Top Questions to Ask to Create Engaging Workshops, Meetings, & Learning Experiences in 2026
Every January, we forget more than we’d like to admit from the year before. Not because these lessons weren’t meaningful, but because our brains tend to only hold onto what is most salient, what leaves an impression, or what we revisit over time.
So in the sprit of practicing what I preach, I pulled together key questions and a simple checklist (with the help of Google’s Notebook LM) to capture the biggest insights from my monthly newsletter, Not Taught in School, in 2025.
If your a newsletter subscriber, I guarantee you don’t remember them all (none of us do), which is precisely why I think it’s so important to revisit key ideas, slowly, repeatedly, and intentionally, to make sure learning sticks.
You can think of this as a quick, practical guide to design your learning experiences in 2026 to feel more human, intentional, and effective.
This guidance is not exhaustive, but they’re all grounded in insights I shared throughout Not Taught in School in 2025. I’m looking forward to updating this list as the year unfolds and new insights emerge in 2026.
If you want the formatted PDF, including links to every resource shared in Not Taught in School throughout 2025 go ahead and scroll to the bottom and download it at the end of this post.
Top Questions to Ask Yourself to Create an Engaging Workshop, Meeting, & Learning Experience in 2026
Learning Foundations
Am I creating the right amount of stretch?
Will participants be challenged in a way that expands their capacity without pushing them into overwhelm?Have I built scaffolding into this experience?
Did I break down the content, model the steps, or provide prompts that help learners move from knowing to doing?Where am I reinforcing consistency?
Did I design small nudges, reminders, or recurring habits that help the learning stick over time?Is this designed for doing or listening?
How am I balancing active, experiential activities with long stretches of passive consumption?Am I using AI to replace human experience or speed up production?
Does the final product still reflect my lived experience and what my learners actually need?
Facilitation and Engagement
How am I opening the space?
Is my introduction grounding, meaningful, and intentionally designed to bring people into a shared mindset or reviewing the agenda?Will every voice have a way in?
Am I providing opportunities that democratize participation instead of relying on whoever speaks first?Am I truly facilitating or am I leading a meeting?
Have I created conditions for interaction, conversation, and shared ownership of the learning?Where have I intentionally built in time for reflection?
Are there moments to pause and reflect or am I focused on filling every minute of the agenda?
Visuals & Design
Have I led with visuals where it matters?
Does the experience help learners visualize the idea and not just read it?Is my content skimmable?
If someone looked at your content for 10 seconds, would they understand the structure, the point, and what matters most?
Behavior Change & Real-World Impact
Am I choosing the right technique for the outcome I want?
Does the design match the goal: motivation, knowledge, or action?Have I incorporated the three pillars of training effectiveness?
Relevance: Do learners understand why this matters right now?
Interactivity: Will they have a chance to apply or test the idea?
Environment: Will their workplace support them in using what they learn?
If these questions help you see your learning experiences differently, the full 2026 Training Design Checklist goes even deeper with links to all the resources mentioned in the newsletter in 2025. It’s beautifully formatted, actionable, and designed to help mission-driven teams create learning that is both research-backed, human, and designed for modern learners. And if you’d like future insights like this delivered directly to your inbox, I’d love for you to subscribe to Not Taught in School.
