The Hallway Blog

Retreat Checklist

Nothing brings a remote team together like some good old-fashioned face-to-face time. Plan some time to eat, work, drink, and be merry with your colleagues. Forge friendships, get to know one another and get some great work done.

Now, of course, planning a team retreat is not a simple thing. When your team is spread out across different time zones, locations, and may not even have an office to meet at, it can be a logistical challenge to get everyone in the same room.

That’s why we put together this four-page checklist of all the things you need to consider when planning your next team retreat. From remembering to ask about dietary restrictions for your team members and bringing enough markers, to making sure you have goals set before setting off, we’ve thought of pretty much everything.

There are two ways you can consume this checklist…

  • Simply see the bulleted list items below
  • Enter your email address below to get a much better designed, prettier, printable PDF version of the checklist



Focus on the big picture

First Steps – Initial Planning Meeting

  • Get management/team leads together to discuss goals and outcomes
  • Assign a point-person to lead organization of the retreat
  • Figure out budget, a general date range, and a list of possible locations
  • Plan for next meeting

Determine your goals

  • Why are you bringing everyone together?
  • What outcomes are desired?
  • What kind of activities you plan help achieve those goals?
  • Will you have a theme for the retreat?

Know your team

  • What is the adventure level of your team?
  • What do they love to do?
  • Are there any activities you feel you should shy away from?

Where and when are you going?

  • Will the retreat be at an office? A destination?
  • Will it be convenient to most of the team?
  • When will they be available or not available?
  • Let the team know once you have a scheduled date

Finances

  • What is your budget?
  • How will the trip be paid for?

Dial in the structure

Collect Information From Potential Attendees

  • Everyone’s home airport (+alternative airports)
  • Preferred airlines
  • Frequent flyer numbers
  • Known traveler numbers (if applicable – anyone with pre-check has one)

Flights

  • Book flights for each team member
  • Share their flight information with them

Lodging

  • Determine your lodging type (hotel, airbnb, etc.)
  • Research and present lodging options
  • Confirm availability
  • Check wi-fi speed
  • Book lodging

Team meetings

  • Where will team meetings and discussions take place?
  • What strategic goals does each team need to accomplish?
  • What big organizational goals need to be completed?
  • Are there any customers in the area you can visit or have come meet you?

Going International?

  • Will you need Visas?
  • Visa/tourist fees – let team members know if they may be required to pay a fee on the way out or in and that you’ll reimburse them for it or if needed, provide them with the currency to do so

Work Activity scheduling

  • How many work sessions will you have time for?
  • Who will be leading each session?
  • What will each session be about?
  • Determine allotment for team sessions, all-hands, fun activities, and down time
  • Schedule in time for “regular work” catch-up sessions

Fun Activity scheduling

  • Plan activities but allow for spontaneity
  • What are the top tourist attractions in the area? Are there any very unique ones your team can try out?
  • Take pictures and videos

Nail the details

Run a pre-retreat team meeting

  • discuss goals
  • discuss logistics
  • address concerns and questions
  • Get the team excited

Information to share before leaving

  • Packing list based on planned activities
  • Dress code for certain events if applicable
  • Itinerary
  • Important points of contact

Transportation

  • How will everyone get to your lodging?
  • Will you rent separate vehicles? A team vehicle? Hire a driver? Take ubers?
  • If people are getting in at similar times, can you set up rideshare?

Eating

  • Are there any dietary restrictions you need to be aware of?
  • Make reservations or ensure restaurants are open on days you plan to eat there
  • If you’re renting an entire place, where will you do the grocery shopping, who will do it, and what do you need to buy?
  • If you’re renting a place and cooking, who will cook? What dishes will be served? Will there be a chore schedule?

Downtime

  • Everyone needs some downtime to relax, talk to family, catch up on work. Make sure to schedule it in and not have team members feel pressure to always socialize
  • Bring some games

Supplies

  • What supplies will you need? Where will you get them?
    • post it notes, writing pads, easel, markers, index cards
  • Retreat swag
    • Get t-shirts made
  • Get travel insurance for everyone or get a group policy
  • Snacks, Coffee, Tea, and other assorted munchies

Handling people who can’t make it

  • Video conference them in
  • Take minutes or pictures of whiteboards, notes, etc.

Create policies or house rules

  • Significant others
    • Create a significant other plan or policy. If they tag along, what are they allowed to participate in?
  • Alcohol & behavior
    • What is acceptable? What isn’t?
  • House rules
    • When is lights out?

If traveling internationally

  • Remind everyone to register with the consulate, make passport copies
  • Check for any travel warnings to the destination

Contingency planning

  • What will happen if your team or someone can’t get to the destination?
  • Do you have all important documents before leaving? Like travel insurance, reservations, itinerary, etc.?

After the retreat

Keep the energy going

  • Collect team photos and do a slideshow
  • Share action items, topics discussed, big takeaways, etc.
  • Schedule any necessary follow-up meetings
  • Incorporate photos from the retreat into your about us page or recruiting efforts
  • Collect evaluations of the retreat asking what went well and what could have been improved for next retreat

Logistics and Minutiae

  • Collect expense reports for any approved expenses
  • Collect reviews and evaluations on the retreat of what went well and what did not

Travel planning tips and tricks

  • Don’t schedule tight layovers or layovers at places where gates are far apart or they may be impacted by weather
  • Plan for social time, but also for chill time
  • Be sure that groups who normally wouldn’t interact with one another have to interact