Upside Down Thinking


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So many great minds in our sector are talking about the need to change, the urgency to transform services and operations in ways that not only fit our chaotic environment but influence its future as well.

We tend to be rather good at seeing what should change and why, but life becomes much more difficult when trying to figure out the how.

It used to be how-type challenges were about improving quality, achieving incremental growth, tweaking a program, or coming up with a better way to do this or that. Sure, we dealt with big changes, too. We transitioned from typewriters to computers, from mailing letters to faxing them to emailing them.

We weathered budget cutbacks and government downloading, found impressive ways to stretch a dollar, and we influenced the emergence of new areas of study in universities.

Our sector has a strong reputation for being innovative, whether it be creating cutting edge social housing programs, launching community wide collaboratives to help kids, crafting new and flexible funding programs, building social enterprises, or pulling off cross sectoral partnerships that benefit community.

That said, there is a sense many of us feel that we are entering a time where the challenges to change are far more complex than ever, coated in risk, and so profound in their implications they seem overwhelming (and a tad terrifying at times).

Economic changes, generational and multicultural shifting, shrinking resources, global influences, an aging population, and a technological revolution that is changing the way we define community, work, friendship, and ourselves — these are but a few of the dramatic factors in a transforming world. Just what the “transforming” will result in is the million dollar question.

Anyway, all of that is a bit of a windy path to getting at the how of crafting change.

There’s a lot being offered up about this and I have no doubt much more than I will ever know about, much less read. That said, I tend to read what helps me think against the grain of convention. Not because convention is wrong, but rather because new ideas, not to mention transformational visions, are difficult to see much less comprehend through conventional lenses.

Our fundamental challenge in our sector is this: what we have created offers up a lot of good stuff but not enough and the foundation on which we built this sector is not sustainable. If we don’t change it (change it, not fix it), all the good folks have built will begin to fall away.

This is personal, not just professional. It is personal to face the daunting task of transforming not only that which we created and believe in but also that which has formatively and profoundly influenced our lives, who we are, and how we see ourselves. In other words we have to use the knowledge, skill, perspectives, attitudes, and emotions that make up our identity and deploy them in ways to create a radically different identity. Another way of saying this is we have to use who we are to deconstruct who we are in order to become who we must become.

Many of us in the third sector are attempting to use tools and mechanisms to kick start transformation. Many of us are familiar with “Wicked Questions” thanks to our friends and colleagues at Tamarack Institute (link). Through my embrace of this particular tool, I have begun investigating the concept of “Upside Down Thinking” which is a phrase I have coined top frame my sense that we need to totally turn ourselves on our heads sometimes to get at the change we need to craft. Both are tools to be used to help approach current understanding in radically new or different ways. Their intent is to identify new, evenb outlandish perspectives that break us out of habits and dogmatic approaches to change.

“Wicked questions do not have an obvious answer. They are used to expose the assumptions which shape our actions and choices. They are questions that articulate the embedded and often contradictory assumptions we hold about an issue, context or organization. A question is ‘wicked’ if there is an embedded paradox or tension in the question.

“A wicked question is not a trick question. With a trick question, someone knows the answer. Wicked questions do not have obvious answers. Their value lies in their capacity to open up options, inquiry and surface the fundamental issues that need to be addressed.”[1]

Tamarack Institutes’ examples of wicked questions include:

  • “How can we commit ourselves to be accountable for achieving specific measurable results, while at the same time staying open to the possibility that we may be measuring the wrong outcomes?
  • “Do we know how to build a movement large enough to achieve critical mass, power and diversity; while also staying true to certain contentious values and principles?”[2]

The website, Liberating Structures, offers another example: “What opposing-yet-complementary strategies do we need to pursue simultaneously in order to be successful?”[3]

Upside Down Thinking is a cousin of the Wicked Question. The term sometimes has a negative connotation in that some people think upside down thinking represents the wrong way to think about the right thing. That is not how I use the term. Quite the contrary. Upside Down Thinking is both a mindset and a tool to use to look at things in a totally different way. One who is engaged in such thinking is bound to deploy wicked questions to be sure, but Upside Down Thinking is a cognitive-creative methodology and is about more than crafting inquiry; it goes further to pose new realities or potential realities that run contrary to how we think and how we see our own identities within the context of our work. Moreover, Upside Down Thinking has no loyalty to the status quo or to current tools or best practices. Its purpose is to give life to the contrarian within us and to see our world through eyes that wish to see something quite different from what is there.

Going beyond inquiry, Upside Down Thinking often begins with a premise most of us would receive as untenable. Examples of premises that flow from Upside Down Thinking include:

  • Anti-poverty activists perpetuate poverty.
  • Outcomes have destroyed innovation.
  • Our program criteria do more to justify the exclusion of those who need our service than help those who meet our criteria.
  • Partnerships cost more in resources than going it alone.

Engaging one another in Upside Down Thinking is not purposed to prove such premises as correct, though at times the premise might just be true, but more so are meant to facilitate new visions and actions that are based on truly testing what we hold to be sacrosanct.

This is not easy. It runs against our nature to contemplate a new reality that on the surface seems to contrary to what we see and how we act. Sometimes, engaging in Upside Down Thinking begins with what makes us angry and often hurt. For example, when some voices in the community accuse people like me of being a part of the “poverty industry” or worse, a “poverty pimp,” I can’t believe someone would think that of me. How dare they?

While such pernicious language does not bode well for collaboration with those who say such things, much less mutual understanding, Upside Down Thinking might have us engage authentically with the premise that those who work to eliminate poverty do create scenarios that perpetuate poverty.

Upside Down Thinking can be deployed in many different ways. For example, I am currently writing a short piece with the working title: “No Agendas Should be the Only Agenda.” My purpose is to explore what might be possible if people just come together to have a conversation rather than prescribe the conversation. This is not about creating a new model that pitches no agendas as the way to go. Rather, through deploying such Upside Down Thinking, I hope to discover new ways to frame important discussions about our work.

Another piece I am working on is tentatively titled, “Upside Down Thinking about Collaboration” and its motivation comes from my sense that we just use the word now for everything we do. And there seems to be a gospel of collaboration that would have us believe it is always good and right and helpful. The dogma is so engrained in us (kind of like outcome measurement is) that anyone who questions it or might suggest that sometimes, if not often, collaboration is contraindicated runs the risk of being seen as some sort of misfit.

Think of the ways you can think upside down. Then work with the premises you come up with and see what happens. You might discover some new truths that you could not see right side up.

More to come.

Other postings you might want to peruse:

Thinking about how I Think

Leadership in Complex Times

Republished with author's permission from original post.

Mark Holmgren
Mark Holmgren Consulting
Mark Holmgren is committed to helping non profit organizations and local governments build capacities for new visions. Mark does this through the provision of custom designed strategic services that fit an organization's culture as well as its aspirations.


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