Welcome back to my series on Rally’s process for annual planning.
In the first post of this 4-part series about our planning, I offered you a glimpse into how we conducted some of the initial planning Iteration approach: from executive visioning through departmental ORIDs into deep preparation for the Iteration 3: the planning meeting. We chose to act as chefs in our approach versus follow a recipe.
Our annual planning has iterations
To reset the stage a bit, let me give a high-level view of our overall planning approach. Think about 5 iterations (not levels, iterations) of planning. We kicked off the annual planning through an executive offsite as our Iteration 1. The outcome of this iteration was a set of proposed Mother Strategies. (To learn about our use of Mother Strategies, checkout Part 1 of this series.) This was followed by Iteration 2: departmental ORIDs. I then touched into the preparation we asked of participants, our customer guests and our team of three facilitators for the 2-day meeting of annual planning, Iteration 3. Iterations 4 and 5 wrapped up the overall planning for the year by setting our cadence for continuous steering throughout the company.
Time for the planning meeting sessions to begin!
As the actual annual planning meeting approached, we stepped up the details of the facilitation processes that would guide the two days of planning. This Iteration 3 of planning included pre-reading as part of the iteration: Escape Velocity by Geoffrey Moore. Moore’s book about applying Horizons 1,2, and 3 in order to “free your company’s future from the pull of the past,” set the stage for all participants in the 2-day planning event. We drew upon Moore’s advice as a guide for our language and our very purposeful intentions for the year and beyond.
Build it and they will come–inviting guests to our “dinner”
It is this Iteration 3 event to which we invited our customer guests. Wow! We had never invited observers to our annual planning before. But we knew we wanted customers to see how we work, gather their feedback, and hopefully give them takeaways for their own agile organization planning. In morning sessions on the two days, we engaged over 60 Rally employees representing their teams. They were guided by 2 main facilitators and 2 assistant facilitators. For these large sessions, the facilitators prepared several weeks in advance to ensure the room provided guidance for all aspects of the meeting. In particular, we posted the purpose and a very detailed agenda. This helped everyone in the room understand the work at hand. 
Afternoon sessions had a smaller gathering and concentrated on what had been learned and discussed in the morning sessions. The sessions were guided by 2 different facilitators. The 25 people in the afternoon represented the extended management team. Our guests were also present as observers. Yes, they saw and heard everything!
In the first morning, the executive team provided a review of their work on proposed Mother Strategies. The larger group of Rally employees created:
- 23 departmental readouts captured on a large wall chart created in the morning
- surprises, risks, dependencies, and recommendations brainstormed and captured in an affinity grouping chart about all the readouts
- votes from all 60 attendees with regard to their reactions to the 5 Mother Strategy proposals that had emerged from the executive offsite

Mother Strategies–trust and safety in the 60-person voting step
We felt strongly about protecting each attendees anonymity as they evaluated the Mother Strategies. as defined in Pascal Dennis’s book “Getting the Right Things Done.” You can also checkout more in Part 1 of this series.) We wanted people to be able to make tough recommendations about the Mother Strategies without influence from others. Trust and safety were critical for the voting to be truly candid. Our anonymous voting system used colored cards and baskets. Each of the five proposed Mother Strategies had a basket into which people placed one of three possible colored cards:
- Green card = “We need this Mother Strategy this year.”
- Yellow card = “I don’t care whether we do this Mother Strategy or not.”
- Red card = “We should not have this as a Mother Strategy for this year.”
Everyone voted on every strategy. They were also invited to write comments on the green/yellow/red small cards to explain why they had chosen a particular color.
During lunch, the team of facilitators counted all the cards for each Mother Strategy. We then used a bar chart to reveal: how many green vs yellow vs red cards each Mother Strategy received. And, we glued some of the cards with comments to a wall chart to show insights from the group. We wanted to provide feedback in both a quantitative and qualitative way.
Always close with a retrospective
Before the morning session was completely over, the facilitators team made sure the group could provide feedback on the meeting. Participants populated a mood chart about each part of the morning’s agenda in the following way: were you glad we had the agenda item; did it not really impact you one way or another; or, were you disappointed in it (it added no value)? This too was captured on a large wall chart. It was completely visible for everyone to see, including our guests.
What do we do with this information?
In the afternoon of the first day, we switched our facilitators and used new processes: a Kanban board of agenda items versus a list of agenda topics. The group of 25, along with our 12 guest observers, had a lot to absorb. Our first step was to quickly build a bridge of empathy about the morning participants and their work. To do this, we turned to Empathy Maps, an approach to learning we’d practiced with people from the Stanford d.school. We also followed guidance from the book Gamestorming. Teams of 4-6 people (including our guests) gathered at separate wall charts to brainstorm about the morning. What did we notice about the 60 participants? What had the 60 people from the various departments heard, said, seen, done, thought and felt during the morning session? The readout, in particular from our guest observers, revealed a great deal about how people were engaged; what they were concerned about; what they valued; what gave them energy; how open were they, and, what they might have taken away from the meeting.
We also re-visited the morning group’s insights and risks as well as the voting on the proposed Mother Strategies looking at the bar charts and comments. This was revelatory. We discovered some strong opinions we didn’t expect. The main revelation? How do these five proposed Mother Strategies help the entire company focus for the year? How do they help the company determine what to stop doing, start doing, and keep doing? In sum, the group of 60 sought assurances and clarity about how to do their steering through the year.
Wrapping up Day 1 of Iteration 3
Our first day of Iteration 3 started to wrap up after open dialogue around the proposed Mother strategies. Each of the 25 participants self-selected which strategies invited their focus. These sub-groups provided more detail around the strategy, outlined initial metrics, and created a 4-minute”stump” speech using a Bert Decker grid for crystallizing their messaging. The results were both stunning and energizing. We were ready to bring our work into the morning session of day 2. We ended the day by holding a retrospective on the overall day and by asking our guest observers to give us their feedback through their own ORID exercise.
Ask a guest customer to tell you about how you are doing. You’ll truly love the experience. Once again, their attention to detail, their observation of trends and their recommendations (for themselves and for us) made us so grateful for their presence.
Dinner and drinks sealed the deal at the day. So, ending this Part 1 of my series on “Guess Who’s Coming to Planning,” I’ll play off of the movie “Guess Who’s Coming to Dinner” a bit more explicitly. We fed liberally off each other’s insights. We challenged one another. We didn’t hold back. And, we held close to our sense of being a growing, learning community.
Stay tuned for Part 3 of our 4 part series on Rally’s annual planning journey. In Part 3, we’ll finish day 2 of Iteration 3. Part 4 will complete our series by wrapping up with Iterations 4 and 5.
Jean Tabaka is a serial collaborator, a relentless facilitator, a well-intended blogger, an author and Agile Fellow at Rally Software Development. If you don’t see her in your town, you can follow Jean on Twitter at @jeantabaka