The EP Debrief

What makes a workplace holiday party feel thoughtful, and what can go wrong behind the scenes? Chris welcomes Sam back to The EP Debrief for an in-person conversation about planning company holiday events, from travel logistics and audiovisual hiccups to food, entertainment, and making guests feel welcome.

Sam shares lessons from organizing large team gatherings, including why planners need to know their audience, keep the agenda moving, and prepare to adapt when something goes wrong. They also debate holiday-party “red flags” and “green flags,” talk about forced fun, and reflect on the invisible work and personal pressures that event planners carry during the holidays.

Whether you’re planning a company holiday party, team celebration, or year-end event, this episode offers candid stories and practical reminders for creating an experience that puts people first.

Chapters

00:19 Sam returns in person

02:46 Planning a holiday breakfast for multiple teams

04:02 When the audiovisual setup fails

05:41 Themes, decorations and guest experience

09:58 The tricky logistics behind holiday events

11:30 Reusing an event template

19:16 Holiday-party red flags and green flags

24:23 The unseen pressures planners carry

29:23 Designing an event as an escape

31:19 Forced fun: does it work?

33:16 A last-minute planning check

#EventProfessionals #EventPlanning #HolidayParty

Everyone wants the Shark Tank moment, but nobody talks about the part before it. In this solo episode of The EP Debrief, Chris shares what he learned from a five-week startup incubator workshop, where every idea gets pressure tested. He turns it into a playbook for event planners and professionals: five questions to ask before event day. 1. Who is this really for? 2. Why now? 3. What would make it fail? 4. What happens if we get cut? 5. What does the guest actually feel? You'll also hear three lessons (trust over being organized, being present over speed, and the value of talking to people outside your industry) and Chris's 60-second rant on why planners should fall in love with the process and not the event-day photo. Which of the five questions does your team always skip? Tell us in the comments. Next episode: Sam Kiley returns in person to talk about planning a holiday party.

Chapters:
0:00 The part before the Shark Tank moment
4:27 The incubator workshop
6:47 Three lessons
8:55 The 5-question playbook
11:59 The 60-second rant
13:03 Final debrief 15:11

Next episode Keywords: event planning, event management, event professionals, Shark Tank, pressure testing ideas, event planning questions, vendor contingency, guest experience

#eventprofessionals #eventplanning #sharktank

The advice every event professional needs right now: stop treating personality like a soft skill and start treating it like the make-or-break factor it is. Alex Davis and Christopher Dela Cruz connect Ultimate Girls Trip chaos to the real-world pressure of staffing, client chemistry, vendor turnover, and why some people are brilliant in one room and totally wrong for another. Alex, who has spent her entire career in event planning and now works at a large agency in Chicago, breaks down what nearly a decade in the industry has taught her about reading the room, protecting your energy, and building the right team for the right event. Chris, who has worked alongside her across multiple agencies, brings the client-side perspective on what actually happens when a planner, a vendor, or a guest is even a little bit out of sync. You’ll discover:

• Why great people can still be a terrible fit for a specific event, client, or team
• How turnover changes everything, especially when trusted vendors disappear, and you have to rebuild fast
• The real ripple effect of being “just 20 minutes late” on transfers, activities, and departure logistics
• Why the best on-site partner is not the person who says “don’t worry,” but the one who helps you problem-solve
• How incentive trips, SKOs, and travel programs are evolving beyond stiff corporate branding into more memorable, experience-first moments

Alex also shares her strongest hill to die on: everyone should work in hospitality for at least a month. According to her, nothing builds self-awareness, empathy, and professionalism faster than being on the front lines of service. And if you’ve ever wondered why some attendees, clients, or coworkers seem completely oblivious to how their behavior affects everyone else, this episode will feel extremely familiar. Perfect for event planners, producer teams, client leads, and anyone who has ever had to smile through a logistical mess while quietly holding everything together. If you love sharp industry truths, Bravo-fueled comparisons, and candid conversation about what actually makes events work, hit play.

Four episodes in, it felt like the right time to stop, look around, and ask: what are we actually learning from all of this?

No guest this time. Just me, the mic, and a little debrief on the Debrief.

In this special solo episode, I’m looking back at the first four episodes of EP Debrief and the conversations that have stuck with me, from surviving chaos and betting on yourself to impossible expectations, boundaries, burnout, and why event professionals somehow always end up being the person expected to “just figure it out.”

And apparently I’ve decided to process all of this while working full-time, going to grad school, building EP Labs, and hosting a podcast… because balance. 😅

We’re talking about what Below Deck taught me about teams under pressure, why Elle Woods will forever be my reminder to bet on yourself before everyone else gets it, what The Devil Wears Prada says about the difference between excellence and impossible expectations, and why learning to say no might actually make you better at your job.

But there’s also a bigger question I keep coming back to:

Why are event professionals still being rewarded for rescuing broken systems?

Because I don’t think the future of events needs more heroes running around putting out fires. I think we need fewer fires in the first place.

That’s where my thinking around AI, data, smarter workflows, and EP Labs starts to come in, especially when it comes to production schedules, repeatable operational work, and catching problems before they become an onsite emergency.

This episode is part reflection, part rant, part “wait… maybe I’m actually onto something here.”

If you work in events, manage a million moving pieces, have ever been handed an impossible turnaround with a smile, or have caught yourself thinking there has to be a better way to do this, this one’s for you.

No polished answers. No pretending we have it all figured out.

Just the debrief.

Can event professionals deliver five-star experiences without sacrificing themselves in the process?

In Episode 4 of The EP Debrief, host Christopher Dela Cruz joins event producer Eva-Marie Kailas to unpack what Below Deck gets surprisingly right about the event and hospitality industries.

From demanding clients and last-minute requests to team dynamics, leadership, managing up, invisible work, and the pressure to make everything look effortless, life on a superyacht can feel VERY familiar to anyone who has ever worked behind the scenes of an event.

Chris and Eva-Marie dive into:

• ️Why every member of the team matters to the final guest experience
• Why burnout and marathon event-day shifts shouldn’t be badges of honor
• What Below Deck teaches us about teamwork, hierarchy, and communication
• How to manage demanding clients without absorbing all of their pressure
• Why great leaders recognize people’s strengths and give them credit
• The realities of managing up, down, and sideways
• Why boundaries can actually create better experiences
• How the event industry’s definition of “professionalism” is changing

Because the attendee may never see the scrambling, stress, last-minute fixes, duct tape, steaming, or chaos happening behind the scenes.

They only know how the experience made them feel.

So maybe the goal isn’t to stop creating five-star experiences.

Maybe it’s learning how to create them without losing ourselves along the way.

What happens when high standards start feeling impossible?

In this episode of The EP Debrief, Chris Dela Cruz sits down with event professional Kristina Mease, CMP, to unpack The Devil Wears Prada through the lens of the events industry, where demanding expectations, constant pressure, imposter syndrome, and the feeling that you always have to say “yes” can feel a little too familiar.

Chris and Kristina break down the Miranda Priestly effect: Is she simply an impossible leader, or is she a product of an industry that rewards perfection at any cost? They explore the difference between mentorship and intimidation, how high-performing environments can impact confidence, and what happens when ambition starts competing with boundaries and wellbeing.

They also dig into Andy’s evolution, the pressure to prove yourself when you’re the least experienced person in the room, and why event professionals sometimes struggle to recognize just how much they actually know.

Plus, with The Devil Wears Prada 2 bringing familiar characters back into a very different world, Chris and Kristina talk about career evolution, changing power dynamics, and what happens when you return to an industry, or a team, after you’ve grown.

And, of course, Kristina takes on the 60-Second Rant.

In this episode:
• Imposter syndrome in the events industry
• High standards vs. impossible expectations
• Leadership, mentorship, and the “Miranda Priestly” boss
• Why event professionals feel pressure to always say yes
• Boundaries, burnout, and protecting your confidence
• Career growth and evolving workplace dynamics
• What The Devil Wears Prada still gets right about ambitious professionals

Because sometimes the biggest event lesson isn’t about executing the perfect event, it’s realizing you don’t have to lose yourself trying to create it.

🎙️ The EP Debrief: Pop culture meets real event lessons.

The confidence advice people repeat most is wrong. Elle Woods proves it, and so does Sam Kiley, a corporate in-house planner who manages internal events for 500+ team members, board travel, off-sites, and incentives. In this episode of EP Debrief, Sam and Christopher use Legally Blonde and the new Elle prequel to unpack what real confidence looks like in events, at work, and in the moments when you feel wildly underqualified. If you have ever sat at a table full of executives, second-guessed yourself after a simple question, or felt like you were "just support," this conversation will hit close to home.

• Why confidence is not the loudest voice in the room
• How Sam went from studying facility management to accidentally building a 10-year career in events
• The difference between external validation and actual self-trust
• Why having your own "Emmett" matters when you're finding your footing
• How to handle vendors, stakeholders, and pressure without letting them intimidate you

Sam shares the career pivots, imposter syndrome, and hard-won perspective that shaped her approach to planning, leadership, and self-belief. Christopher brings the same theme home through her own path in events, from high school prom planning to managing high-stakes conversations, budgets, and career expectations.This conversation gets especially real around the idea that confidence does not have to be loud to be powerful. Sometimes it looks like knowing your event, knowing your worth, and saying, "I am the table" when someone tries to treat you like you are not.If you are an event professional, a student figuring out your path, or anyone trying to stop living for other people's expectations, this one is essential listening. Perfect for anyone who wants more clarity, more courage, and a little more Elle Woods energy in their life.

Most event planners secretly dread the chaos behind every flawless event, until now. What if the key to smoother, stress-free productions isn't just hard work, but mastering behind-the-scenes partnerships? On this episode of The EP Debrief, I unlock the hidden lessons from Below Deck that can transform your approach to event planning forever. Imagine managing a luxury yacht’s every detail, knowing that every miscommunication can turn a perfect evening into chaos. That’s precisely what your team faces at every event. We delve into Below Deck's high-stakes world, from last-minute requests and deck-to-dinner precision to the importance of over communication and vendor collaboration. Chris reveals the surprising parallels between yachting and event production, showing how the fragility of these experiences hinges on tiny gestures, impeccable logistics, and seamless teamwork.

You'll discover:

• The overlooked power of early vendor inclusion and transparent communication
• How to prevent chaos inherited from poor pre-planning and slipped communication
• The critical role of over communicating details for flawless execution
• Why small client gestures (smiles, refills, simple kindness) drive loyalty and better contracts
• The mental and physical toll of burnout, and how to protect your team's well-being

This episode is essential listening for event professionals feeling overwhelmed by last-minute requests, fragile timelines, and the constant pressure to perform. If you’ve ever wondered how to craft experiences that feel effortless while avoiding costly mistakes, this is your playbook for elevating your partnership game, and your sanity. Chris Dela Cruz, host of The EP Debrief, shares his own experiences and expert insights, blending pop culture with real-world strategies. He has spent years in the trenches of event management, knowing that behind every perfect event is a network of hidden heroes, from vendors to support staff. This episode isn’t just about surviving; it’s about thriving by mastering the unseen groundwork that makes every event memorable.Perfect for event planners, vendors, and clients eager to ditch chaos for cohesion. By tuning in, you'll learn how to prevent the common pitfalls, foster stronger vendor relationships, and deliver unforgettable experiences without burning out. Because, ultimately, the secret to great events is great partnerships.Join us as we turn the chaos of Below Deck into your blueprint for success. Hit play and start transforming your events today.

The EP Debrief is officially here. 🎙️✨

Pop culture meets the real behind-the-scenes world of events: the chaos, the strategy, the vendor stories, the client curveballs, the burnout, the big wins, and the moments that never make it into the recap deck. This podcast is for the planners, vendors, venues, production teams, entertainers, and experience makers who know events are never “just a party.”

Expect honest debriefs, industry lessons, pop culture hot takes, and conversations with the people who actually make the magic happen.

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Events. Pop culture. Behind the scenes. No filter. 🎤

#TheEPDebrief #EventProfs #EventPodcast #PopCultureMeetsEvents #VendorVoice #EventPlanning #ExperienceDesign #BehindTheScenes #EventIndustry