5 Event Strategy Problems Nobody’s Naming (And the Curiosity Question That Fixes Each One)

TL;DR

The events industry has a curiosity problem, and it’s quietly killing your event strategy. The metrics you celebrate (sponsor renewals, NPS, session scores, attendance) often hide the structural problems your team has stopped questioning. In this episode of Event About It, New York Times bestselling author Diana Kander joins host Megan Martin to name the five stagnant event strategy problems most leaders are too comfortable to address, plus the curiosity question that breaks each one open.

  • Sponsor renewals at 80% feel like success but mask new-logo growth that’s been stalled for years.
  • A 4.5-out-of-5 session score is the worst feedback you can get — it tells you nothing.
  • Day-three attendance crashes 40% no matter what you change, because nobody’s designing day three to draw people in.
  • “We need a younger audience” is rarely a real strategy. It’s a reactive task with no shared definition.
  • Networking is on every event agenda, but actual connection rarely happens because the format is wrong.

The fix in every case: stop validating what you already think. Start asking the question you’ve been too busy to ask.

The Curiosity Problem Inside Your Event Strategy

The events industry has a curiosity problem. Attendees changed. Buyers changed. Metrics changed. And most event leaders rebooked the same hotel. That’s the central thesis Diana Kander brings to this episode of Event About It — and it’s the diagnosis most event marketers, sales leaders, and growth teams are too comfortable to hear.

Diana Kander is a New York Times bestselling author of All In Startup, The Curiosity Muscle, and her brand-new book Get Curious and Grow. She’s a former senior fellow at the Kauffman Foundation, a Georgetown-trained attorney, and one of the most-booked innovation and curiosity keynote speakers in the country. Her core thesis applies directly to anyone running an event-led growth strategy: “The biggest threat to your event isn’t failure. It isn’t fear. It’s the success you stopped questioning.”

Across the conversation, Diana diagnosed five event strategy problems with a single tool: a better question. Here are the five, plus the curiosity practice that fixes each one.

1. Sponsor Renewals Look Healthy, but New Logo Growth Has Stalled

“Most people never interview the customers that leave. You have certain assumptions about why they’re leaving, but almost never are those assumptions connected to the truth.” — Diana Kander

Framework: Ask the People Who Left, Not Just the People in the Room

Most event surveys go to the people who showed up. Those people are also the people most likely to validate what you already believe. Diana’s methodology, drawn from her work with The Curiosity Muscle, flips the inquiry: interview the sponsors, attendees, and members who left or never joined.

Why It Matters for Event-Led Growth Strategy

If sponsor renewals are flat and new logos are stuck, the data you need is not inside the room. It’s inside the calls you haven’t made yet. Build a no-show debrief into your event ROI playbook. The insights you get from a single conversation with a former sponsor will be more strategically valuable than another year of incremental survey work.

2. A 4.5-Out-of-5 Session Score Is a Red Flag, Not a Win

“Good is the worst possible feedback you can get. If you’re getting a 4.5 out of 5, you’re asking the wrong question.” — Diana Kander

Framework: Question the Questionnaire

Session evaluations are designed to measure satisfaction. Satisfaction is a low-bar metric. What you actually want to know is what changed for the attendee, what they remembered two weeks later, and what action they took as a result. Anecdotal conversations with five real attendees will tell you more than 500 evaluation forms.

Why It Matters for Event Strategy

Survey data also suffers a sampling problem: the only people who fill them out are the most engaged and the most disappointed. The polite middle never weighs in. If you’re making strategy decisions based on 4.5 averages, you’re optimizing for the wrong audience. Replace the post-session evaluation cycle with a small number of structured conversations. Treat it as qualitative research, not customer service.

3. Day Three Attendance Crashes by 40%, and We Schedule It Anyway

“What is the draw? If you know there’s a drop off, how do you create a draw on the last day?” — Diana Kander

Framework: Design the Emotional Arc, Not Just the Agenda

Diana told the story of being booked as a closing keynote at an event that opened with Ryan Holiday. Only 10% of attendees made it to her session — not because the content was weak, but because the event structure didn’t give people a reason to stay. She advised event leaders to think about the emotional roller coaster of a multi-day experience: where are the lows, and what intentional design moves create a draw on day three?

Why It Matters for B2B Event Strategy

If your day-three drop is structural, no amount of content quality fixes it. The question isn’t “how do we make the content better?” It’s “what experience design pulls people into the room when they could be at the airport?” Reverse-engineer the emotional moments your event needs — there are at least 10 of them — and build day three with intention, not inertia.

4. “We Need a Younger Audience” Is a Task, Not a Strategy

“Ask three to five follow-up questions on what younger means and why they think it’s important. If you don’t understand the why, the chances of you succeeding in that task are incredibly low.” — Diana Kander

Framework: Three to Five Follow-Up Questions Before You Move

When a leadership team hands a marketing team an unclear directive (“we need a younger audience”), the temptation is to jump to execution: book a millennial keynote, redesign the lounge, refresh the brand. Diana’s curiosity practice is the opposite. Ask three to five clarifying questions before you spend a single dollar. What does “younger” mean — younger in career or younger in age? Why is this a priority? What business outcome are we trying to drive?

Why It Matters for Event Marketing Alignment

Most failed event strategy execution traces back to unclear initial briefs. The follow-up question is the cheapest, fastest, highest-ROI move on the board. It also reframes the marketing or event lead as a strategic advisor rather than an order taker — which is the leadership transition most event professionals are trying to make.

5. Networking Is on Every Agenda, but Nobody’s Actually Networking

“People are asking the same questions over and over again, and they’re terrible questions. Nobody’s getting to know anybody new.” — Diana Kander

Framework: Engineer the Connection, Don’t Just Schedule It

Putting “networking” on every agenda, building dedicated lounges, and handing out name tags is not a networking strategy. It’s a venue strategy. Diana’s point: the format of most networking events forces people into surface-level questions (where do you live, how many kids do you have) that don’t create real connection. Real networking requires designed prompts, structured introductions, or a connection methodology that goes deeper than chitchat.

Why It Matters for Event ROI and Attendee Retention

Most attendees say “meeting new people” is the most valuable part of an event. If your networking format is failing to deliver that value, your retention rate is going to drop regardless of how good the content is. Treat connection as a designed experience, not a scheduled block.

The Aftershow: How to Innovate Without Inventing

In the Event About It Aftershow companion episode, Diana goes deeper on the curiosity practices that translate her keynote thesis into a Monday-morning operating system for event leaders, marketers, and sales teams. Highlights include:

  • Why innovation isn’t a thing — it’s a mindset, and the “closet of old ideas” test reveals whether your team is actually innovating
  • The Calendar Test for curiosity: your meeting calendar reveals exactly how curious your business actually is
  • The three questions to ask attendees who didn’t come back, and why nobody on your own team should make the call
  • The seven-chapters theory of career reinvention for event marketers and sales leaders feeling stuck on the operational plateau
  • Diana’s $500,000 software failure at 29 and the iteration habit she’d install in every event team today

Listen to the Aftershow on EventAboutItPodcast.com.

The Final Word

The events industry doesn’t have an innovation problem. It has a curiosity problem. Most event teams have stopped asking the questions that would make the difference because the metrics they’re tracking validate the answers they’ve already accepted. The fix is structural, not creative. Build curiosity into your calendar, your debrief process, and your no-show outreach. Then watch how quickly the industry’s “unsolvable” problems become solvable.

“If curiosity killed the cat, complacency killed the conference.” — Megan Martin

FAQ: Event Strategy and Curiosity in Practice

What is event-led growth strategy?

Event-led growth strategy is the practice of designing events as measurable drivers of pipeline, retention, and revenue rather than as marketing line items. It treats live experiences as a portfolio of intent signals and first-party data sources that inform broader marketing alignment and sales targeting.

What is the biggest barrier to innovation in events, according to Diana Kander?

According to New York Times bestselling author Diana Kander, the biggest barrier to innovation is not failure or a lack of resources. It is success. Once a team identifies a way that works, they tend to stop asking whether it could be done better, which leads to a curiosity plateau and stalled growth.

How should event teams interview attendees who didn’t come back?

Diana Kander recommends a three-question structure for no-show interviews. First, set the frame that this is not a sales call — you are not calling to convince them to come back. Second, ask why they decided not to return and whether they attended a competing event instead. Third, ask what their favorite event of the year is and what made it unforgettable. Importantly, the person making the call should not have a job tied to attendance metrics.

What is the difference between innovation and invention?

Innovation is a mindset, not an output. Diana Kander defines innovation as the belief that no matter how things are going right now, they could be going better — and the willingness to ask the questions that surface the improvement. Invention is the creation of something new. You can be highly innovative without inventing anything because innovation lives in how you do everything, not in what you create.

How do I run event experiments when my conference is only once a year?

Run experiments outside the event itself. Diana Kander, drawing on her time as Entrepreneur in Residence at H&R Block, points out that conversations with past attendees are experiments. Ask three years of past attendees their favorite and least favorite sessions. Test hypotheses about what would make next year’s event more valuable. The conference is the production; the experimentation is the year-round work.

What is the Calendar Test for curiosity?

The Calendar Test is a practice introduced by Diana Kander for evaluating whether you have built curiosity into your operating rhythm. If your calendar is back-to-back meetings with no buffer time, no scheduled after-action reviews, and no built-in moments of reflection, your business is not curious. Your calendar reveals exactly what you find valuable, and it does not lie.

Listen to the Episode

Listen to “5 Event Strategy Problems Nobody’s Naming” with Diana Kander on EventAboutItPodcast.com, Apple Podcasts, Spotify, or wherever you get your podcasts.

Related Episodes

  • Catch the companion Aftershow: How to Innovate Without Inventing
  • More on event-led growth strategy at msquareddynamics.com

About the Author

Megan Martin is the founder of M Squared Dynamics, a consulting, facilitation, and content strategy firm helping event leaders, marketers, and sales teams turn live experiences into measurable business growth. She’s the host and executive producer of Event About It, co-founder of Opportunity Hunters, and a two-time PCMA Visionary Award nominee (2022 winner). With nearly 20 years in the industry, Megan operates at the intersection of event strategy, marketing alignment, and behavioral intent signals, turning events from line items into pipeline drivers.

Connect with Megan and M Squared Dynamics:

Keep the Conversation Going

If this resonates, sign up for the Step and Repeat newsletter at msquareddynamics.com/stepandrepeatsignup for more on event-led growth strategy, event ROI, and the curiosity practices that turn events into pipeline drivers. And if you want to hear it in conversation, “5 Event Strategy Problems Nobody’s Naming” is the companion episode to this post — listen on EventAboutItPodcast.com.

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