Strategy Retreat - Day 5

Strategy Retreat - Day 5

This post contains the activities for Day 5 of the strategy retreat. For more information and the links to the activities from other days, please see the strategy retreat post.

Day 5

Before you start - Opening Circle. See day 1.

  1. Closure - "Offline/Online".* To tie up the strategy retreat nicely; we want to make sure that it is clear to all when/how/if the issues arising will be handled

    This is a very quick, visual exercise to make sure that things which were captured in the agenda hack earlier in the week have either been tackled, scheduled for resolution or accordingly parked.

    Instructions: Take four large bits of paper and title them:

    1. Done - Make sure that there is no doubt in the team that they are complete and that there are no outstanding questions
    2. Do before departure
    3. Do "offline (online :) )" (in the next 30 days)
    4. Parking lot (time to completion > 30 days)

    Have someone facilitate a discussion about status on each of the topics remaining on post-it notes from the agenda hack. Then get them to move the postit notes across onto one of the sheets. Each post-it note is visibly moved so that people can see when and where it will be handled.

    You will need to sanity check items b & c and make sure that every post-it is assigned a date and an owner.

    Document this carefully and move to break.

*This exercise is lovingly dedicated to my former colleague, Sam Leon. Sam’s favourite phrase is “let’s take that offline”. The reason it frustrates Sam is that it actually means “Let us, as a team who normally works remotely (online) and today are meeting in-person for once (offline ), not tackle that face-to-face because we can actually tackle it offline (aka for us online ).” Perplexing for all of us, but very fun to wind Sam up with.


  1. Roadmap (Credits: Facilitation folklore suggests Aspiration Tech, though I got this passed down by word of mouth, saw it done by Fabriders and have tweaked it slightly to meet the needs here.) Aspiration Tech are working on a write-up for this activity, which I will link here when it is done, but for the time being, here is a basic overview.

    Why we do this exercise The most precious time after a retreat is the time directly following it, the next 30 days where everyone is still buzzing from the ideas shared and while the conversations are still fresh. The aim for this exercise is to outline tasks for the 30 days - 3 months following the retreat into a roadmap detailing who does what and when.

    1. Decide on your "tracks". Tracks are ways of categorising tasks. Depending on the size of your team, you may want to do this by the person delivering the task or by the headline to which the activity relates. You will ideally need a different coloured set of postit notes for every track.
    2. Mark out some kind of grid (this can be done with masking tape, or physical objects, like using a table for each month)."Time" should be in the header row, "track" in the rows. (See picture below). The first 30 days will be the most detailed, the further you get, the less detail you should factor in, as things are bound to change. This might mean you want to allow more space for the first month to make this clear.

    Roadmap 1

    1. Each person now takes some time to write out all of the milestones which fit into the time period specified. For more on what qualifies as a milestone, read on.

    On Milestones

    A milestone is an output which has some kind of external value.

    That means "publish blog post on new fellowship programme", would count as a milestone wheras "Do research into different types of fellowship programmes", would not. The research may be a necessary precursor, and you will need to capture it - but keeping focus on the external value of what you are doing is incredibly valuable here to remember why you are working on a particular deliverable.

    Each milestone must have 3 pieces of data associated with it:
    1. A full sentence description (yup, you know what that means, you need a verb!)
    2. A due date. Advice here was to only allow two variations: first day of the month, or 15th of the month. The logic is that anything more detailed was likely to be more granular than our estimating abilities could guarantee with any reasonable degree of accuracy.
    3. An owner . The person responsible for the delivery of that milestone.
    If what you are writing is a neccessary activity to support a milestone, but not a milestone itself, place it underneath the postit note for the milestone to which it relates.

    Roadmap 2

    1. Have people place the milestones in the correct place on the grid.
    2. Step back. Discuss. Throw things at the roadmap and try to break it.
    3. Document and deliver.


Make sure to finish early :) Else, this space is left open to:

  1. Complete small tasks highlighted in the morning as Do before departure or
  2. To throw rocks at the roadmap, it is your job to try and break it, and raise any issues with it while the team is all together.


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