Preparing for a Strategy Sprint – A DIY Guide

Preparing for a Strategy Sprint - A DIY GuideThis is the second in a series of five DIY posts on holding a strategy sprint.

The decision to hold a strategy sprint assumes that you’ve come to the conclusion that a new strategy is warranted, that new directions must be explored, and you’ve gotten to this point in a thoughtful and deliberate way. Something has been tugging at you for a while, keeping you up at night. Something isn’t working as well as it should, or as well as you think it should. (A sudden crisis is not the time for a strategy sprint.)

There are a few important items to consider in preparing for a successful strategy sprint. Basically, you’ve got to cover who, what, when, and where.


A strategy sprint team should be three to five people. If you’ve got more than five who must be involved, simply split the group into two sprint teams. As far as the number of teams goes, more than four becomes cumbersome and time-consuming. So set your capacity at twenty participants.

Now, who should be included? The short answer is those most accountable for strategy in the domain you’re addressing. If it’s overall enterprise strategy, you want the key “heads of state.” In many companies that means the senior executive team. If it’s a functional area, you want the key managers.

Beyond that, you want to compose sprint teams that are diverse in makeup, in terms of both intellect and expertise. If you’ve got a team of four, try to have one of each basic intellect:

  1. Thoughtleader: an ideas person
  2. Taskmaster: an process person
  3. Peacekeeper: a people person
  4. Playmaker: an action person

Having teams with these four basic inclinations, along with diverse areas of subject matter expertise (marketing, operations, technology, etc), make for the most prolific sprint teams, and less vulnerable to “group think.”

Make sure the people you select play well with others. A naysayer or disgruntled player, not to be confused with a useful devil’s advocate, might be someone to keep out of the room, but have “on call.”

On that note, there will always be an “extended team” at your disposal–people who do NOT need to be in the room–that you can call on for input. These might be specific knowledge area experts, partners, or even customers.

There’s one other person to consider: an outside facilitator. An outside facilitator is someone who has no vested interest in the strategy, but rather the process of strategic conversation itself. Ideally they have a working knowledge of strategy, ala the Roger Martin where-to-play/how-to-win framework in order to answer tough questions. They are strong meeting leaders, and have a nice quiver of tools and techniques to get things moving if they stall. They’re objective, and don’t share the mental biases of those owning strategy for your company. They also should have a healthy dose of provocateur in them, and have the courage to push the teams a bit beyond their comfort zone.

They should have enough of a context so that the questions they ask have some gravitas to them, and the easiest thing to do is arm them with background documentation on your current situation. They don’t need in-depth knowledge, just enough to be “dangerous.’

You don’t necessarily need to default to contracting an independent person from outside the company…look for people inside your organization with the requisite chops and credibility. Perhaps you’re lucky enough to be in an organizations has a pool of internal or retained skilled facilitators for important meetings. Or maybe you have a friend at another company. Maybe the right person is you, since you’re reading this!


As a pre-meeting homework assignment, I strongly suggest have everyone read Playing To Win, by Roger Martin and A.G. Lafley, or at these articles by Martin/Lafley et al (click on title to download pdf):

Materials-wise, there are a just a few items to gather:

  1. One Play-to-Win canvas (54 x 36) for each team (download printable pdf HERE). Many companies have plotters that can output this wall map. If you don’t have a plotter, have a local print firm that handles blueprints and large architectural printing print them for you.
  2. Good supply of various colored 3 x 3 Post-it notes
  3. Sharpies
  4. Dot stickers. Post-It brand dots work well.
  5. Whiteboard space. Whatever your huddle space is, you need thinking space. If you don’t have whiteboards at your disposal, get a Post-It chartpad and easel for each team. And don’t forget appropriate markers.
  6. Sustenance: breakfast, lunch, snacks for breaks, and plenty of refreshments.

Strategy SprintWHEN & WHERE

You’re going to need three days, minimum. Ideally those days are consecutive. Something magic happens during multi-day immersive experiences…something along the lines of the old maxim that “when two minds come together, a third mind emerges”.

If you must, you can split Day 1 from Days 2 and 3, but don’t split 2 and 3!

If you find yourself saying, “I can’t afford three days no matter how you cut it,” then that explains why your current strategy may not be working. You haven’t made it a priority. (But maybe your competitors have.)

Clear calendars, and get a nice large conference room. Ideally, it’s an offsite location, away from the distractions and disruptions of running your daily work life. If that’s not possible or desirable based on the cultural norms and needs of your company, try to find a convenient and comfortable location conducive to focused thinking and productive collaboration without interruption.

You’re now ready to hold your strategy sprint!

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Matthew E MayMatthew E. May is the author, most recently, of Winning the Brain Game: Fixing the 7 Fatal Flaws of Thinking.

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Matthew E May




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