How To Plan A Fun, High-Impact Strategic Retreat

The WorkBright team just got back from a kick a**, super motivational, game changing leadership retreat. We revisited our foundational direction and re-committed to our purpose, then each team member go to deep dive on what these values and mission meant to our personal and professional lives in 2016 and beyond. Sound heavy? It wasn’t! It was really, really fun too! We each walked away with clarity on our direction, a deeper connection to each other and our customer base, and really sore legs from all the skiing.

While all of this may not be repeatable for the masses – we’re lucky to live just a quick hours drive from some of the best skiing and best views in the world – we did take some time at the end of the retreat to give feedback. And after rounds of genuine “best retreat ever” and “I’m so excited to work here with this team”, we got to thinking… what made this retreat so different?

After a few days of reflection we can honestly say it was planning, participation, and authenticity. But what do those words really mean and how did they play out to create a fun, high impact offsite strategic retreat? This blog post – and the subsequent deep dives on each activity we will do in the coming weeks – are meant to be a definitive, how-to guide to give you meaningful and actionable steps to putting on your best offsite strategic retreat ever!

Tips from Workbright CEO

“Your CEO should be the main owner of this retreat, with perhaps the help of a committee for additional support where needed. I highly recommend the email with the agenda comes from the CEO directly – participation comes from the top and this will set the tone for your retreat!”

-David Secunda, CEO, Workbright


Use the template below (copy and paste if you want!) to outline your offsite retreat. Replace our information with your own, then email it to all team members at least 1 week before the retreat so they can get prepared and know what to expect. The bolded area is the template piece and the rest is exactly what Dave had written in to our WorkBright offsite retreat agenda for some ideas.

Theme: Culture Development and Foundational Directions
This is a great theme for an offsite retreat – customize it if you want but we recommend you just rip it off exactly! Culture is critical to any organization and will trickle down from the key leaders that are likely attending this retreat. While each department inevitably develops their own sub-culture, the offsite is a great time to make sure your companies overall vibe is in-sync. We also recommend keeping your offsite retreat BIG PICTURE. So often we get stuck in the day-to-day of our jobs and getting out of the office is the perfect time to come out of the woods and revisit your foundation. When everyone knows and is committed to the core of what you do and why you exist, your long-term goals take shape much easier.

Goals: Team-Retreat-Goals-Ski-Fun

  • Deepen team relationships and promote open and honest communication
  • Revisit and add to WorkBright Foundational Directions to confirm and/or modify and re-commit
  • Personal long term visioning
  • Have fun

Your goals should be in line with your theme. This may be a bit of a ‘duh’ but it can be easy to include buzzwords, like culture, in your theme and then make all your goals about strategic business planning. Everyone knows that we are going to talk business at the retreat, but by having three of the four goals harken back to that part of the theme, we are setting ourselves up for something a bit different!


Location: Snow Mountain Ranch, 1101 Co Rd 53, Granby, CO 80446 (2 hours from Boulder)


We like just one night away and two full days. It keeps the cost down on lodging and allows people to get back and focused for the majority of the week (i.e. team still has 3 out of 5 full work days). Schedule time for fun on each day! We’ll talk more about the activities later in the agenda.)
(Format: 2-day offsite with work and skiing each day)


  • Tuesday
    • Breakfast: on own before you go
    • Lunch: at cabin
    • Dinner: at cabin
  • Wednesday
    • Breakfast: at cabin
    • Lunch: at cabin
    • Dinner: on own upon return
Our headquarters are in Boulder, CO so dietary restrictions are pretty much a given to maintain that healthy lifestyle. Half our team is gluten free so we discussed some good options that would work for both groups. We landed on Sandwich material (gluten free bread options presented) plus chips for lunch and fajitas with corn tortillas for dinner. Feedback at the end of the retreat was that people LOVED cooking and eating at the cabin rather than going out on the town. It allowed us to mingle while cooking and cleaning and not just getting stuck sitting to the person to your immediate right and left.

Review in Advance:

  • 1 Page Strategic Plan
  • Buyer Personas
  • January 2015 HR Roundtable Meeting Notes
  • 2015 Year in Review
For us, each one of these were links to the google docs which held the information. Sorry, the actual docs are proprietary or we would share! The “1 Page Strategic Plan” held all the values, mission, etc. we would be reviewing through the weekend. The “Buyer Personas” and “January 2015 Roundtable Notes” reminded us of who we are developing, working for, and selling to so we could keep it in context throughout our discussions. And the “2015 Year in Review” was a link to each departments presentations that had been compiled the previous week. We’ll review that process in more detail in a future blog post.This section also allows new members of your team to get up to speed before attending so you spend so much time rehashing how you came to your strategic plan.

What to Bring:

  • Clothing for Alpine skiing and XC skiing. We will have an opportunity to XC ski on Tuesday morning so I suggest that you have your outdoor clothing either on or have it handy in a day pack so we can do a quick change and get out.
  • Skis (if you have them, otherwise rental is on WB)
  • Clothing for hanging out in the cabin for 2 days.
  • Thermic Mug/Water bottle
  • Toiletries/Meds
  • PJ’s
  • Notebook/pen
  • Computer

Ok, some of these sound silly. Whose going to forget PJ’s? You can leave it off but don’t come crying to us when you’re sleeping next to your co-worker in his underwear! All jokes aside, the key information here is about the activities we are doing which are the first two bullet points. We highly recommend you have some physical activity planned in. If you do this, some people may not own the right gear and it’s important to let them know well ahead of time what is covered by your organization (rentals) and what they may need to ask a friend or family member to borrow.

One other interesting note here is to bring a Notebook/pen. We kept a fairly strict – no computers open during our scheduled time to avoid people getting distracted by email. That meant any activities that required writing was done by pen and paper.

Group to Bring:

  • Projector (Cary)
  • Post it notes, Post it Flip Chart and Pens (Dave)
  • SC Notebook & Fast Filters & Unique Naming Exercise & Handouts (Dave)
  • Food (Dave)

If the facility you are staying at has a large TV you can plug in to, you may not need to bring a projector. However it is important that you have some way of communally reviewing documents so you can maintain the ‘no computer policy’. If you missed that, check the notes from the “what to bring” section.

The rest of the items in this list are required for the activities posted below. Dave, our CEO, took on the majority of gathering things. However, these could easily be assigned out to your committee. Only suggestion, if you have a lot of dietary restrictions, have one of the people WITH dietary restrictions shop for the food. I.E. those without gluten issues don’t know which gluten-free bread to get and apparently there are some good ones and some really bad ones.

Schedule: Tuesday

6:30am: Depart Front Range at 6:30 AM to arrive at Snow Mountain Lodge by 8:30.

8:30-9: Check into cabin and change into XC ski clothes

9-11: Rent gear and XC Ski at Snow Mountain Ranch

11:30-1230: Lunch at the cabin and WORK TIME

EEK! 6:30 sound early? The truth is, it is. But if you are going to pack this much in to two days and not make it a 2 night retreat, it’s really necessary to get the most bang for your buck. If you choose a location closer to you, you can bump this time but we recommend you get started on your activity by 9:00am.

On a positive note, starting your retreat with a physical activity is a great way to start bonding with your team. It has been proven that ‘adult play’ relieves stress, improves brain function, stimulates the mind and boosts creativity, improves relationships and connections, and so much more. Cross country skiing is an easy to pick up, not too strenuous activity that we knew would be approachable for the whole group. Half the group had never been before and everyone did great working together. We had planned to stay on the green courses but were feeling so confident we ended up going almost 4 miles on part of a blue track! When picking an activity look for things that can be easy for all skill levels and will leave you with a sense of accomplishment.

Here are some other ideas:

  • Go-kart racing
  • Easy hike
  • Volunteering together
  • Bowling
  • Zip Lining
  • Tubing
  • This could be another blog post so we’ll cut the list right there for now…

The last note on the morning is to make sure to schedule in at least one hour of “Work Time”. Some roles are really difficult to pull away from for 2 days, like a customer service roll. Schedule in time that employees know they can check their emails so they are not tempted too during your group work time.

Tips from Workbright CEO

“Assign time to each exercise and build in break times between. The facilitator of the event (hopefully your CEO) should then review the agenda after each exercise during the break time to see if something needs to be cut because other sections ran over. Most important is to feel like you have flexibility. Look at your exercises before the retreat and identify those that can get cut if necessary.”

-David Secunda, CEO, Workbright

12:30-6: Group Work

Branching Exercise: Think of your life as a branching tree. Branching points are events, experiences, or happenings in our lives that significantly affect the direction or flow of our life. Branching points are experiences that shape our lives in some important way. They may be big events (e.g., marriage, retirement, geographical move) or they may seem small and apparently inconsequential (e.g., reading a book, going on a hike). From your point of view, what were the major branching points in your life? The events, experiences, interactions with people that had a major influence or impact on the way your life has flowed? Each team member will have about 9 minutes to share their major “branching points” in life and how they contributed to who they are today.

If culture and bonding is at all part of your theme, please, please, please start this way! It may sound hokey, but when you hear someone’s story you can’t help but feel connected to them. The stories that were shared here ranged from hilarious to very serious but it kicked off the retreat goal of ‘open and honest communication’ that was carried throughout all other exercises. More about this in a future blog post.
1-1:20: Positive Focus Reflection from 2015 and Team Member Growth Plan (do and share)
Each week we start out our team meeting by sharing a positive focus from the previous week. It can be personal (i.e. I bought a house this weekend!) or professional (we had 150 registrants for our webinar!). Our CEO has been keeping track of these in a spreadsheet and had each person’s previous year printed out in cards for us. We personally reviewed our year which was a great reminder of where we came from and then did a personal growth exercise which we will share at a later point. This session was short and wrapped up the previous exercise before we shifted in to company thinking.
1:20-2: Reconfirm Core Purpose (Mission) & Vision

2-2:10 Break

2:10-3: Revisit Brand Promises – “What we can be best in the world at?”, or, “What can our customers expect us to provide across every experience?” Look at our current Brand Promises and see if these still reflect our unwavering commitments.

    • Set 1-2 KPIs for each

Unlike your core purpose and vision, your brand promises may shift a bit more from year to year. The key here is to set metrics so you can track how you are doing against those promises to your customer. This is easy for some and more difficult for others but you can always find a way! See our brand promises and how we came to them in a future blog post.

3-4: Core Values – What do each of these values mean to you? What are the Top Ways to Infuse Core Values into Company? Team-Retreat-core-values

For example: One of our core values is that “We Listen”. In marketing, we live this by regularly surveying our customers to see what they would like to learn about so we can develop content that fits that. We’ll deep dive on this issue in a future blog post.

4-4:10 Break

4:10-6: BHAG (Big Hairy Audacious Goal) Activity

This was our first time creating a BHAG so we set aside a lot of time to create it. Honestly, we weren’t even able to finish it in this amount of time! We still need to revisit it and finalize but we made some big progress towards defining it which is half the challenge and the discussions that came out of it were awesome!

6:00: Dinner & Hang Out

  • Life in a hat game

Schedule: Wednesday

7:30: Breakfast

8:30: Group Work

  • 2016 Annual Goal(s)
  • Q1 2016 Big Rock(s)

11:00-12: Work Time and Lunch at cabin

While day 1 was VERY big picture, we took the morning of Day 2 to focus on big goals that were more tangible and that we wanted to focus on in 2016. These goals should definitely be displayed in your office and shared with other staff members that weren’t on the retreat so everyone is working toward them. We liked looking at the year and then the quarter so we can start to track how we are coming toward the annual goal within a 3 month timespan.

12:00: Depart and Ski at Winter Park

4:00: Head Home

After your event, it’s important to survey the team members right away so you can get feedback for your next one. This retreat drew on our founder’s experience over many years and has been fine tuned to deliver results. However, there’s always more that can be done to personalize to your team.

Do you have other activities that have been great for bonding your team? We’d love to hear about them! Share them in the comments below so we can try them out at our next one! And be sure to subscribe to the blog so you can follow the detail information on each one of the exercises we did. We promise to be transparent and open with where things went well, and where they could have used a little bit of work. We hope that by sharing this process candidly, we can reveal a bit about ourselves to you and that we can spread the excitement we have about the Mission Critical Workforce to everyone!

If you hire over 50 employees per year and are not currently using WorkBright for your onboarding, reach out to us!