Can a leader be strategic without a consistent contemplative practice?

This question started rolling around in my brain after the first episode of At Work by The Ready (👏 Sam Spurlin and Rodney Evans ).

The work of "strategy" is often supplanted by "planning" - a comfortable alternative to facing the inherent unpleasantness of what strategy requires: making difficult decisions while acknowledging the unknowability of the future. Even differentiating the two terms - planning and strategy - might be new to some. Many organizations simply conflate the two, engaging in a “subtle slide from strategy to planning” (strategic planning!), as Roger Martin calls it, in an attempt to turn strategy into “a thoroughly doable and comfortable exercise.”

This being-in-discomfort is a key competency for strategy work – without the guts to stick with it through the discomfort, it’s too easy to rush toward a solution before understanding the problem you're working on. You'll achieve only a superficial clarity - knowing who's planning to do what and when they want that to happen. Higher-order clarity would be having a fuller picture of reality, comfortable or uncomfortable – a truer understanding of what you're working with.

Per Einstein: “If I had an hour to solve a problem I'd spend 55 minutes thinking about the problem and five minutes thinking about solutions.”

I participated in a 10-day silent Vipassana meditation last year. Vipassana means "to see things as they really are." Those 10 days were the most difficult thing I have ever done and also the most illuminating. One fascinating reflection a fellow participant shared with me once we were finally able to speak at the end of the retreat was that, while a lot of today’s highly-productized mindfulness offerings have the goal of calming down the mind - that is, making the meditator more comfortable - Vipassana is the opposite. It requires intently observing (sometimes extreme) discomfort, and not intervening. No shifting your body. No scratching an itch. No clearing your throat. And no external distractions to soothe you. (I’m really selling it, right?!) To be fair, there can also be states of ecstasy in one’s experience. But in every case, no matter what is experienced, the practice is to simply observe, attentively and equanimously. As you do, you gain a deeper and deeper understanding of reality as it is, and the source of our resistance to it. You build the muscle of not acting reflexively but rather, consciously, deliberately.

Two foundational characteristics required for good leadership are 1) humility, and 2) endurance for discomfort. Humility is an inward skepticism of the self - continuously holding the uncomfortable perspective that you do not know everything and therefore require considering others’ perspectives to give you a fuller grasp of reality. Guiding organizational strategy requires a lot of hanging out in the problem space, with murky futures that can’t be predicted but require difficult decisions to be made nonetheless. 

So to that question - can a leader be strategic without a consistent contemplative practice? - I assert that it is impossible. 

Contemplative practice is like isometric training for the mind. Wall sits for wisdom! Holds for higher insights! Without having built the mental fortitude over time to operate calmly from within an uncertain space, one has to rely on adrenaline to focus, which eventually leads to a crash landing when that finite resource is depleted. 

Beyond ability to hold discomfort, unwillingness to accept the discomfort of uncertainty is another potential pitfall. Contemplative practice leads toward a liberatory acceptance of what we can’t control (that is, just about everything). Without that acceptance, constantly resisting reality wears down the mind and body. (I’m using acceptance here in the sense that we must let go of our desires for some alternate reality - which cloud our ability to understand what reality actually is - before we can work to change it.)

Without building a high tolerance for discomfort, leaders will jump to decisions too fast. They will be all plans and no strategy. They will rigidly hold to the plans they made rather than being adaptive as the world internal and external to the organization incessantly changes. That rigidity makes a leader - and an organization - brittle. 

Contemplative practice allows us the spaciousness of mind to see more of reality and also to accept it. It occurred to me during Rodney and Sam's conversation that scenario planning is a type of contemplative practice*: not a reductive exercise to script how you're going to act when Crises A-Z finally happen, but rather an opening of greater awareness and perspective - and therefore understanding - of "adjacent possible realities." Maybe we could call it “scenario contemplating” or something else - avoiding that distracting P-word again.

*but definitely not the only one you need!