Let Taylor Swift Help You Break Up With Your Strategic Plan

Strategy is messy, chaotic, and transformative. Just like the end of a youthful romance. So who better than the Bard of Breakups herself to offer searing guidance on how to break with your plan?

Let Taylor Swift Help You Break Up With Your Strategic Plan

Several years ago at a Microsoft analyst meeting, Steve Ballmer broke his promise not to go crazy and started flailing around the stage as he described Microsoft not as a mature company, but as a “gangly teenager.”


Ballmer was right, and his description is apt for most companies, even if they don’t want to admit it. Any company that thinks of themselves as mature falls into one of two camps: “delusional” or “one foot in the grave.” A gangly teenager, however, had his or her life ahead of them and plenty to learn. Let the strategic planning learning begin with Taylor Swift.

“Dear John” Speak Now (2010)

Don’t you think I was too young to be messed with?

Young organizations in particular, and even those with longer histories, should resist developing traditional strategic plans that include the capture of organizational state, mission, vision, market, etc. All of those components are important, but they are better as modular, loosely affiliated representations.


Linear exposition confines traditional strategic plans. Strategy, however, is messy, chaotic, and emergent. So if some older guy comes courting, suggesting you get in bed with him to develop a strategic plan, politely excuse yourself–if he becomes insistent, don’t be afraid to toss a drink in his face.

Maybe it’s me and my blind optimism to blame, or maybe it’s you and your sick need to give love then take it away. You’ll add my name to your long list of traitors who don’t understand, and I’ll look back and regret how I ignored when they said “Run as fast as you can.”

Regret. At the end of many a strategic planning processes lies regret. Countless hours spent creating a document that doesn’t get used, seldom gets referred to, and for the most part isn’t applied in day-to-day decision-making. The way to avoid regret: Make components out of the strategic plan, make it accessible and contextual. When making a big decision, run that decision through the mill that is vision and strategy. Build a working relationship with strategy. Learn the nuances and subtitles that run through day-to-day work. If “blind optimism” drives a belief that creating a plan is good enough, you will find that a likely path to regret.

And I lived in your chess game, but you changed the rules every day. Wondering which version of you I might get…

In the future, only the rules of nature remain certain. Economic and political, technological and social, even environmental rules may change dramatically, and in ways contrary to trends and common assumptions. If a strategic plan grounds itself in deep analysis and false surety it will not reflect the changing rules that govern the unfolding of history. Strategy should challenge assumptions constantly, not codify and institutionalize them.


“Back to December” Speak Now (2010)

The last time you saw me is still burned in the back of your mind. You gave me roses and I left them there to die.

Strategy is active. Strategy requires execution. A strategic plan only matters if it results in action. Strategy also requires feedback. Static, aging strategies encourage acting without thinking. Strategy requires constant refreshing, reinvention, and reorientation. A good strategy remains firmly planted in the current reality, not the reality of its conception–or some reality you hope may eventually occur. The present is where life-cycle and renewal take place, and that is where strategies should live.

“All Too Well” Red (2012)


You call me up again just to break me like a promise, so casually cruel in the name of being honest. I’m a crumpled up piece of paper lying here, ’cause I remember it all too well.

The words “dusty notebook” and strategic plan often coexist. Strategic planning documents tend to be the subject of intense deliberation while being developed, but quickly fall into disuse once completed. “I’m glad that is over, now we can get back to work,” people quip at the end of a strategic planning process. The strategic plan can even become a symbol of lost direction as it remembers “all too well” the good intentions integrated into its analysis and narrative.

It doesn’t matter if you change the world, or someone else does–that the world changed is important. Strategy should reflect the starkest image of reality available. Don’t break organizational promises by letting old thinking lie “crumpled up” and irrelevant.

And I know it’s long gone, and that the magic’s not here anymore, and I might be okay, but I’m not fine at all.

Strategy provides a context for co-creating the future. People need to feel a passion for the direction and they need to experience the magic manifest when their personal and team achievements deliver strategic value.


“Better Than Revenge” Speak Now (2010)

Sophistication isn’t what you wear or who you know, or pushing people down to get you where you want to go. They didn’t teach you that in prep school so it’s up to me, and no amount of vintage dresses gives you dignity.

Strategy does not require erudition. Strategies don’t translate well to the rank-and-file employee because they aren’t written for them, and for the most part, they had very little to do with their creation. Strategy stands apart from those expected to execute it, even if one of the strategies focuses on inclusion and communication of the strategy. The solution: Translate strategy into meaningful action that can be incorporated into individual department and personal goals and objectives.

“I Knew You Were Trouble” Red (2012)


And I heard you moved on from whispers on the street. A new notch in your belt is all I’ll ever be. Now I see, Now I see.

Strategy does not require an understanding of trends. Trends whisper promises of futures that may not come to pass. Strategy requires a confrontation and a grappling with uncertainty. Uncertainty leads to the need for multiple possible ways for those uncertainties to play out, which ultimately requires scenarios. Once an organization effectively engages with scenarios it says, “now I see, now I see,” not the answer, but the truth that it can’t possibly foretell the future, and therefore needs to practice active engagement and foresight in order to navigate the uncertain path forward.

“The Way I Loved You” Fearless (2008)

My heart’s not breakin’. ‘Cause I’m not feelin’ anything at all.

The only way to make strategy relevant is to make it the substance that drives the pulse of the organization. If employees aren’t feeling connected, it’s because they don’t understand their role in helping the organization grow and thrive. Management broke their heart by not telling them where they were going, and why they needed them to come along.


“Should’ve Said No” Taylor Swift (2006)

You can see that I’ve been crying. And baby you know all the right things to say, but do you honestly expect me to believe we could ever be the same?

If your last strategic plan failed to deliver results, and when you removed the dusty tome from the shelf you found history, not inspiration or fulfillment, then applying similar structured approaches probably won’t work again. But the consultants will all come courting, saying the right things, flashing their frameworks, telling you they’ve change and assuring you it will be all right this time. You’ve been jilted. Be skeptical.

“You’re Not Sorry Fearless (2008)


And it’s taken me this long baby, but I figured you out. And you’re thinking we’ll be fine again, but not this time around.

The only way you’ll be fine is to reach out and embrace the gangly teenager wreaking havoc and creating chaos. Use strategy to set boundaries, not to shackle innovation, learning, and adaptation.

And for this analysis and reflection on strategy to mean anything, you have to embrace the wonder of the anthem, clench your fist and push it with force into the air, take a deep breath and declare to your stale old strategic plan:

“We Are Never Getting Back Together” Red (2012)


We are never ever ever getting back together!

[Image: Flickr user Jana Zills]


About the author

Daniel W. Rasmus, the author of Listening to the Future, is a strategist who helps clients put their future in context


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