have explored the phenomenon of learning from experience, offering more complex cycles and more expansive descriptions of experiential learning interplay that can be comprised of individual experience, context, reflection, interactions with others, thought processes, emotional engagement, and embodied knowing. A number of practical insights can be drawn from these theories.

Facilitators sometimes attempt to engage experiential learning by walking through a series of debrief questions. They ask: What happened? How do you feel about that? What lessons have you learned? What will you do next time? While useful, these questions are a bit of an oversimplification of what the cycle entails. You can do better by more deeply setting people up and actively facilitating them through the process of learning from experience.

The belief that all genuine education comes about through experience does not mean that all experiences are genuinely or equally educative. ~ John Dewey

Drivers of learning from experience

These are some of the keys to ensuring that the tasks and challenges you assign to employees advance their knowledge and skill, expand their cognitive understanding, and improve their capability to act.


To learn from experience, it’s helpful to go into the assignment with a learning goal. With so much going on around them, employees have to prioritize what they will attend to, where to devote energy. Some projects hold great promise as a testing ground for a developing skill, or an opportunity to pay close attention to experts they may want to emulate.

In their paper on learning better from work, David Perkins, Michele Rigolizzo, and Marga Biller advised people to approach some projects with a “developmental stance” – treat the assignment as an opportunity to shine (to do the job well) and also to take the learning from that assignment into future opportunities. When people take a developmental stance, their learning is intentional, not accidental or incidental. Intentional learning is focused and motivating. The development stance can be taken once people have identified the skills that have staying power – the ones they want to put effort into developing more deeply.

Leaders support intentionality in several ways. They help people prioritize their development goals. Not every project is ripe for learning, and you need to identify the right opportunities. When making assignments, a leader should share desired learning outcomes as well as the needed project outcomes. Or the leader and employee can agree together on learning outcomes for a project and ways to get there.

Scaffolding and support

In theory, when you assign challenging opportunities, you’re placing people in a “zone of proximal development” – a space in which they need support to advance to the next level of performance, and by definition, a space where developers need to take an active role to ensure learning happens. (The ZPD is the gap between what the learner can already do, and what they can do with the support of a more knowledgeable other.) That means leaders have to give people the support they need to get started, to learn the basics, and to get feedback on progress.

Scaffolding comes in many forms: direction, side-by-side coaching, job aids, Q&A support, role models, barrier mitigation, and more. The trick is knowing when to start removing supports (also known as “fading”) and let the learner gain confidence by doing the work on their own. (Teaching a child to ride a bike is a good analogy to keep in mind – eventually, you remove the training wheels and stop holding on while they pedal.)


Every theoretical breakdown of experiential learning has reflection at its heart. It’s in reflection that people make sense of the experience and pull apart its nuances. It’s from reflection that their mental models change and plans for future action are developed.

Reflection also comes in many forms: rational analysis, introspection, inquiry, collaborative meaning-making, deconstruction, assumption-questioning, and checking in on embodied awareness (what your gut is telling you) to name a few. The conclusions that people draw, lessons they learn, and next steps they devise are predicated on how deeply they have reflected on the experience.

Depth of reflection – and the insight gained therefrom – is greatly expanded when people enlist others in the process. Left alone, people may not ask themselves the right questions, or may have limited perception of a situation, or may be too influenced by their own history and biases.

Leaders support reflection by asking reflection-provoking questions (in addition to good coaching questions), demonstrating their own reflection aloud, building reflection into operating procedures. and making it a point to reserve time for reflection. These are simple bits of advice, belying how critical and potentially impactful support for reflection can be.

“We do not learn from experience… we learn from reflecting on experience.” ~ John Dewey

Psychological safety

To step out of a comfort zone into a learning mode, people need to believe that they won’t suffer dire consequences if they stumble along the way. People need psychological safety, the freedom to question, to raise concerns, to make suggestions, and to try new things.

Leaders create that safe-to-learn environment by ensuring that employees know proscribed procedures and have baseline skills before setting them loose on projects. Leaders set boundaries for experimentation and identify projects as learning assignments or pilots to minimize pressure. Just as important, they recognize and applaud good faith tries that nonetheless end in failure, and they ensure that people articulate what they learn from the experience, whether successful or not. At the same time, leaders are open about their own learning projects and mistakes, and they role-model due diligence and involving others in deliberations and decision-making.

Challenge as a developmental move category

As far back as John Dewey’s time, we have understood that “learning comes through experience.” These days, L&D professionals often pass around the mantra that “work is learning” or “the learning is in the work” (possibly started by Harold Jarche). In experience, people gain situational and tacit knowledge that simply can’t be codified and taught through other means.

While challenging special assignments are fertile ground for rapid learning, everyday experience has challenges as well. If leaders take the time to look around, there are no doubt plenty of tasks and assignments that can double as developmental opportunities. In the challenges afforded by the work, you have terrific opportunity to accelerate knowledge and skill development. The work needs to be done; you may as well use it to advantage.

“A mind that is stretched by a new experience can never go back to its old dimensions.” ~ Oliver Wendell Holmes


Some terrific sources for deeper understanding of how to help others learn from work challenges.


This post is part of a series exploring the moves leaders can make to promote development of their teams and employees. Check out the entire developing people series. And please get in touch if I can help you to aquaint your leadership team with these moves and the details of practices that ensure they are effective. I can offer a workshop and other learning materials on the subject.