John Ellison

Day 44: Training Stories Workshop

8 min read

Finally the day of the training stories workshop had arrived. I had to cancel last week's session because of a family emergency, and funny enough, I ended tearing my ankle playing football on the eve of Day 43. So I came to Day 44 with less than four hours of sleep, but I was determined to hold this workshop (even if I was half asleep while doing it).

I have to give many thanks to Monika Bansal for helping me set up the workshop. I crutched into the office on the morning of Day 44 not sure how I was going to setup an entire workshop and get lunch for all participants on crutches. Monika swiftly came to save the day. I could not have done it without her.

monika bansal helping me set the stage

Setting Up The Space

I designed the initial layout of the workshop on Day 18 and had intended to hold the workshop outside on the deck, but unfortunately we had heavy rain so it was bound for the downstairs auditorium.

My aim behind the workshop layout was to create a relationship between space, time and the story itself. I wanted participants to literally walk through the story and feel the progression from one event to the next as they moved through the space. I wanted to have participants feel the progression from high to low and back again as they observed the story events on a spectrum of emotion.

There was something powerful about creating a linkage between space, time and the story's progression. It seemed so much more real and effective than portraying something on a screen.

I think the digital world can be really weak at times and we turn to screens too often. We are humans who can touch and feel, smell and hear, yet too often we resort to simply seeing... That can create unnecessary limitations on our ability to perceive and process information.

Basic layout concept was that we would enter the room and walk through the room clock-wise. At the beginning of each story was the hero persona. The hero persona introduced the character, their key attributes, their allies, antagonist as well as the story's premise.


Inspired by Ben Sauer's consistent use of icebreakers to kick off a workshop, I decided to give it a try on my own. (An icebreaker is an activity that is designed to 'break the ice' and make people feel comfortable.)

At the end of Day 43, I told Ben I wanted to include an icebreaker and after a bit of a ping-pong conversation, we had the icebreaker task well defined:

I want you remember an embarrassing moment from your past that you would be comfortable sharing with the group. Using the piece of paper in front of you, write it down. Keep your story private for now, we’re going to make a little game out of this...

When you’ve finished writing, turn your paper over so no one can see it.

I’m going to collect all the embarrassing moments that people have written down and read them aloud one-by-one. After I’ve finished reading each story, we’re going to play a game and guess who this moment belongs to. Just a fun little something to get us going.

participants getting settled with icebreaker

I am using Evernote to archive all of my workshop activities into modules:

  • Icebreaker
  • Divergent
  • Convergent
  • Decision Making


As we finished the icebreaker and everyone had eaten their lunch, I introduced the purpose of the workshop:

The purpose of this workshop is to generate value propositions for the Training Project.

Before jumping into the structure of the workshop, I’d like to give a little background on the Training Project, or ‘Project Snorkel’ as Andy P likes to call it.

The Training Project began as an exploration into how Clearleft could provide training services to clients.

Over the past couple of weeks, Andy P. and I performed a wide range of user research activities. As an outcome of our research, we created four personas. We experimented with the personas and pretended that they were heroes with superpowers to see how it would affect the stories that we created. With that ‘hero’ lens, we then created stories that we felt represented the larger audience we uncovered in our research.

Today we are going to walk through the stories of each of our heroes and identify opportunities for us to help them along their journey. These opportunities can be personal or impersonal, but the idea is to help the hero make at least one step forward towards their goal.

We're going to use those opportunities as the basis of our value propositions.

Given this is the first workshop I've facilitated and that this workshop is new, we are going to experiment on the process of the first story and iterate and improve with each story along the way. So if something doesn't make sense or you think we could do it better, go ahead and let me know.

Sam's Story

I asked everyone to grab a stack of post-its and a sharpie. We stood up and I introduced Sam and we walked through his story. I set a timer for five minutes and asked people to identify opportunities on their sticky notes and place those stickies where the opportunity arose within the story.

It was amazing to see how many opportunities people generated in the space of five minutes.

I told the group that I felt we needed to work towards a value proposition for Sam and asked how we might go about doing it. I suggested splitting into pairs and grouping the opportunities into categories so we could use them as the basis of our value propositions for Sam. James Bates suggested we group them as a group rather than in pairs, and rightly so. It would've been impossible to reduce categories into pairs, but that's exactly why I wanted to open up the workshop to everyone's opinion because I've never done this stuff before!

I was initially hesitant to remove the stickies from the context of the story because I think that was a huge part of the workshop's strength, but I thought we could at least try it out and see how it worked.

grouping into categories

It took about two mintues to group Sam's opportunities into categories. We had a quick minute of reflection where I asked the group if we should create value propositions for Sam right now, or go through each story and generate opportunities first and then create value propositions for them all at the end.

The group consented to focus on generating opportunities for each story first because we would start to see trends and patterns between the stories and it would be easier to create value propositions after we'd seen all the stories.

Walking Through Each Story

We proceeded to walk through each story and identify opportunities. The group opted not to group them into categories but to leave the stickies in context on the story roll.

nicoles story

I learned something in letting the workshop fall into a natural rhythm: Flow is crucial. I hadn't thought about the workshop's flow when I was working with Andy P to design the specific steps of the workshop. I had imagined a single movement through the space when I designed the workshop layout initially on Day 18, but I didn't use flow as a criteria to design the workshop activities later on.

lisas story

Both Nicole's and Lisa's story worked really well to generate a wide range of opportunities, but as soon as we got to Teddy's story we got stuck.

getting stuck on teddy's story

It became pretty clear that our fourth and final story was broken. As soon as we entered into generating opportunities for the story, our workshop hit a really low energy point and we couldn't come up with any ideas.

Learning About A Story's Significance

Ellen de Vries pointed out that Teddy's story was written in third person and focused on the movement of the organization rather than Teddy as an individual. James Box pointed out that there were really two stories that we were working with. Both of these observations were completely valid and showed that the story was in fact broken.

It was fascinating to see that the quality of a story was largely deterministic of the number and quality of opportunities that participants were able to generate.


The workshop was incredibly successful at generating insightful opportunities for us to help our hero personas along their journey, but ultimately the workshop failed at achieving its main purpose: To generate value propositions.

I asked for feedback from all of the participants, and received some really amazing insights. Here selected notes from my conversations with Ben and James:

Feedback from Ben 1

Feedback from James 2

Debriefing With Andy P

Andy P and I met after the workshop to talk about the outcomes and how we were going to move forward. We also discussed a blog post that we were going to write about what we learned from the process and how we would implement these exercises with clients. By this time of the day I was failing from such little sleep and a swollen throbbing ankle. So I bid Andy adieu and planned on catching up the next day.