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A Tale of Two Offsites, 2024An inside look at the itineraries for our all-company gatherings in Portland and Scotland this yearPublished inThe Medium Blog17 min readJust now--Bass Rock outside our hotel in North Berwick, Scotland. Photo by author.Do you remember high school chemistry class? My husband once told me about a poster in his class. It had an image of a giant elephant teetering atop a tiny beach ball. The key to life is balance was printed underneath. The phrase has since become a mantra for our relationship and our individual lives too. Ah, chemistry, its not just for the classroom!Medium is a remote team, but we meet up twice a year for all-company work sessions, team building, and bonding. We call them offsites. Two offsites a year gives us an opportunity to strike a balance between the vibe and focus of each offsite. When I start planning Mediums offsites for the year with our team, I cant help but have the image of that graceful elephant on a beach ball in my head. Considering the role balance plays in chemistry, I can easily see how important it is for strengthening the chemistry of a large gathering of colleagues.For our offsite locations, we search all over the world for inspiring properties that reflect Mediums values and sensibilities, then choose the place that most represents where we are as a team at that point in time. Some of it is strongly educated guesswork we like to plan our offsites as far in advance as possible, but you never really know exactly where things will be a year from now.In 2024, we went first to Portland then to Scotland. Right before Portland, Medium reached a milestone of 1 million members and we were ready to celebrate our wins, so we knew staying in downtown Portland was going to feel spirited and energetic. This meant we needed a location for our fall offsite that offered a balance. A beautiful old hotel in an idyllic seaside Scottish town was a restorative, quiet counter.As I share our itineraries for these two offsites, youll see how the balance between the two was an essential part of our year.Offsites are a game-changer for companies and are becoming essential for successful remote/hybrid teams. Its true they can feel overwhelming to plan, but they dont have to be! If you work for a remote company and youre thinking about planning an offsite, or are in the midst of planning one now, I hope these two outlines help make your job a little easier. Im not going to go into too much detail about our work sessions, but Ill share with you all the cool things we did in downtown PDX and rural Scotland. If youre planning an offsite, steal this itinerary! Why we chose Portland Itinerary Monday Tuesday Wednesday Thursday Friday Part II: Autumn in North Berwick, Scotland Why we chose North Berwick, Scotland Itinerary Weekend before (Fri-Sun) Monday Tuesday Wednesday Thursday Friday Looking ahead to 2025Part I: Spring in Portland, OregonJust to note: Medium isnt affiliated with any of the companies or businesses we mention below, and were not getting compensated for giving them shoutouts here. We just had a great experience with all of them and would recommend it. But of course, there are so many things to do and you can do your own research, too our experience is just one perspective!Why we chose PortlandPortland is a vibrant city that is bouncing back from hard times. We were faced with the difficult realities of a neighborhood in recovery and gave back in many ways throughout the week. Every employee and staff member at every location we went to was helpful, hardworking, and enthusiastic about their love of the Rose City. The next time I hear someone say they got the most bang for their buck somewhere, I might reflexively think of this offsite in Portland.Going into this offsite, heres what was important to us:A place where we could all be together in one building, with lots of space for work.A focus on fun and playour team loves games, and its a great way to build relationships and trust. Youll see how we leaned into this as a theme for the week.Activities that spark meaningful conversation and thoughtful reflection.A final night that felt like a celebration (in a way that aligns with our values and personality as a company).Heres what our itinerary looked like for the week.ItineraryMondayTravel day! For the folks who arrived early (some got in on Saturday or Sunday), we kept the day free so they could explore Portland on their own terms. Some of us hit up Hawthorne Asylum Food Carts, The Freakybuttrue Peculiarium, the big Pendleton store, and so many other things that we couldnt fit in the official program for the week.In the evening we gathered on the rooftop of The Hoxton, our hotel for the week. The Hoxton has 119 rooms, which was perfect for our company of ~80 people. Shoutout to the Hoxton team (Simone and Jen and the whole front desk crew!). They rearranged their entire restaurant to accommodate our group, set up snacks, and went above and beyond in their attention to detail for our team all week.. Their restaurant, Tope, not only has a terrace with gorgeous views of the city and Mt. Hood to the east, but also had outrageously good food and drinks.Perfect spot for a kickoff speech from our CEO Tony StubblebineTuesdayInstead of having our offsite work sessions in a basement conference center with no light and stale air, we got creative and worked with The Hoxton to have exclusive use of the first floor restaurant for the week. Ive gone into more detail about my disdain for windowless meeting spaces in my previous post, and I must say, The Hoxton knocked it out of the park for us.Just one of the pretty corners of our large workspace.Conversations on a comfortable, plush couch are very different from conversations had on a plastic folding chair.We had a quick breakfast in the hotels apartment space, then kicked off our first work session of the week. Some teams differ here, but we love to get right to it and front-load our week while ideas are fresh and energy is high.Powells historian telling us its historyAfter lunch and another work session, we headed to Powells City of Books. Its likely youve heard of Powells and really, The Hoxtons proximity to the bookstore was a huge selling point. The Powells team gave us a ten-minute talk on the history of the store, then we were off to wander the labyrinthian mecca of books. If you do this part of the itinerary, we highly recommend giving your team members a book stipend! It was fun to see our team recommend books to each other, buy books to bring home to their kids, and pick out books for Thursdays book swap (more on that in a bit). After Powells, we took a short walk to Mox Boarding House, a restaurant where you rent a board game to play while you dine. We love gaming and Mox has a gigantic store in the front of the restaurant filled with obscure board games from all over the world.WednesdayWe like to schedule optional group physical activity at least once throughout the week, so we had a phenomenal early riser yoga class with Sydney from YoYoYogi at the hotel, or folks could join a team-led run. We then went to an incredibly delicious and casual, show-up-whenever breakfast at Mothers Bistro, followed by breakout team time and smaller work sessions back at the hotel.Portland is known for its food truck culture, so we went to the Expensify Midtown Beer Garden for lunch. Usually food halls will ask that you buy gift cards for things like this, but were not into the gift card thing (the single-use plastic, and small amount of money that often ends up on the card, seems so wasteful). Midtown Beer Garden let us use wristbands! Each employee was given a wristband for the day, so after ordering their meal from one of the trucks in Midtown Beer Garden, they just showed their wristband and it was added to the running tab we closed out at the end. Midtown Beer Garden has a lot of picnic tables under big tents and folks gathered in smaller groups on their own.After lunch, we returned to our workspaces in The Hoxton and had small group presentations and downtime. Then we had dinner at Xin Ding Dumpling House and a Medium-themed trivia night, led by our People Team. Our way of dividing up teams was to shuffle different colored bandanas, hand them out one by one at the door, and have folks sit at the table with a corresponding color bandana placed at the center. (As any former camp counselor or teacher will know, assigning teams with objects or colors is a shortcut to a shared identity among a team.) Trivia is pretty interactive, so it takes the pressure off of conversation and can help ease social anxiety or social fatigue from a long workday.Kimberly Ebelt was my rousing co-host!Once dinner was over, we had an optional Spooky Ghost Tour with one of our team members friends from the area. This was one of my favorite parts of our offsite. There is a reason theres a popular, giant mural near our hotel that reads Keep Portland Weird and this spectacular, supernatural tour really gave us the weird factor!We learned so much about downtown Portlands history through our awesome guide!A note on what looks like an extremely busy day its important to communicate the things at your offsite that are mandatory and those that are not, as well as the things that you dont have to be at for the entire time. We really strive to make sure folks are reminded they can do things like sleep in and show up later to breakfast if they want, or come back from lunch early to relax in the quiet of their room, or go home directly after dinner. Empowering folks to find moments to recharge between mandatory work sessions is essential.ThursdayWith the busy Wednesday, we intentionally sought to bring some introspection to the morning of our last full day at the offsite. At 9am after a casual buffet breakfast at the hotel, we walked to Lan Su Chinese Garden, just two blocks from our hotel. The staff there was kind enough to open an hour early for our team to spend time writing and reflecting in one of the most beautiful places Ive ever seen.Our Chief of Staff Brittany Jezouit deep in contemplationWere very keen to consider when an offsite starts to feel overproduced. Were all pretty savvy here at Medium and dont need much hand-holding (though that is nice once in a while) so we decided after the visit to the Chinese garden, a nice choose-your-own-adventure was in order. Want to go for a hike? Grab a Lyft to Hoyt Arboretum and get some forest bathing in. Want to get a bit of a workout in? Go for a brisk, uphill walk through downtown to Washington Park for a walk around the famed Portland Japanese Garden. Want to head back to the hotel to get some work done, pack for departure tomorrow, or take a nap? Do that!We all reconvened at the hotel for a casual, quite delicious lunch (the salmon was truly divine), then had our book swap! Here were the directions:Bring a book to give away (you cant take a book unless you bring one in exchange). It can be any book nonfiction, fiction, poetry, memoir and does not have to be work-related.For added mystery, were going to do this as a Blind Date with a Book style when you take home a book, you wont know which book youre choosing! Well have wrapping paper and markers for you to write a description/clues about your book and why you think another Median would love it.An intriguing way of describing a book ready for swapping.After the book swap, we did one of my favorite things to do at offsites: a two hour block devoted to follow ups and conversations that are best to have in person. Throughout the week there may have been that one thing you need to tie up before you leave and a tte tte is in order.As our week was winding down, we took the opportunity to connect with our larger Medium community and held our first ever Pub Panel with our featured pub editor guests, Debra G. Harman, MEd. and Judy Walker in conversation with our very own VP of Content, Scott Lamb. It was moving, enlightening, and so much fun. We had a coffee and donut social after, with an array of curious donuts from Doe Donuts, Coco Donuts, and Blue Star.For our final dinner of the week, we made it to the cozy but lively Deschutes Brewery Portland Public House where we enjoyed Oregon-centric food and world class brews including my new favorite, Black Butte Porter (the non-alcoholic kind)!I found out Im actually pretty good at pinball!We decided to save one of the most exciting moments for the last night of the offsite. After dinner, we all walked a few short blocks to Ground Kontrol. This place is a sight to behold. A multi-level arcade with vintage games from (and for) all generations. They separate their space into two areas, the blue zone and the red zone. We opted for exclusive use of the blue zone for the night (but could still play for free in the general public red zone). They even set up karaoke for us. We called it Karao-cade. While we were in Portland I asked all team leads and managers to take videos and photos and send them to me via slack. Then I tucked myself away for 3 hours during that donut social and edited the videos and pictures into a recap of the week that we projected on the screen at Ground Kontrol. I use a video editing app on my iphone called VideoLeap. Its shockingly easy to use and really fun!The last night of an offsite is thrilling. After the last work session ends, the final dinner is enjoyed, and the agenda is fully executed, I get this profound sense of accomplishment and gratitude for the effort everyone put into our shared experience.FridayWe had grab-and-go breakfast at the hotel, said our goodbyes to each other, Portland, and the wonderful team at The Hoxton, then all grabbed Lyfts back to the airport home to tell our friends and family of the thrilling week wed had.Part II: Autumn in North Berwick, ScotlandWhy we chose North Berwick, ScotlandIn March 2024, North Berwick, Scotland, a small seaside town outside Edinburgh, was named the #1 best place to live in all of the UK by The Sunday Times. Its idyllic and quaint with beautiful old stone churches, cottages, museums, and chip shops. After our bustling spring offsite in Portland, OR, North Berwick gave perfect balance to our offsites of the year. Our hotel was spectacular. With 83 gorgeously designed rooms, banquet hall and workspace, spa, gym, restaurant, bar, and even putting green on site, Marine North Berwick was one of the more luxurious places weve stayed. The staff is all top notch (shoutout to Gina, Megan, and Laura!) The town of North Berwick has many noteworthy historical highlights. In the 1590s King James the 6th claimed to have been assaulted at sea by a group of witches from North Berwick, saying they tried to sink his ship by conjuring a storm. It set off a pretty nasty series of witch trials that caused the murder of at least 70 women. Much later, Robert Lewis Stevenson drew inspiration from the islands off the coast of North Berwick as he wrote Treasure Island.North Berwicks harborItineraryWeekend before (Fri-Sun)Knowing our offsite was to take place close to the incredible city of Edinburgh, we encouraged our team members to arrive there the weekend before to acclimate to the time zone as well as explore the historic city. We reserved a hotel block for everyone so we were all in the same place. We opted to leave that part of the journey unstructured and unprogrammed. I did however share my own personal itinerary for that weekend in a Medium post so anyone could join me as I explored. This opt-in approach took the pressure off folks who were wanting some independence, but also gave me some company and connection with the folks who met up along the way.MondaySome folks skipped the weekend in Edinburgh and headed straight to North Berwick. Once your flight has landed on the isle, the fastest way to travel in the UK is by rail. Its so convenient, timely, and a more eco-friendly way to travel! North Berwick is at the end of the line on a 25-minute train from Edinburgh, then Marine North Berwick is a 10-minute downhill walk through a charming and safe neighborhood. We let folks mosey over to the hotel all day and explore the town of North Berwick at their leisure. We really enjoyed the Coastal Communities museum (where I learned about those cool witches!) and the Scottish Seabird Center.The Original St. Andrews Church in townIn the evening, we had our first gathering in the hotels plush bar, Bass Rock, with handheld bites, mocktails/cocktails, and a traditional Scottish band.TuesdayIn the UK, its customary for a full breakfast to be included in your stayeven in hotels with fewer stars than the one we stayed at! Every morning we had a huge breakfast buffet with fruit, cheeses, breads, granola, yogurt, and so much more. There was also an a la carte menu with full Scottish (yes, haggis and black pudding!) We kept breakfast optional and casual dining style to allow folks who may have still had a bit of jetlag to sleep in if they needed. We appointed leaders for a run/jog club on Tuesday and Thursday, so some folks got a run on the beach and through town on those days.Marine North Berwick has a fabulous banquet hall we used as our meeting space. Like most locations, they offer different table arrangements. I always opt for large banquet rounds for work sessions. I wont go into detail about our work sessions, but know that we usually like to start with the most important work sessions on Tuesday morning. This is an important part of setting the tone for the week, and its when most folks energy is highest.Scotland knows a thing or two about beautifully patterned carpets. The view out the work spaces window is of the Firth of Fourth, a stunningly gorgeous Scottish inlet. (photo courtesy of the hotel)I loved the unconventional nature of the Portland offsites meeting space, but Ive found that more traditional work spaces can be just as effective for focused, productive teamwork. But this only works when they have great natural light, or better yet, awe-inspiring views of the sea.We had a quick grab-and-go lunch in the foyer of the workspace and got right back to it. I totally need to give a shout out to Marine North Berwicks team here. When I worked with their head chef to decide our menu, we discussed the need for lighter fare for lunch. No one wants to come back to a work session all sleepy having eaten a big bowl of pasta. They brought us creative lunch wraps, interesting salads, light pastries, etc.We also did the Medium book swap we love to do at every offsite during this lunch. We changed the timing of the book swap from Thursday to Tuesday so people could read their books throughout the week.We set up our Friday departures on Tuesday, too. Some folks had early flights out of Edinburgh and trains wouldnt get them there in time. As an easy way to coordinate this, we put a simple sign up sheet for them to choose which hour theyd like to leave and booked enough cars for them.WednesdayAnother delicious breakfast in the restaurant kicked off our third work session of the week. The hotel offered multiple breakout areas and a property as large as Marine North Berwick, many of our meetings were able to be held in a comfy corner of the lobby or in the sundeck of Bass Rock Bar.A still from a video Cassie McDaniel took of Cameron Price chasing birds during sunrise!Maintaining the balance with the Portland offsite, we opted for all our official meals taking place at the hotel. That didnt mean all our meals happened in the same place around the same times. For our Wednesday lunch, we gathered for Scottish high tea, but instead of doing it in the foyer of the meeting space or in the restaurant, we held it in the lovely and cozy lobby. Towers of treats adorned the space, making it feel casual and playful.Ill never forget those Dulce de Leche tarts on the top rightWe returned to smaller work sessions for brainstorming and smaller group discussion, then broke before dinner. When you have offsites centered around crucial work sessions, its important to add even more break time to your schedule so folks can rest and recover.Being that we were in a magnificent, old Scottish hotel we felt we absolutely had to hire a murder mystery troupe for the evening. Trying not to ruin the surprise, we told everyone it was a theater troupe with macabre and adult themes. This was so fun, especially with the Scottish accents. The show started in the hotel lobby before dinner, dinner took place in the restaurant, then we finished the show back in the lobby.ThursdayBreakfast and lunch were in the same locations as Tuesdays meals, so we could focus on our last day together. We closed out our last work sessions with an all-team meeting and sendoff, then took a much-deserved break before dinner.Bagpipes are a must when throwing an event in Scotland. We booked Roddy (Reel Time Events) to announce dinner by playing his bagpipe at the entrance to Bass Rock Bar where the team got a drink before dinner. Then, he led us back to the banquet hall. We had flipped the room while everyone was away and it was turned from work stations to a dining room! Roddy did the address to the haggis.Its quite a show and the poem is great funAs is becoming customary, we designated the time after dinner a Medium game night. Folks played games of Werewolf, cards, and had quiet conversations throughout the hotels many cozy corners.FridayWe had grab-and-go breakfast at the hotel, said our goodbyes to each other, and headed to EDI. Some folks chose to stay on to explore the UK that weekend to visit the Scottish Highlands or Glasgow. A great thing about bringing your team to far-off places is they are given the opportunity to explore and deepen their understanding of the world.Looking ahead to 2025I think of the two offsites we do each year as companion pieces, so it makes sense to look year-over-year with a similar lens. Were laddering together. What havent we done? Whats out there for us to find? What does our team need most? Bolstered by our learnings and team experiences from this years offsites, what is our next frontier? I know were all chomping at the bit to find out.
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