Fog Creek

The Definitive Guide to Planning a Company Off-site

Last year Fog Creek decided we wanted to have an off-site. As I’ve previously written, our company is remote; in the previous years, we’ve had remote weeks in our office in New York. The setback there was our remote employees were essentially ‘on vacation,’ while HQ Creekers went home at night, some to their kids, mostly maintaining their normal schedules.

We wondered – because we’re always trying to improve on the remote experience – if taking everyone out of his/her normal routine might produce a more consistent experience across remotes and HQers. Also, when we looked at the numbers, we realized it would cost about the same to fly the entire company somewhere else and put everyone up for 3 days, as the travel & housing for a week in New York did for ⅔ of the company. So, we decided to bite the bullet. Cut to me planning an off-site for 34 of my closest friends (aka my coworkers).

Before I began, I scoured the internet for help – How do I do this? Where do I even begin? Let me tell you, there aren’t many answers out there.

Thankfully, I’m lucky because I have the benefit of a sister company like Stack Overflow. Coming off a successful off-site of their own, I had a lot of information to pick from their substantial brains (Shout out to Alex Miller, Cassie Stone & Jess Pardue on Stack’s awesome Operations team).

Between their help, and my general love of planning and organization (for realz!), I was able to create an excellent experience for my people. And lucky for you, I’m going to tell you exactly how I did it… down to the minute! So here goes:

A Planner’s Best Friend is a Timeline

3 Months Out

Pick a Date

This is relatively easy. I looked at our Office & Vacation calendars for a week in November or December when no-one was out of town. I made sure to avoid national, international and religious holidays, and then I went to my team. We agreed 3 days and 3 nights was the appropriate duration; it’s enough time for bonding, but not so long that the families of our employees would feel the strain. With those things considered – Boom, the dates were set.

Pick a Venue

This part proved to be a bit more difficult. Initially, I wanted to go to Maine. My thinking was most of my employees live in the North East, so travel will be cheap, and Portland is cool! We could maybe go skiing! Thinking I was nearly done, I announced to the company “I think we’re going to Maine!” Then I heard an actual record scratch. One of our founders, Joel said, “Maine? In December? No. We’re going somewhere warm.” So back to the drawing board I went.

I used Expedia’s Group Travel service to find a hotel. Here’s how it works:

  • You tell them where you’d like to go, your travel dates, what accommodations you need, and your budget.
  • They send that information to hotels in the area where you’re traveling
  • The hotels respond with bids for your business

For my trip, I needed to have 34 available rooms, each with a king or queen size bed, a great Internet connection, a conference room, and all the other amenities you’d expect from nice lodgings.

I was willing to go anywhere balmy – North Carolina, Texas, Tennessee… I just needed a hotel and an airport. Lucky for me, I found so much more.

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A hotel in Austin called Travaasa bid on my new quote request. Actually, calling Travaasa a hotel is a major understatement. Travaasa is an “experiential resort”. All of their rooms sit on a gorgeous expansive campus along with a spa, a pool, various meeting spaces, a farm, and a fantastic restaurant. Travaasa also employs a staff of activity leaders who lead a wide range of activities from horseback riding to hatchet throwing, zip-lining to wine tasting. It. is. fabulous.

Rather than a hotel, what I’d found was essentially a camp; it was a place where my team could live for 3 days, secluded from the real world (though we had Internet, of course) and enjoy the closeness that kind of short-term isolation brings. We had every meal together, walked the campus together, did activities and spent our free time sipping cocktails and lazing in the hot tub – you guessed it – together.

If it’s in your budget, I highly suggest finding a place like Travaasa for an off-site. Not only is it more special than your run-of-the-mill hotel, but it’s equipped with spaces, activities and most importantly a staff dedicated to meeting your needs.

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2 Months Out

Get to the heart of it

The most important questions to answer before your off-site are the ones at the heart of it all: What is an off-site? Why are we having it and why is it important? The answers to these questions seem obvious, but try quickly talking them through with yourself. You’ll find they don’t come as easily as you might think!

Figuring out what you’re trying to achieve is essential and worth a good think. When you’re scheduling your off-site, you’ll find that you won’t have time to do everything you want. It’s much easier to prioritize though when you can ask yourself, “What’s essential for what we’re trying to do here?”.

For Fog Creek, our goal was super simple. We’re two-thirds remote, so we had the off-site to build bonds. Here are the actual blurbs the leadership team at Fog Creek wrote down:

  • What is the offsite? 3 days of talks, discussions and events organized around bonding with your coworkers.
  • Why have one? Building bonds between coworkers is important. Doing that over the Internet is hard. At the off-site, every Creeker should have a chance to interact with every other Creeker.
  • Why do we think this is important? Having deep bonds between co-workers creates a productive, motivating environment of trust where innovation can flourish. Also, it’s easier and way more fun to work with people you know and like.

We shared these with the rest of the team immediately after we wrote them. Step 1 of the process is setting the tone for the off-site way before it began… but more on that later.

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Shout out to Opie’s in Spicewood, Texas, and their amazing Tater Tot Casserole.

Book travel early

It’s important to begin booking travel early because: money. My team is small, and I wanted all the Expedia points on our company account, so I chose to book all the travel myself unless someone specifically requested to book his/her own. The first thing I did was email my team and give them a deadline to decide their travel dates.

Here’s a snippet of my email:
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As you can see, I used Trello to gather the information for travel dates and times, then booked in bulk when I could. This extended over flights and cars – I had 15 people arriving in Austin around the same time on Tuesday and leaving at the same time Friday, so I booked SuperShuttles to take us from the airport to Travaasa and back again that Friday.

Get Some Swag

Every good company event deserves a kick-ass piece of swag. Because our off-site was in the winter, in the Texas hill country, and was going to be relatively laid back, I chose super comfy sweatpants. I made the decision about what I wanted super far in advance to give our awesome Designer, Enrique, enough time to create this adorable logo:
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Then my Office Assistant, Kyle, ordered the swag and had it sent directly to our contact at Travaasa along with a list of each Creeker and his/her pant size. Before we arrived, the staff put each person’s pair in his/her room, along with this little note:
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I also sent logo notebooks and pens to Travaasa ahead of time. Each Creeker got one of each at check-in. Little touches like this made everybody feel – from the get go – really welcome and like a lot of thought had gone into it, which obviously was very true. That kind of cred goes a long way.

6 Weeks Out

Start building excitement amongst your team

At 6 weeks out I started to get really jazzed about the trip, and I wanted my team to share the feeling, so I provided them with all the information about Travaasa and the amazing activities in which they could participate. Then I opened a room in our Slack instance called #Offsite and invited the whole company to join. The room was a place for talking about the off-site, asking questions, and for communicating during travel and while we were in Austin.

#Offsite turned into a super-useful planning tool and a great sounding board for me as I put together the trip’s schedule. Also, it was just really funny. Here’s a snippet of a conversation we had about the restaurant where we were set to have BBQ, and the copious amounts of meat we planned to eat:
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This kind of anticipation 6 weeks away made planning way more fun for everyone.

Make a Schedule

Creating a schedule is one of the most difficult parts of planning your off-site. I started by creating a Google Spreadsheet and breaking out each day into 15 minutes chunks. From there on, it’s basically a puzzle – each activity is a piece that needs to fit somewhere. It’s really about a combination of flexibility and prioritization.

For ideas on what to actually do, I suggest using your resources. Talk to your management team about potential sessions. How much time do you want to dedicate to meetings? Do you want your team to do any actual work? How much is it just about fun? That’s your starting point. For us, we aimed to strike a balance between fun, team-building activities, meetings about high-level stuff, and downtime when people could hang out casually.

Let me break it down further:

  • Work stuff

    In terms of actual work, we decided first what we didn’t want: no time dedicated to the day-to-day stuff (with the exception of our support team, who dipped into the queue a bit each day) and no strategic planning – we’re a remote company, so if we need to all be in a room to make big decisions, we’re doing it wrong.

    Then we turned to what we did want. Because our time was limited, having a theme to which all our sessions could roll up really helped us act purposefully and pack a punch in each hour. Our VP Sales, Jordan, led a welcome session the first morning to reintroduce the off-site’s theme and again, set the tone. We had a breakout session after Jordan’s session so people could do some getting-to-know-you stuff in smaller groups. The groups were made to be a mix of remotes / HQers / old timers / newbies/ and people on different teams. Later that afternoon, our CTO talked about the future of Fog Creek and our mission.

    The following day, I lead a discussion and activity about communication, how we do it at Fog Creek, and how we can better use our tools to communicate respectfully and functionally with one another; that afternoon our VP of Product, David, ran an exercise to remind us of all the amazing things we did in 2015 and encourage people to set our sights even higher for 2016. Lastly, we set aside time for team meetings, and because the bulk of the company are developers, a Hackathon involving a new product we’re currently incubating. Both of those were optional.

  • Activities

    Travaasa has a number of insane activities they offer to companies staying on campus. We did a few all-company bonding activities (hiking, dodgeball, our holiday party) and the rest were optional and employee chosen (zip-lining and hatchet throwing – because nothing helps you bond like trusting each other with a hatchet). We also took a trip to a barbeque restaurant to soak up some local Austin flavor.

  • Hang out time

    We had free time during the day so people could nap, call their spouses or jump in the pool with coworkers, and we had an open bar every night from dinner until midnight so those who prefer to bond over a beer (or 4) had ample time to sit and chat with one another.

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My overall advice: customize! There are no right answers. The fun will really come from creating your own thing. A few more tips:

  • Establish yourself as the host from the get-go. Have a welcome dinner, give a proper hello to the whole group. Use this as an opportunity to reinforce the tone of the off-site, get everyone hanging out right away, and establish yourself as the point of contact if anyone has an issue.
  • Incorporate traditions that make people feel at home: our off-site was around the holidays, so we included a game of “white elephant,” (which we do every year on holiday party day) and our traditional holiday bash.
  • Free time is key, especially for tech companies. Whilst every group has extroverts who can hang out all day, there are introverts too who need alone time to rejuvenate between social engagements. Think of both, and encourage people to take care of themselves. Encourage participation, but make a lot of things optional.
  • For activities, I used a Google Form, had everyone pick 2 from a list of 10 possible options, then did my best to schedule time for the top 5.
  • Do a night-time, post-cocktail activity. We played drunk dodgeball, and it was hysterical. Definitely a bonding moment.
  • Make time for a company photo! Who knows when you’ll all be together again! Usually, you can get names of photographers and other vendors from your hotel contact. If not, Yelp is your friend.

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4 Weeks Out

Nail down the details & set things in stone

A month away, I had a 3-hour phone conversation with my contact at Travaasa, the purpose of which was setting my schedule in stone. We went day by day, item by item to make sure every meal had a menu, every activity had a room to take place in, every meeting space had a whiteboard, etc. etc. The more detailed you can be in this phase, the less actual work you’ll have to do while you’re on site, and the more seamless the entire experience is for your team. I can not stress enough the importance of this step!

Get the Information Out

Now that your travel is booked, your philosophy set, your schedule good to go and your brain ready to explode, it’s time to share all the information with your team and prepare them for their upcoming trip.

I used a Wiki page on our company’s instance of FogBugz, a Fog Creek product (maybe you’ve tried it?) to disseminate all the information my employees needed.

Section 1 was a mental preparation list because I wanted to continue the job of putting everyone in the right mindset to achieve the goals we set for the trip. Here’s what I asked:


Here’s What You Can Do To Prepare

Get in the mindset!

  • Make a mental list of all the people you want to connect with and be ready to make a concerted effort to get to know them.
  • Be available and ready to share random ideas & persistent frustrations
  • Think about what you’ve accomplished this year
  • Think about what you’d LIKE to accomplish next year!
  • Get ready to chat about communication, the remote experience, and how to better them both
  • Think about how you can be a thought-leader at Fog Creek. What are you contributing? What COULD you be contributing?

And while you’re at the off-site:

  • Go all in
  • You get what you give – commit to being fully present!
  • Take care of yourself
  • Don’t overdo it! Know thyself – there are lots of breaks built into the schedule, take advantage of the downtime when you need it.
  • Be responsible and behave!
  • While in Austin, you are representing Fog Creek Software. Please make us look as good as possible.


The rest of the information in the Wiki was purely logistical and included:

  • What costs Fog Creek was covering, including travel, hotel rooms, food and drink and Travaasa amenities
  • A list of everyone’s cell phone numbers
  • A map from the Austin airport to Travaasa (in case anyone got a particularly dense Taxi driver)
  • Complete lists of everyone’s travel organized by day and time, including home airports, departure times, arrival times, color-coordinated by people sharing flights
  • A map of the Travaasa property
  • A description and photo of each venue on the Travaasa campus where we were having a meeting, meal or activity
  • A list of hotel amenities
  • A complete offsite schedule in list form (for those who didn’t like my spreadsheet)
  • A blurb explaining what each work session was about and who was leading it
  • Menus for every meal
  • An FAQ

I wish I could share this whole thing with you, but unfortunately, it would make this blog post 20,000 pages long so… oh well.

2 Weeks Out

Start Rehearsing

Keeping the sessions light meant each one had to be excellent, pointed toward our goals, and most importantly, well rehearsed. Our leadership team met twice to present in front of one another and get notes. If I had it to do again, I would have rehearsed even more. There’s no overstating the importance!

While You’re There!

Meet Everyone

Immediately when you check in at the hotel, ask to meet your contact. Have him/her introduce you to the staff. Meet EVERYONE. Get cell phone numbers, email addresses, etc. The more people you can call on to help you when something (inevitably) goes sideways, the better.

Enjoy yourself!

The best way to make sure everyone has a good time is if you yourself are able to relax and enjoy the experience. If you’ve done enough work ahead of time, you should be in a good spot to really engage, not just facilitate.

And Finally… after the Off-site

Get Feedback

After you’ve packed your bags, returned home, overcome the complete shutdown your body has undoubtedly experienced, make sure you get feedback from your team. Find out what worked, what didn’t, get a wishlist for next year, etc. Make sure you thank those who helped you, compliment the people who worked hard, and remind those with influence to follow through on any promises / initiatives the genesis of which you set up at the off-site.

For those not in need of a step-by-step timeline, here’s something a bit more digestible:

TL;DR: 10 Secrets to Amazing Off-site Success

  • 10. Use Your Resources: sister companies, friends, coworkers who’ve gone to off-sites before, anyone who can help, pick everyone’s brain! You never know where a good idea will come from.
  • 9. Set a mindset way before you go – Figure out your why, and give your employees homework. Letting everyone know what you expect of them greatly enhances your chances of actually getting it.
  • 8. Make best friends with your lodgings contact: Get the names of his or her team, emails, cell phones, be tough! Remember you are giving your venue money, and if you enjoy your experience, you might give them a lot more down the road… I promise you: they want to make you happy, so ask for everything you want!
  • 7. Good food and drink – enough said. Good food makes everyone happy. Everyone.
  • 6. Rehearse! – You only have so much time to make your work sessions impactful, so make sure every minute counts!
  • 5. Delegate – get other people involved whenever you can.
  • 4. Eliminate obstacles – make missing events or not participating basically impossible by using communication tools like Slack during the trip, providing notebooks and pens, handing out maps to each venue, etc.
  • 3. Be flexible – something will go wrong. It’s ok! Be ready for that.
  • 2. Be a Host(ess): Take care of your people by making sure they’re being taken care of. Check in with people casually when you interact. A real simple, “Are you having a good time?” oughta do. Let ‘em know you care (there’s another tip: care!)

And the #1 most important thing:

  • 1. Make yourself unimportant – Make all information available. Create a spreadsheet and highlight who’s traveling together. Share menus, blurbs, times, confirmation numbers, policies, the works. Gather every piece of information in one easily accessible place, so that if anyone has a question when you’re not around, someone will know the answer, or at least, know where to look it up.

I hope my guide has given you the courage to jump head first into your planning. If you’d like more information on what I did or how I did it – you can find me on Twitter. Send me a little message, or let me know what you did that worked well! I always love a good idea from a fellow planning aficionado.

Good luck, from my team to yours!

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