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    Home»Business & Economy»US Business & Economy»Here’s Why Most Employee Training Workshops Fail
    US Business & Economy

    Here’s Why Most Employee Training Workshops Fail

    News DeskBy News DeskOctober 14, 2025No Comments8 Mins Read
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    Here's Why Most Employee Training Workshops Fail
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    Opinions expressed by Entrepreneur contributors are their own.

    Key Takeaways

    • A successful training workshop needs to tell a good story. Framing lessons as narratives helps participants connect ideas, remember concepts and see how challenges lead to solutions.
    • Establish a learning environment where people feel safe to make mistakes and try again without beating themselves up for it.
    • Leaders should also encourage better teamwork and insert a bit of showmanship into their lessons to make them stick.

    After decades of guiding enterprise brands through the design process and running internal workshops to help cross-functional teams function better, a friend who was teaching in Stanford’s continuing studies department suggested that I should be teaching, too.

    My “Design Thinking and Innovation” course became one of the department’s most popular classes. The success of the course came down to four key principles that lay the foundation for an impactful curriculum:

    1. It told a good story

    2. It gave students the freedom to be curious

    3. It encouraged better teamwork

    4. It had a bit of theatre

    What does this look like in practice? Let’s dig in.

    Telling a good story

    While the methodologies that I’ve formed throughout my career do not have to be done linearly, it really helps to cement an idea in people’s minds if they know how each element builds off the other. You need to explain how a challenge or design problem becomes a tested solution that builds value for an organization and its customers.

    Start by using Joseph Campbell’s time-tested storytelling framework with your hero, a place and an inciting incident. Then, introduce conflict: The action builds with challenges until you reach a solution, and your hero comes home a changed person. Humans have relied on stories for millennia to make sense of our world and form memories, so be sure to craft all lessons as a story arc.

    In one workshop, I teach teams to start with empathy and problem-finding before they start brainstorming, because they first need to have a full understanding of their users and the jobs those users need to do. We start with the user as the hero, outline the problem they are facing, identify potential solutions and then experiment to arrive at an inspiring outcome. That last element is key: The solution always needs to be tested.

    Little stories throughout the teaching also help to cement learning. Things like case studies, storyboarding techniques or scenario-based learning moments are all helpful tools to reinforce training material.

    Establishing a safe learning environment

    Today’s companies tend to operate with a CYA (Cover Your Ass) mentality, but the most innovative businesses are the ones that are inherently curious, and that starts from the top down. The same applies to teaching. When teaching, you need to lead by example. If your students go about things in the wrong way, there’s no need to panic — it’s your job as the teacher just to help them course-correct a bit.

    I’ve written about psychological safety before. It’s the belief that you won’t be embarrassed or punished for speaking up. Part of learning is doing something wrong and being corrected; however, you need to establish an environment where people feel safe to make mistakes and try again without beating themselves up for it. Learners learn through trial and error and iteration.

    Some ways that you might sense low psychological safety are if folks say things like, “This might be a dumb idea, but…” or “You may have said this, but I am confused by…” As the person leading the learning, I work to eliminate those insecurities by admitting when I don’t know something and sharing moments of my own failures. This gives people permission to do the same.

    Another way I try to create psychological safety is to get to know people. Set aside 15 minutes before each session so that you can greet each person who comes in and work on building a rapport with each of them. If you can’t get to everyone in those 15 minutes, make an effort during break times. We want teams to do this with each other, so I like to model it.

    Teammates need a safe space to think big, bold and beyond, where they can feel comfortable ideating without judgment. Celebrate the journey with them, and you’ll get a better outcome.

    Encouraging better teamwork

    I’ve heard it said that, “In great teams, the lightbulb isn’t over one head, it’s over the whole table.” This requires learning to not only have empathy for the customer/user, but also for each other. When people feel empathy for each other, they collaborate more freely and eliminate friction.

    I once sat in on a fireside chat at Stanford with Jony Ive, Apple’s former Senior Vice President of Industrial Design and Chief Design Officer. He spent a good part of the discussion talking about how he got his team at Apple to work better together. For example, every Friday morning, one person on the design team would make breakfast for the whole team, and they took it in turns. I thought this was brilliant. These small acts of kindness for the team inspired things like vulnerability, reciprocity and gratitude — all key elements of building a solid team.

    While it helps to encourage teams to do things for each other — even if it’s just picking up coffee — I’ve also found success in assigning people simple roles in the classroom so they understand how the activity translates to real-world experiences. If we split into groups for a project, I like to assign a facilitator, a timekeeper, a scribe, etc. The balanced participation helps tremendously in teaching teamwork.

    Being the greatest showman

    I believe that the best teachers are not just smart people and educators; they are also stage directors, live theatre actors and magicians. When you combine what you know with a little showmanship, you create memories that people carry back to their work.

    Some elements of this are simple, like using your hands, varying your verbal speed, pacing your intensity, pausing to avoid monotony and not apologizing for stuttering or tripping over your words. I also find that deliberately moving throughout the room helps keep the energy alive, as do a few jokes. Think about the last time you saw a play or musical and how so much of the above was key to the entertainment of the story.

    Other elements are more complex, like meticulously preparing your class plan, timing your curriculum to fit a class length and term and learning how to read the room. Showmanship does not mean showing off.

    I had a friend who was in a big training session for a law firm. He told me that one of the speakers always showed up in a big Uncle Sam hat and crazy overcoat to deliver his lecture every day. The costume and props did not have anything to do with his topic. While the crazy get-up was clearly memorable, the lecture was not. My friend has never gotten over the silly outfit.

    All roads should lead to fun

    The combined purpose of these four principles is to make training fun. When people are having fun, they are not just enjoying themselves — they are learning better, remembering more and applying what they’ve taken away to their day-to-day beyond the workshop.

    Business is changing so rapidly. Your workforce needs to constantly learn new techniques, tools and methodologies if they’re going to build, market and sell products, programs or services. And they are only going to learn from training that moves them.

    Key Takeaways

    • A successful training workshop needs to tell a good story. Framing lessons as narratives helps participants connect ideas, remember concepts and see how challenges lead to solutions.
    • Establish a learning environment where people feel safe to make mistakes and try again without beating themselves up for it.
    • Leaders should also encourage better teamwork and insert a bit of showmanship into their lessons to make them stick.

    After decades of guiding enterprise brands through the design process and running internal workshops to help cross-functional teams function better, a friend who was teaching in Stanford’s continuing studies department suggested that I should be teaching, too.

    My “Design Thinking and Innovation” course became one of the department’s most popular classes. The success of the course came down to four key principles that lay the foundation for an impactful curriculum:

    1. It told a good story

    2. It gave students the freedom to be curious

    3. It encouraged better teamwork

    4. It had a bit of theatre

    What does this look like in practice? Let’s dig in.

    Employee Training employees Entrepreneurs leadership Managing Employees Training
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