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Beyond Training: How to Design Transformative Learning Experiences

Sean Acklin Grant

March 10th, 2025

Most corporate training solutions don’t live up to their promise because they transfer knowledge instead of transforming thinking. Deep learning happens when leaders are pushed to wrestle with tough decisions, challenge their own assumptions, and apply knowledge in real-world contexts. It’s uncomfortable. It forces reflection. And it’s exactly what’s missing from most L&D programs.

This article breaks down what makes learning transformative and offers practical tips to create experiences that actually change behavior. From mapping learning goals to choosing the right methods and facilitators, here’s a primer on how to deliver leadership development that sticks.

The Problem with Traditional Training

Most leadership training is built on a flawed assumption: that knowledge leads to action. Organizations spend significant time and money on programs that are content-heavy, overly structured, and focused on information transfer — expecting that leaders will somehow apply what they've learned to create value. If information alone created better leaders, we’d all be flawless after reading a few HBR articles. The reality is that people don’t change just because they’ve been told what to do. Leadership is not a set of static skills that can be memorized; it’s a complex, adaptive practice that requires decision-making, reflection, and application in unpredictable environments.

Consider the last time you faced a difficult decision at work. You probably weren’t thinking about a framework from a slide deck you saw once. More likely, whether you recognized it consciously or not, you drew on your past experiences to project possible outcomes. It’s how we’re wired to learn from childhood. Traditional training often fails because it doesn't match the way we're designed to learn.

It’s passive. Sitting through a workshop or watching a training module doesn’t change behavior. Learning happens when people actively engage and experiment with new ways of thinking.
It lacks real-world context. Leadership is situational. Training that isolates skills from their real-world application creates leaders who know about leadership but don’t know how to lead in their own unique environment.
It focuses on retention. Most programs measure success based on attendance and knowledge checks rather than shifts in mindset and behavior. Learning that doesn’t challenge assumptions and reshape decision-making rarely leads to meaningful change.

Leaders don’t develop by passively absorbing information. They develop by making decisions, facing uncertainty, and engaging in difficult conversations. Transformative learning is about creating experiences that allow leaders to practice.

What Makes Learning Transformative?

Transformative learning challenges existing mental models by giving us new experiences to draw on. It’s why we ask for "years of experience” in a job description – because those years translate to perspective. If you’ve put in the time, you’re more likely to have already encountered similar situations when faced with a high-stakes challenge. Designed correctly, transformative learning allows you to accelerate and compress those years by testing decisions in a risk-free environment. Three key elements make learning truly transformational.

Active, immersive experiences

Learning happens when leaders are forced to engage, make decisions, and take ownership of their growth. “Experiential” learning is the buzzword — in practice, this means cases, simulations, role-play, coaching, and problem-solving exercises.

Cognitive and emotional engagement

Learning that is personally relatable and emotionally charged creates a deeper impact. That’s why we remember embarrassing situations for years despite the mistake having been long-forgotten by those around us. People learn best when the material is relevant to their lives, engaging both the head and heart.

Reflection and sense-making

Taking time to process, debate, and extract personal meaning from an experience is critical to retention. Transformative learning requires structured reflection that helps leaders connect insights to their own leadership challenges. Talent assessments can help with this process.

The guideline is that if leadership development doesn’t challenge assumptions, stretch comfort zones, or require active decision-making, it’s not transformative and it’s significantly less effective.

Mapping Learning Goals to Transformative Experiences

To design a transformative learning experience, start by defining what kind of change you want to create. Instead of asking, “What skills should we teach?” shift the focus to:

What mindset or behavior shift are we trying to create?
How should participants think or act differently after this experience?
What real-world leadership challenges should this program help solve?

Once the goal is clear, the learning format must match the type of transformation you’re aiming for:

For complex decision-making, use case-based learning. Present leaders with real-world dilemmas that force them to analyze trade-offs, make tough calls, and defend their reasoning.
For leadership under pressure, use simulations. High-intensity, real-time scenarios help leaders develop resilience and decision-making in uncertain environments.
For interpersonal skills & communication, use role-playing & peer coaching. These methods create safe spaces for practicing difficult conversations and leadership presence.
For strategic thinking, use live problem-solving challenges. Bring in real business problems and have leaders collaborate on solutions, applying their learning in real time.
For self-awareness, use self or peer assessments. Give leaders a framework to evaluate their own habits — not for evaluation, but for reflection.

Just as important as choosing the right format is measuring impact beyond participation. Instead of relying on post-training satisfaction surveys, consider the following dimensions of success.

Measure improvements in confidence. Do leaders feel more prepared to handle complex challenges? Confidence in applying new skills is a strong predictor of long-term behavior change.
Note application in real work. Are leaders using what they learned to make different decisions? Personal commitment to applying learning can be a strong indicator of the likelihood of applying learning.
Track behavior change over time. Do colleagues notice a shift in how leaders approach challenges? Revisit structured peer assessments like 360s to track perceived improvement.
Evaluate business impact. Has the learning led to tangible improvements in performance, collaboration, or decision-making?

Designing the Experience: Key Elements of Transformative Learning

As strange as it may sound, a transformative learning experience is often focused more on how learning is delivered than what learning is delivered.

This is a tough mindset shift for many HR leaders because organizational systems like competency models and development pathways often push us towards a checklist of topics that map to knowledge. It’s important to read between the lines and think about the unwritten impact of a learning experience.

Here’s what separates high-impact learning experiences from forgettable training:

Introduce discomfort in a safe way

The best learning happens when participants struggle just enough to push their thinking but feel supported in the process. At work, you might get this safety from a great leader who supports you when you make mistakes. In a learning environment, the ground rules are key. A facilitator must create an atmosphere of mutual respect, inclusion, and openness for this method to succeed. Start the session with 5 minutes of brainstorming on what learners will expect from one another – this inspires group ownership over the dynamic and culture in the room.

Use real-world complexity

Leadership is messy. Learning experiences should reflect that by incorporating ambiguity, competing priorities, and real trade-offs. Wait until the end of a session to introduce knowledge and frameworks. Allow learners to struggle and debate, then use theory to help them make sense of the experience.

Facilitate deep reflection & discussion

Leaders don’t just need to experience something new; they need space to process and make sense of it. Use structured debriefs, group discussions, and personal reflection to amplify learning. A common pitfall in learning design is feeling like you need to create a jam-packed day of learning to make it worthwhile. Give people time to absorb. For example, instead of presenting a bullet list of takeaways at the end of a session, you can instruct your learners to split into pairs and find a quiet spot to synthesize their personal insights.

Make it personal

The best learning happens when leaders can connect new insights to challenges they are facing right now. Use exercises that tie learning to real-world leadership situations. If the group all work together in one organization, use a real situation for action learning (being mindful not to make it too personal with a contentious topic). If the learners come from different organizations, use structured sharing like buzz groups to encourage a free exchange of ideas and insights. A good case study can also make the learning personal if the themes are relatable enough that most leaders will have encountered a similar situation in their careers.

Transformative learning is about creating similar conditions to those a leader might face at work. Your goal is to create memories, not memorization. But again, this should always be done in a structured, safe setting led by an experienced facilitator.

The Role of the Facilitator: What Skills Matter Most?

Even the best-designed learning experience will fall flat without the right facilitator. Great facilitators create the environment for transformation and guide learners through their discomfort. Here’s what sets them apart:

Guide, don’t lecture. Instead of acting as the expert, great facilitators pose the right questions, challenge assumptions, and create space for exploration.
Step aside when necessary. In a room of 30 leaders each with 20 years of experience, you have 600 years of combined knowledge to draw on. An expert facilitator centers the ideas and contributions of the learners.
Create productive tension. Learning happens when people wrestle with new ideas. Strong facilitators push participants to engage in difficult conversations and rethink their perspectives while still maintaining the all-important ground rules.
Adapt to the room. No two leadership groups are the same. Great facilitators read the energy in the room, pivot discussions, and adjust based on what’s resonating. It’s OK for the session to diverge from the plan as long as your facilitator is also comfortable with ambiguity.
Help leaders connect the dots. The best learning experiences aren’t about what’s taught; they’re about what’s discovered. Skilled facilitators help participants link insights to their real-world leadership challenges.

A facilitator shouldn’t just be a source of knowledge. You need someone who can catalyze and shape the learning experience in the moment. Now that we’ve set the stage for transformative learning, what’s next?

How to Get Started with Transformative Learning

To move beyond traditional training and design learning that truly transforms, start with these steps:

Audit your leadership programs. Are they passive or immersive? Information-driven or transformational? Identify where you need to introduce more engagement, challenge, and application.
Pilot a small change. You don’t need to overhaul your entire program overnight. Start by integrating case-based learning, live problem-solving, or deeper reflection exercises into an existing workshop. As long as you learn from your experiments, you can’t fail.
Get feedback and iterate. The best learning experiences evolve. After each session, ask participants: “What challenged your thinking the most?” If nothing did, it wasn’t truly transformative. Think about what success looks like, and design your measurement around those metrics.
Consider your facilitators. This is where theory meets application. Invest in facilitators who can challenge, adapt, and create meaningful learning moments.

If your leadership programs aren’t changing behavior, improving decision-making, or driving real business impact, they’re just checking a box. The best leadership development isn’t about training — it’s about transformation.

Sean Acklin Grant (MA) is a talent development leader who helps global organizations build leadership readiness. As Director of Open Executive Programs at Ivey Business School, he works with the faculty to create immersive learning experiences that drive real impact. Leveraging a background in public policy, entrepreneurship, and brand strategy, Sean challenges leaders to rethink assumptions and apply insights to real-world problems.