5 Event Strategy Problems Nobody's Naming
June 19, 2026
27
00:13:29

5 Event Strategy Problems Nobody's Naming

The events industry has a curiosity problem. Attendees changed. Buyers changed. Metrics changed. And most of us rebooked the same hotel.

This week on Event About It, New York Times bestselling author and innovation keynote speaker Diana Kander joins host Megan Martin to diagnose five stagnant event strategy problems nobody in the industry is naming out loud, and the curiosity question that breaks each one open.

If you're building an event-led growth strategy, leading a marketing team, or running B2B events that need to drive measurable pipeline, this is the diagnostic you didn't know you needed.

What You'll Learn

  • Why "the biggest threat to your event isn't failure. It's the success you stopped questioning."

  • The one question that turns flat sponsor renewals into new logo growth

  • Why an attendee NPS of 72 every single year isn't a win, it's a warning sign

  • How to design a day-three draw before you lose the room

  • Why a 4.5-out-of-5 session score is the worst feedback you can get

  • What Snoop Dogg's business model teaches the events industry about staying relevant decade after decade

About Diana Kander

Diana Kander is a New York Times bestselling author of All In Startup and The Curiosity Muscle, with her new book Get Curious and Grow available now. She came to the U.S. as a refugee from the Soviet Union at age eight, became a Georgetown-trained attorney, founded around ten companies, served as a senior fellow at the Kauffman Foundation, and is one of the most-booked innovation and curiosity keynote speakers in the country.

Connect with Diana:

  • Website: dianakander.com

  • LinkedIn: https://www.linkedin.com/in/dianakander/

  • Instagram: @dianakander

About Your Host

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:

  • Podcast: EventAboutItPodcast.com

  • Newsletter (Step and Repeat): msquareddynamics.com/stepandrepeatsignup

  • Consulting and strategy: msquareddynamics.com

  • LinkedIn: https://www.linkedin.com/in/meganmartincmp/

  • Instagram: @m2dynamics and @eventaboutit

  • TikTok: @eventaboutit

Keep the Conversation Going

Subscribe to Event About It so the Aftershow lands in your feed the second it drops. Diana and Megan go deeper on why innovation isn't invention, the curiosity practice every leadership team should install tomorrow, and the three questions to actually ask the people who didn't come to your last event.

Send this episode to the marketer, sales leader, or event strategist who keeps telling you their last event "went great."

The events industry has a curiosity problem. Attendees changed. Buyers changed. Metrics changed. And most of us rebooked the same hotel.

This week on Event About It, New York Times bestselling author and innovation keynote speaker Diana Kander joins host Megan Martin to diagnose five stagnant event strategy problems nobody in the industry is naming out loud, and the curiosity question that breaks each one open.

If you're building an event-led growth strategy, leading a marketing team, or running B2B events that need to drive measurable pipeline, this is the diagnostic you didn't know you needed.

What You'll Learn

  • Why "the biggest threat to your event isn't failure. It's the success you stopped questioning."

  • The one question that turns flat sponsor renewals into new logo growth

  • Why an attendee NPS of 72 every single year isn't a win, it's a warning sign

  • How to design a day-three draw before you lose the room

  • Why a 4.5-out-of-5 session score is the worst feedback you can get

  • What Snoop Dogg's business model teaches the events industry about staying relevant decade after decade

About Diana Kander

Diana Kander is a New York Times bestselling author of All In Startup and The Curiosity Muscle, with her new book Get Curious and Grow available now. She came to the U.S. as a refugee from the Soviet Union at age eight, became a Georgetown-trained attorney, founded around ten companies, served as a senior fellow at the Kauffman Foundation, and is one of the most-booked innovation and curiosity keynote speakers in the country.

Connect with Diana:

  • Website: dianakander.com

  • LinkedIn: https://www.linkedin.com/in/dianakander/

  • Instagram: @dianakander

About Your Host

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:

  • Podcast: EventAboutItPodcast.com

  • Newsletter (Step and Repeat): msquareddynamics.com/stepandrepeatsignup

  • Consulting and strategy: msquareddynamics.com

  • LinkedIn: https://www.linkedin.com/in/meganmartincmp/

  • Instagram: @m2dynamics and @eventaboutit

  • TikTok: @eventaboutit

Keep the Conversation Going

Subscribe to Event About It so the Aftershow lands in your feed the second it drops. Diana and Megan go deeper on why innovation isn't invention, the curiosity practice every leadership team should install tomorrow, and the three questions to actually ask the people who didn't come to your last event.

Send this episode to the marketer, sales leader, or event strategist who keeps telling you their last event "went great."

[00:00:00] The events industry has a curiosity problem. Our attendees changed, our buyers changed, our metrics even changed, and then we booked the same event. The biggest threat to your event isn't failure, it isn't fear, it's the success you've stopped questioning. If curiosity killed the cat, completency killed the conference. It's Event About It with Diana Kander.

[00:00:24] Hey everybody, welcome to Event About It. I'm your host, Megan Martin, and our guest this week turns curiosity into a competitive advantage, and we've always done it this way into the four most expensive words in the industry.

[00:00:44] She'll convince you your favorite meeting belongs in the zombie pile, that the most dangerous question in your business is the one you stopped asking, and the expert in the room is the one with the most to unlearn. Diana, welcome to the studio. I am so glad to have you here. Thank you so much, Megan. I'm excited for it. This was almost a podcast that never happened. The amount of times we've rescheduled to get here is quite impressive.

[00:01:12] And I'd like to give credit where credit is due because I want to shout out Nathan Hermiston from Kansas City, which is where you're from and live. He connected us because you just knew we would be fast friends and that I would be a super fan, and he was not wrong. So thank you, Nathan, for making today happen. Okay, well, before we dig in, I too have a fascination with Snoop Dogg. Beyond loving his music, I think he's an incredible businessman.

[00:01:39] And you posted recently on your Instagram that you got contacted by his team to go to an event. Yes, I'm a big fan of his business acumen. And if you think about it, he is the captain of reinvention. He has reinvented himself so many times, which I think is the most important skill set for the future. So yes, I got to go to a Snoop Dogg ice cream party. Was he there? Did you get to meet him?

[00:02:06] He was there. It was a really super fun experience. I don't know. What question can I answer for you? Is he as enthusiastic and enthralling in all the things that you expected when you saw him in person? Yeah, he's a super awesome guy, but really he has an incredible team all around him, including... Most of them are in their 20s, including his son.

[00:02:31] And he has like a really competent team that is really focused on bringing in opportunities that he isn't even aware of. And while most people use younger people to execute on the work that they know needs to be done, he uses young people to teach him about things that he should know about. And, you know, one of the many things I admire about him. Yeah, he's incredible.

[00:02:56] And in your new book, which we're going to talk about in the after show, you talk about the time he turned down Michael Jordan to DJ a party, which like who would ever do that except for Snoop Dogg. And I think it just shows like just how incredibly committed he is to like his vision and what he's doing and what serves him. And as much as he probably would love to do it, it wasn't necessarily worth it for him and what he was building. So I love that story. Well, given our love for Snoop Dogg, we're going to play a game called Curious Like It's Hot.

[00:03:27] So here's how it works. I'm going to read you a stagnant problem the events industry has been ignoring for a long time. And you dropped the curiosity question that could crack it open to help people solve that. Great. All right. So first up, our flagship event renews 80% of sponsors every year, but new sponsor logos are nearly impossible to land. So I would find out why people are leaving.

[00:03:54] Most people never interview the customers that leave. And you have certain assumptions about why they're leaving, but almost never are those assumptions connected to the truth. And I think there is diamond in the answers to that question. Yeah, agreed. Next one. Day three attendance drops by 40%, no matter how strong the content is. No one ever comes past day three. I think it's about designing thinking about the emotional roller coaster of the experience.

[00:04:24] It could be because there was a karaoke party at 10 p.m. on day two. And the way that the event was structured is like people got flights home on day three. So it's about I once did an event where Ryan Holiday opened. Do you know him? He's like the stoicism guy. And then I was the closing speaker and there was nothing else at the end. It was just me at the end of the conference.

[00:04:49] And there was like 10% of attendees because who knows who I am, you know, but they all showed up to his session. So thinking about it, what is the draw? If you know there's a drop off, how do you create a draw on the last day, a drawing or whatever to get people in the room? Yeah, great point. Post session evaluations come back at four and a half out of five. Two weeks later, attendees can't name a single takeaway. I think good is like the worst possible feedback that you can get.

[00:05:18] If if you're getting a four point five out of five, I think you're asking the wrong question. You're not getting the kind of feedback that's going to help you improve the event. So I would actually question the questionnaire. And if you're getting so many positive responses, I would talk to individuals and find out the anecdotal stories about their experiences and the value that they got, because oftentimes they're going to be different than the response you get. And we know that people don't answer surveys and evaluations anyway.

[00:05:47] So that four and a half out of five is what just your sponsors or just your evangelists. So like I don't think it actually gives you an accurate reflection of how people evaluated your event or your program. OK, next on the executive team has decided we need a younger audience. They tell marketing to, quote, figure it out and book a millennial keynote. So I anytime I get a request and I'm like, what? A lot of people will jump to trying to solve the problem.

[00:06:16] But you probably don't even understand the task that you've been given. And so I would ask at least three to five follow up questions on what younger means and why they think it's important and the value that that will provide to the organization. Because if you don't understand the why, the chances of you succeeding in that task are incredibly low. Yeah, agreed. And I think younger is so subjective. Is that younger in their career, younger in age? Like that's such a vague term.

[00:06:42] OK, we put networking on every agenda, build dedicated lounges, provide name tags, but no one talks to each other. I would say let's go. Yes. And most people will say that meeting other people at an event is the most useful time in their event. But if you go to those events, people are asking the same questions over and over again. And they're terrible questions. Nobody's getting to know anybody new. And so how do you I think we're going to talk about this later.

[00:07:10] It's like how do you engineer an event where people genuinely connect with new people and hear each other's stories rather than where they live and how many kids they have and what they have planned for the summer. These are high level not getting to know you questions that most people stick to at networking events. Yeah, it's all very surface level. So how do we get there faster? Yeah. OK, last one. Again, attendee NPS sits at 72 every single year.

[00:07:39] Whether we have better content, worse content, it doesn't matter. It always comes back the same. I think, again, you before you go to the qualitative data, you go to the quantitative data and you understand specific stories in the room. Who's getting what value? Why are they coming back? What were the moments that made the biggest impact? And out of those, you're going to hopefully identify pain points of, well, what didn't quite hit the mark.

[00:08:07] And there's going to be some repeat pain points that I think are going to be the low hanging fruit of making for an exceptional follow up event. Yeah, couldn't agree more. You need both data sets to really understand the full picture. Well, thank you for playing curious like it's hot. And here's the thing I want everyone listening to sit with for a second. You just rewrote three huge industry problems with one question. And it's basically why? Like ask better questions.

[00:08:35] And if we did that, I think people would have a lot better understanding of their programs and where they should go. Well, now it's time for my favorite session, the vent of the week, because sometimes the only thing tighter than a load in schedule is our patients. So this is your safe space to tell us what bugs you the most about going to events.

[00:09:00] We have like a saying in our family, candors don't complain, you know, so it's very difficult for me to answer this question. But you have to give people enough breaks in the day. You can't create content in three hour chunks because people can't pay attention in that period of time.

[00:09:19] So I really want people to be generous with their breaks and just think about what it's physically like to sit in a chair for hours upon hours and days upon days. Yeah, not just for your body, but your mind needs white space to comprehend. So one of the things we talked about in the curious like it's hot was like no one remembers after two weeks after the event.

[00:09:43] Well, you didn't give them time to actually process or apply anything they learned because they were just rushing from session to session. There was no time for reflection. Yeah, and that's the key. You know, it's like in your workday. If you have like meeting, you're not learning anything. You're just jumping from thing to thing and giving people that kind of space and prompting to help think through what they're taking away and what they're going to act on is key.

[00:10:09] Yeah, they kind of need the white space for the so what moments like what does this mean for me and my work? I love that. I think we can all learn something there. Well, next up it's time to event about it. The part of the show where you get to spill the tea on a memorable event moment, whether it was a huge success, total disaster or simply chaos. Give us a fun behind the scenes story.

[00:10:31] I had an event this year where something happened to the to the teleprompter right before I went on stage. And to address this, they decided to reboot the entire AV system. So all the monitors in the back and I was like, this is a terrible idea. Just like don't use the teleprompter, you know, just let me go. And of course, it took 20 minutes to reboot the system. And then they couldn't find my slides. So and then they started just introducing me. So I was like, OK, well, here we go.

[00:11:01] Like, I'm just going to go on stage and hope for the best. And it worked out great. So do you typically use a teleprompter or? No, I wasn't for me. It was for the session before me. Oh, even worse. And then they lose your slides. That's horrible. Yeah, there's like an award segment, you know. Got it. Did they finally find your slides and like put them up 20 minutes halfway through your talk? Yeah. Oh, my God.

[00:11:30] That's almost more distracting, I think, because now you're like in the flow and then all of a sudden like your slides reappear. And then you have to like catch up to where you are. And it was great. They were trying their best. But there should be like there should be somebody in the back that's like, no, we're not going to reboot the system. You know, we're just going to we're just going to go with whatever we have. Yeah. And if you didn't need the teleprompter, they could have done that on a break, like after your talk. Like schedule a break and be like, we're going to we'll be back. Take a commercial break. I don't know.

[00:12:00] Craziness. Oh, my gosh. Well, tell everyone a little bit about yourself, where they can find you, where they can engage with you online. My name is Diana Kander. I'm a serial entrepreneur. And for the last 12 years, I've also been an author and keynote speaker on curiosity and innovation. So in my non speaking role, I work with large organizations to help them do exactly what we're saying, get to know their customers better, grow the bottom line.

[00:12:26] And on stage, I get to show some key ideas and practices that I think can have immediate impacts for their organizations. That's amazing. And where can people find you like online? Anywhere. I mean, Diana Kander dot com is my website, but the most fun content is on Instagram and the most professional content is on LinkedIn. Amazing. Well, that's all the time we have for today's episode of event about it, where we connect events, marketing and prove that live experiences aren't just logistics, they're a growth channel.

[00:12:56] If this episode made you think differently about how events drive pipeline, brand or growth, make sure you subscribe. That's how you'll catch what's coming next, including the event about it after show where Diana and I dig deeper into why cameras are scarier than stages, the curiosity practice that should be installed in every leadership team, and what questions to ask the people who didn't come to your last event. Until next time, keep growing, keep laughing and keep eventing about it.