The Most Important Strategic Question You Can Ask

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We’ve all seen them: The pipe dreams that are presented as “strategic plans.” Plans that seem to have no tether to reality. Plans that nobody believes in (but that somehow get approved).

There are many reasons such unrealistic plans survive. The organization may encourage activity, not results. Leadership may not be grounded in the planning process, and are thus unable to guide it. Politics may replace objectivity. And so on.

No matter the roots of the issue, I’ve found that one question is particularly useful in making a huge leap toward strategy that truly works.

That question is four short words:

How will we win?

How Will We Win 2Once I started to think of strategy as “the specific intent to win,” I became a better strategist.

When your starting point is nothing less than winning, everything changes. It doesn’t take much thought just to play in a market. But to win, you must think much more creatively. And strategy is, at its core, an act of creation.

Considering entering a new market? Ask “How will we win?” first. (And often.)

Has your growth rate been at or below the category average? Shift your focus from merely competing to winning.

Evaluating a line extension? Consider it not in terms of expanding your brand, but of winning with the consumer.

Asking “How will we win?” forces you to answer a series of interrelated questions, all of them critical to good strategy. These questions include:

  • What exactly does winning look like?
  • With exactly whom do we intend to win? How exactly will we do that?
  • What do we value as an organization?
  • How will we prioritize among competing objectives?
  • Do we have the resources to win? If not, what will we change?

When I’m leading strategic planning workshops with my clients, I’ll often start by asking attendees to share their answers to “How will we win?” along two dimensions:

  • “What We Get”: What does winning look like for us? What do we accrue? What outcomes do we most value? This is where companies typically start. It’s not usually the best departure point for creative strategy, but it is useful for objective-setting.
  • “What They Get”: How do consumers win? Who and how do we serve? What does their world look like when we succeed? The answers to this question force us to look beyond our walls, and are great starting points for determining where you’ll play and how you’ll win with consumers. Ultimately, this is the question that must be answered first.

Winning DefinedI encourage answers that are aggressive and bold here. Safe targets and small dreams aren’t very useful for spurring new thinking.

Depending on the level of consensus within the group, it may take an hour to a full day or more to define what winning looks like. (Note that high initial consensus is not necessarily better. It could mean that the team is pointed in the same direction, or it could mean that members are sharing only what they know leadership wants to hear.) In any event, make sure there’s plenty of time for healthy, open discussion. The answer to this question shapes everything that follows.

Once you have clearly defined what winning looks like – especially in terms of how you will serve your chosen market – you’ll have much more clarity regarding the specific actions to take to make winning a reality.

Throughout the strategic planning process, look for a cohesive fit between your objectives, your decisions and your resources. Adjust as needed, but remember that the big victories won’t come unless you plan for them.

It’s not too late to take a last look at your 2016 plans. Do you have a clear answer to the question of “How will we win?” Do you believe your own plan? If not, make the necessary changes to ensure yours is a plan not just to play, but to win.

About Matthew Fenton: Matthew helps challenger brands to focus, grow and win.  Since founding his consultancy, Three Deuce Branding, in 1997, he’s helped hundreds of brands to achieve “brand clarity.”  His consulting services and speaking engagements help brands to focus on what matters through positioning, strategy and ideation.  Contact Matthew here.  He calls Chicago home.

Copyright 2016 – Matthew Fenton. All Rights Reserved. You may reprint this article with the original, unedited text intact, including the About Matthew Fenton section.

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