This is a legacy provincial website of the ATA. Visit our new website here.

The Two Questions at the Heart of Strategic Thinking

May 30, 2018 Wilson Winnitoy

From English teacher to strategic planner; how did that happen? What was the journey from pondering Hamlet’s “we defy augury” to getting into the augury game myself? It mostly happened in the Calgary public school system and was always about learning, sometimes very steep learning.

At the beginning of September 1963, I was a newbie standing at the back of the gymnasium at Henry Wise Wood Senior High. It was the school opening assembly. As the principal read out my home room class list, a dapper, otherwise composed and obviously seasoned colleague on my right began muttering under his breath. It seemed that, in his view, I had been handed a crate of bad eggs with whom to begin my career, and he took me aside to share some advice. I was grateful. I not only survived, but found I liked teaching, and many of the bad eggs turned out to be rather good ones once I got to know them. And the advice helped.

A few lines above I used the word career. Back then I believed that stable and predictable careers existed and that I should have a plan. I decided that I would like to become an English department head, with maybe a successful textbook or two along the way. That did not happen. Over the coming years I was to learn that I would not have a career as much as be had by one, a rather interesting, challenging and unpredictable one as it turned out, for which I am grateful to the Calgary Board of Education. We call them career paths now; expect choices and surprises.

I liked exploring the power of poetic language with my students. We grappled with the idea that poetry doesn’t have to have verses and rhymes. “Well then, what is it?” they asked. Not the time or place for a poetry lesson here, but …

Perhaps these were signals, with the benefit of hindsight, that my journey would take me toward the kind of thinking we call strategic planning. It could be that my 1960s idea of a career turned into a personal and professional process of coming to grips with change and uncertainty, and the pitfalls of linear thinking. And it could be that working with imagery and symbolism and discerning layers of meaning and disentangling ambiguity was, who knew, part of my early preparation to be a strategic planner.

The Problem with Planning

In 1968 I left the classroom for a two-year appointment at the romantically titled central office, the place we hardened staffroom types referred to dismissively as “downtown.” I should have spoken more sweetly of it. I did not know that my two-year appointment would extend to more than 30 years. Perhaps I needed the extra time to get it right.

Increasingly my job titles had the word “planning” in them: “educational planning,” “corporate planning.” What was going on? Our school system, like many other organizations, was leaving the old world of administration and entering the new world of management. In the old world, having a plan meant knowing the culture and “how we usually do things around here,” with maybe a nod to any new twists on old problems. The magic words were certainty and predictability.

In the new world, we were preparing reports on alternative schools, sex education, drug education, school discipline and employee burnout. Change and complexity were increasing as evidenced by frequent references to turbulence and white water. Management consultants appeared and suggested we should improve our research and planning by, well, actually doing more of it. We began to do comprehensive long-term plans that were meant to be more integrated with a clearer picture of multi-year outcomes. But there was a problem.

Plans should not be answers in search of a question, desperately trying to connect with the world that has spawned them. It turned out that the time it took to create five-year and seven-year plans began to exceed the validity of the assumptions and problem definitions that had launched them. Their half-lives of relevance shortened as the time to debate and approve them lengthened. These plans and their long lists of recommendations trudged off to live in dark and quiet spaces at the back of filing cabinets. Words such as adaptiveness, resilience and organizational learning began to adorn the spines of management texts. And just in time, along came strategic planning, and my career turned another corner.

Enough history. In 1992, I was invited to join the ATA’s newly formed Strategic Planning Group (SPG). The ATA already had a track record of moving beyond linear into anticipatory planning. The SPG brought very good people to the planning table to do important work. What did I bring to that table?

I have a two-word definition I like to work with. Strategic planning is “against fatalism.”1 The soul of brevity, you might think: a two-word definition. But some explanation is required.

First of all, when an organization decides to think forward strategically, a fundamental decision has been made. That decision is a declaration, “We can intervene in our future. We can shape it in positive and deliberate ways. No matter how solid, seamless and relentless the forces acting on us may look, we can and will find the cracks and openings where we can create change.”

Co-Creating Change

Truly intervening in the future should not be confused with just getting better at anticipating threats and girding up the organizational loins to deal with them. The result is only a more strategic version of fatalism. “Yup, the same stuff keeps comin’ round, but now we’re really prepared.” The strategic thinking decision signals that the organization is committed to a long-term organizationwide effort to learn about and shape its future in profound and enduring ways.

More than that, the decision declares that the organization will not work just internally, but will step out into the world as a cocreator of change. The operating environment is a source of learning and the locale in which enduring change will be created. Working outside the organizational boundary as well as inside is how the merry-go-round of reacting to threats and issues begins to be changed to fruitful engagement with opportunities and a positive influence on the interplay between the organization and its environment.

Secondly, the decision to think strategically commits the organization to a new discipline of learning in two significant areas that are defined by these questions:

What kind of future do we want?

What kind of world will we be creating it in?

Answering the first question requires the organization to express its ideals, values and beliefs. It should look at its history, policies, commitments and stands it has taken on important issues. It should talk to lots of people, internal and external. It should wordsmith and road test carefully; language so often falls short or misrepresents. The result should be a vivid depiction of the preferred future, sometimes called a vision statement. It should not be an elevator speech, a silly term that only made sense when elevators were hand-cranked and took a long time to get to the top floor. But it should be kept brief. Hint: if you like telling people about it with only a slightly crazed look in your eyes, you’ve probably done a good job.

Answering the second question requires the organization to study its environment to see what forces are at work and how they are unfolding through time. Scanning news and events to discern trends is great organizational learning. It also helps us understand that although we may have different perspectives, we see essentially the same world out there and by putting our heads together, we can decipher the changes. The result will likely be some sort of statement of trends or meta-narratives that describes the road we are all on. If you share this work, people will want to come to your meetings. Hint: mild stimulants help; order extra coffee and doughnuts.

Learning Leads to Influence

There are bags of tools and techniques. Other forms of learning such as scenarios can be very useful. But they ultimately feed the two questions I have described above. If you don’t know what you want or the kind of world you will journey through to get there, actions will disappoint. The culmination will be a plan, probably called a strategic plan, with papa, mama and baby bear–sized outcomes covering the next three to five years of the organization’s life. Yes, some of the paperwork may trudge off to live in dark and quiet spaces at the back of filing cabinets, but if the learning has been done well, the plan will be influential and will change the life of the organization as well as the lives touched by it.

This has happened with strategic planning at the ATA and it has been a privilege to be a part of it. Alberta teachers can rest assured that their professional organization is anticipating change, not just reacting to it, and is ensuring the futurity of its policies and decisions.


Wilson Winnitoy was a member of the Alberta Teachers’ Association’s Strategic Planning Group from its inception in 1992 until 1999. Since then he has been an advisor to the group. He has 40 years of experience in strategic planning and policy development.

Also In This Issue