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Where does strategy come from?

And do we even need it?

12 min read

I’ve missed writing to you. It’s good to be back.

What have I been up to? Well, in addition to fascinating-but-secret nda work, Dr Fox has been manifesting at leadership events and strategic offsites once more. ‘Onsites’, too, because they’re now novel. Here he does his thing with all the wit and charm you’ve come to know and love; bringing thoughtful provocations and spice, inverting paradigms and generally unravelling ossified thinking into something more bemused yet enthused, elated and ripe for emergence.

But then what? Ha! I would love to say that poetic sensibilities blossom within all, that folk awaken to the constructs and illusions they have been caged within, casting off cognitive shackles, standing bolt upright, quivering with enthusiasm; and that we all arise, flourish, frolic and coordinate at higher orders of complexity, forward not backward, upward not forward, twirling, twirling, twirling and questing towards future relevance and profit with curiosity, warmth and wit; paragons of life, wonder and virtue all. But that would a stretch.

Instead of the glorious polymythical uprising I might hope for, the Typical Offsite would move on to morning tea for carb-loading, and then onto information-dense powerpoint presentations (including a presentation about how ‘hybrid work’ is intended to work) followed by high-energy-yet-slightly-infantile ‘collaborative visioning’ or ‘ideation’ sessions, replete with butcher paper posters, post-it notes and hokey-yet-endearing group presentations. Late afternoon these posters and post-it notes are dutifully blu-tac’d upon walls, photographed and promptly uploaded to the intranet, never to be looked at or spoken of again. Some sort of dinner ensues, wherein a good portion drink a bit too much to compensate for social anxiety and the buzz generated by all of the caffeine and sugar of the day. If we are lucky, some late night conversations happen at the bar.

This—along with corridor conversations and roundtable cheek—is where The Real Magic happens. It’s in the structureless spaces, the ‘negative’ space, that the truest connections, conversations and conjurations emerge.

There’s a balance to this, of course—it can’t be all structureless, of course. But the better offsites optimise for emergence by not crowding out this space with content that could otherwise be disseminated via video, podcast or pdf. The best strategic offsites, in my experience, have been 20–40% structured and 60–80% emergent. Yet the norm seems to be the complete inverse of this—highly structured experiences (with little room for emergence) that produce a predictable yet underwhelming kind of success (and, perhaps, a rich delusion of progress).

And then Day Two is ‘All About Execution’. We awake dusty, with a mild-yet-persistent headache in a too-bright room, scoffing hot stale-yet-welcomed coffee from synthetic-smelling paper cups whilst hunkering down to play our part—namely; nodding along to the optimistically neat/linear plans, metrics, milestones. Smart goals; pre-ordained, polished, perfected. Clarifications, but no real objections. Mentos mint packets pop throughout the day.

The event concludes and we leave exhausted yet very glad for our time together. But also feeling a vague kind of… hollowness. But maybe we’re just tired.

Back at work our inboxes are brimming and there are petty fires to put out from the nincompoops you left in charge. You tell yourself you’ll get onto some of the notions from the strategy offsite—just once you clear this mess and carve out some time for yourself. Some time to think. But the work just multiplies. Meetings spawn more emails, which spawn more meetings, which spawn more emails. Somehow, in amongst all of this, a strategic offsite happened; and yet still you and everyone around you are too busy for meaningful progress. You are also still left feeling that the important stuff—the real stuff, the subliminal stuff, the things we’re pretending to not know—wasn’t ever addressed. And that the genuine strategic opportunities—the inklings glimmering just at the edge of our awareness—weren’t ever given the space to emerge, let alone be voiced.

Perhaps the curious amongst you are left wondering…

Where does strategy come from?

Hoho! I painted a grim picture of a strategic offsite just now. It’s mostly cognitive sleight-of-hand to make my thesis shine brighter—for, verily: offsites are genuinely mythic in their potential. They’re just hard for many to do well at scale because anything at scale becomes a bit of politicised theatre.

Nature abhors a vacuum, and as an Archwizard of Ambiguity I can assure you: The Emptiness That Begets Emergence is… a hard concept to sell.

Long time subscribers (or readers of my book) will know the general arc of my quest-beckoning thesis, which still holds today. I’ll lay it out in succinct form—please skip past the following if you are familiar. Fascinating as it all is, I have become so accustomed to the thesis that I am impatient for what lies on the other side. Curse of knowledge, I suppose. Anyhoo, ahemness:

  • We’ve all become busier than ever before, thanks to the internet. Now, the boundaries between work-life and home-life have all but disappeared. Expectations of our availability and responsiveness have gone through the roof; even more so now that the pandemic-spawned work-from-home ‘new normal’ means that the chthonic tendrils of the egregores we serve have worked their way into our very homes.
  • This busyness leads us to feel as if we are time poor. And when we are time poor it’s natural for us to favour quick fixes, familiar solutions and default ways of doing things. These defaults are the options we choose automatically, in the absence of viable alternatives.
  • Defaults are associated with fast and instinctual ‘type 1’ thinking, and are key to our survival. We need defaults; they save us time and cognitive angst.
  • We learn such defaults via pattern recognition. The more familiar we become with certain patterns, the less resources we need to expend to maintain competence within them.
  • Organisations need defaults; they’re what contribute to operational excellence and efficiency-at-scale. My lazy heuristic for most (but not all) organisations is that ~80% of our time ought be invested in the default ‘modus operandi’ of work. The remaining time is where we venture beyond the default, and tend to the more nuanced, nebulous and emergent things that aren’t easily categorisable, measurable or even effable.
  • The trouble is, most organisations in Enterprise Land are now cursed with efficiency, where the vast majority of our time (I’d say: ~98%) is invested in default (safe, predictable, familiar, measurable) activities. Mature organisations have policies, procedures, rules, systems, templates, guidelines, precedence—established default ways of doing most things.
  • This is where curiosity begins to die—it’s just not efficient. Why waste time exploring new ways of working when we already have a heap of evidence that suggests that what we are currently doing is working? Just stick with the defaults; it’ll save you time (also it’s what your performance is measured against).
  • Here is where we also experience the atrophy of empathy—again, it’s just not efficient. We become embroiled in insular politics, and our inward focus means we are no longer empathising with the emerging needs of our clients, the market, or the wider world in which we live. Oh and forget about climate change and similar-such existential crises—who has time for that?
  • And so we collectively maintain a rich delusion of progress, busily working away, like automaton-golems, towards that what I call ‘The Inevitable Kraken of Doom’—an Eldritch beast that feeds upon the sweet nectar of our impending irrelevance.
  • No one sets out to become irrelevant—but many well intended teams find themselves irrelevant when they become ‘too busy’ for meaningful progress.
  • The path to irrelevance is littered with safe, prudent (default) decisions. Whilst neither curious or courageous, these decisions are easy to defend in hindsight. Everyone’s donkey is thus suitably covered. There’s no goat to ‘blame’. Cool, right? (No. Not cool.)
  • The only way to circumvent the inevitable Kraken of Doom is by introducing ‘new thinking’ into the mix.
  • But this is incredibly difficult to do because our motivation, attention, focus and behaviour will naturally gravitate to the things that provide the richest sense of progress. And yet the things that provide the richest sense of progress are often the default activities getting in the way of meaningful progress (hence: a rich delusion of progress).
  • Furthermore, the incentives that underly the game theory of Enterprise Land optimises for selfish and myopic behaviour. In many organisations it is also much more of a career advancement strategy to broadcast that you are doing the work than it is to actually do the work. Hence we see emails, emails about emails, meetings, meetings about meetings—a grand pantomime of busyness.
  • Which begs the question: what is meaningful progress? Ah-ha! Now we are closer to the domain of strategy—and the point of a strategic offsite. We need to disrupt default thinking—to lift our gaze beyond the immediate—so that we can contemplate what meaningful progress might be.
  • Meaningful progress is that which brings us closer to future relevance.
  • ‘Relevance’ is a state in which our activities makes sense given the context we find ourselves in. Many of the things we do today are already incoherent to our context. Many more things will make absolutely no sense in the very near future.
  • ‘The future’ is infinitely complex (and thus, not singular)—but we can look toward the intersection of trends and the various attractors to get a sense of the futures more likely to unfurl. All complex adaptive systems (and self-organising complex intelligences—of which we are a part of)—‘seek’ metastability (either via the the transformation into higher orders of complexity—or degradation into lower). Our task is to find the common incoherencies betwixt our existing modus and multiple possible futures, so as to develop a sense of directionality towards future relevance (and similar or higher orders of complexity).
  • But what is future relevance? Ah, now that is the question. And it’s not an easy one to answer. It takes curiosity, empathy and wit to decipher—and even then, any insight must be held tentatively, with sincere-irony. This is at the heart of Quest Leadership.
  • If our defaults are the options we choose automatically in the absence of viable alternatives—a quest is the search for alternative options.
  • Without questing, strategy looks like incrementalism (doing what you have done before but with tweaked numbers so it seems aspirational) and bandwagonism (scanning the zeitgeist for whatever buzzwords are hot and peppering the strategy with that; “transformative agile hybrid and human-centred disruptive future of work where the customer is at the heart of everything we do”).
  • Quests are driven by questions. Every question literally begins with a quest.
  • Questing is what makes for breakthrough innovation. Because you are venturing beyond the default—harvesting curiosity, imagination and wit—you are working with a wider and more varied data-set than the default trends and themes everyone else is paying attention to.
  • This is what begets competitive advantage, via the cultivation of optionality; a quiver of options, if you will. Strategic initiatives we may deploy in the future, should the right conditions manifest.
  • Of course, the only way we can tell if the options within our quiver are viable is to experiment. A multitude of small, safe-to-fail experiments that can be scaled up to the point at which they are viable enough to be integrated into our core strategy.

There’s some context for us. We are—most of us—very, very good at mission-critical work. A mission has a clear objective and linear path that is easily measured—which is fine for focused sprints of work.

I’d love for us to make a little more room for that which informs strategic decision making.

Strategy is that which serves to focus and coordinate our efforts towards relevance realisation. But… where does strategy come from?

This is one of those infinitely recursive questions that will ultimately send us back to the origins of the universe and a deep questioning of free will itself. Some might say that strategy comes from ideas—but I have always found the notion of an ‘idea’ to be problematic. For ideas are neither discrete or atomic; they are—like all things—nebulous, inter-contingent and emergent. First sensed as inklings, then developing as hunches, then being ‘realised’ as if they were sudden epiphanies… but wait; where do ideas even come from? Are they not but a poetic acuity for want and need? Something more?

I could wax philosophical to much further degree here, but it would be an indulgent distraction. Mayhaps over a whisky by the fire and under the stars, sometime.

Instead, we need to return to the land of heuristics.

Questing is the precursor to strategy

It begins with questioning: are we on the right path? Is there a better way? What’s changing in our landscape? What are we pretending to not know? What aren’t we seeing? What does the world need? What if…?

There are canvases and frameworks we can use to catalyse this questioning. I mention some in my book, and Brave New Work also lays out a nice canvas for Enterprise-level antics (the OS canvas). The point here is to not get too caught up in the tools and props (lest we collapse the possibility-space of our thinking).

Rather, the point is to cultivate the conditions in which quality thinking (curious, complex, empathetic, imaginative, attuned) is more likely to flourish.

This is what a strategic offsite can help catalyse—if done well.

But that is only a part of the puzzle.

If questing is the precursor to strategy, then…

Fellowship is the precursor to questing

You can’t quest effectively—that is, you can’t cultivate optionality beyond the default—if you are surrounded by folk you don’t respect, trust or enjoy the company of.

Questing requires scenius (collective genius), thoughtful provocation, and time to think.

According to the Cambridge Dictionary, ‘fellowship’ refers to a friendly feeling that exists between people who have a shared interest or are doing something as a group. This isn’t quite the mythic definition I have in mind, but you get the idea.

Questing requires that you be a member of a small yet diverse set of bright minds; sensemaking to a rhythmic cadence in a spirit that is warm and mutually encouraging. It requires something akin to the days of intellectual speakeasy salons, where there is time to wonder, debate, imagine, jest, hazard, pontificate, ponder, explore whilst staying in the tension of constructive discontent. No quick fixes, familiar solutions or banal defaults. No leaping to conclusions. But rather; the antifragile pursuit of better questions. And from this: the proliferation of optionality.

The ideal questing fellowship is 5±2 people. At least three*—but no more than seven. This is your crew, your coterie, your posse.

* A warrior, wizard and a rogue.

The temptation is to make questing A Big Thing. A Big formalised Program rolled out within the Enterprise. I wrote a few thousand words on the hazards of this notion—but then deleted it during my edit because this museletter is already way off track. (This happens when I haven’t written in a while.)

My point being; not everyone needs to quest—and that’s okay. Just as you wouldn’t hire a questing wizard to be the engineer-architect of your operational excellence (a world where things actually need to get done)—you also perhaps wouldn’t hire the certainty-seeking, metric-driven ‘let-me-fix-it’ engineer-architect to be the leader your quest. Questing is instead where we learn to love the volatility, uncertainty, complexity and ambiguity of our unfurling world. It’s wherein we relish in the unknown, pioneering amidst the uncharted waters in unprecedented lands of the aether—systematically stumbling upon profound insight and transmuting these glimmers into Options. Options to be cultivate and explored further, so that they may enrich our strategic decision making in the everquest for enduring relevance.


It seems I’ve been writing books in reverse order

The Game Changer is a book for managers looking to change the dynamics of work, and is focused on execution and progress. How to Lead a Quest is very much about that which informs strategy (questing and experimentation)—one oughtn’t rely solely on external consulting firms to bring new thinking into the mix; it’s possible to cultivate this capability internally.

But it’s not enough to simply know How to Lead a Quest. The precursor to this is: do you even have fellowship? An adventure party. A group of warm, brightly minded, curious and respected peers—folks you trust, to whom you can be genuinely vulnerable in your thinking with—ready willing and able to venture beyond the default?

Fellowship > Questing > Experimentation > Strategy > Execution > Progress

I’m not sure I am the person to write this book—my friend Joe writes of this with much wisdom. But I do know that fellowship is the key to questing—which is key to strategy, which is sometimes the key to meaningful progress (if we stay nimble and attuned).

I spoke about the notion of fellowship/scenius recently with my friend and fellow philosopher Jeff Schwisow on The Difference Project. You can watch the discussion here. The first 10 minutes is Jeff’s intro—which features a mighty endearing rap—and then we get into the conversation proper. It was a wonderful jolly spar. Both Snorri and π made an appearance on the show.

In summary

This musing was longer than intended, even after I edited it down. (My editing is of the mildly dyslexic sort so, word sleuths: enjoy the typos interwoven throughout!).

I was motivated to write this musing because the theme I am seeing in Enterprise Land is that momentum is returning. Momentum inhibits reinvention. And whilst I know Strategy Has Happened—I’m not sure if much has been invested into the questing that informs such strategy. Which makes me wonder as to the directional thrust of this newfound momentum. Furthermore, too; I’m not sure if I am getting as strong a sense of fellowship within Enterprise Land as we all might like to see. Instead… it seems like most folk are busy again.

There’s nothing wrong with being busy—just as there is nothing wrong with default thinking. We need defaults for ~80% of what we do. But… just mind that we don’t become cursed with efficiency once more. And perhaps lets retain some sort of coordinated curiosity for what meaningful progress might look like—lest we meet the Kraken. 😘

The Inevitable Kraken of Doom, in pursuit. As illustrated by the dangerlam. (Yes I know it looks dark on this site but part of me thinks it’s cool like that, in an edgelordy way).

PS: I didn’t quite know where to slip this in, so I will just leave the following on the table before I depart: Luke Webb recently penned an elegant and refreshingly original, deep and contextualised review of How to Lead a Quest—honing in on the notion of ‘failure’, and how some of the principles from the book pertain to leadership in the Air Force. Enjoy!



A rogue philosopher.