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Hello From Hawaii! How We Planned a Weeklong Meetup for 90+ Teammates, Partners and Kids

Imagine getting off a plane in a new state or country, heading to a place you’ve never seen, to spend a week with 70-plus coworkers you’ve never met (plus some of their partners and kids).

That’s what happened to more than half of the Buffer team over the weekend.

This week, our fully distributed team is all in one place—Honolulu, Hawaii—for our 7th all-team retreat.

We’ll spend a full week of work together (and a weekend of fun activities) before going back to our homes or travels.

Between costs, time zones, visas, Buffer babies and kids, our actual work, and many other factors, it’s quite a challenge to pull off an event like this twice a year.

And yet, a growing number of remote teams do. (Otherwise, we’d never see each other in person!) Even non-distributed, non-startup teams are getting in on the action.

As this trend grows, many remote teams like Zapier, Automattic, and Baremetrics have been kind enough to share some of the secrets of how they bring their whole staff together for working and fun, and we’d love to do the same!

What follows is definitely not the “right way to do it”—we’ve certainly yet to figure out lots of the answers. But in case it’s helpful to other teams, here are all the ins and outs of planning a workcation, Buffer-style.

Scheduling: Every 6-7 months, lots of advance notice

Planning for this week in Hawaii began in August of 2015, just after we finished up our sixth retreat in Iceland.

We try for a retreat approximate every 6-7 months, and the first order of business is determining which dates the most number of full-time teammates are available (Buffer bootcampers are invited to retreats after they join the team fully—even if that means hopping on a plane last-minute).

We do this by choosing a range of weeks and asking folks to select which ones might be available.

picking a date

No matter how much time and consideration we put into choosing the date, at a certain team size some conflicts are inevitable.

While we’re in Hawaii, we’ll have two teammates enjoying family leave and unable to make it. A third teammate will join us part of the time. Here’s a sweet note from our awesome teammate Roy about his tough decision to skip the retreat:

roy and retreat

Weddings, babies and all the wonderful stuff of life is always happening. :) All of this is understandable and great and encouraged!

We’ve begun having smaller, more frequent regional meetups to make sure no one goes too long without seeing at least a few teammates in person.

Location factors: Safety, size, internet reliability

Once a winning week is chosen, we share it with the team and begin the exciting process of figuring out where to go. We’ve written about this part of the process before, but it seems to keep evolving as we grow.

In the past, we’ve simply taken a vote and chosen the top destination. But with a bigger team than ever, the challenge to find a good location for our retreat increases.

For this week, our amazing “retreats team” of Åsa and Rodolphe wrote a great note to the team explaining why we might lean towards slightly more established and potentially less “exotic” areas as we continue to grow.

factors of location

They did a bit of pre-scouting and presented us with a short list of places where they felt we had the best chance of having a great get-together at our size. Here’s the list from which Hawaii was chosen:

2016 destinations

Including everyone: Partners and families are invited

We’re always looking for ways to make families feel even more part of the team. On our most recent retreat in Iceland, we officially invited partners (and one brother) along for the first time. In Hawaii, we’re excited to add Buffer kids into the mix too.

Buffer offers a financial boost to help those who want to invite partners and dependents to the retreat, paying 50% of flights for dependents, full accommodation costs and for some meals.

How things work with partners and kids is still a bit unformulated since it’s so new. In Iceland, all the significant others hung out a lot together and planned their own sightseeing trips and agenda, as well as participated in lots of fun times with the whole team.

We’ve been hard at work gathering advice from people who have different requirements, such as disabilities or families that may come with or without their kids—it’s certainly been a great learning experience!

Getting there: Visas, hotel booking and lots of flights

With a location chosen, the retreats team gets to work finding an accommodation that can suit the whole team. Over time we’ve moved from one house to multiple houses to boutique hotels to bigger hotels.

Åsa says this work entails a lot of scouting and researching hotels and restaurants—she and Rodolphe have the plentiful spreadsheets to prove it.
Meanwhile, anyone who might need to get a visa or have other special travel considerations is given lots of help and support (some countries are tricker than others!).

About 6-8 weeks out, all teammates are cleared to shop for their own plane ticket and expense it at their leisure. (Expensify makes this super easy and quick!)

We do this to give everyone the freedom to plan their own way, but we can understand how the upfront costs could cause a potential financial burden for some. (Would love any ideas on improving this process!)

Teammates generally arrive the Saturday or Sunday before the week of the retreat and are encourage to stay until the Monday following retreat week. (If you’re coming from further away, it’s great to arrive on Saturday to get into sync with the new time zone).

The retreats team strives to get a schedule of the week to all of us in advance so everyone knows what’s in store.

The workweek: Space for conversations and learning

So what’s the week actually like? Monday-Friday, teammates tend to work together on a 9-to-5(ish) schedule. We have worked from both houses and co-working spaces in the past. In Hawaii, we’ll be working in a hotel conference area.

The actual “work time” is often more centered on conversations, sessions, and ad-hoc syncs than a normal week might be—we like to take advantage of the time in person to have lots of chats. (I always come with my notebook filled with specific conversations I want to have with specific teammates.)

While a lot of progress is made and new ideas are often birthed on retreats (Buffer for Business is a product of a retreat week!), there’s often less tangible work that gets done during this time.

This is great for the future of Buffer, but often a bit challenging for the present—for example, for customers who rightfully deserve to have their questions answered and problems solved promptly during this week.

We’ve yet to figure out a great solution to this challenge—our response time to our wonderful customers often slows down during this time, which doesn’t feel ideal. We’d be keen to hear your ideas on this!

Not-work time: Organized and free-form activities and outings

An incredibly important element of retreats is the time we spend not working but instead getting to know one another.

Rodolphe shared that this is a big factor in the retreat planning process:

“Balancing work and social interactions is fascinating, since getting together is just as much about cultivating company culture and Buffer values as it is for planning and executing on what is to come for the next 6 months.”

We haven’t planned a lot of formalized ice-breakers or exercises to make this happen thus far. At least a few days a week there are optional group activities in the afternoon and/or evening. These are generally things that are special to the place we’re visiting—like surfing lessons in Sydney or a volcano tour in Iceland.

There’s also a team dinner on every retreat (the occasion of many millions of silly photos and selfies) and our (more-or-less) official team photo. Here’s our last one in Iceland:

iceland team pic

On this retreat, we’ll also have an “Orientation Day” for the first time, to make sure that our many new team members are well taken care of. Some of them might be meeting up to 90 people for the first time!

In addition to pre-planned activities, there are plenty of self-organized activities—book clubs, board game nights, morning yoga, evening whiskey tasting—that anyone can spearhead or be part of, depending on their interest. Time to chat during meals and coffee breaks is plentiful, as these are usually self-organized in small groups as well.

One thing we’ve discovered is that retreat weeks can sometimes be a bit of a challenge for the more introverted members of our team (I count myself as one!). As a result, we’ve tried to build in more options and flexibility for those who need a bit of alone time to restore their energy.

Cost: Here are the totals for our last 4 retreats

There’s no way around it—retreats cost a lot. When we tallied up all our expenses to break down what each cent of a Buffer Awesome subscription goes toward, retreats were toward the top of the list:

Buffer costs

And as we grow, so does the cost. Our previous retreat in July 2015 was around $150,000 altogether, and the estimated budget for Hawaii is about $400,000.

Click the image below to see the tally for each of our last 4 retreats:

retreat costs

Retreats typically also have quite a lot of various expenses that teammates pay for personally and get reimbursed for, like meals, transportation, and activity costs.

A handful of folks have Buffer credit cards, and they try to pay for everyone with them as often as possible to cut down on teammates’ upfront costs.

Scaling retreat growth

It’s fascinating to see how Buffer retreats have grown and evolved over time:

  • 8 teammates in Lake Tahoe
  • 11 teammates in Thailand
  • 17 teammates in Cape Town
  • 25 teammates in New York
  • 26 teammates in Sydney
  • 31 teammates and partners in Reykyavik
  • 91 teammates, partners and kids  in Hawaii

Our team more than doubled in 2015, which means even more changes to the experience. Rodolphe explains:

“We’ve been trying to to re-think the retreat experience, and be mindful of placing ourselves in the shoes of a person that just joined Buffer—how would attending a retreat for the first time feel for them? If you joined Buffer over the last 6 months (half of the company has), you haven’t quite met the entire team just yet. So we’re trying to make the retreat as smooth and social as possible.”

On to the next one!

It’s astounding to me that all the work to bring us together is done by only two Buffer teammates who have other full-time roles in addition to retreat planning!

Our amazing “retreats team” of Åsa and Rodolphe work tirelessly to make each event better than the last. (It probably doesn’t hurt that they’re two of our most well-traveled teammates.)

“We just learn from each one and take everything onto the next retreat,” says Åsa. “Both us of really love to organize these types of things, so, to me, it’s one of the most exciting things to be involved in.”

In the future, Åsa shared that this could potentially become someone’s full-time role at the company, particularly if we begin to do more, smaller retreats and meetups in different spots around the globe.

And almost as soon as one retreat is completed, it’s on to the next one.

On the last day of the Hawaii retreat, Rodolphe said he’d like to poll for availability for the next retreat.

“It’s a balance between planning ahead and trying to include as many people as possible (including bootcampers) to make sure we have an almost accurate picture of team member availability.”

So: Is it all worth it?

There are definitely a lot of logistical challenges involved in getting all of us to one place in the world for a week.

But there are so many more moments of joy, serendipity and learning together that make it all worthwhile (at least in the eyes of someone like me, who gets to enjoy the week).

After planning this latest retreat, Rodolphe told me his favorite part of the experience:

“Getting to spend face time with our Buffer teammates is the best part—we get to discover fascinating new people and catch up with friends; it really feels like a family get-together! I especially enjoy team dinners and randomly bumping into people. In Sydney, some team members had decided to spend a bit more time in the city post-retreat. A few days after most people had gone home, I randomly walked into Joel and Leo strolling down the streets of Sydney—even large cities feel just like home when you get to catch up with friends!”

Over to you!

Have you ever been part of or planned a work retreat for your team? Do you have any recommendations for us? We’d love to hear them in the comments!

  • Tracey

    Thanks for sharing this, Courtney. As our distributed team grows – both through hiring and because there are a lot more kids now! – I’ve already found organising meetups to be a lot more challenging than when I started. This post is really helpful, even though we’re not quite at 90 employees yet!

    • Hey Tracey! Yep, I could see that being an interesting challenge for sure. We love to share everything we’re up to for just this reason–hope it might help you out a bit!

  • Joe O’Hara

    This is a really interesting breakdown, thanks! New Zealand could potentially check all of your boxes next time, especially somewhere like Queenstown.

  • Michael Jenkins

    Courtney, that is absolutely amazing. Not only that Buffer has dedicated themselves to do a retreat every 6-7 months but the amount of thought that goes into it. I have heard of other companies doing similar things but the fact that you try to make it available for all employees depending on their schedule is a huge undertaking. Bringing in kids is an amazing advantage. Traveling for that long can be very hard without your kids and it is a great option if chosen. Plus, what a huge bonding experience. When you work remotely you can have all the video and phone conferences you want but when you meet up with your team it is a whole different ball game. I know it creates a stronger bond and makes work more enjoyable once you get to know your peers on a personal level as well. Hope you all enjoy the weather there vs. the snow we have here!

    • Yes to ALL of this, Michael; I absolutely agree. Meeting up in person is so very special and definitely changes the team dynamics moving forward. Very grateful to have the opportunity to have our expanded Buffer family be part of the time together as well.

  • felicia.cristofaro


    AMAZING! What an incredible effort from Buffer (especially the retreat team!). This is awesome! I love that Buffer does retreats and such for their employees, it inhibits bonding and team-building, particularly in new
    environments. As to team members booking flights, have you thought of a
    corporate cred card? I understand that Expensify is used for keep track of
    funds, but a company issued credit card could be used solely to charge flights.
    This would eliminate any upfront costs and financial burdens for team members. I know you mentioned that a “handful of folks” have company cards, but it may be
    beneficial to issue them to the entire team.

    I can’t believe all that work is done by two people! I’m sure the Buffer team is quite grateful for all that hard work. I can’t wait to see where the next destination
    is! Thanks for the updates.

    • I can’t quite believe it either! Great thoughts on the credit card; I do think this would help alleviate any financial concerns upfront. We’re exploring this now and will continue working on this!

      • Katie Garcia

        To offer a similar idea, PEX affords lots of control and flexibility for companies with needs like this. Everyone can be issued a card when they’re hired to keep in their possession. Then cards can be funded, zeroed out, turned on or turned off completely, all from the central admin account online. This could provide the opportunity for staff to have budgeted allowances on the trips themselves as well, like for meals etc. Or when not on retreat, cards can be used as needed for corporate purchases (equipment, etc.) or just deactivated until they’re next approved for use. Deactivation prevents accidental purchases when staff are out and about in the world (cleaner for your accountants). Plus PEX is integrated with auto feed to Expensify so it feeds into your existing pipeline. I’ve used it extensively with a large staff and it’s incredibly helpful. Love the corporate retreats, and the Buffer culture!

        • Wow, great information! Thank you so much, Katie; this feels like a great one to consider!

  • Carolina Rosabal

    You should totally come to Costa Rica! Funny thing: I’ve been thinking about this Hawaii retreat recently because I saw one of the pics you posted in Facebook and I thought “why don’t they choose Costa Rica as one of their retreat locations?” It would be great to have you here, I’d even volunteer to meet you at the airport wearing the lovely Buffer t-shirt I got on the mail last Friday :D (thanks again for that!)

    I think these retreats are awesome, both for employees and their families. I had the chance to attend last year’s Akamai Technologies Titans Club as a family member and it was a blast. You can feel the love from the company and how they truly value their best asset: their people. (We went to Cabo, by the way. It’s a great location for this type of retreats, I highly recommend it!)

    It’s also great to see your transparency in action once again. Sharing those costs and some details about the logistic is really helpful for other companies and start ups that might want to plan a similar activity. I hope you all enjoy this retreat, you really deserve it!

    • Oh wow, I would love to come to Costa Rica! It’s on my list for sure. :) How awesome that you’ve had such awesome retreat experiences!

  • Gretchen Roberts

    True the retreats cost a lot, but what do they cost compared to what an office would be for this size of team? It would be interesting to see that difference.

    • pj882

      That’s an interesting perspective, and it’s gotta be very true! One advantage of no office is extra money to spend elsewhere!

    • Great point; that’s how we look at it as well. It would be neat to price some office space in San Francisco, New York and London (the spots where the most team members happen to be) and see what that comparison looks like.

  • pj882

    I’d consider this kind of thing as one of the perks for working at Buffer!

    • Absolutely! It’s a huge perk; feeling tons of gratitude. :)

  • I suspect Buffer has the world by the tail. The product is sweet and the culture/philosophy seem sweeter. Here’s to much success in the coming years!

    • You are so kind, Melissa; thank you so much for this note!

  • João

    Awesome post Courtney! Have you considered promote the ideia of Costumers delivering Costumer support during that time? I know that it would difficult to measure, but what if y’all asked the users to help other users on twitter using an #bufferhelp during the retreat and then maybe offering 6 months of Buffer for Business for people that helped, and have been useful to other users? Maybe the users would feel part of the “team” and really help other users and at the same time the response time could stay awesome as always :)

    • Whoa, what an awesome idea João! This is so inspiring to think about; I’m really excited to share it with the team! Thank you so much for sharing this with us!

      • João

        Glad my idea is inspiring! That’s so great to read! Guess I will have to wait for you to tell me what the team thinks about this :)
        Hope y’all have a great retreat!

  • Susan Pauls

    It’s absolutely amazing to read about this whole process–the reasoning behind doing the retreats a couple times a year, the planning, everything! Kudos to the two folks who do the planning, and in addition to their regular responsibilities! I also think your efforts to include families/SOs are so cool. Travel can be such an incredibly educational experience, and by including SOs and kids, you’re investing not only in the growth and development of your employees but also in their familes.

    A thought about customer service during retreats. Maybe keeping up w/ customer service requests could rotate among the people at the retreat, like every few hours or so (meaning have a “changing of the guard” every few hours), so no one has to miss out on too much of the retreat? I’ve read that occasionally even your programmers and developers do customer service. Would this be a good opportunity to include them, while everyone’s together?

    But then I read Joao’s suggestion in the comments about inviting customers to help other customers for that short amount of time (the week), and I kinda like his idea better. :)

    • Hey Susan, thanks so much for all the excellent thoughts here! I really appreciate your suggestion on serving our customers during retreats! We’re trying something that’s quite a bit similar to your thoughts this week, where everyone on the team picks a time to deliver some happiness throughout the week. Keen to report back on how it goes!

  • I’ve traveled for work, but never attended a retreat. And as my state is recovering from Snowzilla, I’m so jealous of the fact that you’re in Hawaii right now. I’m so excited and can’t wait to read what changes will come out of this retreat.

    As for future retreats, I think they’ll eventually go away. While I do understand the benefit of a retreat, as the team grows it just seems too expensive to justify.

    Oh, and congrats Roy on your new bundle of joy. God bless you and your family.

    • Thanks for these thoughts! Yup, they are getting quite costly. We’ve been inspired by Automattic, which is quite a bit bigger than us and still going strong with retreats. I hope that model could possibly work for us also :)

  • Good grief @courtneyseiter:disqus !!!! I feel a combination of tiredness and excitement just reading that :)) I’ve been following the #BufferRetreat on Instagram – it’s a unique way to see the retreat – through different Bufferoo’s eyes. Totally recommend people have a look at it there to see how everyone is experiencing it differently. Hope you are all energised and feeling really good about the great things you’ll have done together.

    • Oh, that’s such a great tip, Liz! Yes, it’s a blast to see all the photos on Instagram; we’re collecting lots of them on Facebook too. We had quite the epic karaoke fest last night; should be some fun pics!

  • Samantha Fauver

    @@courtneyseiter:disqus we need to chat! My brother works for Buffer (Alex Ray) and was telling me about your retreat. I can make your life SO much easier. Can I have your email address or Asa’s so that we can chat? You guys are doing an amazing job!

  • Brendan Moore

    Courtney this sounds amazing – I can’t believe it’s pulled off by only two people for the most part! Way to go Åsa and Rodolphe!

    As Susan suggested, I like the idea of rotating duties amongst the team. But rather than just being “on duty” why not make it a learning session? Pairs or small groups of Happinness Heroes could lead sessions through the week with groups from other Teams. Here they could be kept up on the current voice for customer service, bring up any suggestions for improved tooling and provide demonstrations. More than just keeping up with customers, this might be really valuable for both teams involved to better understand each others work and struggles.

    Jealous of the Hawaiian sun from up here in Toronto!

    • Yup, this is a super awesome thought, Brendan! I was able to do a little “delivering happiness” this morning with the aid of the happiness team, and it was awesome to be able to be in the same room to ask questions and learn. Feels great to keep going with this!

  • Great to see the breakdown @courtneyseiter:disqus Saw Joel talk in NYC at a small event and he provided some insight into this trip and board control. Really amazing stuff you guys, Automattic, Zapier, and 37 Signals are doing. :)

    • Oh, neat! I know Joel loves to talk about all these issues; cool that you got a chance to chat with him!

  • Wow this is an amazing post. I love how transparent and straightforward you guys are!

  • @courtneyseiter:disqus Thank you so much for explaining this all! A good way you might want to take a look at customer service during retreats is to assign a 1-2 hour window to each team member during the retreat and that will be their window to handle customer emails. For example, on the schedule, they will know that Tuesday between 2 & 4 p.m. they will participate in the retreat activities but if customer emails come in, they are directly responsible to be on it. I hope that helps in the future. :)

  • Gotta LOVE work boondoggles! Heading to Hawaii end of February for my small business retreat as well.



  • Sylvia

    Wow! Only 2 people organize this whole event? That’s amazing! It sounds like a fun job, actually, though full of challenges :)

    It’s crazy to see how the numbers have gone up drastically. I remember I started following Buffer a little before the Iceland retreat and thinking that a group that size feels perfect for traveling. And now you’re 90! Do you think there might be one a retreat just for teammates and one for family and kids? Or are you all staying on course for all-inclusive retreats?

  • I may have missed it, but how do you deal with working visa issues – as in this is a “working” holiday, you are working in the country Mon-Fri, do you have issues with immigration etc?

  • Kathryn Presner

    Hey @courtneyseiter:disqus ! Really enjoyed reading how Buffer plans its retreats, thanks for sharing the process and evolution. :)

    re: booking travel, at Automattic we use Egencia (Expedia’s corporate edition) and it works quite well, avoiding the need for employees to lay out funds for travel. We can book our own travel online via Egencia, and the account is tied to a corporate credit card. For our Grand Meetup (annual company meetup), all flights are first verified by a meetup organizer to make sure they make sense. :) It’s all pretty painless.

    • Hiya @kpresner:disqus! Thanks so much for sharing this great tidbit with us, it’s super helpful! (Apologies for catching it so late!) I’m curious if any folks on your team ever happen to plan personal vacations or side trips immediately before or after the retreat and how you might work though the divvying of those. That’s one that comes up a good bit on our team, though it might be specific to us! Thanks for being so generous with your process here!

      • Kathryn Presner

        Definitely, some folks do take vacations or side trips before or after meetups, whether it’s our annual Grand Meetup or smaller meetups during the year. Our general rule of thumb is that booking flights later or earlier than the meetup is OK as long as there’s not a significant price difference between flights.

        • Excellent info, thanks for all the great help here! We’re always super inspired by Automattic!

  • Wow, we though planning a retreat for 9 was tough! Just wanted to say thanks for all the great insights. We’re developing our own remote culture and have learned a lot from Buffer along the way. Here’s a write-up of our first retreat:

  • Love the boondoggling retreats and the fact that you guys spend more on retreats than you make in operating profits. Inspiration for my own small business! Best, Sam

  • Melissa

    Your post is a great explanation and I think the retreats are amazing. My mom planned trips for us in scouting for years and my sister is an event planner so I know how much work must have gone into the planning. I really like the way you have broken down the costs as a portion of the Awesome plan, that is a really nice way to see the costs. Does Buffer update that type of metric often?

  • Catherine Gibson

    Great tips! I’m part of a small team developing a flight search to help companies with with distributed teams search for flights from different departure airports to a common meetup destination. Our idea is to make it easier to coordinate similar arrival and departure times for different teams. Let us know what you think and any feedback is much appreciated!

  • Sheldon Schumer

    I do use an alternative to Expensify which is Penny Inc ( I’m an owner of a small business and recording expenses for team building has been another task that is taking my time. With the help of Penny Inc, managing finances was easier.

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