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14+ Steps to Running a Successful Offsite (I Mean…Advance)


In the last 12 weeks, our teams at Stride have run two Advances for the Company.  What is an Advance?  Well, we don’t like calling it 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 don’t really mean anything other than you are going somewhere that is literally, “off site”.  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 gameplan for helping your team establish the Critical Success Factors (CSF’s) necessary for the next 6 month execution.  For a primer on what Critical Success Factors are, click here.

Team Advance Steps for Establishing Critical Success Factors:

1. Operate in a space that creates energy. 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.

2. Fuel the team. You need food so plan in advance.  A light breakfast, snacks and lunch are key.  People will graze.  That’s fine.  Fruit, coffee, nuts, trail mix, M&M’s, popcorn.  Lunch should be pre-ordered and delivered at a specific time (do not deal with logistics like this in the middle of the Advance).  Breakfast should be already set up by the time people arrive.  The environment needs to be well controlled.

3. Set ground rules. You can either solicit input for the ground rules or lay them out up-front.  Key ground rules for our Advances include:

  • This is a safe place to speak openly and honestly.
  • Respect the voice of a single person expressing a thought.
  • Share your experience. Speak from first person
  • Celebrate a success or a breakthru
  • Cut out the technology and be present
  • Have fun

4. Run an icebreaker. Here are three icebreakers I like:

  • If you could travel anywhere in the world, where would you want to go and why?
  • My one wish for the future of the Company is…..
  • We are going to simply count to 10 but here is the catch – 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 can’t say the next number.

5. Give people homework in advance. It makes everyone feel invested.  Examples might include:

6. 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.

7. Throw down the gauntlet. The leading executive needs to present on the desired outcome for the business over the given timeframe.  Without knowing what mountain the team is supposed to climb, it is hard to build strategy. That should be a well thought out and articulated presentation because it is out of that presentation that the power of the group comes into play.

8. Facilitate the dangers.  I really like the exercise of facilitating all the reasons that the objective that the CEO or executive leader rolled out won’t work or where the big obstacles exist. To make sure you get full participation in laying out dangers, have each person write down 2-3 dangers on a piece of paper and go around the room and get that input (note, you should be scribing this on a big white board of sticky pad).

9. Set up a voting system. Wisdom of the group (“WOG”) is a powerful theme for any Advance.  It says that together as a group we will be able to prioritize better than any one person acting alone.  The voting system works like this:

  • Each person has 5 green post-it notes and 5 red post-it notes. People come up to the board and vote for what they believe are the top 5 dangers and what they believe are the bottom 5 dangers.
  • Once posted, if there is conflict, people can defend their positions and conversation ensues.
  • Once conversation is over, remove the post-its and re-distribute post-its. People vote again.  Ideally there is clarity on what rises to the top.

10. Set up working group teams (with a team leader). Now that the priority dangers have been determined, create breakout groups with a team leader to go attack and prioritize the solutions to that danger.  Breakout groups should be led by the person most likely to lead that initiative ongoing.   The breakout group brainstorms on plans, prioritizes them, sets timelines and measurable outcomes.

11. Team presentations. Teams come back to the group and present their action plan. These action plans will be documented, organized and be the driver of ongoing weekly / bi-weekly CSF meetings.

12. Set a theme. The Advance is a great place to set a theme as a company.  You can use wisdom of the group to set a theme but that theme is a powerful glue for the organization to keep their sites set on the goal.  Our current theme at Stride is, appropriately, “Hitting Our Stride”.

13. Save time for reflections. After plans have been laid out and a theme established, congratulate yourselves on hitting such an awesome milestone.  Reserve time for reflections.  Go around the table and ask what people learned from the day.  I often like to do a one word close, “What is the one word that captures how you are feeling?”  It is important to wind these days down in a reflective way.

14. Have a rallying cry. At Stride, we have a Stide clap sequence which is pretty fun.  It’s a way to connect people to a shared ritual.  Figure out something fun that you can use as a reminder of the power of the day.

15. Complete a visual report and distribute. This may be the most critical piece.  You have a ton of content on sticky pages around the room and that needs to be organized.  Also, make sure to have taken pictures of people working and discussing (and take picture of all the content up on the walls).  Put that together in a visual report that can be distributed and memorialized.  You don’t want to forget the enormous strides you made that day.  It is also helpful for new people that join the organization as something to review.

While this may seem a little overwhelming, I assure you that it can be 😉  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 me at russell.benaroya@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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