How to organize a Team Meetup

When you’re working from home, you’re losing an important part that it’s normally born when your setup is in an office or any other working space: the human touch. Connecting with your team, knowing them better, what they like, dislike, what kind of jokes they make, how they react when they’re frustrated, anxious, happy, etc. Some people may prefer (or like) to work alone without distractions, but knowing the people you’re working with defines the line of success and motivation within your team. What to do when your whole team setup is remote? The answer is Team Meetups.

Team Meetups must be one of the most important things within your organization, especially if you’re working remotely. The kind of relationships that you can create with a person in “real life” can’t be compared with the one behind Slack or any other sync/async communication software.

However, organizing a Team Meetup for a group of people from different cultures, nationalities, or religions can be challenging¹Especially if you want to keep everyone happy!. I was always interested in knowing the ins and outs of organizing such gatherings, so I stood up for the challenge, and I volunteered to organize my team’s for the first time in 2018, and I’ve been doing that every year until now.

From my experience, this is by far the most exciting part for yourself and for your teammates (and it’s regrettably the easiest to arrange). There are a few things to keep in mind here:

• The size of your team.
• Where your peers are based in.
• Country and city you’d like to go to (and timezone!).
• Overall distance via plane between yourself, your colleagues, and the destination.
• Budget.

If your team is mostly based in Europe, perhaps it is not convenient budget-wise to cross the whole world to visit Asia + adding long travel hours + dealing with jetlag for a few days. On the other hand, if your team is small and mixed with people from different continents, perhaps you’ll find more willingness to find an “exotic” destination that might be good for everyone. In my personal case, I’m okay with spending 14 hours on a plane to visit some hidden part of Asia, but maybe your colleague living in France just prefers to go to a closer destination. There’s an undeniable truth that rules here: you won’t be able to please everyone. So you will need to communicate with your teammates and use that fantastic and incredible way that always work in all kind of setups and never disappoints at all: democracy.

We came up with a system, which is very simple, based on a spreadsheet:

On the columns on the right, you’re writing down the names of your peers. On the column on the far left, you’re listing the possible locations for your meetup. Time to vote! Each one can add a “Yes,” “No” and “WANT” vote. “Yes” gives 1 point to the location, “No” gives -1 point, and “WANT” adds 2 points. We have a special “VETO” vote as well; veto will automatically exclude that location for a meetup destination. No questions asked – if someone vetoes a city or country, we won’t go to that place. We limit the “WANT” and “VETO” just to 1 per person to keep it fair.

Once all your teammates leave a vote, you will have a rough list of 2-3 (sometimes 4) interesting locations. You can start doing the research with the “winner”, keeping in mind that you can always go with the second most voted one if it doesn’t make sense budget-wise. My recommendation is to keep it to 2 locations of your will invest plenty of time and, as I said before, you won’t manage to please everybody anyway.

Alright, you have a few potential places you can go. Before going further into checking the hotels, prices, etc., it’s essential to decide a few things that will define the accommodation and work setup you need for those days you will spend abroad:

• How many days? The standard is usually 7 days, where 2 of them are for traveling, and the rest is for the meetup itself. From those 5 days where you are actually together, you’d need to decide if you want to focus your reunion on the social side or maybe more on the “working together” one. My recommendation is to simply find a balance – it’s okay to have an activity day where you can actually engage and have fun with your peers, but it’s also important to work together since it’s something that you don’t usually do in person. You can learn a lot from working a few hours with your colleague next to you (workflows, processes, task management, tips, etc.).
• Communicate with your team about specific personal details so everybody feels comfortable and integrated. Is there any dietary requirements (based on religion or personal choice) or allergy in any of your teammates? Do they prefer a hotel, or are they okay with spending those days together in a big apartment? Don’t assume that everything you know or want applies the same to everybody, so don’t be afraid of asking questions.
• Create a schedule for those days. Include your workdays and your activity days. Schedule everything: breakfast, coffee breaks, work time, workshops, keynotes, etc. The success of a team meetup heavily relies on planning, so don’t be afraid of overscheduling, however²Italic time., be also flexible to make changes and improvisations on the spot if needed.
• Where would you work? Business hotels generally offer meeting rooms, but you can also go with the hotel Suite and use it as an “operation center” and work all together from there. Some others prefer to rent a coworking and work from there. My recommendation would be with either the meeting room or the hotel’s big suite. The suite might sound expensive, but in practice, it’s not much expensive than a meeting room, and you can normally fit 1 or 2 colleagues from your team in there to spend those nights (as usual, the suite has separated rooms – but again, ask your colleagues first about the idea before placing them together in the same space). The meeting room, on the other hand, can also have some different accommodations such as a projector, paper and pens, etc., and it also sets a more “serious” environment – choose whatever suits your needs in a better way but, whatever you decide, make sure you have a good wifi connection. Arrange a private wifi network for your meeting; this small thing can basically define the line where your meetup can be a success or a complete failure.

You know what you need to make your stay an awesome experience; now it’s time to start arranging the logistics. Check hotels³Or apartments, though I’ve always arranged hotels. according to those needs you previously defined. Keep in mind your budget and also the distance between the place and the airport + the public transport to get there. I’m always checking by using Booking or Tripadvisor, as they’re a good source of information; however, don’t make the booking through them, only use them for gathering information. If you wish to make a business booking, it’s much better to make these arrangements with the hotel directly – they’re usually going to offer something adapted to your needs and at a better price.

Pick a few hotels, check their websites and collect their emails. Then prepare a snippet with a generic message addressing your needs and send it to all of them. Be straightforward and communicate your budget and needs. If, after hearing back from them, the offer is not satisfying, don’t be afraid to negotiate and try to lower the price – they’re generally open to cooperate and find common ground. I’m usually using something along these lines:

Hi there!

My name is XXX, we’re looking for a reservation price for a business meeting. We’re a team of XXX people, and we’re looking for prices for XXX individual rooms. However, it can be the case that we increase our team members by XXX; maybe we will be XX or XX. In that case, would it be a problem if we book more rooms (i.e., can we ‘prebook’ them and update you in XXX or XXX)?

We’re also interested in a meeting room, one where we can work together and with a good wifi connection (important), and I’d like to know if that room has a water/coffee supply, a projector, pens, etc. The dates would be from XXX XXth to XXX XXth. We’re looking for the lowest prices in our meeting in XXX, so we appreciate any proposal you may have for us.

Looking forward to hearing from you!

Thanks!

Once you formalize the deal, make sure you start tracking everything. Ask the hotel what information they need from you and your teammates, so the check-in would be as smooth as possible for all of them when they arrive. Track their flight numbers and hours in case there’s an emergency or delay, and you’d like to check the status of their flight. Add the price of the tickets and all the company expenses incurred during the trip (lunches, dinners, activities, etc.) – you will appreciate having all this information added beforehand when the time to submit it to HR comes.

Follow up with the hotel a couple of days before traveling. Make sure everything’s in order and that there are no pending issues. I had a misunderstanding once with an invoice that was issued incorrectly, and I had to deal with that in record time with the hotel + the accountant department of the company. Imagine how stressful the situation can turn if you’re dealing with that on the site after traveling – always follow up with the hotel before leaving.

If you want to give the extra mile and make the stay even more joyful, create a Google Map with the location of the hotel + contacts in case of emergency. I usually add the person to contact in the hotel and my personal contact, but it’s also good to have a second person to go within your team (maybe I am the one needing help!). Highlight the routes of trains and buses to get to the hotel and add potential places to visit with your teammates and restaurants. Don’t forget to share the map with everyone⁴Captain Obvious intensifies..

Delegate tasks. Don’t handle everything on your own, or you will go crazy. Your peers are smart and reliable human beings, so don’t be afraid to give them tasks, like finding the restaurants, planning activities and workshops, creating the maps, arranging meetings with local businesses, etc.

And finally… meet and have fun!

P.S. If you’re interested in the famous spreadsheet I’m talking about in this post, you can download it from this link⁵You’re welcome..