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How to Plan an Impactful Corporate Retreat

There is probably no more expensive investment for a firm or company than a retreat. Not only do you lose the productivity of your entire team for a few days, but that is compounded by the expense of travel, hotel, food, and entertainment.

So why do I love them? Because it is a rare opportunity to bring my team together to form bonds that will dramatically increase productivity and provide an opportunity to take a hard look at what is working and what isn't and dial in the strategy for the next year.



I have four priorities for my annual offsite:

  1. Review past results
  2. Create a shared vision
  3. Play together
  4. Plan out the execution of the vision in the next year.

Here is how we scheduled out our two-day event: We arrived the night before to stay in a big private cabin in Park City. It was pretty late by the time everyone arrived, so we encouraged everyone to get some sleep and get ready for a long day.

Waiting in their designated rooms was a welcome gift-bag with treats, lotion, chapstick, and a Clearview Social down coat.

Day 1

(Play) We started early with yoga instruction run by lovely sister-in-law Annie. This was a great start for us since it had a dual purpose of getting our blood pumping, while also preparing us for the first day that would be jam-packed with a lot of hard work.


Then we had a delicious breakfast including a smoothie bar and bacon. Mmmm, bacon.

(Welcome) For the introduction, I reviewed a few ground rules for the retreat. We discussed the Five Dysfunctions of a Team and particularly focused on the need for everyone to be open and honest, and not to fear conflict.


(Review) Next week did a Lifeline exercise that I learned about from the Entrepreneur Organization (EO). In this exercise, each person takes a white poster board and uses colored markers to draw out a "lifeline" that goes up and down with the highs and lows of a person's life.

This was an awesome way to get to know the new members of our team, and it also gave people a chance to both be vulnerable and to see the other members of the team open up as well.

It's the second time I've done this exercise, and each time it has been a big hit. It was amazing to my team how many things they had in common that they hadn't even realized before: losing parents at a young age, divorce, and serious health problems.


(Review) After a short break, we had each department report on their numbers and performance for the past year. We concluded by having me as the Founder giving a report on 2018 and since we missed one of our key goals, we had a discussion about what went wrong.

Everybody was open and honest and it was productive, even though some of it was difficult to hear. The morning was dedicated to looking back, and from that time on we would spend our time looking forward.


We had our lunch catered by Andy West, a close childhood friend of mine who happens to be a gourmet chef and a rising star in the Utah cooking world.

He will be launching a new food truck soon called "Mother's Fried Chicken" and we got to try out the menu which included fried chicken, bone broth, homemade biscuits, brussel sprout salad (epic) and macaroni and cheese.

(Vision) After lunch, we brought in Brigham Dickinson from Powerselling Pros to share his story and inspire us to look beyond artificial limits we have set for ourselves. My favorite story he shared was that of his grandfather who expected to die by the age of 65 and ended up living well into his 90's.

He had a limiting belief that turned out to be completely wrong. How many of us limit ourselves by our own mental hurdles? After his talk, we had a discussion about limiting beliefs and we each wrote down one limiting belief for us personally and for us professionally. This was a perfect warm-up for our next session planning out our five years.

(Vision) 1-3-5. In this session, we planned out our next five years of growth. Our vision session required the most planning in advance of the retreat because we needed to completely dial in our unit economics to know how much revenue we could reasonably expect from each department in setting our goals.

We set our five-year goal and then worked backward to anticipate hiring needs, funding needs and growth targets each year to get where we needed to go. Many of the new hires loved this exercise because it helped to clarify for them exactly how we would achieve our long-term goals.


AD Vision


(Vision + Strategy) For the final session, we took the top three weaknesses/threats/opportunities that Clearview Social is facing in next year and divided into three cross-functional teams including members of each department to develop three strategies to address one of these top issues.



This was a great exercise because it got engineers working with sales, customer success, and marketing in a way that doesn't happen enough. After about 50 minutes, each team had to present their findings, including the name of their group.

The group names were: "Appalicious," "White Men Can Jump," and "The Party Planning Committee." They didn't know it at the time, but they would be working together again with these teams the next day and into 2019.

We concluded the first day with some words of inspiration and then gave everyone some free time before we would be heading into Main Street in Park City for a company dinner. We ate at Tupelo, a great farm-to-table restaurant, got to see a Banksy painting, and finished up with dessert at Java Cow & Ice Cream.

Dinner 1



Day 2

We gave the rest of the team free time in the morning while the executive team met to plan and make adjustments to the afternoon schedule which would focus on execution.

In past offsite meetings, we've heard complaints that "we make big plans, but then nothing changes." We wanted to make sure we had an execution plan in place to act on our vision. With the rest of our agenda set, we loaded up into our 18 passenger van to have some fun together.

We decided to hit the trails snowmobiling together. It was epic! Seriously, we had so much fun. Instead of writing about it, I'll just share with you a few of the pictures.

 Snowmobile Meadow

 Shawn Pointing
It was awesome to play together and do something that was both challenging and fun. It was honestly one of the most fun things I've ever done with my team. We used Red Pine Tours for the activity, and they had access to some amazing terrain right next to Park City.

We returned to the cabin for a hearty lunch including some amazing soup by Andy West and got everybody fueled up for the final afternoon dialing in our plan for the coming year.

(Execution) Right after lunch we broke up into our departmental teams and planned out our Q1 strategy. We also had each team choose a theme for Q1.

I met with the marketing team and since we are launching a new marketing team and multiple new initiatives in 2019 we decided this would be our quarter to get a baseline that we would base all other quarters, so we fittingly called our theme, "All About that Base." And we played the song by the same name through the stereo system as the marketing team came out to present their plan.

(Execution) For the next session, we had the cross-department teams get back together and plan out the execution of one of their key strategies and present those to the team as well.

We set deadlines, and scheduled weekly check-in meetings for each "power team" to track progress on their set goals. We will continue following these initiatives throughout the rest of the year.

(Vision) For the final session of the offsite, we did an exercise called Your Vision Board where each member of the team took a giant post-it sticky, posted it on the wall and answered five questions.

  1. Why is it important to you that we achieve our goals five years from now?
  2. Who else will be impacted by us hitting our goal?
  3. How will it feel if you transported yourself into the future and we finally hit this goal?
  4. What will it mean to you? What will you have proven to yourself/others in the process?
  5. How will you grow/change/evolve as a person in this process?

Then we had everyone share their answers to each question. This is a powerful exercise to finish on because it really focuses everyone on why our goals matter to them individually. We definitely finished on a high.

We gave everybody some time to prepare for a semi-formal farewell dinner which was prepared and served by Andy West and his team. The dinner was incredible food and the low light with music playing in the background made it a perfect way to end our two-day offsite.

We shared toasts, compliments for members of the team and then we finished with having everyone share two things:

  1. What was the best thing that happened to you in 2018?
  2. If you were looking back on 2019 a year from now, what would you like to say is the best thing you accomplished?

This was another powerful conversation that put a great exclamation mark on the event.

My team absolutely loved the event, here are just a few of the notes we received after:

"Thanks for working so hard to make this an unforgettable off-site. Best one I’ve ever attended."

"Big thank you to EVERYONE for these past few days. It was far better than I could have imagined and it really has me excited about the future of our company and our team."

"2019 is going to be a great year!"

Half our team lives in New York and the other half is in Utah, and many of them had never met each other in person, so this event was a great way to everybody on the same page, grow as a team and as individuals. It required some major sacrifices to make it happen, but it was absolutely worth it.

Team Clearview

If you are wondering whether or not to have an annual offsite, I highly recommend it and would be glad to provide any other insights that would be useful, feel free to email me at

What has made your offsite meetings great? Feel free to share it in the comments below.

Adrian Dayton is the Founder of Clearview Social, a software platform that makes it super easy to get your employees sharing your content to social. He is also an internationally recognized speaker who has spoken at conferences, retreats and offsite events in over a dozen countries.


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