Questions, the engine of understanding

Big picture strategy may belong to the C-suite, but strategic thinking must take place throughout the organization. Basically, strategic thinking is the deliberative thinking that takes place when you ponder how you, your team, your department or your company will succeed now and into the future.

My dilemma.

I’ve been facilitating strategic thinking workshops for over twenty years, but I was at a loss as to how to organize a planned guidebook aimed at helping emerging leaders become better strategic thinkers. 

I could launch into a description of industry successes and failures and try to tease out some lessons learned. But if the stories were from another industry or time the reader may find them boring or mysterious or non-relevant. So, although stories are helpful, they are not a good organizing tactic.

I could summarize the workings of the famous strategic thinkers and identify common threads and explanations. But some of the best-known thinkers of the past are not very relevant to young, emerging leaders. What was brilliant twenty-some years ago may be boring today. So, although we have plenty of famous thinkers to choose from, their models and suggestions are not necessarily a good way to organize a new book. 

I could try to glean the best thinking about strategy by studying the best and most successful companies in the 21^st century. But this would situate the learning in the context of today’s competitive ecology. Consider the recent books about Elon Musk, or Instagram, or Samsung, or Jeff Bezos. They will soon be gathering dust and being ignored as new books are being written about “the secrets” of success to be learned from Nvidia and other “AI” companies. Sitting at the feet of currently successful companies would lock-in thinking to today’s reality.

So, I decided to ask some questions.

Going back over the many workshops I’ve conducted I tried to align and summarize the questions from the attendees that drove some of the best conversations.

And I came up with fifteen great questions that opened the eyes and minds of the people engaged in the conversation. Are there only fifteen? No, but these will provide a rich starter-set to improve your strategic thinking.

Answer each question with an honest Yes, No, or Not Sure. Use your answers to prioritize your efforts to improve your strategic thinking.

Are we working on our most important challenges? All organizations face challenges, both good and bad. However, urgent challenges often get in the way of ones that are more important.

Do we understand why these challenges exist? Challenges are often a symptom of a more fundamental set of circumstances. Are you dealing with root causes?

Does the workforce understand and accept our stated vision, values, and goals?  Vision, values and goals are the very foundation of planning but, unfortunately, they are “just words” to many of the people in organizations.

Do we think big enough?  Change generally comes from outside your organization so you need to consider conditions in your industry and the economy at large. Learn to think in “bigger boxes.”

Do we think far enough into the future? There are three zones of strategic thought: the reaction zone (today’s problems and opportunities), the adaptation zone (existing trends), and the anticipation zone (clues about the future). Unfortunately, too much leadership time is spent in the reaction zone and the future arrives as a surprise.

Do we examine multiple approaches to resolving our challenges? There is always more than one way to resolve a challenge and too often we default to the least risky approach or to the approach that senior leaders like.

Do we regularly ask tough questions of ourselves and senior leadership? Questions are the most powerful tool you have. Unfortunately, we often leave questions unasked because of an organization’s “hands off” attitude. What questions are we afraid to ask?

Do we know what key assumptions we are making and if they are (still) correct? All plans are built on a set of assumptions. When they are correct, they are a great aid to strategic thinking. But when they erode, they will kill your strategy. What assumptions are dangerous?

Do we know who have different points of view and do we listen to them? It’s rare to find an organization wherein all the stakeholders agree on the definition of the challenge, much less the solution. Unfortunately, stakeholders who disagree with the popular point of view are often labeled as naysayers and ignored.

Have we discussed both the intended and unintended consequences of our favored approach? Solutions always produce a ripple effect throughout an organization, resulting in unintended consequences. Sometimes these are good and sometimes not so good. Your job is to at least think about them before they occur.

Have we tapped into the decision wisdom of our entire organization? The “wisdom of the crowds” is a real phenomenon that is too often ignored. Go back to Question 9 and consider the points of view you are ignoring.

What should we change and what obstacles exist to making these changes? Strategy is all about deliberative change and there are numerous factors that will determine your future success. You can change some of them, but barriers always exist.

Do we have the right capabilities to implement our solution? The capabilities that got your organization to today may, or may not, be the capabilities needed to get your organization to tomorrow. Think in terms of capabilities needed for the future.

Do we have sufficient capacity to implement our solution? For the past twenty-some years many organizations have stressed the need to be “lean and mean.” However, when it comes to dealing with the future, some have become lean and anorexic.

Do we know if this solution is aligned with our culture? An organization’s culture will either accept or reject plans for change. My challenge to you If you answered Yes to all the questions, I’d be suspicious of your honesty.   Triage your fifteen answers. Work on the No answers first, then address your Not Sure responses.   Happy summer,   Bill