Mastering Corporate Retreats for Startups: Part III - Sustaining Momentum After Your Team Retreat

February 15, 2024
Milana Martinovic

Milana has been involved in hospitality and events her entire career. Her journey in operations, support and distributed work started with Airbnb and continues among other startups in the ever evolving tech space. The two worlds connected 6 years ago when Milana got involved with building one of the frontrunners in the company retreat market in the evolving space of remote work. OnsiteHub was created as a culmination of 20 years experience in hospitality, tourism and startups to help distributed teams get together and enhance culture and connection.

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group of people running in the desert at sunset

After triumphantly returning from your company retreat, exhausted but exhilarated, everyone is usually flying high. You made some wonderful memories through engaging activities, and hopefully learned more about the company and the role you play within it. 

Only…now what? How can you continue the momentum that grew from your time together? 

As an event manager with experience crafting a team event for a remote company, I have seen first hand how important it is to continue building upon the innovation that came from the retreat. 

Yet it’s so easy to fall back into old patterns after just a few weeks. People begin working within their silos, some start turning their cameras off during video calls, and they may hesitate to reach out to that new connection they made who works in a different department. So it is extremely important to find ways to maintain the energy and connections that were created during the in person retreat.

Otherwise, the investors and c-suite may start to question why they approved the retreat in the first place. It may be harder to advocate for it again next year

See below for some strategies to make your retreat not just a memory but a catalyst for ongoing success! 

Debrief and Encourage Feedback

There’s a sweet spot about one week after your return, when the memories are still fresh but people have had time to catch up on their work. This is a golden opportunity to send a short survey asking a few questions about the experience. 

Ask for an overall rating, but also ask more specific questions — do they now feel more connected to the company, or, were they inspired by the trip. Giving their name and position should be optional, in case they wish to remain anonymous. 

TIP: You can use the answers from this survey to help advocate for another retreat in the future. 

Goal Setting and Follow Up

 It may be easy to let your ideas from the team retreat get lost after coming home. So be sure to take all of the wonderful creative ideas that were incubated during the retreat and turn them into reality. Ask each department head to present what they came up with to the rest of the staff. 

TIP: Use project management tools like Monday or Asana in order to ensure follow up. 

post it notes showing the words "to do", "doing", "done"

Cultivate Team Bonding 

In order to continue fostering a strong team bond, implement various initiatives that will continue to bring your remote team together. 

Ideas include:

  • Weekly cocktail hours: These can provide a relaxed setting for casual conversation and connection. 
  • The Donut app on Slack: This facilitates random coffee chats between colleagues, encouraging cross-channel bonding. It also introduces weekly topics such as "favorite ice cream flavor" and "most beautiful place visited" to spark interesting conversations.
  • Virtual escape rooms are great for team building and can bring back that sense of teamwork and play cultivated during the retreat. 
  • Monthly themed days can allow your team to end early and enjoy hanging out together.
  • Host a round table featuring rapid-fire questions like "show something on your desk," creating a dynamic space for personal interactions. 

Digital Skill Development and Training Sessions

Now that you are working again remotely, you will see the need to prioritize understanding how to work best together without “actually” being together. 

To facilitate knowledge sharing in this way, host "brown bag" meetings, where team members are encouraged to present their ongoing projects for the benefit of the entire company. This not only enhances transparency but also fosters a culture of continuous learning and collaboration, ensuring that our remote team stays connected and informed about each other's contributions.

coffe mug and laptop showing a zoom call with a large group of people

Everyday Best Practices

Emphasize best practices to maintain a cohesive remote work environment. 

  • Ask everyone to keep their cameras on during meetings in order to foster a sense of connection and engagement. 
  • Prior to weekly team gatherings,  encourage a 5-10 minute window for small talk, to create a more relaxed and personable atmosphere. Provide topic ideas for those who may need a conversational prompt. 
  • When communicating asynchronously with team members, emphasize the importance of providing comprehensive information to ensure clarity and efficient collaboration. 

These practices contribute to a positive and effective remote work culture, promoting both interpersonal connections and streamlined communication.

Promote Inclusion

Ensure that each new team member has the opportunity to meet everyone at the company. They may feel excluded if they joined after the team retreat has ended. In fact, they may have even joined because of that employee branding video you made from footage from the trip! (See tips from part one of this article series). 

Carry the Momentum Forward

The strategies outlined here can transform the retreat's impact into a lasting force, propelling your team toward continued success. As you move beyond the retreat, let these straightforward approaches guide your team towards sustained triumphs.

If you are an in-house corporate event manager that needs a little assistance, consider working with a dedicated company retreat company like OnsiteHub, whose mission it is to create meaningful retreat experiences across the best locations in Europe that foster unity, enhance communication, and spark innovation.

Having help from an outside company who specializes in planning team retreats can allow you to focus solely on creating an impactful event strategy that will have an undeniably positive impact on your company. 

Good luck!


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