Event Planner Confessions

Your attendees may have decided your event interests them long before they register. What happens between those two moments can reveal whether your marketing is giving them a compelling reason to commit.

In this episode of Event Planner Confessions, Ashley Currin talks with Ken Holsinger, EVP of Industry Research & Insights at Freeman, about newly released research on the participant journey and what event teams should reconsider for 2027.

Ken challenges the industry’s definition of “late registration” and explains why current patterns should be treated as normal attendee behavior. He explores the difference between deciding to attend and completing registration, along with the information people want before committing their time and money.

The conversation moves into practical changes: sharing meaningful program updates earlier, communicating relevant benefits, and using registration questions to improve the attendee experience. Ken also shares an example of how a clearly differentiated VIP offering changed registration behavior at one event. Ashley and Ken discuss how AI is influencing event discovery, why planning processes need room for timely content, and what makes face-to-face experiences valuable in an increasingly digital world.

In this episode, you will learn:

• Why deciding to attend and completing registration can happen at different times
• What attendees want to know before committing
• How regular content announcements can build momentum
• Why registration questions should create value for the person answering them
• How to leave room for relevant updates without abandoning your event strategy
• Why Ken remains optimistic about the future of face-to-face experiences

Give attendees a clearer reason to commit, and make sure the experience delivers on that promise. Stronger planning for 2027 starts with understanding what people need before they arrive.

A destination event should feel like more than a meeting that happens to be in another city.

In this episode of Event Planner Confessions, Cara Pratt, Ashley Currin, and Sam Monroe explore how event planners can build a real sense of place into an attendee experience without relying on obvious themes or destination clichés.

From creating an authentic Las Vegas experience for 10,000 attendees to transforming a Tampa ballroom after rain forced a beachfront event inside, the team shares how local knowledge shapes the decisions planners make when circumstances change.

They also unpack the less obvious ways a destination can influence an event, including transportation and permitting, regional food experiences, local musicians and performers, general session entertainment, community giveback, and the small details that help attendees actually connect with where they are.

And in true Event Planner Confessions fashion, Ashley shares what happened when a Maryland crab feast was planned for a large group of international attendees who did not know how to crack a crab.

In this episode, you will learn:

• Why a destination should influence an event rather than simply serve as its backdrop
• How local expertise can change venue, transportation, food, and entertainment decisions
• Why involving a DMC early can prevent logistical problems later
• How regional food can become an interactive and educational attendee experience
• Why local entertainment can sometimes create greater impact while reducing unnecessary cost
• How community partnerships can make an event feel more meaningful and connected to place

The strongest destination experiences do not simply show attendees where they are. They give them a reason to remember what it felt like to be there.

Every event planner has a Plan B. But what happens when Plan B is not enough?
In this episode of Event Planner Confessions, Cara Pratt, Ashley Currin, and Sam Monroe share the behind-the-scenes contingency stories their attendees never saw.
One indoor event was disrupted when a storm contributed to a generator failure and an electrical fire at the host hotel. Another required 500 attendees to be rerouted through a hotel gift shop after protesters blocked the primary transportation area. The team also revisits an island downpour, a limousine staging challenge, an 8,000-person block party, and a Hawaii experience that had to be completely repositioned because of rain.
The conversation reveals why a contingency plan is only useful when the people, vendors, routes, layouts, and decision process behind it are ready to move.
In this episode, you will learn:

• Why an indoor event may still require a separate backup venue
• How to make event investments transferable across multiple plans
• Why alternate floor plans should be completed before the disruption
• How to identify the people authorized to change the plan
• Why decision deadlines should be placed directly on the production schedule
• How transportation and attendee flow can become contingency issues
• How to preserve the intended experience even when the original format changes

The strongest Plan C does not call attention to the disruption. It protects the experience so well that attendees never know how much changed behind the scenes.

Modernizing an experienced event team does not mean starting over. It means knowing what to preserve, what to change, and who needs to be involved earlier.
In this episode of Event Planner Confessions, Cara Pratt talks with Dawn Wesley, Senior Manager of Agency Operations, Agency Awards and Recognition at Allstate, about team modernization, attendee experience, AI, supplier strategy, procurement, and the capabilities future event leaders will need.
Dawn has spent more than three decades at Allstate and 16 years in sales leadership. Before leading the company's event-planning team, she experienced its incentive programs as an attendee and award winner. That background gave her a direct view into how event policies, recognition programs, guest experiences, and family inclusion feel from the other side of the plan.
When Dawn moved into event leadership, she inherited a team with roughly 100 years of collective experience inside Allstate. Her job was not to dismiss that history. It was to modernize the work while respecting the knowledge and relationships that had already made the programs successful.
The conversation then turns to supplier strategy and procurement. Dawn explains why planners must help procurement understand the purpose behind event decisions and why procurement should be involved before scopes, suppliers, and contract positions are already locked. When both teams understand the same business outcome, procurement can become an extension of the event team rather than a final approval step.
Finally, Dawn shares what she looks for in future event professionals and why grit, curiosity, energy, and the willingness to learn can matter more than a traditional event-planning background.
In this episode, you will learn:

• How attendee experience can reshape event policies and family programming
• How to modernize a team without dismissing its institutional knowledge
• Why diverse professional backgrounds can strengthen an established event function
• How AI can improve standards, analysis, planning, and work-life balance
• Why new supplier relationships can unlock ideas an experienced team has not seen before
• When procurement should enter the event-planning process

The future event team is not built by replacing everything that came before. It is built by preserving what works, opening the door to better ideas, and aligning the right people earlier.

AI can generate content at extraordinary speed. It cannot recreate the trust, spontaneity, and shared memory of a live room.
In Part 2 of this Event Planner Confessions conversation, Ashley Currin continues her discussion with Jimmy Knowles, Global Head of Experiential at Canva, about artificial intelligence, human connection, experiential marketing, and the future of live events.
Jimmy explains why he is not afraid of AI and how his team uses it to reduce administrative work, improve planning, generate meeting agendas and recap emails, and create more time for creative thinking.
His goal is not to make AI the center of the experience. When the technology is being used effectively, Jimmy believes it should almost disappear into the background.
As AI becomes integrated into every tool and digital content becomes harder to verify, Jimmy believes live experiences may become one of the last trusted platforms available to audiences and brands. A physical event provides something generated content cannot: a moment people know happened directly in front of them.
The conversation also explores Jimmy’s push for greater experiential recognition at Cannes Lions. Although experiential marketers create the environments and activations that power the festival, the discipline continues to receive limited recognition through its stages and awards program. Jimmy shares the progress being made and why formal recognition could help experiential teams become part of the strategy instead of another budget line.
Ashley and Jimmy then discuss how Canva’s experiential team grew from a team of one into a group of ten marketers with complementary strengths across strategy, production, and agency work.
Finally, Jimmy shares two unforgettable Event Planner Confessions. He recounts the crisis that unfolded during Airbnb Open when thousands of attendees were spread across Paris during the terror attacks and explains why event insurance and crisis communication are now among the first things he considers.
He also takes listeners behind Canva’s polarizing Enterprise rap battle and explains how the criticism unexpectedly revealed the strength of Canva’s community and gave the company permission to become even more unapologetically itself.
In this episode, you will learn:

• How Canva’s experiential team uses AI behind the scenes
• Why effective AI should almost disappear into the background
• Why live experiences may become more valuable as digital trust declines
• What “Less URL, more IRL” means for the future of events
• Why Jimmy is advocating for experiential recognition at Cannes Lions
• How experiential can move from a budget line into the strategy
• How Jimmy built Canva’s experiential team from one person to ten
• Why crisis communication and event insurance must be established early
• What Canva learned when its rap battle divided the internet

The more AI creates, the more valuable real presence, trust, and human connection become.

Canva is one of the world’s most recognizable digital platforms. Jimmy Knowles is responsible for making it something people can walk into, explore, and feel.
In Part 1 of this Event Planner Confessions conversation, Ashley Currin sits down with Jimmy Knowles, Global Head of Experiential at Canva, to explore how creative careers are built and how digital-first brands can create meaningful real-world experiences.
Jimmy shares the unconventional story of being offered his first events job from a commencement stage in front of approximately 11,000 people. That opportunity led him to the Macy’s Thanksgiving Day Parade, Fox, Civic Entertainment Group, Airbnb, and eventually Canva.
He takes listeners behind the scenes of Airbnb Open, which grew from approximately 1,000 attendees into a 20,000-person experience spanning seven venues in downtown Los Angeles. Jimmy explains how that work shaped his approach to community building, audience connection, and designing experiences at scale.
At Canva, the goal is not simply to place logos and brand colors inside a venue. Jimmy and his team want every physical experience to feel colorful, playful, inclusive, and unmistakably Canva.
That philosophy helped shape Canva Create as an “un-conference conference” built around how audiences should feel, not only what the program needs to communicate. Jimmy explains why the strongest experiential marketing should create something audiences could not imagine coming from another brand.
The conversation also explores how Jimmy’s theater background continues to influence his work. From collaboration and improvisation to reading the room and recovering in real time, he explains why the skills learned onstage remain essential to event planning and experiential leadership.
Finally, Jimmy shares what is ahead for Canva’s experiential portfolio, including the continued evolution of Canva Create, Canva Originals, the Canva World Tour, and new opportunities to expand Canva’s creative ecosystem.

In this episode, you will learn:

• How Jimmy Knowles built his career in experiential marketing
• What Airbnb Open taught him about community and scale
• How Canva transforms a digital-first brand into a physical experience
• Why Canva Create was built as an “un-conference conference”
• Why curiosity remains one of Jimmy’s most important creative tools
• What Canva is building next through events, content, and community

Part 1 explores how Jimmy learned to build experiences people can feel. Part 2 continues with AI, trust, industry recognition, leadership, and his Event Planner Confessions.

More content is not always more valuable.

In this episode of Event Planner Confessions, Cara Pratt talks with Tavar James, vice president of global events at Forrester, about why the company introduced shorter, more intimate Forums alongside its flagship Summits and shortened experiences across parts of the portfolio.

Tavar shares how a listening tour with attendees, sponsors, clients, and internal teams exposed the real friction around event participation: higher travel costs, tighter budgets, too much time away from work and family, content overload, and sponsorship value that was not always obvious enough.

He explains how Forrester responded with more accessible formats, bi-coastal options, shorter agendas, more flexible sponsorships, and a stronger focus on relevance. He also discusses how the team is measuring the change through satisfaction, content scores, NPS, ticket revenue, sponsorship revenue, and the ability to act quickly on yellow and red signals.

The conversation then turns to leadership. Tavar breaks down how a clear point of view, commercial thinking, and transparency with both executives and the event team helped build buy-in before the strategy had a long results history.

And in true Event Planner Confessions fashion, Tavar shares the emergency that changed how he thinks about empathy, executive communication, and having a plan before anyone believes they will need it.

In this episode, you will learn:

• Why Forrester added shorter Forums without eliminating its flagship Summits
• How attendee and sponsor feedback shaped the new event formats
• Why accessibility includes cost, geography, time, and the option to self-fund attendance
• How shorter events change content, scheduling, team recovery, and sponsor value
• Which attendee and commercial signals Forrester is using to evaluate the strategy
• Why event leaders need a point of view tied to commercial outcomes
• How transparency can close the trust gap between leaders and their teams

The best event size is not the biggest or the smallest. It is the one designed for the outcome the audience and the business actually need.

Anaheim is one of the most recognizable destinations in the country, but recognition does not always lead to consideration.

Visit Anaheim’s research found that roughly nine out of ten people knew the city, yet there was a 64 percent drop between awareness and the number of people who would consider bringing a meeting or convention there. The challenge was not getting people to recognize Anaheim. It was helping them understand everything the destination offered beyond its most famous icons.

In this episode of Event Planner Confessions, Ashley Currin and Sam Monroe sit down with Scott Oklin, Chief Marketing Officer of Visit Anaheim, to unpack the strategy behind the city’s new A-City unscripted positioning.

Scott explains how Visit Anaheim used research, local partnerships, unexpected creative agencies, experiential campaigns, and Anaheim’s real community to build a more emotional and complete destination story. He also shares how local restaurants, breweries, entertainment venues, cultural communities, and unexpected spaces can become part of the event itself.

In this episode, you will learn:

• Why Anaheim’s challenge was consideration rather than awareness
• How Visit Anaheim used research to guide its new destination positioning
• Why emotional connection can influence destination decisions
• How iconic attractions can introduce attendees to a city’s broader culture
• Why local restaurants, venues, and communities should become part of the event experience
• How destination marketers and event planners can tell a more complete story together

The real opportunity is not simply getting people to recognize a destination, but helping them see, feel, and experience everything it can become.

Most event problems do not begin on-site. They begin much earlier, when expectations are misunderstood, important details are missed, or everyone leaves the same conversation with a different version of what was decided.

In this episode of Event Planner Confessions, Cara sits down with executive coach Evan Roth to explore the communication and leadership skills event professionals need when the pressure is high. Evan is also Cara’s business coach and helped her shape the original vision for the podcast.

Together, they break down why active listening requires more than staying quiet, how planners can create shared understanding across clients and vendors, and why clear follow-up can prevent small communication gaps from becoming major execution problems.

The conversation also explores emotional regulation, written communication, feedback, trust, and conflict debt, the unresolved tension that continues building when difficult conversations are avoided. Evan explains why emotions spread through teams, when a conversation should move away from email or chat, and how trust can take months to build but only seconds to damage. Cara connects each lesson directly to the event world, where one missed delivery, absent vendor, or off-script speaker can test an entire team.

In this episode, you will learn:

• Why listening failures create execution problems
• How to establish shared understanding
• When to move a conversation off email
• How emotions affect an event team
• Why unresolved conflict becomes conflict debt
• How trust helps teams recover from mistakes

The strongest event teams are not the ones that never experience pressure. They are the ones that know how to listen, regulate their reactions, address conflict, and protect trust while working through it.

A packed calendar can look like ambition from the outside while quietly becoming the very thing that is burning you out. For event planners, every open space can quickly become another client call, site visit, internal meeting, networking event, travel block, or after-hours obligation. The work keeps getting done, but the margin disappears, the recovery time gets pushed aside, and eventually even success begins to feel exhausting.

In this episode of Event Planner Confessions, Cara sits down with burnout and peak-performance speaker Erin Stafford immediately after her “Burn Bright, Not Out” keynote.

Drawing from her experience as a bestselling author, Cambridge-trained social psychologist, and former hyper-growth executive, Erin explains why the same habits that help high achievers succeed can eventually leave them overwhelmed and depleted.

She also shares practical ways event professionals can protect their time, reduce unnecessary pressure, and create careers that feel as strong on the inside as they look from the outside.

In this episode, you will learn:

• Why removing one small commitment can change the way your entire week feels
• How shorter meetings create more margin without reducing productivity
• Why travel, focus, and recovery time need to be protected intentionally
• How saying no without guilt can improve your performance and energy
• Why JOMO may be more valuable than FOMO for high achievers
• How defining success helps you decide what truly deserves your time

Burnout rarely begins with one dramatic moment. More often, it builds through hundreds of small commitments that leave no room to breathe. The question is not whether you can keep pushing, but what might change if you finally took one thing off.