This is the fourth in a series of five posts devoted to a DIY guide on running a strategy sprint.

You now have a few strategic possibilities to explore. Each deserves it’s own 5-question cascade. But you will only cover the first three of those questions today, for two reasons.

First, these questions require thoughtful exploration. Second, each of the teams will be “pitching” their thoughts to the larger group throughout the day, to not only keep everyone else informed and up-to-date, but also to feed the strategic conversations and give them the breathing room they need. This is not a “lone genius” exercise.

Day 2 Objectives

The three main objectives of the day are:

  1. Choice of winning aspiration
  2. Where-to-play choices
  3. How-to-win choices


Here are resources that will help you:

Previous Posts:

What Is Your Winning Aspiration?

Where Will You Play?

How Will You Win?


Play-to-Win Canvas

Free YouTube Webinar on Play-to-Win Canvas


Here’s my agenda template, easily tailored to your requirements:

1. Brief review of the day’s objectives (5 minutes)

2. Revisit yesterday’s work, confirming thematic possibilities (5 minutes)

3. WINNING ASPIRATION, Part 1 (20 minutes)

I time box this tightly, because I don’t want people to get caught up in endless discussion and wordsmithing. That’s why I use the Playing to Win canvas…limited space in the size of 3X3 Post-it notes. And, I have the teams revisit their aspirations at the end of the day, because the downstream work on playing spaces and competitive advantage choices often enable better clarity on a winning aspiration.

I like to have teams think about the wining aspiration as two items: the “what” and the “so what.” It’s fine to say you want to be #1, for example, but why does that matter specifically? What is the happy story that comes from achieving the aspiration?

There is time to do both in this twenty-minute window, and space on the canvas to explore the “so what,” labeled “Value Produced.”

4. QUICK PITCHES (15 minutes)

I allow each team one minute each to share their winning aspiration (and value produced) with the larger group, and just three minutes max of questions and answers.

5. WHERE TO PLAY (45 minutes)

There are a half dozen or so generic categories to consider: segments, channels, product and service offerings, geography, stage of production, etc. Yours may look different, especially if you are exploring specific functional strategies, like branding.

The point is, more than six is probably too many to think about. I prefer to have teams spend 15 minutes exploring one kind of space, then move them on to the next. Again, the 2X2 “white space” on the P2W canvas aids this greatly.

Remember, this activity is also very much about identifying where NOT to play.

In addition to the above resources, these posts may help clarify this exercise.

5. Break (15 minutes)

6. WHERE TO PLAY, cont’d (45 minutes)

Teams continue their exploration of potential playing spaces. Included

6. QUICK PITCHES (25 minutes)

In my experience, the discussion around potentially new playing spaces tends to be lively and often somewhat heated, as distance from the current (and comfortable) strategy creates dissonance and discomfort. Therefore, allow a little extra decompression time.


Following quick pitches and discussion around initial playing field choices, it makes sense to give the teams time to not only revise their choice of spaces, but to revisit the winning aspiration.

8. Lunch break (60 minutes)

9. RINSE & REPEAT (same timing as first 8 steps)

The afternoon session uses the exact timing and template above, but is focused on HOW TO WIN.

10. DAY 1 CLOSE (5 minutes)

It’s been a long day, with six solid hours of strategic exploration, but it’s worth a quid recap and preview of what’s coming tomorrow…capabilities, systems, and reverse engineering all of the logic thus far, including the identification of an initial experiment.