How and When to Un-Strategize

The other day I exhumed the memory of something which really should have remained buried. But if specters of the dead can be roused in order to instruct the living then the lesson imparted from one of the earliest learning strategies I ever put together was that I shouldn’t have created a strategy in the first place.

Having rattled the ghost of this strategy and a couple of others, I now see that the biggest issue was not that the act of strategizing itself is wrong — it is, in fact, vital — but issues can arise when strategizing happens at the wrong time and in the wrong way. That early strategy gave me — and perhaps my hapless colleagues — a false sense of security. It also diverted time and energy away from more purposefully interrogating what we were trying to accomplish and why — among other questions. But because the wisdom of strategizing is often unquestioned, as is any attempt to beat back the darkness by wielding a plan as a torch, it could be that organizations need a deliberate act of un-strategizing.

What would un-strategizing look like? At its inception un-strategizing would start with a dose of awe, curiosity and wonder for the giant hairball that is any social issue. Next would come the recognition that even if the hairball cannot be fully penetrated, it must be detangled to some degree, and that creating any strategy prior to doing some of this detangling could be a waste of time and resources.

One might point out that good strategic planning already entails a process of learning and exploration. However, this is often done with a mindset of strategizing and a certain impatience to get to the “real” work. What is required of un-strategizing is a contrary posture to “doing,” a loosening of the muscles in order to float rather than to swim; a concentration and leaning into the powers of deep listening and dialogue with the unknown. In addition to activating a vigorous and earnest inquiry process, (guided by hard-hitting learning questions), it means going beyond the walls of the organization to find the answers.

In short, un-strategizing is a form of doing with a semblance of standing still. While several organizational management approaches speak to this need for deep and active learning and unlearning, what is often lacking is a permission structure or mandate for organizations to fully lean into this process.

What do organizations have to gain from un-strategizing in an environment when they are judged (and funded) according to signs of motion, of appearing to be forever in mid-stride? A non-profit about to make an investment in fundraising may find that its staff and supporters would rather question existing models of philanthropy and switch to a social enterprise model. Another, originally intending to create a strategy around marketing, may find that it first needs to shape a central story and metaphor that reflect its core values.

Un-strategizing may only need to happen at certain times: Early in an organization’s existence, when it doesn’t know what it doesn’t know. Late in an organization’s existence when it has become too reliant on what it knows. In times of crisis, when it has lost its balance. In times of stuck-ness when equilibrium has become a prison.

Like the yin to strategy’s yang, like the un-learning which slowly unwinds learning and allows something new to take its place, un-strategizing does not exist solely as foundation-laying to a strategic planning process — though it can. It is rather about permission for organizations to move by standing still, to reach deep into the well of the unknown in order to draw out insights they never had before.

This piece was first published as an Ignited Word blog.