Over the last 5 years, I’ve done more than 130 live events in industries like healthcare, defense, agriculture, executive coaching, non-profits, and tech (plus a bunch of others, but we’d be here all day with the list). Each is different, and often amazing.

Watched an intelligence community team realize they were telling a story about who they were that hadn’t been true for years. But no one had named it out loud until they saw it sketched.

Captured the somewhat unspoken tension between two departments at a leadership offsite, and that visual gave them a neutral way to address conflict instead of finger-pointing.

Helped a small group of software developers who couldn’t explain their work to outsiders suddenly have the language and imagery to pitch donors and partners with confidence.

All of this through the process of listening and sketching, listening and sketching.

It’s wonderful to see these breakthroughs, these “aha!” moments. But in those years, I’ve also noticed something else: there’s a crucial next step to all of this.

Think about when you’ve been to a training or learned a new concept. In this case, you leave energized, armed with beautiful visual artifacts and genuine insights.

Then it’s back to the desks or offices, the urgent takes over, and those breakthrough moments become distant memories filed away in folders. Or worse, forgotten entirely.

The sketches are transformative on their own. They capture breakthroughs, create alignment, and become lasting visual anchors. But I’ve discovered that adding strategic reflection multiplies their impact.

The live sketching creates immediate clarity and connection. The reflection ensures that clarity translates into lasting change.

What has struck me over the years is this: The most valuable conversations I’ve had with clients didn’t happen during the event.

These conversations happened afterward, in the reflection, when we worked to make sense of what they’d experienced.

Prep. Deliver. Reflect. Repeat.

In this world of visual sketching, there’s a four-part system ensuring necessary insights don’t disappear into the void.

Prep. This is the research into team dynamics, industry pressures, and unspoken tensions happens upfront.

It starts by understanding what people are afraid to say, so the sketching captures context, not just content.

Deliver. Live sketching draws out meaning, not just words. The illustrations become emotional, thoughtful artifacts grounded in the specific situation.

Memory anchors that hold the moment in place long after everyone returns to their desks.

Reflect. Red Teaming (more on this in a sec) is a concept where you examine your own strategy through the eyes of an adversary or outside observer. In business, it’s strategic and thoughtful reflection: seeing what was missed, what was implied, and what could break if left unspoken. Most services stop after the sketching session.

This approach starts something after.

Repeat. Insight works as a cycle, not a one-off. Teams that embed this rhythm into their culture build something more lasting than good ideas.

Clarity isn’t a one-time moment. It’s an ongoing practice.

The Session After the Session

Red Teaming is where insight goes from felt to followed.

The military uses Red Teaming to examine its own strategies through the eyes of an adversary. It’s how they spot weaknesses, blind spots, and assumptions that could be fatal in the field. They need it because lives depend on seeing clearly.

If you’re reading this, you probably aren’t under attack from a foreign adversary (that you know of). But your business strategies, team dynamics, talent management, and organizational blind spots still benefit from that same kind of outside perspective.

It’s the post-game film. The mirror. The listening. The rapport. The conversation (sometimes great, sometimes tough, always insightful) that happens after everyone thinks the work is done.

These are the visual recaps that synthesize what emerged, a strategic memo outlining what to explore and what’s next, and a conversation to turn insight into actionable next steps.

This transforms drawings and sketches into strategic mirrors. Now the artifact is used to make decisions, guide conversations, and stay aligned on what actually matters.

There’s something powerful about seeing your event sketched in hindsight.

The practical implications of what was said, and what wasn’t, become clear. It’s the part no one budgets for, but every team needs.

From Decoration to Decision-Making

Most people leave with notes. You should leave with a mirror.

This isn’t decoration. It’s decision-making fuel. Over the years, my work has shifted. It started with capturing what happens. Now it’s helping teams understand why it matters and what comes next.

The system creates lasting alignment and trust, not just documentation. It’s turning insight to action. Moving from inspiration to implementation.

Because the drawing is just the beginning.

If you’re planning an event and want the insights to stick, let’s connect.

Prep. Deliver. Reflect. That’s how change becomes lasting.

Grateful you are here,

Wade

PS - If you’re running events and don’t want the insights to fade, if you’re tired of breakthrough moments becoming distant memories, we should talk!

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