As event professionals, we're constantly seeking that elusive "wow factor" that transforms a good celebration into an unforgettable experience. With AI becoming increasingly sophisticated, I decided to put ChatGPT through the ultimate test: could it rise to the challenge of creating a truly bespoke event concept?

I presented it with a demanding scenario—planning a surprise 70th birthday celebration for a retired sailing enthusiast and CEO at a Chicago skyscraper restaurant overlooking Lake Michigan, complete with his love for French cuisine and fine wines. The results were both impressive and revealing, highlighting what I call the "AI hospitality paradox"—the tension between leveraging technology's efficiency while maintaining the deeply human connections that define exceptional hospitality.

What ChatGPT delivered might surprise you, but where it fell short offers crucial insights for every event planner navigating our AI-augmented future.

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Using Technology to Create More Human Connections

How smart automation can free event planners to focus on what matters most

In the last edition of Event Pulse, the exploration of Will Guidara's "unreasonable hospitality" sparked an insightful question from reader David M., who wrote: "Guidara's playbook makes me think about how AI's growing ability to anticipate preferences could help scale small personalized moments without losing warmth. What routine tasks would you hand off so you could spend more time crafting those surprises and which manual processes eat most of your day?"

David has identified something crucial: the tension between leveraging AI's efficiency and maintaining the human touch that makes hospitality truly unreasonable. As event planners, we're facing a fundamental question - not whether AI will change our industry (people, let’s face it, it already has), but how we can harness it to amplify rather than replace the personal connections that define exceptional events.

The Great AI Misconception in Event Planning

Before diving into practical applications, let's address the elephant in the room: AI's reputation for "hallucinating" or generating inaccurate information. I recently asked ChatGPT about their current hallucination rates. Here is their key takeaway:

• GPT-5 represents a notable improvement over prior models—especially in its “thinking” variant with browsing enabled—often hovering around or under 1–1.5% hallucination rate.

• Still, hallucination rates can vary widely depending on context (e.g., summarizing docs vs. medical reasoning) and evaluation method.

• Human oversight remains essential, particularly in high-stakes areas like medical, legal, or financial tasks.

This concern is valid and critical for our industry, where a single error can damage client relationships and event success. For this a 1-1.5% chance of a hallucination is too high. However, dismissing AI entirely would be like refusing to use email because spam exists.

The key is understanding where AI excels and where it falls short. AI is exceptional at pattern recognition, data processing, routine communication, and predictive analytics. It struggles with nuanced decision-making, reading emotional context, and handling unexpected situations that require creative problem-solving - exactly the areas where human hospitality shines.

Think of AI as a sophisticated assistant that never gets tired of organizing your filing system, but you wouldn't trust it to comfort a distressed guest or improvise when your keynote speaker's flight gets cancelled. The magic happens when we use AI to handle the predictable so we can focus on the personal.

The Smart Delegation Framework: What AI Should (and Shouldn't) Handle

Not all event planning tasks are created equal when it comes to AI delegation. Here's a framework for making smart decisions:

Green Zone: Safe for AI Automation

Data Processing and Analysis AI excels at parsing registration data to identify patterns and preferences. It can analyse past attendee behaviour to predict session popularity, dietary requirements, or networking interests. Unlike human analysis, AI can process thousands of data points simultaneously without fatigue or bias.

Example in action: An AI system analysing registration data might identify that 40% of attendees have registered for sessions on sustainability, suggesting an opportunity to incorporate eco-friendly elements into catering or create an impromptu networking group for environmentally conscious participants.

Routine Communications Standardized confirmations, reminders, and logistical updates are perfect for AI handling. The technology can personalize these communications at scale while maintaining consistency in tone and timing.

Example in action: An AI system can send personalized pre-event emails that reference each attendee's specific session selections, dietary preferences, and networking interests, creating a sense of personal attention without requiring human intervention.

Schedule Optimization AI can analyze multiple variables - room capacity, speaker availability, attendee preferences, traffic flow patterns - to optimize event schedules in ways that would take humans days to calculate.

Basic Customer Service Chatbots can handle routine questions about venue directions, schedule changes, and general event information, freeing human team members for complex issues.

Yellow Zone: AI-Assisted but Human-Supervised

Personalization at Scale AI can identify opportunities for personalized touches - noting that an attendee mentioned celebrating an anniversary in their registration comments - but humans should decide how to act on this information.

Example in action: AI flags that John from Chicago mentioned missing deep-dish pizza in a pre-event survey. A human team member uses this insight to arrange for a Chicago-style pizza delivery during the networking lunch, complete with a note referencing his comment.

Content Curation AI can suggest relevant content, speakers, or networking matches based on attendee profiles, but humans should validate these recommendations against the event's broader goals and context.

Crisis Communication Templates AI can draft initial responses to common crisis scenarios (weather delays, schedule changes, technical issues), but human review ensures appropriate tone and accuracy.

Red Zone: Keep Human-Only

Emotional Situations When attendees are upset, confused, or dealing with personal emergencies, human empathy and judgment are irreplaceable.

High-Stakes Decision Making Decisions that could significantly impact attendee experience, budget, or safety require human oversight and creativity.

Relationship Building The conversations that turn attendees into advocates and clients into partners require genuine human connection.

Creative Problem Solving When your venue floods an hour before the reception or your keynote speaker tests positive for COVID, you need human creativity and adaptability.

Real-World AI Applications: From Theory to Practice

Let's examine specific ways event planners are already using AI to enhance rather than replace hospitality:

Intelligent Registration Systems

Modern registration platforms use AI to streamline the signup process by predicting likely session choices based on job titles and past behavior. This reduces friction while gathering more accurate preference data.

One corporate events company uses AI to analyze registration patterns and automatically suggest relevant networking connections, which are then reviewed by human team members who add personal context before making introductions.

Predictive Catering Management

AI systems can analyze historical consumption data, weather patterns, and event schedules to predict catering needs with remarkable accuracy. This reduces waste while ensuring adequate supply - a behind-the-scenes improvement that enhances guest experience without being visible.

Dynamic Content Personalization

Event apps now use AI to customize the content each attendee sees based on their interests, session attendance, and networking activity. However, the most successful implementations combine this automation with human curation to ensure recommendations align with event goals.

Smart Resource Allocation

AI can optimize staff deployment by predicting crowd patterns and identifying potential bottlenecks before they occur. This allows human team members to be positioned where they can have the greatest positive impact on attendee experience.

The Time Liberation Strategy: What to Automate First

Based on feedback from event planners who've successfully integrated AI, here's a priority order for automation that maximizes time savings:

Week 1-2: Start with Communications Implement automated registration confirmations, reminder sequences, and basic FAQ responses. This typically saves 3-5 hours per event while improving response consistency.

Month 1: Add Data Analysis Use AI tools to analyze registration data and identify trends or opportunities for personalization. This intelligence gathering previously took hours of manual spreadsheet work.

Month 2-3: Optimize Scheduling Implement AI-assisted schedule optimization for sessions, staff deployment, and resource allocation. The time savings here are dramatic - what used to take days of manual coordination now happens in minutes.

Month 4+: Advanced Personalization Once comfortable with basic automation, begin using AI to identify opportunities for personalized touches, always with human oversight and execution.

Risk Mitigation: Protecting Your Reputation While Innovating

The concern about AI hallucination is legitimate and requires specific safeguards:

Never Fully Automate Client-Facing Communications Always have human review for any communication that goes directly to clients or VIP attendees. AI can draft, but humans should approve.

Implement Verification Systems For any AI-generated recommendations or insights, create verification processes. If AI suggests that 70% of attendees are vegetarian, manually cross-check this against registration data.

Maintain Override Capabilities Ensure that human team members can easily override or modify any AI-generated decisions. Technology should enhance human judgment, not replace it.

Start Small and Scale Gradually Begin with low-risk applications like internal scheduling optimization before moving to customer-facing implementations.

Document AI Usage Keep clear records of where and how AI is being used, so team members understand when they're working with AI-generated insights versus human analysis.

The Hospitality Amplification Effect

When implemented thoughtfully, AI creates what we might call the "hospitality amplification effect." By handling routine tasks efficiently, AI frees human team members to focus on the spontaneous, creative, and emotionally intelligent work that defines unreasonable hospitality.

Consider this scenario: Instead of spending two hours manually analysing dietary restrictions and seating preferences, an event planner uses AI to complete this analysis in minutes. The saved time is invested in personally calling three attendees who mentioned in their registration that they're first-time conference goers, offering to connect them with relevant peers and providing personalized orientation.

The AI handled the data processing, but the human connection - the part that turns a good event into a memorable experience - remained entirely human.

The Human-AI Partnership Model

The most successful event planners aren't choosing between human touch and AI efficiency - they're creating partnerships where each amplifies the other's strengths.

AI provides the intelligence: identifying patterns, predicting needs, and surfacing opportunities for personalized attention. Humans provide the wisdom: interpreting context, making nuanced decisions, and executing with emotional intelligence.

This partnership model is already showing results. Event planners report that AI automation allows them to spend 40% more time on strategic relationship building and creative problem-solving - exactly the activities that differentiate exceptional events from merely functional ones.

Looking Forward: The Evolution of Event Hospitality

As AI capabilities continue to expand, we'll likely see even more sophisticated applications: virtual assistants that can engage in natural conversation while maintaining consistent brand voice, predictive systems that anticipate and prevent problems before they occur, and personalization engines that create individualized experiences at unprecedented scale.

But regardless of technological advancement, the fundamental truth remains: people attend events to connect with other people. Technology's highest purpose in our industry is enabling and enhancing these human connections, not replacing them.

The event planners who thrive in this AI-augmented future will be those who master the art of strategic delegation - knowing when to let technology handle the predictable so they can focus entirely on creating those unreasonable moments of hospitality that transform events into experiences.

Your Next Steps: Practical Implementation

Ready to explore AI integration in your event planning? Start here:

1. Audit Your Time Drains: Track how you spend time for one week. Identify repetitive tasks that don't require creative thinking or emotional intelligence.

2. Choose One Low-Risk Automation: Begin with automated email sequences or basic data analysis - something with minimal client-facing risk.

3. Establish Review Protocols: Create systems for human oversight of any AI-generated content or decisions.

4. Measure the Impact: Track not just time savings, but how automation affects your ability to focus on relationship building and creative problem-solving.

5. Scale Thoughtfully: Add new AI applications only after mastering existing ones and maintaining service quality.

The goal isn't to become more efficient at the expense of becoming less human. It's to become so efficient at the routine that we can be more human where it matters most - in the moments of connection, surprise, and delight that transform events into memories.

AI won't replace event planners who understand hospitality. But event planners who understand AI will replace those who don't. The question isn't whether to embrace this technology, but how to use it in service of the fundamentally human work of bringing people together and creating experiences that matter.

I Put ChatGPT to the Test

As event professionals, we’re constantly challenged to exceed client expectations and deliver that elusive “wow factor.” Continuing on from the previous article, I decided to test whether AI could rise to the occasion.

The scenario: I imagined myself as a customer service professional at a major restaurant perched atop a Chicago skyscraper overlooking Lake Michigan, tasked with planning a surprise 70th birthday celebration. The guest of honor? A retired CEO, once an avid sailor, with a deep love for French food and fine wines. My challenge for ChatGPT was simple yet demanding: could it create a celebration concept that feels not only bespoke, but truly unforgettable?

Here are the 3 scenarios that it came up with:

Option 1: “An Evening in Saint-Tropez” – French Riviera Yacht-Inspired Celebration

 Theme & Décor: Transform your restaurant space into a luxurious French Riviera yacht club with nautical accents: navy-and-white linens, brass lanterns, polished wood finishes, and touches of sailcloth. Projection mapping can create the illusion of being docked in a Mediterranean harbor, with Lake Michigan’s view as the backdrop.

 Culinary Experience: A curated menu of French coastal cuisine—think bouillabaisse amuse-bouches, Niçoise-inspired salads, and a main of grilled Dover sole with lemon beurre blanc. A Champagne and rosé tasting station featuring Provence wines.

Special Touch: A memory wall designed as a "sail" where guests can pin photos and handwritten notes celebrating his achievements and adventures. A surprise French chanteuse performing classics like “La Vie en Rose” as the evening finale.

Option 2: “A Grand Cru Journey” – Private French Wine Cellar Experience in the Sky

 Theme & Décor: Create an immersive wine cellar atmosphere within the restaurant. Dimmed lighting, rustic French wine barrel décor, and elegant candlelit tables. Guests are greeted with a personalized wine passport on arrival.

Culinary Experience: A five-course French fine dining menu paired with premier wines from Burgundy, Bordeaux, and Champagne, introduced by a Master Sommelier. Each wine is tied to a milestone in his life (e.g., Bordeaux for his corporate achievements, Burgundy for family milestones).

Special Touch: For dessert, unveil a “wine bottle” cake decorated with his initials and birth year. As a keepsake, each guest receives a custom-engraved wine stopper or crystal glass etched with the event date.

Option 3: “Legends of Leadership” – A Parisian Salon Celebration

Theme & Décor: Inspired by the intellectual salons of Paris, this event celebrates his legacy as a leader. Elegant chandeliers, velvet draping, and gilded accents set the mood. Each table named after a great French leader, sailor, or philosopher.

 Culinary Experience: A French haute cuisine menu featuring dishes such as foie gras terrine, coq au vin, and a cheese course with artisanal selections flown in from France. French wines paired thoughtfully with each course.

Special Touch: A short tribute film with messages from family, friends, and former colleagues played during dinner. A string quartet performs French classical pieces. The evening ends with a Champagne toast overlooking the glittering Chicago skyline, led by his closest family member.

While each option ties together his personal passions (sailing, leadership, French cuisine and wine) with the luxury and exclusivity of the venue, I felt they all fell flat, missing the, well, the human touch. So, I told Chat GPT to consider bringing in Michelin starred chefs or award winning sommeliers. This is the revised version:

Option 1: “Sailing into Seventy” – Michelin Star French Riviera Experience

Headliner: Fly in a Michelin-starred chef from the South of France to design and personally prepare a bespoke menu inspired by the French Riviera. Each dish tells a story connected to the sea, tying into his passion for sailing.

Culinary Journey: A seven-course tasting menu (e.g., sea urchin custard, langoustine carpaccio, Mediterranean turbot with saffron) paired with rare vintages from Provence and Corsica.

Showstopper Moment: Between courses, a live jazz trio performs French seaside classics. Dessert is served on the rooftop terrace, with a surprise Champagne sabrage ceremony performed by the sommelier.

Personal Touch: The final course, a delicate gâteau Saint-Honoré, is presented with his initials engraved in spun sugar.

Option 2: “Grand Cru 70” – Private Vertical Wine Tasting with a Master Sommelier

Headliner: Invite a world-renowned Master Sommelier (perhaps one from France or Napa) to host an exclusive vertical tasting of Bordeaux Grand Crus spanning several decades, including the year of his birth.

 Culinary Journey: A Michelin-level French chef (local or flown in) creates a five-course haute cuisine menu crafted around the wines, such as duck à l’orange with a 1982 Château Margaux.

Showstopper Moment: Each guest receives a bespoke leather-bound wine journal to record tasting notes. At the finale, the sommelier presents the husband with a magnum of Bordeaux labeled and etched for his 70th.

Personal Touch: A custom “wine passport” stamped at each course tasting station as if the guests are traveling through France’s vineyards.

Option 3: “Parisian Salon of Legends” – An Evening with Culinary Royalty

Headliner: Bring in a French Michelin-starred chef and pastry chef duo for a one-night-only Parisian salon dinner. The chefs introduce each course themselves, as though the guests are dining in their own maison.

Culinary Journey: Classic French haute cuisine elevated: foie gras torchon with Sauternes, lobster thermidor, côte de boeuf carved tableside, and a show-stopping dessert cart of mille-feuille, macarons, and soufflés.

Showstopper Moment: After the meal, the lights dim and a surprise French cabaret performance (or Edith Piaf-style vocalist) brings the magic of Paris to Chicago.

Personal Touch: A tribute film plays on hidden screens mid-evening, celebrating his journey from sailor to CEO, ending with a toast led by his family. Each guest departs with a box of hand-crafted French chocolates designed by the pastry chef.

The Verdict: Where AI Falls Short

While ChatGPT delivered polished, thematically cohesive concepts that checked all the boxes, something crucial was missing—the spark of human intuition that transforms a good event into an extraordinary one. Each proposal, despite its sophisticated details, felt constrained by the parameters I initially provided. The AI focused exclusively on maximizing the restaurant space rather than reimagining the entire experience.

Take Option 1, for instance. A human event planner would have immediately recognized that a sailing enthusiast's 70th birthday deserves more than nautical-themed décor—it calls for an actual connection to the water. Why not charter a yacht for cocktails and sunset cruise on Lake Michigan, then transition to the restaurant for an intimate dinner? This multi-location approach creates narrative flow and emotional crescendo that AI simply didn't consider.

This limitation reveals AI's current role in our industry: it excels as a brainstorming partner and detail generator, but it cannot replicate the experiential thinking that makes events truly memorable. As event professionals, our greatest strength lies not in following formulas, but in seeing beyond the brief to craft moments that resonate on a deeper, more personal level.

The question isn't whether AI will replace event planners—it's how we'll leverage it to amplify our uniquely human ability to create magic.

What would you have planned for this celebration? Share your ideas in the comments below.