The offsite is officially next week, and for once, I’m not in panic mode. Usually by this stage I’m running through a mental checklist at 2am wondering if I forgot to confirm transportation or if the hotel remembered my 47th email about gluten-free snacks.

But this time, we’re ahead of the curve. We’ve got the team excursion locked, meals planned (yes, even breakfast, I’ve learned the hard way that hungry attendees are not engaged attendees), a photographer lined up, and onsite support secured so I can actually sit in and participate in the sessions. Like a true strategic partner, not just the person sprinting around trying to fix the Wi-Fi.

And because this past month has been all about offsites here at OOTEA, I wanted to go deeper than my own checklist. So in this issue, I tapped into the experts at Offsite, the people who do this day in and day out, and asked them to spill their best-kept secrets on what really makes a killer offsite.

With love and lots of Coffee, ☕

Chrissy

P.S. This week’s “Week in My Life” is brought to you by Offsite, the only reason I’m not crying or pulling my hair out from stress. 🫠

When you’re knee-deep in planning an offsite, it’s easy to obsess over the “big” stuff — the venue, the agenda, the flights. But the experts at Offsite reminded me that the things we tend to underestimate are often what make or break the experience.

🍽️ Food & Beverage

“Food and Beverage is one of the number one pieces of feedback we see on event surveys,” says Harlie Walfish. “Hotels often set a minimum that looks fine on paper, but in reality you’ll spend more — and it’s worth it, because better food = happier, more engaged attendees.”

🚌 Logistics, Not Just Location

According to Kali Bradford, “Companies often underestimate the logistics around transportation and timing. How people actually get from point A to point B can set the tone for the entire event.” Smooth flow matters more than flashy venues.

🎯 Clear Goals, Clear Culture Fit

Cash Graner pointed out that the agenda only works if it maps back to business objectives and the company’s tone in that moment: “If leadership isn’t aligned, the agenda will feel scattered — and the offsite won’t land the way it should.”

💰 Budget Realities

Between AV, service charges, resort fees, and even breakfast (yes, people do eat it), you’ll almost always spend more than you think. “Budget realistically,” advises Kali, “because those hidden costs can swing numbers significantly.”

⏱️ Breaks That Actually Matter

“It’s the informal opportunities — meals, coffee breaks, walks — where the most valuable conversations happen,” says Harlie. Pack the agenda too tightly, and you miss out on the real ROI.

👉 Translation: Don’t just obsess over the venue contract. The things that look “small” on paper, meals, breaks, buses, are the things your team will actually remember.

I was lucky enough to be introduced to Ebony Belhumeur back in 2019 when I was running a small EA community called Elite Assisting. Fast forward to today, and it’s been incredible to watch her step into her role as founder and absolutely crush it.

In a recent piece for Business Insider, she shared the 4 career lessons she learned as a former EA to CEOs, from embracing a little “delusional” ambition, to treating curiosity as a superpower, to focusing on outcomes over compliance. It’s a reminder that the EA vantage point doesn’t just prepare you for the next role, it can shape you into a builder, a leader, and a force in whatever space you step into.

👉 Read the full article here.

Keep killing it, Ebony, we’ll happily be here cheering you on!

An offsite can have the perfect venue and agenda, but what attendees remember is how the experience felt, whether they felt engaged, included, and not completely drained. Here’s what the experts at Offsite say makes the biggest difference:

📣 Communication is Everything

“You’ll have attendees who read every single document… and others who don’t even open the email with their flight info,” says Harlie Walfish. “That’s why you need a communication game plan: a Slack channel, daily TL;DR updates, and a calm, service-with-a-smile approach when people inevitably miss details.”

🧭 Flow, Not Frenzy

“The biggest difference is attention to flow,” notes Kali Bradford. “When attendees don’t feel rushed or confused about where to go next, they can be fully present. That means building buffers into the schedule, providing clear at-a-glance agendas, and balancing structured sessions with downtime.” For hybrid events, she adds: “Dedicate a tech partner to monitor virtual engagement — it prevents awkward lags and ensures remote attendees feel included.”

🤝 Leadership Tone & Culture

For Cash Graner, the most memorable offsites are the ones that reflect where the company is in its journey: “The event should map back to the business objective and fit the tone of the culture at that point in time.” When leadership is aligned and the offsite feels authentic, the impact lasts well beyond the event itself.

👉 Translation: Memorable offsites don’t just happen because of great agendas, they happen because of great experience design. Communicate clearly, build a schedule that breathes, and make sure the tone matches the moment.

When you’re new to planning offsites, the big picture feels obvious, book a venue, set an agenda, feed people, done. But the truth? The details are where first-timers trip up, and it’s those tiny decisions that make or break the experience.

We asked a few seasoned event pros to share the one insider tip they wish every rookie knew before stepping into the role. Their answers are equal parts practical, humbling, and exactly the kind of advice you only get from someone who’s lived through the chaos.

💡 Cash Graner – “Overestimate AV and food costs, underestimate how many people will eat breakfast, and never forget that this industry is tiny. Everyone knows everyone—how you treat people today will circle back tomorrow.”

💡 Harlie Walfish – “Most of the time your attendees have no idea something went wrong. Stay calm, carry on, and they’ll think it was the plan all along.”

💡 Kali Bradford – “Always build a Plan B—especially for outdoor events. Weather and tech will betray you when you least expect it, and having a seamless backup makes you look like a genius.”

We’ve got a packed month ahead, and we’re excited to share what’s coming up for the community:

October 17 – Philly EA Dinner
An intimate community dinner bringing together local EAs and operators for connection and conversation.

October 23 – AI & Automation Session with Lauren Bradley (The Officials)
We’re thrilled to be partnering with Lauren Bradley, founder of The Officials, for all things AI. Lauren will walk our members through practical ways to implement AI and automations into daily workflows—whether you’re running Outlook or G-Suite. Think smarter scheduling, faster inbox management, and automations that actually stick.

✨ Special Note: Next week’s newsletter issue will be written by one of our own Inner Office community members, Justine Carucci. We can’t wait to share her perspective and give you all a fresh voice from within the EA world.

Because sometimes, offsite planning feels like juggling knives on a tightrope. But when you nail it (or at least look calm while the AV implodes), you deserve an anthem that celebrates the fact you’re still standing, still smiling, and still looking good as hell doing it.

Follow our Spotify playlist for inspo! 🎧