Hi there!

Last week, I attended an AI Executive Dinner at the exclusive SF restaurant, One65. Typically, when deciding whether attending one of these events will be worth my while, I ask the organizers to review both the agenda and the guest list. In this case, both seemed promising: The evening would feature a Michelin star 5 course dinner, an AI panel (featuring one female CMO), networking with ~30 leaders from companies like Meta, Apple, Google, and a number of AI startups. In short, it had all the right ingredients to make a successful night.

But…as I’ve blogged about previously…having the right ingredients doesn’t always guarantee a great event.

During the cocktail hour, I was asked by the Executive host of the dinner for suggestions on how to run the evening’s event. This was part flattering, part horrifying…yet, didn’t come as a surprise as this was actually the second time I have attended one of these dinners in the past few months where the event organizer asked me for the best way to run the evening while AT THE EVENT. And that’s why I’m focusing today’s Gem on the reason why it’s important to think through the flow of an event, and not just the ingredients BEFORE you have a room full of executives.

When planning an executive gathering, it's tempting to focus on the ingredients only: impressive venue, check!t Great guest list from impressive companies - check! Entertainment - check!

Gianna’s Gem: Here's the truth many planners miss: you can nail every ingredient that should make for a great event, but if the event isn’t thoughtfully planned with the attendee journey and outcome in mind, it might easily fail.

The Executive Event Paradox

I've witnessed this scenario countless times. A stunning rooftop venue with skyline views that would make anyone's jaw drop. A chef flown in from another continent. Entertainers who have performed for royalty. A guest list consisted of the most influential leaders in the industry.

And yet... something felt off.

The executives weren't connecting. Conversations remained surface-level. People checked phones discreetly, wondering when they could politely exit. Despite ticking every box on the luxury event checklist, the experience failed to deliver what executives truly seek: meaningful connections and valuable exchanges done in a manner that is intentional and efficient.

What Executives Really Want

Let's be honest - executives don't attend your dinner for the imported truffles or branded swag bags. Those elements might pique their interest, but what keeps them engaged and ensures they'll accept your next invitation is something far more valuable:

Genuine peer connections with others who understand their unique challenges
Insights they can't Google shared in an environment of trust
Space for authentic conversation without the constant pitch
Efficient use of their limited time

The Over-Indexed "Wow Factor" Trap

Many planners fall into what I call the "wow factor trap" - spending disproportionate time, budget and energy on creating Instagram-worthy moments that ultimately distract from rather than enhance meaningful connection.

Example: At this event last week, there was a magician. I have blogged previously about how magicians can be a great event element. But you can’t just toss a magician into the mix without a purpose. In the case of this event - it was unnecessary and a distraction. The magician approached me in the middle of a conversation I was having, which became an annoyance rather than a delight. And then the magician started off the dinner portion of the evening while the AI panel was saved for the dessert course (at which time I personally had to depart and missed it!)? The miss here? The executives are too busy watching the performance to speak with each other or . The magician compromised valuable conversation and content time. It's was supposed to be engaging, but did it facilitate better connections which was the point of the dinner? No.

On the other hand, I used a magician at my husband’s 50th birthday (Check out Dennis here), but I was intentional about why he was there. As people gathered, he helped provide some entertainment, but only when people looked like they weren’t talking to other people. This warmed them up to him so that when we all sat down, he performed 3 tricks, one of which included my son so he would have a part in the special evening, one which involved my husband, the guest of honor, and the other involved the entire group. This sparked people’s attention and created delight all while servers were taking dinner orders so it didn’t interrupt the rest of the Jeffersonian style dinner I had planned.

Designing the Attendee Journey with Intention

The difference between forgettable and transformative executive events isn't found in bigger budgets or flashier elements - it's in the thoughtful design of the attendee journey from start to finish:

1. Pre-Event: Set the Foundation: One of my favorite authors, Priya Parker, writes in The Art of The Gathering about why it’s important to communicate with guests in advance about what they should expect from the event and prime them.

Communicate the value proposition clearly - executives need to know exactly why this gathering deserves their time. One of the biggest complaints I hear from Executives is no clearly communicated agenda or value proposition in advance.
Provide just enough context about other attendees to spark curiosity. Bonus: Curate connections in advance. Summit Series does a great job of personally introducing attendees to each other on a 1:1 basis in advance so people know at least one person they can connect with at the event.
Set appropriate expectations about the format and flow and just like a good marketing campaign - don’t bury the lead! If the main point of the event is the content, don’t save it for the dessert course!
Gather meaningful input that shapes the experience. When Execs are giving up their time to attend your event, it’s a nice touch to ask them what they’re hoping to get out of the experience or any topics they’d like to see covered. It's a simple but highly strategic step and just takes a little extra time and thoughtfulness..

2. Arrival: Reduce Friction Points

Streamline check-in to minimize administrative tasks and have a passed drink (I recommend sparkling wine, white wine and water) at the ready so people don’t have to spend the first 30 minutes networking on the way to the bar (pain point alert!)
Facilitate immediate connections rather than leaving people to fend for themselves. It is such a next-level move to have your team ready to personally introduce whoever arrives to someone you feel they’d benefit from speaking with. Again - this requires no extra time, simply extra thoughtfulness.
Offer a moment to transition from the outside world to your experience (I always offer where the restroom is, or have a personal host offer to take people’s coats and see if they need anything or a moment before escorting into the reception.

3. During: Orchestrate Without Controlling

Create conversation catalysts that spark meaningful discussion with conversation starters or a common question to get the group warmed up like “What was your first job”? Or “If you had 50 years more to live, what would you do”?
Design seating arrangements that foster new connections and are strategic for both the company and enjoyable for attendees. Birds of a feather also works if you don’t know who will be best suited to sit together so people can self-select the peers they want to engage with.
Balance structure and spontaneity throughout the agenda. If you have content, keep it light and add in opportunities for people to mix and mingle so they’re not stuck in one seat all night.
Read the room and adjust when energy shifts - always have a pivot in mind.
Build in reflection moments that help insights crystalize or a takeaway for attendees. A personal favorite of mine is to have people write themselves a note or key takeaway that they want mailed to them in 3 months. Then you collect and mail them - it’s a great way to remind people of their intentions and also follow up with them!

4. Departure: End with Intention

Provide closure that honors the time invested and if including a survey ask people if there was anyone they’d like an introduction to (with permission of course)
Capture commitments or insights while they're fresh and distribute in a meaningful way. If you take professional photos, send the photos of attendees directly to them with a thank you note for attending.
Create a delightful exit experience - I had to leave the Executive Dinner before dessert and it would have been lovely to have had a truffle and decaf coffee to-go! I love building in a sweet treat or warm drink for folks as they depart, especially if they have a long commute home.

Success Without Spectacle: A Case Study

One of the most successful executive dinners I've facilitated featured none of the typical "luxury" elements. The venue was a private dining room in a moderately-priced restaurant. The menu was simple but well-executed. There were no entertainers, no surprise moments, no elaborate gift bags.

What it did have was a thoughtfully designed attendee journey:

A pre-dinner exercise that surfaced each executive's most pressing challenge, moderated by a very skilled host.
A seating arrangement that positioned people next to others with complementary experience and affinities
Conversation prompts that progressed from easy sharing to more vulnerable discussion
Facilitated moments that ensured everyone contributed without putting anyone on the spot in an un-conference style format that ensured the topics that evening were relevant to those in the room
A simple mechanism for capturing insights and connections made and sharing out afterwards.
A thoughtful gift at the end which was a professional headshot and a bag with some artisanal goodies, a beautiful artisanal journal and pen that I will actually use, and a credit to take an Uber home (nice touch).

The result? Executives who typically duck out early stayed past the scheduled end time and the room was truly engaged. Multiple business relationships formed that night have led to partnerships. And the host received unsolicited messages of thanks for an "unusually valuable" evening. I’ve kept in touch with two people from that event personally who have reached out to make sure they stay on my mailing list!

Making Your Next Executive Event Count

Whether you're planning a dinner for 20 or a summit for 200, consider these questions before locking in the details:

Have you mapped the entire attendee journey, or are you just working off a mood board?
Does each element of your event contribute to or detract from meaningful connection?
Are you creating environments where authentic conversation can flourish?
Have you built in mechanisms to gauge engagement throughout and pivot if necessary?
Are you providing the right balance of structure and space?

The bottom line: Executives don't need another fancy dinner to attend. What they crave are experiences that deliver authentic connection, valuable insights, and efficient use of their time. When your attendee journey delivers those elements, you've created something truly valuable - with or without the bells and whistles.

What I’m Loving this week: For all my favorite vendors, partners and products, visit: https://www.giannagaudini.com/gianna-recommends

Bespoke Interactive Entertainment - meet Haikuists. As a lifelong writer, I was thrilled to be introduced to this amazing team through The Battery. They are like a photo booth for your soul, delighting guests with personalized haiku poems crafted on vintage typewriters! Not only that, their poets are elegantly dressed and engage with guests, turning their stories into unique, memorable haiku. How it works: Over the course of just a few minutes, guests share a piece of their life and receive a bespoke haiku which captures their essence in a haiku. Each haiku is a concrete memento—a symbol for guests that their story is worthy of being turned into a small but mighty work of art. Poetry is a gateway to more meaningful connection between humans, allowing them to unlock creativity that they didn’t know existed within. I love that Haikuists mission is to make poetry accessible to everyone so that they may experience the joy of connection that comes along with it. They are providing my gems with a 10% discount code if you apply GiannaVIP to any order when you reach out here.

Gianna

P. S. Need to chat? Book a 1:1 using my link for Expert advice on intro: intro.co/GiannaGaudini

Gianna's Gems

Gianna’s Gem - Beyond Caviar: Why Attendee Journey Makes or Breaks Exec Events

Gianna Gaudini