Strategy: Shoulda, Woulda, Coulda

Watching reruns of Sex and the City last night, I saw a great title for an episode “Shoulda, Woulda, Coulda”, that perfectly describes the stuff I’m teaching in Strategy.  One of the first things we teach in Strategy is analysis of the internal and external environment. The first question I always get is, Why? Why do we bother with environmental analysis? And the answer to that question, like most important life questions, can be found in Sex and the City.  The answer is, Shoulda, Woulda, Coulda. 

Analysis of the external environment, the political, economic, social and technological (PEST) as well as the industry environments, determines what the organization Should Do. Analysis of the internal environment, the organization’s resources, capabilities and core competencies, determines what an organization Can Do. And finally, managerial preference determines what the organization Wants to Do.  The primary challenge of strategy development is to reconcile “Shoulda, Woulda and Coulda”. 

The biggest challenge in reconciling these three elements is to admit that they exist and to admit that there are gaps and inconsistencies between the three.  For example, many for profit organizations are great at analyzing the internal environment but don’t do a great job understanding the external environment, and would prefer to pretend that managerial preferences weren’t really part of the picture at all.  Some not-for-profits do the reverse, it’s all about managerial preferences and the external environment, but they completely ignore the internal environment — resources and core competencies.  So step one — do the analysis and understand the gaps between Shoulda, Woulda and Coulda.


2 replies »

  1. I mean this in the nicest way, but honestly, do we really think we can teach strategy. I mean I have been in business for 30 years and the word strategy is probably the most abused word in the business world.
    I do not even know what it means in the academic world. To me the word most synonymous with strategy is “failure”. It is only through failure that we make the world better than it might otherwise have been without the aforementioned failure. Let’s see someone put together a case study course on strategy that studies only business failures and not successes. Or better yet, give students cases where the only possible outcome is failure. Get them to admit the failure and then mark them based upon what they learned. If they cannot admit failure then they would “fail” the course. Maybe the real lesson of shoulda, coulda, woulda is that we need to admit that our plans ( read strategies) are for naught and when they unravel before our very eyes that best than we can do is learn from our mistakes and try, try again.

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