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Yac's Remote Company Retreat

A recent survey of CFOs found that only 20% of companies offer company retreats. Company retreats have become even more important since the growth of remote work. Anecdotal evidence suggests that remote companies provide for retreats at much higher rates. Maintaining an engaged, distributed workforce isn't easy and company retreats help.

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What is a company retreat?

A company retreat team is an opportunity for team members to work together in person. Company retreats facilitate reflection, connection and collaboration. A spectrum of intentions exist for company retreats. Some retreats focus on social interaction between colleagues. Others focus on producing a work deliverable that is best accomplished while colocated.

Group picture of Yac employees who attended the company retreat

What are the benefits of a company retreat?

At its core, a company retreat fosters person to person connection among co-workers. In-person interactions speed up this kind of social bonding and cohesion. Companies should invest time and money into connections between employees. Companies should hold open the space for their employees to connect with one another. Additionally, certain types of collaboration are ideal for in-person. Some examples of company retreat activities that are better done in person:

·      Aligning company values

·      Communicating long term vision

·      Goal setting as a company or department

·      Culture building

·      Initial social connections

Benefits of Corporate Retreats

How do you plan a company retreat?

Company retreats have 4 key components that need planning:

1. Focus and timing

2. Location

3. Accommodation

4. Itinerary

Companies should first decide what the focus of the retreat should be. Will this retreat focus on a work deliverable or social connection? Deciding this first will help decide other components. A key factor in deciding what the focus should be is when the retreat will happen. Is a new product releasing soon? Did the company hire several new employees? The timing of a retreat has significance for other aspects of planning. The timing and focus of a retreat are linked.

Once a company decides on what the focus of the retreat will be, location is the next consideration. Should the retreat be in a rural location or an urban setting? Should the retreat be in a central location to the company's workforce? Or should the retreat be in an attractive tourist location? Many of these decisions follow from the focus and timing of the retreat.

Next, company retreat planners will book accommodations that will serve the focus. Company size will influence what kinds of accommodations will serve the purpose. Finding accommodation that will serve the purposes of the company isn't easy. Key considerations include:

·      How many attendees are coming?

·      Will organizers want many kinds of meeting spaces?

·      For multi-day events, what sleeping arrangements are best?

·      Will leaders want large convention spaces available?

Planning a company retreat requires balancing several factors. Deciding on the focus of the company retreat clarifies many other decisions.

Notion page for Yac 2022 Retreat overview

What did Yac do during our company retreat?

Yac is an early stage startup that raised a series A round of funding in January 2021. We have hired several new employees in the following months. Onboarding key new team members is hard without the benefits of a company retreat. As a result, we prioritized having an in-person company offsite as soon as possible to help with building social connections and group cohesion.

Face to face conversation between two Yac employees while enjoying leisurely time during the company retreat

World cafe

World Cafe is an excellent way to achieve one of the main benefits of a company retreat: getting to know your teammates as people and brainstorming together. 

“The World Cafe is a method which makes use of an informal cafe setting for participants to explore an issue by discussing it in small table groups. Discussion is held in multiple rounds of 20-30 minutes, with the cafe ambiance intended to allow for more relaxed and open conversations to take place (source).” 

Yac employees gathering around a table for World Cafe

Reverse Brainstorming

Reverse brainstorming is a great method for maximizing the benefits of a company offsite. Reverse Brainstorming is a technique that builds on our natural ability to more easily see problems than solutions. Instead of asking a group to brainstorm ideas that would work, the group brainstorms all the ways that they could cause a plan to fail. This technique is used because it can be easier to criticize and see gaps in a plan than to outline a strategy for success. Once the group has this list, they can look at these specific examples and come up with ways to achieve the opposite effect (source).


A Hackathon event can be a fun way to encourage team bonding through collaborative brainstorming and execution of ideas. For Yac’s retreat hackathon, our team members were split into small groups and had a 3-hour window to create and submit a design responding to a prompt from one of Yac’s co-founders. While the actual Hackathon took place synchronously - in real time - submission and judging was completed asynchronously through Yac. Submissions were uploaded into a Yac discussion channel where off-site team members, who were unable to attend the retreat, were able to judge each design and come to agreement on the winning idea. The winning group was announced at the company dinner the following evening and received Amazon gift cards as a prize.

View of Yac Co-founder Hunter and his viral tweet in the foreground during the Hackathon

Cook outs

What could be better than sharing a home cooked meal with previously remote teammates. Cooking a hot breakfast for your teammates.

One-on-One’s with Leadership

An important interaction scheduled during Yac’s company retreat were one-on-one meetings between Yac leadership – the Co-Founders - and team members for in-person interfacing. The time blocks for these one-on-ones were important to streamline each interaction using approximately 15-minute time slots allowing each co-founder to have enough time to have an in-depth enough conversation with each person while maintaining a flow of efficiency. The one-on-ones encouraged face to face discussions improving morale and giving team members opportunity to discuss items that may not always be forefront during remote interactions.

Hybrid offsite

While many of Yac’s team was able to attend the in-person component of the company retreat, we ended up having some attendees join us from afar. We have an international team and the difficulties of arranging for visas and travel prevented them from joining us in person. In addition hybrid events broadly and hybrid retreats are more difficult than our small team could accomplish. Frankly, we did not do a good enough job of planning ahead to make sure that remote attendees could be included.

Fun offsite activities

An afternoon excursion to the Dali Museum in St. Petersburg, FL brought Yac’s remote team together in one place with the anticipation of artistic interest and dialogue. Walking through the museum, seeing original works of art created by an unarguably talented human, and discussing the impact and appreciation of different pieces gave the Yac team a chance to bond even further throughout the retreat experience.

Additionally, a fun, casual way to encourage friendly competition and interaction between team members included a TopGolf experience on the Yac team’s last evening together. For 2 hours of play, 2 TopGolf bays were rented where team members could choose to play a game as casually as they wanted, enjoy conversation with fellow team members, eat delicious food, and meet with investors and other involved parties that wouldn’t normally have in-person interactions with a remote team. Overall, Yac’s TopGolf experience was well received by the team and seemed greatly enjoyed by all parties involved for a relaxed interactive experience.

Yac 2022 retreat attendees posing at TopGolf Tampa

Throughout the duration of the Yac Pack’s time together, bonding over delicious meals became a welcome and fun experience for the team. At one point, the co-founders were able to break away and have a nice dinner together to discuss goals, plans, and leadership ideas for the future. The remaining team members were treated to a nice, intimate dinner gathering allowing each member to get to know one another on a more personal level. Additionally, a more elegant dinner for the entire team took place at Del Frisco’s Grille where the group enjoyed each other's' company, more delicious food, laughs and announcements regarding the previous day’s Hackathon.​​


Executing an effective company offsite isn’t easy. Planning a company retreat that serves the company and its employees requires deep thinking and intention. Ensuring that your team gets all of the benefits of a company retreat means planning ahead and making sure that the company has done all it can to include everyone in person. Yac’s recent company retreat was a success, but we are hoping to improve on future iterations by planning our company offsite further in advance. Our biggest takeaway as we reflect on our time together is that while we appreciate our location-independent work lifestyles, we also enjoy the benefits of coming to the same place and working together in a co-located environment, too!