Team Trips

Experiencing something together is vital to any team’s culture. You not only have a shared experience, but you begin to have a shared language; a shared framework/outlook; and deeper understanding of a place/people/content. These experiences build the exposure necessary for a team to deepen a shared identity and culture.

My background as a military officer was rife with these opportunities – staff rides, field exercises, and deployments; times when the entire unit (the entire team) was immersed in a shared experience. Yet, in the business world, rarely does this occur.

There may be conferences your team attends together…but unless it is constructed truly as a shared team experience, it becomes an individual experience in a shared place with familiar people.

Therefore, for years, I have included team trips in our annual team rhythms at Access Ventures and they have become one of the highlights of the year. I say team trip and not conference because the purpose is more than the destination, and…they are not always around a conference. I believe there are four types of team trips that need to be considered (and even rotated throughout the year or from one year to the next):

Learning – This can be a conference, a site visit or even a course. For us, there is always a conference that most of the team is attending so we will often wrap our team trip around that experience. But, this could be a university professor coming to the experience and teaching something specific. Or, it could be a city/partner/portfolio company site visit to deepen the team’s knowledge of that aspect of the business to gain deeper insight into what we are about.


Team Building – This can be something random and fun (escape room or skiing) or it can be highly experiential or even challenging (fly fishing or a wilderness guided trip or a leadership reaction course, or an urban scavenger hunt or paintball). Changing this up and pushing people has a way of bringing them together.

Rest/Refreshment – Sometimes stepping away and focusing on refreshment is key. The military would call this R&R or a critical time units are pulled from the front line to rest and recharge before being sent back out. Business can sometimes feel intense and the pressures often require an outlet. Sometimes “retreating to advance later” is the best medicine. This would ideally be a very strategic amount of individual and group time with well-thought out ways to truly rest. Location and amenities are often key to this type of trip (ie spa or beach or mountains…beauty/aesthetic and good food/drink are super important).

Strategic Planning – This is a team trip for sure. It is often the first thought in business and I intentionally put it last. This should be more of a rhythm throughout the business and should be the last choice perhaps to structure a trip around. If you are rotating through these annually, then every 3-5 years for this type of trip feels reasonable. That becomes a good cycle to think about, 3-5-10-15 years into the future for your team and for your organization. We could do an entire series on strategic planning but as it pertains to a team trip, try to avoid this becoming the dominant purpose.


While each of these four things will (and should) be present for every team trip, it is important when planning a team trip to define the dominant purpose. This will guide your planning and priorities given any time constraints. So, if you have a Learning Team trip…you will still want to understand how to have the elements of rest, team building, and strategy present on the trip…but, keep in mind the key purpose is for team learning. Now you can see why it is super important to really plan out these trips – otherwise, what was thought to be a team trip becomes yet again, an individual experience surrounded by familiar faces.



  • Flow is important. Plan ahead and map out the time (make sure you leave in down time and bio breaks…often overlooked 😉
  • Fly together
  • Ride together where possible (get that 15 passenger van or bus if needed). The more time you create with the team, the better. Go the extra mile to ensure this is possible.
  • Mealtime is key…have whole-team meals but also look at assigned seats and then smaller “dine arounds”. Dine Arounds are planned small groups that spread out and go to various restaurants. This makes reservations easier but the intentional group, and the smaller sizes, make conversation possible. Ensure you have a leader that can help facilitate table conversations to avoid 1:1 discussions. This can be a critical 1-to-many time. Also, having pre-planned topics for discussion.
  • Share rooms where possible (airbnb or vrbo are other great options if you can find the space). Many people on work trips are used to private rooms (and you may elect to still have this) but you have a small window to build the team cohesion you are hoping for and having a roommate can help facilitate this.
  • Swag or gifting people sets the tone…but nothing of poor quality. This is a great time to prepare a thoughtful gift or bag. Could it be coordinated and left in their room upon arrival? Is it distributed at the first night team dinner or right before heading back? This can be a great way to signal unity and affection for their contribution to the team.

Team Building.

  • Always plan something fun. Laser tag. A live band. A ballgame. Something fun should be factored into each team trip. It will allow people to switch on another part of their brain and learn to enjoy one another as human beings.
  • When possible, don’t share the agenda in advance…allow people to show-up and depend on the team for the next step. If you do share something, perhaps it is large blocks or high-level but getting them to simply show up and to be present is the key.
  • Plan far enough out and make it as “mandatory” as possible. Life happens and inevitably someone may not be able to make it, but stress the importance of attending the trip and by focusing on building a great experience, they won’t want to miss it!


This article was originally published on Bryce Butler’s Substack, More Than ProfitSubscribe to be the first to access new articles.

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