I keep showing up to digital events where it feels like no one remembered I was invited.

Dropbox ran one recently. Two people on black backgrounds, talking to each other like they were recording a podcast. The chat was lighting up. Questions piling in. They never looked at it once. I sat there thinking, “Do they know we’re here?”

Canva did one with impressive production value—polished graphics, professional setup, great speakers. Completely pre-recorded. The chat figured it out in five minutes and lost it. People weren’t mad it was pre-recorded, they were mad no one told them. They showed up expecting a conversation and got a broadcast with a comments section.

Airtable tried a product demo. The presenter was fine. But the UI was microscopic on screen. You couldn’t see anything. And he was alone—running the demo, watching chat, trying to answer questions flying by in real time. It felt less like an event and more like watching someone drown while you yell suggestions from the shore.

These weren’t scrappy startups. These were well-funded companies with real event budgets. And they all made the same mistake:

They thought digital events were easy. Just open the room and start talking.

No curiosity about what makes it work. No thought about what the audience actually needed. Just: we have something to say, so let’s hit go.

Here’s what actually happens when your event fails:

Your audience doesn’t come back. Not because they’re angry. Because you taught them your events aren’t worth their time.

Your budget gets cut. Leadership looks at the numbers—low engagement, no pipeline, nothing moved—and decides virtual events don’t work.

Your sales team gets frustrated because you’re marking everyone as an SQL when half the room was just there to listen. Now your data’s polluted and no one trusts the metrics.

And the whole thing is embarrassing. You spent weeks on invites, emails, calendar holds, asking AEs to bring their customers—and it landed flat.

I kept seeing this pattern. Well-funded companies with real budgets, running events that just... didn’t work. And I’d sit there thinking: they have the resources, why doesn’t this land?

Then it clicked: it is not the execution that failed. It was the design.

The format didn’t match the problem. And once the format’s wrong, no amount of production polish can save it.

I’ve spent years producing events for Adobe, AIGA, General Assembly, HMCT—digital and in-person. And for a long time, I made the same mistakes everyone else was making.

Then I started asking a different question.

Not “what should we talk about?” Not “who should speak?” Not even “how do we get people to register?”

But: What problem are we solving for the people in the room?

Not what we need from them. Not how we hit our goals. But what do these specific people need that we’re actually positioned to deliver?

Once I started designing from that question, everything shifted.

The events started working. People showed up. They engaged. They came back. And the business outcomes—adoption, trust, pipeline, community growth—happened as a side effect of actually solving a real problem.

Most events are solving the organizer’s problem, not the audience’s. Once you flip that, everything changes. Let me show you what that looked like.

We had a problem at Adobe. Our stock library had millions of assets. People were already customers. But they weren’t using it. Downloads were flat.

The usual playbook would be: more emails, better tutorials, feature spotlights. “Here’s why this matters!”

Pffft. Nobody cares.

We tried something that felt kind of wild: what if we just... stopped talking about the product?

What if we made something people actually wanted to show up for? Not a webinar. Not a demo. Not enablement. A competition. A game.

We built The Perfect Match—a full 1970s game show. Vintage set, bright colors, contestants competing with design directors for $1,000 prizes.

60,000 people watched live. A quarter of them downloaded from the library for the first time—people who’d never touched it before. Product marketing hit their goals.

Not because we convinced anyone. Because while they were having fun, they were doing the thing we needed them to do without being asked to care about it.

The format solved the problem: We needed behavior change. So we designed a moment where the behavior was the fun part, not the ask.

We had a different problem with the hybrid Adobe Creative Jam events. It was working—local campus events, real engagement, actual skill-building. But it was one university at a time. Leadership wanted scale. Thousands of students, not dozens.

We couldn’t be everywhere at once. So we redesigned it.

Open Creative Jam LIVE wasn’t about removing structure. It was about removing geography. One Adobe-sponsored event. Registration open to any university student, anywhere. Teams could form across campuses—and they did.

For the Netflix Jam, we got 7,500+ registrants, and 1,600 entries from teams. Teams of three. That's over 3,500 students creating together in one coordinated window. Ten finalists. First place got $500 each.

The prizes weren’t massive. But the structure created engagement, excitement, and fun. When you give the students freedom, they organize themselves. And when people organize themselves, they recruit. They spread the word faster than any marketing campaign could.

The format solved the problem: We needed scale without losing quality. So we designed one arena that could hold thousands instead of trying to be everywhere at once.

AIGA had a trust problem. A new board had come in. New direction. The design community was confused. Skeptical. Some had checked out.

A blog post wasn’t going to rebuild that. Neither was a mission statement. People needed to see the leaders. Not polished. Not scripted. Just human.

So we created AIGA Real Talk—a live show where AIGA national leadership and local chapter leads sat down for open dialogue. No keynotes. No talking points. Just real questions and real answers.

We ran eight episodes over four months. Topics like AI ethics and career advancement. Some episodes got 445 RSVPs. Others sparked 225 comments in live chat—people debating, disagreeing, sharing their own experiences.

Average conversion rate held at 39%. People weren’t just registering—they were showing up, consistently, week after week.

And AIGA’s LinkedIn following grew by 3,700 in five months. Not because we posted more. Because we became visible. The show created a recurring touchpoint. People knew when and where to find us.

The format solved the problem: We needed trust and visibility. So we designed a recurring conversation where leaders showed up vulnerable, not polished. And that built audience as a side effect.

The speaker from Disney dropped out five days before our digital event.

We’d already promoted his name. His title. His expertise. 500+ people had registered.

Leadership asked: Should we cancel?

It was a fair question. We had 5 days, no speaker, and over 500 people expecting someone from Disney.

If we were going to cancel, we needed to decide fast. Marketing ops would have to stop the campaigns. The email team would have to write an apology. Our PMM stakeholders would have to approve the messaging. It was going to take coordination across multiple teams.

But before we made that call, my team wanted to look at what we actually had.

A demo artist who knew the tool cold. A host who could run a room (me). And a system we’d built specifically so one missing piece wouldn't break everything.

We decided to keep going.

Instead of scrambling to find a replacement speaker, we combined the interview with a working session. We built the story around our demo artist’s perspective on the problem, not just the product features.

The demo artist walked through actual problems and solved them live. I asked the questions I actually wanted answered. No script. No performance. Just a real conversation.

Our system held up because we’d designed it with flexibility built in. The run-of-show had modular pieces we could move around. The structure could adapt without falling apart.

When the show began, I opened by telling everyone the truth: our guest wasn’t going to make it. But here’s what we were going to do instead. And then we showed them how to solve the exact problem we’d advertised, just without the guest.

The people who stayed engaged. They asked questions. They participated.

And that wasn’t even the only time.

A few months later, we lost a guest speaker mid-interview. Not figuratively. Literally. His internet cut out halfway through. Frozen mid-sentence. Gone.

I was hosting. Hundreds of people watching.

Tech director in my ear: “Stretch.”

But we didn’t panic. We kicked off what we call the Houston Protocols. (Yes, that’s actually what we named our crisis SOP.)

Engagement manager kept the chat busy. Line producer tried to reach the speaker. Broadcast tech queued a backup video. Content producer fed me updates.

I stayed with the audience. Asked what they'd learned so far. Called out a few names in the chat. Made it feel like improv—because sometimes, that’s the job.

But the plan was already in motion. The team knew exactly what to do. We didn’t break the spell. We kept the experience intact.

That’s when I knew: well-designed events don’t just work when everything goes right. They hold up when everything goes wrong.

Not because we got lucky. Because we’d built systems with failure modes already mapped. Modular run-of-shows. Clear protocols. Teams who knew their roles even when the plan changed.

Most digital events break the moment something goes sideways. We kept going. Twice.

Once I knew what to look for, I saw it everywhere: The events that worked weren’t better executed. They were better designed.

Each one started with a specific problem:

The format carried the solution. Not the speakers. Not the budget. Not the promotion. The structure itself—who participates, how they participate, what they create, how stories travel afterward.

When you match the mechanics to the problem, the event stops being a cost center and starts being a system that keeps working.

Here’s what I wish someone had told me years ago: Events aren’t content delivery. They’re tools.

And like any tool, the structure you choose determines what you can actually build.

A hackathon solves a different problem than a fireside chat. A game show fixes something a product demo can’t touch. A live show with audience participation does something a pre-recorded webinar never will.

The question isn’t “should we do an event?”

The question is: “What problem are we solving, and what mechanics does that require?”

Once you know the problem, the format designs itself.

When you design events this way, something shifts.

Your audience shows up because they need what you’re offering, not because you convinced them to.

Your metrics improve because you’re solving a real problem, not just optimizing for vanity numbers.

Your team gets excited because the event actually works—it changes behavior, builds trust, creates momentum.

And your budget becomes easier to defend because the event isn’t a cost center anymore. It’s a system solving an ongoing business problem.

The event programs I’m most proud of—The Perfect Match, Open Creative Jam LIVE, AIGA Real Talk—they didn’t just “go well.” They became things people talked about. Things people came back for. Things that kept working long after we’d moved on. (We still get requests for Creative Jams)

Not because we executed flawlessly. Because we designed from the problem, not from the template.

If you’re sitting on an event that needs to work—or a business problem you think events might solve—start here:

What problem are you solving for the people in the room?

Not for your KPIs. Not for your exec team. For the actual humans who will show up.

Once you can answer that clearly, you can reverse-engineer the format. And once you have the right format, everything else gets easier.

The event designs itself. People show up because they need it. The outcomes happen because the structure is doing the work.

That’s when events stop being expensive mistakes and start being systems that actually solve problems.

If you're trying to figure out what format would actually solve your specific problem, that’s exactly what we work through in the Digital Event Strategy Sprint. We reverse-engineer the structure from your business pain. Email me to talk through your situation.