15 Lessons We’ve Learned from Building Transformational Learning Programs

Over the last decade, our team at Assemble has been a part of designing and managing nearly a dozen transformational learning programs — startup accelerators, student leadership programs, MBA programs, communities, and more.

We’ve made mistakes, and gained a good deal of insight; here’s a summary of what we’ve learned so far.

Getting Started

1. Forget most of what you think about education.

Traditional education is about demonstrating knowledge — what you know. It has little way of really recognizing what you can do, and doesn’t care who or what you are becoming. Transformation is all about the doing and being — the knowing happens along the way.

2. Identify one meaningful and hard challenge.

The easiest way to create a transformative experience for people is to put them in a challenging situation or give them something hard they have to accomplish together. Kurt Vonnegut had a rule about storytelling: Be a Sadist. Basically, make awful things happen to your characters so you can know what they’re made of. It’s kind of like that.

3. Give them something to help them find a way out.

Next, create some type of feedback loop they can use to know whether they are getting closer or further away from solving the challenge.

4. Get out of the way.

Most of what happens next will be driven by the learner’s own curiosity. If you designed the challenge and the feedback loop effectively enough, most of your work is done.

Principles As You Go

5. Respect the learner.

At the end of the day, they are the one who gets to decide what they need. If you don’t pay attention to the needs and desires of the learner (even if you don’t believe it’s what they really need), you’ll kill momentum. Adult educator Jane Vella framed this principle by encouraging others to answer the question: Who needs what as defined by whom?

Try This — Before starting your next session, send out (or write on a board): “By the end of this session, what do you want to have done?”

6. Don’t design a program, build a community.

Though we have created learning experiences that involve individual learners progressing through a concrete skillset, we’ve found that the best design focused on creating learning communities and is less like a teacher planning a linear curriculum and more like a bunch of people co-creating a play together in real-time. Learning communities function as complex adaptive systems — you don’t really know what’s going to happen until it happens.

Try This — Start a group or a session with the question, “If you were me, how would you help you learn this concept?” Then, go from there.

7. You have much less control over the community than you think.

Learning communities are living organisms; let them expand and shift however they need to. Your plan will change. The outcomes will likely change too. This unpredictability is a feature, not a bug. Great learning is an exercise in improvisation, and the job of a learner is to pay attention enough to see where the community wants to go, and go with it. See mistakes and surprises as opportunities.

Try this — Make it a habit of saying “yes, and” to all new ideas and hold the same expectation for participants in the community.

8. Think like a beginner, not an expert.

There are two big problems with being an expert if you want to create learning. First, you being really good at something makes it really easy for you to forget what it’s like not to be good at it. You suffer from the curse of knowledge. Secondly, as an expert, you probably care much more about optimizing the most minute and intricate aspects of your craft. But a beginner could care less about the most optimal way of doing something — they just want to get it to work. Think like a beginner and pay attention to what works.

Try this — If you’re introducing a new skill, boil everything down to a binary, and teach that binary. (i.e. “Business is about two things: sales and operations”, “Wax on, Wax off”)

9. Don’t create anything you wouldn’t want to experience yourself.

Unfortunately, we’ve all experienced classroom moments that bore us to tears. If we know the pain of a lesson created without taking the learner into account, why do we, when given the podium, decide to create equally painful experiences? Yes, it’s more difficult on the facilitator to create learning experiences that respect the learner — but if the true motivation is for real learning to occur, it’s all that matters.

Try this — Anytime you’re talking for more than three minutes, record it before hand. Listen to it. Getting bored? Trim the fat.

10. Moments create meaning. But change only happens over time.

We all have memories of powerful moments that solidified big transformations in our lives — finishing a marathon, attending a retreat, giving a big presentation or pitch. These experiences, although essential and deeply meaningful, are just the bookends of real transformation. What happened in the days, weeks, and months before and after are what determine whether or not real change occurred.

Try this — Pick one or two key habits or phrases you want learners to turn into muscle memory. Work them into the learning experience at least five times.

11. Live the experience.

We owe the language for this one to Steve Wanta, founder of Just. Try something as if you were the learner yourself before building it for someone else. Keeping yourself accountable to only asking others to do what you’ve already done yourself is especially critical in communities where status or power dynamics vary between student and teacher.

Try this — Instead of practicing or roleplaying, do the exercise. Actually do it. Seriously. Do it.

12. Repeat what matters over and over and over again.

The stickier the idea, the better — create sturdy handholds for your learners. Then, find ways to show that same idea over and over again, in different and increasingly complex contexts. There’s a difference between being able to do something and gaining mastery of that thing. We’re looking for mastery.

Try this — If a concept, skill, or mindset is starting to feel boring, change the context and change the stakes. Challenge the learner to use it in ways that are unfamiliar to them.

13. Examples and contrast are two of your most powerful tools.

Don’t just tell me about it. Show me. And don’t just show me — show me what it looks like do it well and what it looks like do it horribly. The contrast helps me know the difference.

Try this — Have a “like this” and “not like this” example for every new skill or artifact you’re asking the learner to create.

14. Do real work together.

Apply new knowledge and learnings to actual tasks members of the learning community are responsible for — this is far more effective than teaching a concept through fictional exercises. Make this about their world as it is right now and increase the stickiness of new ideas exponentially.

Try this — Invite each learner to submit a relevant item on their current workload prior to your gathering, and invite them to apply the new knowledge learned on that task. This both invests them in the outcome and deepens understanding.

15. Whoever is reading, writing or speaking is who’s doing the learning.

Eliminate the gap between the speaker and the audience — the more people participating, the more learning.

Try this — Anytime a moment arises when you feel like you should read something, write it down, or discuss it — don’t — invite the learners into as much of the activity as possible. We remember what we do more than what we witness.

Tools & Resources to Help


  • Notecards — give you the freedom to sequence and resequence experiences.
  • Spreadsheets — can help you create high-level overview/story arc of what you’re building.


  • Whiteboards — capturing a conversation on a board as it happens creates a visual demonstration of the progress you’re making. It also lets you create connections between ideas and help you realize when you’re off track.
  • Sticky notes — let you capture a lot of input from each person in a short amount of time. You can then ask people collect and synthesize their thoughts by gathering their sticky notes together.
  • iPhone — take photos and record any live session for reviewing.


“I liked, I wish, what if?” — After each experience, ask your learners to write three short sentences beginning with “I liked…”, “I wish…” and “What if…” so you can tweak future learning experiences based on their needs in the moment.

What approaches, principles, tools, or resources have helped you?

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