A Step-by-Step Guide to to Running a Successful Team Advance (Retreat)

Key Points:

Strideā€™s "Advance" approach transforms team retreats into forward-thinking events, emphasizing alignment, collaboration, and strategic progress.

In the last 12 weeks, our teams at Stride have run two Advances for the Company. What is an Advance? Well, we donā€™t like calling it a retreat or an offsite, that sounds too passive. An Advance is the term we use when we allocate dedicated time outside of the office to focus on driving our company forward.

Offsites donā€™t really mean anything other than you are going somewhere that is literally, ā€œoff siteā€. But to what end? If you really want to align your teams toward shared goals and shared culture, run an Advance! They are so powerful, moving and energizing. If you want to move your company forward faster, do this!

Here is a A Step By Step Guide to Running a Successful Team Advance (Retreat)

1. Start WithĀ the End in Mind

  • Unambiguous Objective for the Day: There should be no misunderstanding about what success looks like for the day. That is your compass so that when things go a little off the rails (very common), you can keep coming back to staying on point.
  • Feel all Feelings: I often will ask how people want to feel at the end of the day. I put this up on the Board so we make sure that the heart, head and gut are working together. Advances trigger a lot of emotions, but knowing which ones to end on is important.

2. Operate in a Space That Creates Energy

  • Space Matters: It should be open and have multiple places for breakout groups to connect. Avoid meeting around a large rectangular table. Consider something U-shaped that is open in the middle. Breakout spaces should be round tables or comfortable couches.

3. Know Your Audience

  • Strategic or Execution Oriented: If your Advance is to set Strategy then the focus should be on Critical Success Factors and prioritization. If your team is made up of mostly line level producers, then they may want to hear what the priorities are but not feel like they need to help create them. Once informed, you can spend time talking about the kind of organization we want to create where we can hit our goals and thrive.
  • Embrace the Entropy:Ā  You will definitely have people in the room that are going to be skeptics or naysers. That is natural but they have an important role to play but it has to be done delicately. First, establish your norms of behavior up-front and get them written up. That way, everyone is accountable to the ground rules. Second, make sure that you solicit input that is non-voluntary (no one can hide) so that people are forced to contribute. Third, check-in periodically with a hand vote of 1-5 (1 being this sucks and 5 being this is awesome) to gauge where people are at. Anyone at a 2 or below should be able to share.

4. Point to the Top of the Mountain

  • When CEO’s point to the “Top of the Mountain” they are communicating WHAT we need to do and WHY we need to do it. They are NOT communicating the HOW and the WHEN. That’s why a team exists to figure that out. But they need to be clear what the mountain is.
  • Pointing to the top of the mountain could be around one or all three (depending on the time you have):
    1. Setting vision: where are we going?
    2. Establishing critical success factors: What are our critical priorities in pursuit of our vision?
    3. Creating company principles: How are we going to conduct ourselves as a living organism, aligned toward the vision?
  • You may only have time for a day-hike here vs. a multi-day expedition so plan accordingly. To get to a point of resolve for most teams, Advances should be no less than a half day and up to two full days. With two full days, real work product can get created in the form of beginning to build the plans.

5. Bring It Home

  • Document your playbook in advance.Ā  I create a detailed roadmap of how I want the day to go in 15-20 minute increments. I often have to deviate from the Plan but it provides a good grounding so that we keep people on point.
  • Facilitation. Facilitating discussion is a bit of an art but you want to solicit wisdom of the group (otherwise why have people there). I will often facilitate an exercise called “Dangers” where people communicate all the things that could go wrong. I then ask people to vote (with sticky notes) for their top 5 highest priority dangers and lowest 5 priority dangers. That fuels discussion to narrow down to what is critical.
  • Presentation.Ā  The CEO should have a few slides for presentation because it will force him to think in advance and clarify his thoughts to communicate.
  • Gratitude. I always try and integrate an exercise of gratitude and appreciation. It warms the room and allows people to feel a bit more vulnerable.
  • Theme. Advances are often great opportunities to come up with a shared theme as a Company. What is our theme for the year or the next 6 months that we can rally around? Our current theme at Stride is, appropriately, ā€œHitting Our Strideā€.

6. Details Matter

  • Give people homework in advance. It makes everyone feel invested. Examples might include:
    1. Have people read a few relevant articles and then be prepared to speak and summarize the key points. Here are a few articles I like:
      How to start the task you have been avoidingĀ ,Ā Building a StoryBrand,Ā andĀ Managing Oneself.
    2. Have people do a strengths assessment like a Clifton Strengthfinders. Summarize the findings on a grid so people can see how peopleā€™s strengths overlap and differ. A very good visual for discussion.
  • Run an icebreaker. Here are three icebreakers I like:
    1. If you could travel anywhere in the world, where would you want to go and why?
    2. My one wish for the future of the Company is…..
    3. We are going to simply count to 10 but here is the catch ā€“ only one person can say a number at a time. If two people say the same number you need to start over. No eye contact and the person next to you canā€™t say the next number.
  • Create a little delight. At one advance, I hid $5 Starbucks gift cards under every other seat. I asked people to reach below their seat and if they had the gift card, they had to give it to the person next to them and say one thing that they appreciated about them.
  • Have the supplies ready.
    1. Pens and paper
    2. Post-it notes
    3. Big sticky pads where you can post throughout the room
    4. Easels so you can write on those pads
    5. Camera (for taking photos)
    6. TV/projector if there is going to be a presentation
    7. Clock/timer to make sure you stay on time
    8. A jar with names (if you want people to participate, have a jar of names that you can pull out and call on)

What Is Most Important Is That You End on a High Note

Be mindful of the Peak End Rule – humans remember the peaks and ending of experiences so make sure to end on a very high note. <- yes, mention this strategy and also end with it, cause you’re spicing it up w a little Behavioral Science Knowledge bombing which is a good way to end your post/session.

Read the Article: 15 Steps to Running a Successful Offsite

While this may seem a little overwhelming, I assure you that it can be šŸ˜‰ But it really is about creating a fun and effective environment at the same time and yes, that takes planning. These Advances are very expensive (a lot of people taking time off work) so don’t leave it to chance. Commit to action out of this because it will set the stage for your execution over the coming quarter or two. You want people feeling somewhat exhausted but also energized and accomplished. At Stride, we know the critical importance of aligning the right execution with the right strategy. You do too. Go for it.

If you would like to discuss Advances in more detail, please reach out to us at hello@stride.services.

Supplies you will want/need:

  • Pens and paper
  • Post-it notes
  • Big sticky pads where you can post throughout the room
  • Easels so you can write on those pads
  • Camera (for taking photos)
  • TV/projector if there is going to be a presentation
  • Clock/timer to make sure you stay on time
  • A jar with names (if you want people to participate, have a jar of names that you can pull out and call on)

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