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Planning a Company Retreat for a Growing Team

· Posted by Francesca in Company and tagged · Add a comment

We keep on growing, and this brings new challenges for our company. Company retreats are no exception: we need bigger locations; preparing a timetable requires more attention; we need to split the team in groups for some activities, etc.

Let's take a closer look at how we plan our retreats and what happened in April 2017.

Put together a (small) planning team

If there's anything we don't want to change, it's the way we organize the retreat. We chose to have a small internal team taking care of everything. No one knows better than we do what we like and how we like to do things.

Some professional event planners seem to have a certain pre-set agenda, so at times they can be a little more generic or touristy feeling. Having an internal team is a guarantee to have the warm touch we love and the right amount of camaraderie we need.

Heads-up: Be aware that organizing a retreat can be very time-consuming, especially during the final weeks before the retreat.


  • Start planning well in advance (at least 6 months before) so you won't feel rushed and can fit in the tasks with your regular work.
  • Find a local organizing assistant that you can coordinate with. Sure, we want to take the reins of the planning, but having someone on the spot to help us out was fundamental. (Thank you, Matteo, for the excellent job!)

Choose the right location

Until this year, we were always able to avoid hotel accommodations: we stayed at a family estate home for the first retreat in 2010, we rented a castle in 2015, and a 21-country-cottage B&B in 2016.

This year we had to give up on the idea of non-traditional housing and face the obvious: since the company is constantly growing, from this point forward we'll need a hotel. I have to say I was a little sad, because I loved the crazy-cozy locations we have stayed at in the past. However, my wistfulness was lessened by the beautiful options we found, and the one condition we set: having the entire hotel to ourselves.

After our previous retreat in California, we decided to come back to Italy. We wanted something close to Bologna (where many of us live) to reduce driving time and be easily accessible for the non-Italian colleagues. The city of Florence, full of culture, comfort, and fun (and equipped with an airport!), seemed perfect. We also liked the idea of having a city retreat, after the country retreat in the Loire Valley and the woodsy retreat in California.

Google helped us find Hotel Villa Agape, the PERFECT place for us to stay. Not only is the Villa remarkably beautiful, with plenty of space both inside and out, and countless rooms for us to unwind and mingle, but also the staff at the Villa was amazing. They went above and beyond and played a huge part in making the retreat unforgettable.

Heads-up: You may fall in love with a dreamy location that is not 100% tuned in to the big picture. That's what happened to me: I thought another hotel in the middle of nowhere was perfect for us, but actually it would not have been ideal. Since the retreat was scheduled in April, staying close to a city allowed us to find activities in close proximity in case of bad weather.


  • Site visits still remain the best way to get a clear idea of the location.
  • If you're organizing the retreat internally, rate the proposed location's facilities, but also their staff and their willingness to help. Because you'll need help 😉

Add some bells and whistles

I'm a big fan of them! ❤️ I believe they add your personal touch and make retreats memorable, year after year.

We loved Balsamiq Summer Camp so much we continued the tradition of selecting a theme. It was pretty easy to choose the 2017 theme: Florence and its history, a beautiful Villa from the 15th century, a planned tour to the Uffizi... everything suggested "Renaissance!"

And this is how we expanded the theme:

  • We created a logo in perfect Florentine style.
  • We made a rollup to show at the Villa reception (and so, Villa Agape became Villa de' Balsamici for a week.)
  • We assigned an Italian name and a Florentine, Renaissance surname to every balsamico. For example, Liz Green became Lisabetta Gherardini, while Florian Brauer became Floriano Barberini.
  • We created beautiful signs for our room's doors, with the original family crests.
  • We rented Renaissance costumes! Costumes always add some fun, and we use them to create our annual Easter egg on the Company page (click on the team photo to see it.)
  • We had a magnificent Renaissance dinner at the Villa. The cook and his staff used old Tuscan recipes such as Caterina de' Medici salad and Pesceduovo al Melarancio (little frittata stuffed with cilantro cream and citrus fruit sauce).

As usual, we also got gifts. There is always a great deal of expectation about them, at least for me!

Gifts were related to the theme and planned activities, but also to our everyday life. This year we had:

  • a long sleeve T-shirt with the retreat logo
  • a pocket size transparent umbrella with our smiley face - we thought it could be useful, considering the retreat dates and the weather
  • an inflatable travel cushion and a beauty travel case with Balsamiq logo (we all take long trips, at least every other year)
  • Balsamiq apron with the retreat logo and a chef's hat for the cooking class
  • a box of Cantucci di Prato to take home to family and friends
  • a gym sack with retreat logo to hold all the gifts.

Heads-up: When it comes to gifts, you may be biased by your personal preference. Try to put yourself in your colleagues' shoes instead and ask yourself: Is this gift really useful? Will they like it? Will they use it?


  • Get inspired by your location when choosing the theme. Every inch of this world can tell you a story!
  • Something we didn't do, but should have: when ordering gifts, order a couple extra of every item. You never know if there's a damaged article, and you might not have time to send it back and get a new one.
  • Related to the point above: order the gifts in good time, especially if you are having them embroidered or printed with your logo.

Enhance the retreat experience with small details

We know from experience that little details are relevant and can make a difference in how the retreat is experienced. Here is a random list:

  • Nobody likes to feel dazed by the jet-lag during the retreat's first day. This is why we always have a pre-day jet lag recovery for the colleagues who come from far and wide.
  • Try to include families in some way if you can. Since half of the team lives in Bologna, this year we hosted a casual family pizza get together the day before the retreat.
  • Give information and advice to the team: create a what-to-pack checklist and give them some basic rules of the place where you're going.
  • Wi-Fi has to be GREAT, of course. Ask the property to send you a speed test while planning the retreat, and if it's not good enough, ask if they can set a temporary upgrade. At Villa Agape we had the best Wi-Fi we've ever had!
  • Pick unusual activities to do together, like the cooking and ceramic painting classes we had this year.
  • Give some space for unplanned and spontaneous moments together. That's where the magic happens most of the time. ☺️

Prepare for the unexpected

Someone can't come

This year, for the first time, a balsamico couldn't join the retreat for a very good reason (welcome to the world, Manoé!) It was hard for everyone, because we really enjoy spending time together, but we knew this was coming, sooner or later.


  • Wait as long as you can before booking expensive activities for everyone.
  • During the retreat, arrange video calls for the most important moments for those who are at home. We did it for the Villa tour, the presentation meeting, and Peldi's keynote.
  • After the retreat, send them all the gifts! Let them feel part of the team.

Someone joins the team close to the departure date

The 2017 retreat was a retreat of firsts, because this happened, too (welcome on board, Luca!) Though some changes could have been organized to add Luca to the trip in the final two weeks, many arrangements would have been difficult and stressful to fix.


  • When booking hotels, events and ordering gifts, plan ahead to be able to easily expand for additional attendees.

Someone gets sick during the retreat

It could be a small injury, or it could be something more serious. (We have needed to treat 1-2 colleagues at almost every retreat.) Bad things happen, and you probably won't be prepared for them. But you'll learn a lot in the process, as we did.


  • Save emergency contacts and personal identification documents for every employee. We have a "Staff Contact Info" page on our wiki and ask every new hire to list one or (even better) two people there, with their telephone numbers and email addresses. We also store personal documents on Dropbox.
  • We can't collect employee medical information for privacy reasons, but going forward, we're going to ask everyone to keep a note inside their passport during the retreat, just in case. Sometimes, basic info, such as your weight or things you are allergic to, could be of great importance.
  • Refunds for cancellation for retreat activities and meals are a good option, so don't forget to ask for it.

That's it for the 2017 Balsamiq retreat! I'm looking forward to what challenges next year will bring us, since there will probably be 10 more Balsamici! Stay tuned for more update about new hires. 😀


Francesca for the Balsamiq Team

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