Creating Engaging Workshops on New Tech

Back in 2017, my team had a simple but powerful ritual. We held "I have a design challenge" meetings, where someone would bring a project they were working on, and we’d workshop it together. These sessions weren’t just about fixing problems. They helped us grow our skills as a team and learn from each other’s perspectives. In 2024, I wanted to bring that same energy to learning designers looking to level up their skills in a fun and engaging way. This time, I turned to Tim Slade’s eLearning Challenges but took a different approach. Instead of just participating, we started doing live reviews of the challenge winners. How It Works One person drives the meeting, screensharing the challenge winner’s eLearning project while recording the session. We pause at each screen and ask two simple but high-impact questions: ✅ What worked well and why? ✅ What would you do differently and why? This sparks rich discussions on everything from instructional design and accessibility to visual design and interactivity. Everyone brings their unique expertise, turning the meeting into a collaborative learning experience. Want to Try It? Here’s What You Need ✔️ A web conferencing tool with recording capabilities ✔️ Adobe Premiere Pro or a transcript tool (optional, but helpful) ✔️ A generative AI tool like ChatGPT, Gemini, or Claude (optional for extracting themes from discussions) After the session, we take the recording and import it into Adobe Premiere, which generates a transcript in seconds. Then, using GenAI, we pull key themes, quotes, and takeaways, turning raw discussions into actionable insights. Why This Works This approach takes learning from passive to interactive. You’re not just seeing best practices. You’re critically analyzing them with peers, learning through feedback, and refining your own instructional design instincts. Would you try this with your team? Have you tried something similar? What worked well? #InstructionalDesign #GenAI #LearningDesign #eLearning #AIinLearning #CourseDevelopment #DigitalLearning #IDStrategy #EdTech #eLearningDesign #LearningTechnology #InnovationInLearning #CustomerEducation

Another AI tool that we've been exploring internally at Dropbox is Cursor. While there had been a few workshops on Cursor in the past, adoption among designers remained relatively low. That’s when Tuyen Truong decided to step in and do something about it. Instead of waiting for top-down support, she launched a grassroots initiative. She curated a small group of Cursor champions internally and brought in Jacob Ketcheson, an engineer from our design systems team, to help co-lead the session. But what truly set this workshop apart was how it was run. Tuyen created a space that was explicitly safe for beginners—acknowledging up front that yes, tools like Cursor, especially with Terminal and Git integrations, can feel intimidating if you're new to them. That moment of empathy changed everything. The result? One of the most engaged sessions we've seen, where designers not only asked questions but also successfully set up Cursor and began using it immediately.  ✨ The takeaway: If your team isn't adopting a tool, it may not be a lack of interest—it could be a lack of support, space, or psychological safety. We’re all learning as we go. The more inclusive we make these conversations—especially around AI—the more perspectives and creativity we get to tap into. And that’s the real win. #AITools #Cursor #DesignTools #ProductivityTools #AICollaboration

Last Friday, I sat around a table with district leaders from across Central Ohio designing a series of workshops on disciplinary-specific AI literacy. These are some of the most thoughtful educators I know. People leading real implementation work in their districts, not just writing policies. And we spent most of the meeting sitting with uncertainty. Here are the genuine design tensions we're navigating: The sequencing question: Do we lead with creative engagement (showing what's possible with AI) or with demystification (how does this actually work)? One approach generates excitement and buy-in. The other builds the functional understanding teachers need to make good decisions. We're not sure which comes first. The flexibility problem: Teachers enter this work with vastly different levels of readiness and willingness. Some are already experimenting. Others are skeptical or overwhelmed. How do we design for that range without either boring the experienced folks or losing the hesitant ones? The accountability tension: We need teachers to actually implement what they learn and report back so we can refine the approach. But we also need flexibility for teachers to adapt to their specific contexts. How do we structure accountability that supports learning rather than compliance? The coherence challenge: We want discipline-specific approaches because history teachers need different things than math teachers. But we also want some consistent framework so students aren't completely confused when AI expectations differ across classes. We made decisions. We're moving forward. Teachers will build chatbots that complement their disciplinary work. They'll learn to position AI as an interactive source students interrogate using existing critical thinking practices. But we're also honest about what we're still figuring out. This is the actual work of implementation. Not having all the answers. Designing with uncertainty. Building in public with educators who trust the process enough to pilot approaches that aren't fully formed yet. Two days later, I stood before over 200 educators at the Ohio School Boards Association conference. The energy was extraordinary. Not people anxious about AI. People committed to preparing students for engagement with AI that maintains intellectual agency. The work is hard. The questions are real. And we're doing it together. What design tensions are you navigating in your AI implementation work? #AILiteracy #EducationalDesign #TeacherLeadership #ProfessionalDevelopment Mike Taubman Mike Kentz Alex Kotran Andrew Rotherham Amanda Bickerstaff Alfonso Mendoza Jr., Ed.D. David H. Dr. Lance Cummings Rob Nelson

One thing I've started doing for my 2-4 hour workshops... Before I ever step in front of the team, I survey them. Not about what they know about AI. About what's eating their time. "What's your most repetitive task?" "How many hours a week does it take?" "What do you dread doing every Monday morning?" Then I build the workshop around their actual workflows. Not generic demos. Their stuff. After the session, I send the same survey. And here's what keeps blowing my mind: 40%+ productivity increases. Tasks that took 3 hours now take 45 minutes. Weekly reports that used to steal entire afternoons are done before lunch. This is why I don't believe in "AI awareness" training anymore. Awareness doesn't move the needle. Implementation does. If your team can't point to a specific task that got faster after an AI training, the training didn't work. #ai #aitools #aitraining

I'm heading up to LA this week for my first AI workshop of the year. Most companies think they have a technology problem. Usually, they have a silence problem. When leadership announces a new initiative (especially one as volatile as AI), the room often goes quiet. The engineers are worrying about technical debt. The operations team is worrying about job security. The managers are worrying about undefined ROI. The result is usually a top-down mandate. Everyone nods their heads in the meeting, but no one actually believes the plan will work. This is why I structure my workshops differently. The goal isn't to lecture on LLMs or show off cool demos. The goal is to bring the people on the sidelines into the game. Real innovation requires psychological safety. It requires a space where the quietest person in the room feels safe enough to challenge the loudest. In Grow Up Fast, I wrote about how interpersonal dynamics shift as a company scales. In the early days, alignment is free because everyone sits at the same table. As you grow, you have to intentionally manufacture that alignment. If you don't, you end up with "milquetoast outcomes" because everyone is too afraid to speak the truth. To break this silence, I use a framework of conversation starters. We don't start by talking about AI. We start by talking about pain. We put specific, hard questions on the table: 1. What keeps your typical customers up at night? 2. What repetitive questions or problems do your clients frequently encounter? 3. If everyone in your organization suddenly became 50% more productive, what would you do with the excess capacity? These questions shift the focus from "How do we use this tech?" to "What problem are we actually trying to solve?" It forces the team to translate "we should use AI" into concrete, prioritized opportunities tied to real business objectives. When you facilitate this kind of dialogue, the dynamic in the room changes. You stop seeing AI as a threat to headcount. You start seeing it as a solution to the "grunt work" that burns people out. You identify the bottlenecks that are slowing down decision-making. You find the areas where the business is making decisions without adequate information. Most importantly, the team leaves with a shortlist of pilotable projects they actually own. They aren't executing a mandate from above. They are executing a plan they built together. That is the difference between a tech demo and a transformation.

35 people. 3 workshops. 90% adoption. We just wrapped up a training series for a new customer. They wanted to go beyond demos and get their hands dirty. To take them further, we adapted our Bootcamp Series and ran a custom workshop track for their team of 35. Here’s what we did: Workshop 1: Demystify AI Set the foundation. How AI works, what it’s good at, where it’s risky. Workshop 2: Prompting & Bot Building Merged our prompting and GPT builder sessions. Everyone built bots. Workshop 3: Automation & Agents New session focused on AI at work...building automations to scale AI. That was just part of it. As part of our engagement model, we also met weekly with their leadership team. Talked trends. Showed live demos. Explored practical use cases. Results? 4.4/5 --> confidence using tools like ChatGPT 4.4/5 --> better understanding of how to apply AI at work 90% --> of the team using AI in new ways just weeks after training What they told us mattered most: - "Building GPTs together, having something we could use at the end." - "Learning how to prompt properly. The lightbulb finally went off." - "Understanding personas and tone really helps get quality outputs." - "Automation tied it all together with actual process improvements." And here’s how we can improve: - Break the sessions into shorter blocks. - Give more structure around automation tools. - Add more “what to do when it doesn’t work”. - Create more space for small group hands-on time. This was one of our favorite engagements to date. When coming to us, this company had a clear appetite to learn AI. Now, they have real momentum. If you're looking to do something similar, then get in touch! [This post was Human Generated, Human Approved]

The Power of Design Thinking in AI Education Workshops Inspired by Jerry Crisci's insights on AI in Education keynotes (if you're not following Jerry yet, you're missing out on an incredible thought leader in this space!) I've discovered that approaching every workshop through the lens of Project-Based Learning and Design Thinking creates magic. Here's how I break it down: Empathy: I start by acknowledging the elephant in the room - the fears and uncertainties around AI in education. It's real, and it matters. I say that it's okay to feel lost, or behind. I then ask for the audience to have an open mind and just be curious about what I might have to say. - 5 minutes Define: A concise AI briefing that cuts through the noise, is simple, and is easy to understand. Eg. Large language models are advanced computer programs that learn from HUGE amounts of text data to understand and generate human-like language, enabling them to perform a wide range of tasks like writing, translating, and reasoning. (Think like a chef - There is a pan, you put it on the stove, you turn the gas on, it cooks) I provide links for further exploration of AI if people are interested. - Maximum 3 minutes Ideate: We get into creative exercises (like "Choose your AI superpower!") that spark imagination and break down barriers. The idea is to rethink AI from the definition. - Gives me a break to involve the audience and engage them, I set a growth mindset, the power of yet, and off we go. I discuss their answers, and connect to how these crazy ideas are becoming reality, and why we need to think out of the box with AI. - 5-10 minutes Prototype: Together, we build an AI-enhanced project from scratch. I scaffold, but the audience drives the creation, choosing something like "Jazz", making it real and relevant. - 10-20 minutes Test & Reflect: I read through the AI output. I show how you can re-iterate or extend, or even just push AI to make a better output. We close by mapping concrete next steps. - As long as needed until end Next Steps - I provide my book, guides, e-mail, AI Tools to create better prompts etc. If we have time, the audience is welcome to use the prompt / learning designer tool etc, and we reflect, or I take them through the process as if we are making this in real time. To me, the audience has built something tangible, something they can implement tomorrow. I'm not a huge fan of Q&A's at the end, I try to integrate reflection points throughout, but it's always open if someone has a question that is related or unrelated (I often get random PBL questions, some questions about getting started with AI, and some questions about the PBL packs I have created) My goal is to introduce PBL and showcase how amazing AI can be integrated with PBL. What are your tips for success in AI in Education workshops/keynotes? Matthew Karabinos, MAT #AIinEducation #ProfessionalDevelopment #DesignThinking #EdTech #TeacherPD #Education #ArtificialIntelligence

I've been involved with conferences for years – even on Shoptalk's Advisory Board when it was small. But still, facilitating a workshop at a brand-new conference from the founders who sold Shoptalk? That still had me nervous. A few weeks ago, I facilitated a workshop at Retail Tech Club – the new conference from the team behind Shoptalk and Grocery Shop. Over 500 people by the ocean in Huntington Beach. I led a discussion with 15 participants – retail leaders, brand executives, AI champions, and tech changemakers – on navigating the AI hype: Tech Fit, Data Fit, and ROI. Here are five things that help me facilitate workshops that work: • Set the framework and expectation upfront. Be crystal clear: why they're here, what they'll take away, what the boundaries are. Without it, everyone has different expectations – and even an amazing discussion can feel like a failure if you missed theirs. • Ask open-ended questions and stay dynamic. Give others the mic. Don't dominate, and don't let anyone else dominate either. • Don't fear the silence. When no one responds immediately, we panic. But people just need time to process. Wait with them. • Move around the room. I was the only one standing. Moving adds flow. When someone asks a question, I walk closer. If someone's disengaging, I move toward them. Use your hands, be theatrical – body language is another tool. • And most importantly – let everyone contribute. A successful workshop means everyone feels they had something to say and learned from each other. They didn't come to learn from me – they came to learn from each other. Your role as facilitator is different than presenter. It's almost group therapy: everyone wants to share their "yes, me too, here's my story." What made this workshop work? Hearing how everyone faces the same problems. McKinsey says 75% of organizations think AI is important, 78% are implementing it, but under 20% generate real value. In the room, you could see it – everyone knows there's something here, but not everyone knows how to work with it yet.

We created 5 startups in 60 minutes in a FULLY-ONLINE class with ZERO slides! That's 5 startups with a pitch video AND a landing page in just an hour! I conducted my first-ever online-only Entrepreneurship Workshop. From a personalized AI-stylist to a contact lenses cleaner for the lazy folks out there, we saw it all! While Universities struggle to create in-person engagement, I managed to do this fully online. Here's how: 1. The Right Tools ↳ It’s not about comfort ↳ It's not about debating over Zoom vs. Teams ↳ It’s about engaging students, even if there's a learning curve :) 2. Engagement Techniques ↳ Techniques and timing are key ↳ They must involve interaction and not information-delivery ↳ Student Engagement is a skill, not a mere role :) 3. Feedback (not AI-generated) ↳ Feedback has to be constructive ↳ NO to AI-generated feedback templates ↳ I was a student too. I paid too much money to deserve GenAI feedback. Don't be that person :) 4. Time Management ↳ Online sessions are "always going wrong" ↳ Spend time driving learning, not setting up ↳ Use no slides. You're to be focused on. Not the slides. Look at your students, not slides :) 5. Growth Mindset ↳ Encourage students to fail fast & frequently ↳ Create a safe space for them to try new things ↳ This applies to you, me and everyone else. In every context :) I'm building What's On! Campus to help University Academics engage their students better. Need help engaging your students? Comment or DM me.

Great training does not happen by chance. It happens by design. After years of conducting workshops across industries, I have realized something simple but powerful. People do not learn when you speak. They learn when they engage. The most memorable programs I have delivered, the ones people talk about months later, all had one thing in common. Participants did not sit and listen. They moved, reflected, discussed, practiced, and applied. Here are the seven training methods that consistently create the strongest learning experiences for teams: 1. Experiential Activities People learn best by doing. Simulations, team challenges, and real scenarios create instant connection with the concept. 2. Case Studies Real stories make learning real. When participants analyze situations they relate to, insights come naturally. 3. Role Plays This is where theory becomes skill. Whether it is feedback, negotiation, or communication, practice builds muscle memory. 4. Group Discussions People bring more wisdom than any slideshow ever can. Peer learning is one of the most underrated tools. 5. Games and Gamification Competition adds energy. Games break inhibitions and make even serious topics enjoyable. 6. Video Based Learning A thirty second clip can spark more reflection than ten slides. Videos trigger emotion and emotion drives change. 7. Reflection Tools Journaling, self assessments, feedback rounds. This is where participants internalize what they have learned and turn insight into action. A training session is not a presentation. It is an experience. The richer the experience, the deeper the learning. If you want to conduct engaging training workshops for your organization, connect with me