It’s officially sweata weatha 🍂 which also means it’s officially planning season. Q4 is looming, and suddenly every leader wakes up and decides this is the perfect time for a team offsite.

I got the classic Monday morning ping: “Can you plan an offsite?” No details, no budget. Just the expectation I’d figure it out (and I will.)

Instead of panicking, I 💭 thought … why not take you with me? This month, I’m running a little experiment: a “Week in My Life: Planning an Offsite” series. Each issue, I’ll walk you through how I’m tackling a different piece of the process, from finding venues, to stretching a budget, to surviving the inevitable last-minute curveballs. ⚾

Think of it as a mini-vlog, but in newsletter form. And yes, I’ll share the tools, hacks, and shortcuts I’m leaning on along the way.

So buckle up, if you’ve ever been voluntold to plan an offsite (without info, without time, and definitely without extra pay), this one’s for you. 😉

With love and lots of Cafecito, ☕

Chrissy

P.S. This “Week in My Life” mini-series is sponsored by Offsite, because even I need backup when the “Can you plan an offsite?” message lands in my inbox. 🫠

First step on my list: get the attendee list from HR and map out where everyone’s flying in from. Direct flights only, because no one should have to start a team retreat with a 7 am layover in Dallas. 🥴

From there, I started shortlisting cities with major airports and potential venues. Normally this is where I’d fall into Marriott’s three-RFP-at-a-time black hole (truly a nightmare for anyone with a deadline). But this time I had Offsite.com in my back pocket.

The platform instantly felt familiar, kind of like Airbnb, but for team retreats. The UX is clean, user-friendly, and made it easy to filter based on exactly what I needed. I seamlessly submitted RFPs for hotels through their system and, along the way, realized I could also loop in things I’d normally stress about later- restaurants, speakers, facilitators, travel logistics, even photographers and swag. All the stuff that usually means another 10 tabs open was right there in one place. 🥹

I’ve already submitted a few RFPs for hotels, and in next week’s issue I’ll share how quickly the responses (and rates) come back. Stay tuned.

Once the first wave of venue research was in motion, I shifted gears to the internal side. My rule of thumb: if you don’t centralize communication from day one, you’ll be chasing Slack DMs until the offsite is over.

So I spun up a dedicated channel: #tmp-offsite-nov-2025. Everyone on the attendee list got added, and I set the expectation that this would be the place for updates, questions, and anything offsite-related. No more “Wait, which thread was that in?”

To kick things off, I dropped a quick input form and asked everyone to complete it. That way I can gather preferences, dietary restrictions, travel notes, and ideas in one place instead of piecing it together from random pings.

👉I’m a firm believer that sharing is caring, so I’m giving away my input form template for free! Use it, tweak it, make it your own!

🎤 Demo / AMA with Offsite!
At the end of this month, we’re teaming up with the Offsite crew for a live demo + AMA. They’ll walk us through how their platform makes planning team retreats way less painful (goodbye, endless RFPs 👋). If you’ve ever been voluntold to plan an offsite, you’ll want to be in the room for this one.

💻 Tech Talk with Lauren Bradley (community exclusive)
Our next Inner Office session is with Lauren Bradley (aka the queen of tech hacks for EAs). She’ll be dropping her favorite G-Suite + Outlook tricks to help you shave hours off your week. This one’s only for members inside The Inner Office — our private EA brain trust. Membership is just $20/month if you’re ready to join the crew.

📢 For my Philadelphia-based EAs (go, birds 🦅 ), we’re planning an in-person dinner in October. Consider it your chance to step away from your inbox, grab a glass of wine (or three or none), and meet other local assistants IRL.

More details will drop in the next few weeks!

This week’s pick: “Under Pressure” by Queen & David Bowie.
Because nothing captures the energy of planning a 200-person offsite with no budget, no attendee list, and 17 Slack pings asking “any updates?” quite like this track. Consider it your unofficial offsite-planning anthem.

Follow our Spotify playlist for inspo! 🎧