🔮 How to Host a Strategy Offsite

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If you work with people—and you sense that the context within which you operate is changing—you’ll want to revisit your strategy from time to time, so as to ensure it continues to make sense. A strategy offsite is one element of how strategy might be developed. In this essay and podcast, I show you how to do it well.

I have written about this in many ways—where does strategy come from?, alluded heavily to it in How to Lead a Quest, and recently had some of my perspectives featured on Change Signal. Eight years ago I wrote Get Away to Get Ahead—the many benefits of a strategic offsite, and how to not screw it up. The article still mostly holds.

Over the years, I’ve worked with c-suite executives of multinationals, vice-chancellors and their teams, founders of medium-sized enterprises, heads of research organisations, skunkworks project leads, military, police, law firms, agricultural innovators, FMCGs, franchise chains, co-ops, banks, fintechs, big pharma, med-tech, insurance, regenerative orgs, decentralised autonomous orgs, governments, big consulting firms—and more. I have many happy clients.

Listing it like this feels a bit mercenary. But my point is this: there are patterns you’ll come to recognise. Things that tend to hold apt, true, and useful across multiple contexts. Over time, these have become sensibilities—a kind of ‘meta-savvy’. I’m going to attempt to share this with you.

I offer this in the trust that you receive it not as a ‘mandate’ to follow—for there are no rules—but rather: as a set of potential ‘ways’ you might provisionally integrate into your own approach, if and as and when they may serve. 

I don’t have ‘a’ way; but I have found ways that have worked for me.

It’s as Lewis Hyde exemplifies of Trickster:

Better to operate with detachment, then;
Better to have a way but infuse it with a little humor;
Best, to have no way at all—but to have instead the wit constantly to make one’s way anew from the materials at hand.
— Lewis Hyde, Trickster Makes This World

If you’ve followed my work, you’ll already know the distinction between established and emergent domains.

Strategy within established domains 🦔

Strategy in established domains presumes a relatively stable, certain, simple, and clear context. Here, precedent abounds. You have “gold standards,” “best practices,” and plenty of credentialed consultants with well-worn industry-specific maps to follow.

The work, then, is largely in attending to known-knowns and known-unknowns. The bias is toward continuity and incremental improvement.

A strategy offsite under this regime will be a mostly formal affair intended to inform the wider team of plans, goals, targets and scenarios, along with the analysis that went into them. 

This is strategy for “closed” systems.

Strategy within emerging domains 🦊

Strategy within emerging domains usually presumes a relatively volatile, uncertain, complex and ambiguous context. Within this world, you don’t have much precedence to draw upon, nor any established ‘best practice’ methods to turn to. It’s pioneering work; uncharted, and unprecedented. 

There are consultants, of course—but the most valuable among them don’t trade in pre-packaged expertise. Their experience arises from a bricolage of heuristics, intuitions, and patterns discerned across many contexts. It’s less about mastery of “content,” and more about stance and sensibilities—a kind of poise suited for fluid sensemaking amidst both known and unknown unknowns. The bias is toward emergence, epiphany, and relevance-realisation.

A strategy offsite under this regime will be a mostly informal affair intended to provide contexts for astute and bright minded questers to come together and sensemake ways forward. It requires the cultivation of scenius, collegiality, mutual enthusiasm, encouragement, respect, and shared rapport. 

It also demands active participation in the cultivation of what I call “in-house intelligence.” Rather than outsourcing strategy to external firms, the capacity to sense, interpret, and adapt is grown from within.

This is strategy for open, porous, permeable systems.

The Hedgehog and the Fox

Isaiah Berlin’s essay, The Hedgehog and the Fox, remains an apt parable for contrasting dispositional preferences. To paraphrase:

In the forest, the fox devises a thousand clever ways to outwit danger. It watches, learns, shifts shape. The hedgehog, slow and simple, knows only one defence—curl into a ball of spines. And yet, when the fox attacks, the hedgehog’s one strategy often proves effective.

In essence: the fox knows many things; the hedgehog knows one big thing.

Much of the world is comprised of hedgehog disposition—thus I need to be careful with what I say here, lest ye bristle.

I love hedgehogs. Chances are, you work with hedgehogs (you might even be one!). Most of the world is shaped by them—and rightly so. Hedgehogs are structured thinkers. Deep specialists. Systematisers of complexity. They bring coherence and conviction to enterprise.

You want hedgehogs at the helm—especially in roles like CEO or CFO. Hedgehog-style thinking can be understood as a mode of cognition and sensemaking that prizes coherence, unity, and a singular narrative arc. The world would not function without them.

But.

But in emergent contexts, the hedgehog’s strength—their singularity—can become a constraint. Strategy offsites for hedgehog-led teams often become performative theatre, with scripted roles.

We go through the motions. We follow best practice frameworks. We map scenarios, and do our SWOT analyses (over-emphasising strengths, glossing over weakness, identifying predictable opportunities and threats). We manufacture confidence from premeditated plans. And then we feel assured that we have everything thought through, creating an illusion that holds well in stable contexts—but falls apart in the face of actual change. 

The fox, on the other hand, thrives in change. And while the world may be built by hedgehogs, it is navigated by foxes.

Allow me to contrast a little further. Much of what I share here was originally inspired by provocations detailed in an ancient essay by Venkatesh Rao.

I trust that you’ll remember that life is always more complex than such binary constructs as this-or-that. But I’ll also trust you know that sometimes it’s useful to create false dichotomies anyway, because of what it reveals. You are never fully one thing or another—hermetic yin-yang, and all that—yet still; there may be patterns to discern, and tendencies to notice.

🦔 The Hedgehog

—monist, systematiser, ideologue

Core Disposition:

• Seeks unity, coherence, certainty
• Filters complexity through a single organising principle (e.g. capitalism, reductionism, individualism, materialism, etcetera—aka: CRIME 😎🆒)
• Prefers grand narratives and universal explanations
• Values depth over breadth, often pursuing mastery in one domain

Strengths:

• Brings clarity, confidence, and conviction
• Skilled in institution-building, ideology formation, and paradigmatic anchoring
• Can inspire movements via a compelling singular vision and disciplined focus

Challenges:

• Often blind to complexity, anomaly, or nuance. Distrustful of novelty (where’s the evidence?), emergence (let’s wait until things are settled), and mystery (there must be an explanation!)
• Curiosity can be limited to confirmation-seeking within a bounded domain
• May become dogmatic, brittle, or lost when their One Big Idea no longer maps to reality
• Vulnerable to narrative ossification

The risks of narrative ossification is partly why I developed The Ritual of Becoming (so that we might reintroduce necessary disruption into our own mythopoetic unfurling). As I’ve written elsewhere, negative capability may be the antidote to calcified experience.

In summary: hedgehog is who you want in most contexts, for most of the time. When things are changing, and when you’re questing amidst emergence—you’ll want to have the fox with you, too.

🦊 The Fox

—pluralist, bricoleur, trickster

These rapscallion characters, what with their wily ways and irreverent wit! It’s fox you look for when you turn to the safety of trouble in times of change. 

I wrote of tricksters, jesters and fools just recently. And it’s probably worth remembering: in this podcast and post I am sharing how to host a strategy offsite with a bias towards emergence here.

When you read the following, imagine I am highlighting qualities within you. Qualities you may possess but may not always embody or express. 

Core Disposition:

• Embraces ambiguity, multiplicity, and emergence
• Draws on a bricolage of insights, tools, heuristics, and stories
• Rejects reductionism and single-lens ideology for pragmatic emergentism, contextually-attuned
• Inquiries are non-linear and often playful, improvising and intuiting

Strengths:

• Highly adaptive and well-suited for complex, changing environments
• Skilled at polymathic lateral thinking, improvisation, and fluid strategy
• More likely to see the pattern behind the pattern, without reduction
• Keen sense-making acuity for weak signals—can follow threads others can’t yet see

Challenges:

• Can suffer from fragmentation, paralysis, or lack of conviction
• May fail to inspire or lead when clarity and coherence are demanded
• Oft-times too clever, baffling, and diffuse—missing the moment for decisive synthesis
• Exasperating within closed contexts where goals and expectations are tightly constrained—in other words, not good at “getting shıt done”
• Tactical cowardice—even if in service to strategic courage—can diminish trust

Foxes are needed—particularly when the old maps fail. But foxes don’t tend to stick around when things need to be established in actuality—they dwell in the liminal and emergent.

So—hedgehog and fox. Two archetypal orientations. Both useful. Both limited. The key is knowing when to work with which disposition.

For a strategy offsite? You’ll want to heed to the fox. Especially if you are questing amidst complexity and change.

Can we talk about how to host a strategy offsite already??

Ha! Sure. But remember:

Momentum inhibits reinvention.

I know—you want to cut to the chase. And this is precisely why I’m taking my time with you. I promise, it’s not just to vex.

So far, we’ve looked at hedgehogs and foxes. We’ve explored the difference between established and emergent domains. But I could just as easily draw the contrast between:

• finite and infinite
• machine and garden
• closed and open
• artificial and living
• complicated and complex
• metric and mythic
• mastery and mercuriality
• mission and quest
• literal and lateral
• fixed and fluid
• reductionist and emergent

You get the idea.

Unless you—and your organisation—can adopt a disposition toward the latter of these pairings, the best you’ll ever achieve is predictably underwhelming, incremental success.

In other words: no true strategic differentiation or advantage.

Okay, let’s dive in.

Questions to ask before hosting a strategy offsite

Before you consider hosting a strategy offsite, it is helpful to know:

• Who’s calling the offsite? What’s their role? What’s at stake for them? How are they incentivised? And—broadly speaking—are they more hedgehog or fox?
• What’s the context—established or emergent? Are they genuinely developing strategy? Or is it already set, and this is just a space to discuss, digest, test, or challenge? Or—let’s be honest—is this all strategy theatre?
• What level of strategy are we talking? Product strategy? Business model strategy? Operating system strategy? Enterprise strategy? Something more existential?
• How do incentives flow here? Who benefits from what? Are we dealing with an invested leadership team with long-term skin in the game? A salaried team with performance bonuses? Tensions between divisions? Or an external firm brought in to 'do strategy'?
• What’s the level of discourse they can hold? Does the leadership team have the capacity for meta-rational, meta-systemic thinking? Or will they want to “keep it simplistic and stupid”? (as I believe the saying goes.)

The answers to these questions will shape your stance, tempo, and approach.

Now, as a brief aside, let me describe the ideal client.

Working with sleeper agents + career executives

Your dream clients are “meta-aware” (for desperate want of a better term). Folks who have enough ironic distance so as to discern the:

• meta-narratives they operate within (internally—aka “the Kool-Aid,” plus the subversive thread; within their industry; and within the wider world—essentially: the ability to take a 4th-person perspective);
• how power works within their own sociopolitical context (including informal and hidden kinds of power);
• the ‘capital’ available to affect change (financial, social, political, etc).

They also have a sense of the ‘myth’ they temporarily reside within.

“Greatness is a transitory experience. It is never consistent. It depends in part upon the myth-making imagination of humankind. The person who experiences greatness must have a feeling for the myth he is in. He must reflect what is projected upon him. And he must have a strong sense of the sardonic. This is what uncouples him from belief in his own pretensions. The sardonic is all that permits him to move within himself. Without this quality, even occasional greatness will destroy a man.” —Frank Herbert, Dune

Sleeper agents have this awareness. These are folk who have been quietly, patiently, working their way towards positions of influence and authority. This is a long-term play, where the real challenge is not losing yourself along the way. If they do become a warlock, they do so with their wits about them.

I’ve worked as accomplice to sleeper agents, and via their savvy have been placed—at just the right moment in time—in contexts where I can be their lever to enable “big change” to happen. Like that one time a team with a very large investment portfolio decided to divest from weapons manufacture and the fossil fuel industry.* Sleeper Agents are driven by more than just profit—there is a deep sense of purpose they bring to their work.

* Admittedly, technology that accelerates our metacrisis, ecological collapse, and the self-termination of our civilisation and species—fossil fuels, weapons manufacture, artificial intelligence, etcetra—are currently very “profitable” investments.

Career executives are also a delight to work with. They may have started as a sleeper agent, and then—after revealing themselves and affecting Great Change—taken themselves to the wider market. These folk often have meta-rational and meta-systemic sensibilities, and are able to embody fluid mode—able to adopt hedgehog perspectives whilst maintaining fox-like fluidity.

The result of this is that they can make unprecedented progress on complex goals that would be otherwise impossible for others to achieve. They can quest, and venture beyond the default.* This is partly because they are usually hired to get results, and aren’t inculcated to established biases or limiting beliefs within an enterprise. Influence, authority, investment and remit serves as a catalysing force.

* These folk are the target audience for my book, How to Lead a Quest.

But then here’s what happens once they have made significant progress—the fox within them gets restless. And so:

1. They get bored—they achieve the thing, the patterns become learned, and the magic of the first 18–24 months has waned. This is when they start looking for their next role.
2. They get booted—either because they’ve left a mess in their wake (the unintended consequences of narrow goals), or the embedded political creatures have become jealous and engineered the ousting.
3. They get burnt—enterprise change is hard. Fatiguing. There’s a magic and momentum that can be channelled—but sometimes, it can burn you out.

Boredom or booting will normally soon see these mavericks work their magic in a new context. Becoming burnt out will often have them quietly resume a sleeper role—or a different career—until the timing is right once more.

I love working with sleeper agents and career executives. I serve as advisor-accomplice: basically helping them look cool(er) and sound smart(er), and sometimes coming in to help facilitate complex stakeholder entanglements, or to catalyse key decisions and the beginnings of new chapters (whilst also playing a part in the performative elements required to mobilise large groups of people).

Fascinating plug—I’ll pass—but now, back to hosting a strategy offsite

Very well. I will get to describing how I approach strategic offsites, but let’s remember: strategy doesn’t come from strategic offsites. It comes from relationality and scenius.

The best way I have worked with clients is in a full quest-augmented strategy (as I write about in How to Lead a Quest). This takes three months at a minimum—but ideally it’s a process that takes 18 months to have its own cycles and momentum. Here we set up the relational contexts for participatory learning and sensemaking in emerging domains, cultivating in-house intelligence and wisdom with a core innovation team bolstered by rotating secondments,

But sometimes, all you’ve got is a day.

And if someone has called for a “strategic offsite” (air quotes)—this mercenary wizard isn’t going to say no! I love this work. Anything that lets us dance amidst emergence—on the edge of knowledge, in the confluence of divergent perspectives, in service to future relevance.

A previous client of mine—and absolute legend in her own right—recently reached out to me with the following question.

‘[…] When you're facilitating strategy off-sites: How much are you a facilitator and how much do you give inspiration/ input/ challenge them on the content?

I just facilitated a workshop for a segment team and found myself well equipped to take them through the thought process - but totally lack the intuition/ ideas to bring "out of the box" thinking in. Luckily we had someone who's good at that stepping in on occasion to add that novel spin that'll help them set themselves apart from the competition.

Would be curious about your approach/ role in such situations!’

Here’s how I replied:

As for strategy offsites, I’d say that for the first third I’m offering provocation and frameworks to deepen the conversation (along with pattern-disrupts and frame-breaks to keep the more sceptical/senior/jaded folk on board).

Then, for the second third, I’m mostly facilitating—but listening closely for where tension could be held longer, and where ideas might be challenged. The goal here is to resist premature collapse of the possibility-space, and to create the conditions of generative ambiguity, so that unforeseen, novel, and truly emergent options might reveal themselves. But this requires that things ‘cook’ for a bit.

Usually, in this middle third, “The True Agenda” reveals itself—along with hidden commitments and conflicting values.

Then, in the final third, I’ve hopefully made myself redundant and am focused on staying out of the way, letting the group self-organise and flow.

That answer was far too simplistic. Hence: this post.

But at this point I’m beginning to worry that this post is too lengthy for the average reader’s attention span. I shall now summon and employ the services of a shoggoth to metabolise my loquacious writing into a more succinct form. 🐙

Note: I’ve edited the shoggoth edit, but just wanted to flag it, in case you’re wondering why the tone has shifted. You can garner more nuance from the podcast or video itself.

~~~~~<shoggoth>

Before the Offsite

Ideally, there’s already been groundwork laid:

• A cultivation of options leading in.
• A shared sense of the real questions. (Usually non-obvious and entangled.)
• Some priming—perhaps a hand-written letter, or a private podcast—to prepare for the transition.
• High-trust leadership who’ve cleared time to be fully present. (Operational distractions have a constricting effect on thought.)

And ideally, the location is designed for flow—low distractions, good regulation, a sense of occasion.

When I help organise these, we ease in gently. People arrive on day one, settle in, enjoy an early dinner, and set the context. We weave in the place—walks, sidebars, surreptitious settings, perhaps a late-night bar session on day two.

But let’s assume you’re coming in fresh. A one-day offsite. No prep. Maybe even some strategic pantomime on the cards.

In this case:

• During your briefing call, ask your client: What do you want people to think, feel, and do differently as a result of this session?
  Also: Any essential deliverables? (And how essential are they really?)
• Be wary of imposed outcomes. They often guarantee a well-executed, underwhelming success.
• Pay attention to the energetics of the room. How are people arriving? What’s the space doing? What needs tweaking?

And with that: we begin.

There are three acts.

Act I: framing, provocation, and subtle disruption

The first act is about opening the field.

Here, your role is to set the tone, establish context, and build rapport. You’re offering provocation and frameworks to deepen the conversation—while gently pattern-breaking and frame-shifting, especially for the more sceptical, senior, or jaded executives.

Above all: help people feel safe, seen, and settled.

There will be sceptical folk. There will be distracted folk. There will be shy and intimidated folk. There will be posturing folk. That’s okay—you’ll work your magic to have everyone level and warm.

Early on, I often introduce the notion of quests, and provide distinctions between meaningful progress (that which brings us closer to future relevance) and the delusion of progress. I’ll also often bring in frameworks like the Business Model Canvas (Strategyzer) or the Operating System Canvas (The Ready). These offer lenses through which we can ‘see’ the business model and operating system we’re in. From here, we hunt for incoherencies—things the team or business does that don’ make sense. Or won’t make sense across multiple possible future contexts.

This sets the scene for the second act.

Act II: holding tension and courting emergence

This is where things deepen.

Your role now is to attune and attend to the unfurling dynamics. You are to listen closely for where tension could be held longer, where things are too neat, and too practiced. You’re sensing when to jilt the momentum, when to invite dissent, when to let silence simmer.

This act is about resisting the premature collapse of possibility, and the emergence that beckons.

We are creating conditions of generative ambiguity—a space where something truly novel can surface. But for that to happen, things need to cook. This can be uncomfortable—that’s okay. It’s also largely the point.

It’s during the second act that “The True Agenda” reveals itself.

Hidden commitments surface. Conflicting values make themselves known.* The polite mask of organisational harmony slips—enough to reveal the real work.

* I’m referencing Robert Kegan and Lisa Lehay’s Immunity to Change concept, here.

If you’re doing this well, there will be moments of palpable tension, which is good signal—far more worrying when things remain passive and polite. At the same time, you’re not the inquisition. It’s more evocation than inquisition, anyway.

At this point, your role becomes subtly ‘shamanic’. I say this with appropriate humility, irony, and reverence. But really—you’re holding the field, attuned to all the subtle energies, non-verbal cues—and novel entities that seek to emerge. You have, by now, a deep acuity for where the conversation needs to go.

Profound things can happen here. Simmering feuds are surfaced. Long-held assumptions are transformed. Perverse incentives and misaligned metrics come into view. And someone finally gives voice to the thing everyone’s been circling around—but no one dared name.

Or—if the team has healthy scenius, and already has a deep sense of fellowship, camaraderie and rapport, with mutual enthusiasm, encouragement and respect—then this is where genuine novel pathways surface. And it feels like a jam session, where all leaders are the contributing artists.

This is where emergence happens.

Because, remember: emergence occurs when a system reaches a certain threshold of complexity. It is through the process of intentionally tending to the conditions of emergence—rising to the complexity of our times—that allow novel pathways to reveal themselves.

Your job is to bring the team to that threshold, and to keep the door open.

Not to force an outcome, nor synthesise prematurely—but to hold the generative tension and immersive ambiguity long enough for something new and novel pathways to manifest.

“Trickster is among other things the gatekeeper who opens the door into the next world; those who mistake him for a psychopath never even know such a door exists.” – Lewis Hyde, Trickster Makes This World

Act III: dissolve into flow

By now, if all has gone well, your primary job is to step aside and allow things to unfurl. You’ve done the work of framing, disrupting, and deepening. Now you (mostly) trust the group to carry it forward, offering light nudges here and there, where appropriate.

Your presence shifts from catalyst to caretaker. You tend the tempo, keeping the energy flowing. But mostly: you stay out of the way.

This is when the group starts to self-organise in the way of the wondrous disruption you’ve wrought. The insights emerge sideways, and everyone has their voice. The novel threads are picked up and woven into the tapestry of strategy.

There’s no guarantee we’ll ever get to this sublime moment, of course. Brilliant emergence is the goal—but underwhelming success is always the fallback.

Oh, and also—here’s the neat thing about this work: you don’t get to claim credit.

You helped create the conditions, yes—but the outcome is emergent. It belongs to the whole. This is one of the gifts of complexity work. All complexity practitioners know this.

Besides—you don’t want to be the kind of consultant who creates dependencies.

Good facilitators makes themselves redundant.
Good leaders do the same.

And just as a good teacher wants to be surpassed by their students, and we complexity practitioners want to stand in humble awe of higher-order emergence.

~~~~~</shoggoth>

It’s as easy as that

Ha! Not really. But maybe—sort of.

It might seem effortless—but a lot of work goes into being prepared to wing it. And by winging it I mean: being present and attuned to emergence—not slaved to a script or tight agenda. This is why you won’t see much in the way of ‘content’ from me—other than light scaffolding. The content is itself emergent.

Also: a strategy offsite is never ‘just a workshop’. It’s an experience that might take us to and through a threshold—and into a whole new chapter—if we attend to the conditions of emergence.

Not all know such thresholds exist. Groomed within containers, some of us can’t see beyond the increment. And—that’s fine. This is not for them. Not yet. Not until they are ready.

What I’ve shared here—in this post and in the video/podcast soliloquy—is a kind of mythopoetic scaffolding. I can’t tell you exactly what to do—no one can!—but maybe this will help you sense into what’s needed. If even a few threads here have sparked an inkling, you’re well on your way.

The rest, as always, is ꧁emergent꧂.

If you want to go deeper, the podcast version of this piece dives into more nuance and story. Or you can reach out—especially if you're a fellow fox, perspicacious hedgehog, mercenary executive, or sleeper agent holding the line within a system not quite ready to change (but trembling at the edges).

Until then: may your questions be fruitful, your colleagues collegial, and your context conducive to emergence.

Warmth,
dr. fox ◊ foxwizard
🧙🏻‍♂️🦊✨