Venture ✨beyond the default✨ with

Quest Leadership

To quest is to find meaningful progress amidst

the unprecedented, uncharted and unknown

True leadership is found within volatility, uncertainty, complexity, ambiguity, paradox and doubt. But most do not venture here—they wait until the path is stable, certain, simple, clear, neat and obvious. They wait for questing leaders to shine a light on the path to follow.

Are you leading—or waiting?

I assist clever teams who seek to lead meaningful progress—beyond the default.

In addition to the thoughtful provocations offered via keynote presentations and my bestselling books, I develop ‘quest leadership’ savvy in the following ways:

  1. Questing Masterclasses + the “Quest-Augmented Strategic Offsite”

  2. “Sensemaking with Sidequests” in emerging domains

  3. “Into the Storm”—The Everquest Leadership Program

  4. Enterprising Quest Leadership + “Wizardly Sparring”

Allow me to elucidate upon each…

“We first engaged Jason to facilitate an important strategic offsite with our senior leadership team. The opportunity for such offsites is rare, and the time senior leaders have together at such offsites is very precious. It was essential we engaged someone who could not only cover the agenda, but also provide space to explore new possibilities. Jason did this and more. He immediately built rapport with the team, and was able to challenge us to think beyond our defaults. The result was a strategy that was refreshing, courageous and differentiated, and a leadership team that was inspired to make it happen. We couldn’t have predicated this, but Jason’s unique approach allowed it to happen. We have since then engaged Jason to help us build momentum with our people. He delivered a keynote to our business in support of the strategy, and the feedback was overwhelmingly positive. We loved that he was able to tailor it serve the strategy. Then, recently, we engaged Jason again to facilitate further strategic development. And it just gets better and better! We look forward to such experiences, and will be working with Jason again in the near future.” Alli Smith Executive General Manager Suncorp

“We first engaged Jason to facilitate an important strategic offsite with our senior leadership team. The opportunity for such offsites is rare, and the time senior leaders have together at such offsites is very precious. It was essential we engaged someone who could not only cover the agenda, but also provide space to explore new possibilities. Jason did this and more. He immediately built rapport with the team, and was able to challenge us to think beyond our defaults. The result was a strategy that was refreshing, courageous and differentiated, and a leadership team that was inspired to make it happen. We couldn’t have predicated this, but Jason’s unique approach allowed it to happen. We have since then engaged Jason to help us build momentum with our people. He delivered a keynote to our business in support of the strategy, and the feedback was overwhelmingly positive. We loved that he was able to tailor it serve the strategy. Then, recently, we engaged Jason again to facilitate further strategic development. And it just gets better and better! We look forward to such experiences, and will be working with Jason again in the near future.” Alli Smith Executive General Manager Suncorp

1. Questing Masterclasses +

the “Quest-Augmented Strategic Offsite”

I offer the following ‘masterclasses’ as half-day standalone experiences, or as a sequenced bundle—aka your “Quest-Augmented Strategic Offsite”. ~(˘▾˘~)

Here’s how it works. If time or budget are a constraint, you can choose one of the following interactive masterclasses to integrate into your next team development day or strategic offsite. Or, if you are able to invest in the quest for enduring relevance, all of the following masterclasses can be used as the starting point for a Quest-Augmented Strategic Offsite.

Note: the following is a draft starting point. The bundled “Quest-Augmented Strategic Offsite” includes: pre-reading materials, an optional priming video/podcast, up to two briefing calls or working sessions, along with a comprehensive debrief with next steps.

Also note: strategies are not formed within such offsites; but it is where they are cultivated, catalysed or coalesced. Regardless of your disposition, the Quest-Augmented Strategic Offsite will bring about real and meaningful progress, and will set the stage for further investment.

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. • ☆ . ° .• °:. *₊ ° . ☆ .• °:


The Prequel

Priming material is developed and delivered.
Patterns disrupted; curiosity piqued.

—Day One—

Part I
The “QUEST MINDSET” Masterclass 🏮

In this masterclass we heighten our appreciation for complexity, and develop a language to navigate emergent phenomena. We see ambiguity as a mystery to be navigated (not a problem to be solved). We make the vital distinction between meaningful progress and the delusion of progress. In doing so, we understand why quick fixes and familiar solutions are seductive but hold us back. The result of this masterclass is a group with greater comfort and capacity for venturing into the unprecedented, uncharted and unknown—without a map to follow. Note: as a stand alone this is the perfect way to kick-off any strategic offsite. Learn more.

Part II
The “(IN)COHERENCE MAPPING” Masterclass 🧭

Here we collectively review the existing business model and operating system, contrasting this against emergent futures to see where common incoherencies exist. We also explore where conflicting values and hidden commitments may be creating ‘an immunity to change’. In doing so, we surface avenues of adjacent possibility—domains in which innovation is both needed and feasible. This masterclass will grant you a refreshed perspective of where your business model and operating system is coherent (i.e., where it ‘makes sense’)—and where your biggest opportunities for strategic innovation lie.

Part III
The “FUTURECRAFT” Masterclass 🔮

The future is infinitely complex and impossible to predict—but humble futurists and complexity practitioners can (tentatively) point to the confluence of meta-patterns and trends. And—within these shaping forces—futures can be envisioned and explored. And so, in this masterclass we do just that, ‘backcasting’ condensed insight with narrative so as to evoke new possibilities in the present. This masterclass will have your team actively exploring how your collective endeavours ‘make sense’ and remain relevant across multiple possible future contexts. The seeds of whole new avenues of value emerge here.


The Dinner + Fireside

With any strategic offsite, “The Dinner” has the potential to be mythic and profound.

—Day Two—

Part IV
The “QUIVER OF OPTIONS” Masterclass 🏹

If our defaults are the options we choose automatically in the absence of viable alternatives—questing is the process of seeking viable alternative options to the default ways of doing things. In this masterclass, cultivate a ‘quiver of options’—strategic initiatives you might deploy in the future (should the right conditions manifest). We also explore living knowledge management, and how “sneaky experimentation” can be used to establish the viability of options. This masterclass ‘makes real’ the otherwise hidden opportunities and threats to your business model and operations—ensuring you can proactively anticipate and integrate insight into strategic decision making.

Part V
The “CONTEXTUAL MOMENTUM” Masterclass 🌿

Contrary to popular belief, strategies are not created at strategic offsites—they are developed. Unless it is an architected piece of propaganda, true strategy is never quite ‘created’—it is an emergent set of sensibilities tentatively woven together into narrative form as a means to coordinate efforts amidst complexity. Thus, to ensure that strategy continues to develop, it is essential we carve out the rituals and milestones that allow for meaningful progress (beyond the default). This masterclass will equip your team with the structures needed to maintain meaningful progress amidst complexity and change.

Part VI
The “FELLOWSHIP & SCENIUS” Masterclass 🌳

Where does strategy come from? It comes from quests. Questing is the precursor to strategy. And fellowship is the precursor to questing. Without healthy relational accord amidst your team (kinship), your most courageous thinking will be incremental at best. A safe recipe for predictable, undifferentiated and underwhelming success. In order to develop scenius (collective genius), we must intentionally cultivate the conditions that give rise to it. This masterclass seizes the opportunity to embrace a deliberately developmental approach to the way we encourage, inspire, and bring out the best in each other at work.

. • ☆ . ° .• °:. *₊ ° . ☆ .• °:

. • ☆ . ° .• °:. *₊ ° . ☆ .• °:

Each standalone masterclass can be conducted over 2–3 hours.

When blended as part of a Quest-Augmented Strategic Offsite, negative space will be built in to ensure ample time for reflection, integration, complexity, serendipity, and the emergence of novel paths.

These events can become a catalysing new chapter for your organisation.

Are you ready to make clever happen?

Get in touch to find out more.

“We first engaged Jason to facilitate an important strategic offsite with our senior leadership team. The opportunity for such offsites is rare, and the time senior leaders have together at such offsites is very precious. It was essential we engaged someone who could not only cover the agenda, but also provide space to explore new possibilities. Jason did this and more. He immediately built rapport with the team, and was able to challenge us to think beyond our defaults. The result was a strategy that was refreshing, courageous and differentiated, and a leadership team that was inspired to make it happen. We couldn’t have predicated this, but Jason’s unique approach allowed it to happen. We have since then engaged Jason to help us build momentum with our people. He delivered a keynote to our business in support of the strategy, and the feedback was overwhelmingly positive. We loved that he was able to tailor it serve the strategy. Then, recently, we engaged Jason again to facilitate further strategic development. And it just gets better and better! We look forward to such experiences, and will be working with Jason again in the near future.” Alli Smith Executive General Manager Suncorp

“We first engaged Jason to facilitate an important strategic offsite with our senior leadership team. The opportunity for such offsites is rare, and the time senior leaders have together at such offsites is very precious. It was essential we engaged someone who could not only cover the agenda, but also provide space to explore new possibilities. Jason did this and more. He immediately built rapport with the team, and was able to challenge us to think beyond our defaults. The result was a strategy that was refreshing, courageous and differentiated, and a leadership team that was inspired to make it happen. We couldn’t have predicated this, but Jason’s unique approach allowed it to happen. We have since then engaged Jason to help us build momentum with our people. He delivered a keynote to our business in support of the strategy, and the feedback was overwhelmingly positive. We loved that he was able to tailor it serve the strategy. Then, recently, we engaged Jason again to facilitate further strategic development. And it just gets better and better! We look forward to such experiences, and will be working with Jason again in the near future.” Alli Smith Executive General Manager Suncorp

2. Side-Quests to Cultivate

In-House Intelligence

Side-quests see a fellowship of 5±2 leaders partake in a curated sequence of salon-style ‘sense-making’ sessions over 2–3 months. Interlaced with apt and contextually relevant assignments, these sessions imbue the questing team with the kind of wisdom and insight that can only be gleaned via direct participation in emerging domains. That is: applicable knowledge well beyond what can be gleaned via online punditry, cookie-cutter consulting firms or chatGPT. Your enterprise will be smarter, wiser and all the more savvy for it.

I currently offer wizardly assisted Side-Quests in seven domains:

1. Blockchain technology and decentralised finance (an inevitability)
2. Applied artificial intelligence (implications and opportunities)
3. Decentralised coordination and governance (aka: the future of work)
4. Nature-based regenerative finance (a glimmer of hope)
5. web3 street smarts and savvy (into the dark forest)
6. The metacrisis (sensibilities in a time of collapse)
7. Metamodern wizardry (what comes after post-modernity)

If you suspect one of these domains may be of relevance to your endeavours—reach out and let’s see what we might conjure.

3. “Into the Storm” ⛈️

—The Everquest

Leadership Program

A storm is coming (it’s already here). We’re in The Exponential Age, now. As artificial intelligence continues to usurp roles and ways we once held sacrosanct—it behooves us to develop the wit, wisdom and wiles to stay savvy in this time of great change and collapse.

For true leadership is a subversive act. Only that which can change can continue—but many leadership programs simply perpetuate the kinds of low-order thinking that celebrate banal incrementalism, delusions of progress and “the current thing”. We now live and work within an age of artificially intelligent deep-fakes, audience capture and manufactured want—in a distraction economy engineered to keep us dumb. To genuinely lead, we must rise to the challenges of these times.

The Everquest Leadership Program is designed to develop the skills and savvy to lead meaningful progress amidst volatility, uncertainty, complexity, ambiguity, paradox and doubt.

This program is designed for mid-to-senior level managers and leaders. This is not for everyone. Some (many) will find themselves lost, baffled and confused. This is intentional—and something we work through, as means of developmental transformation. “The mind that is not baffled is not employed,” poet Wendell Berry once wrote. “The impeded stream is the one that sings.”

The Everquest Leadership program is designed for small cohorts, and is paced over one to three seasons. Here is a sample of the living curriculum (in no particular order).

Complex Adaptive Systems: Understand the interconnected nature of challenges and the fluidity required to navigate them.

Ambiguity Aplomb: Cultivate efficacy, adaptability and ease in the face of the unknown.

Wit, Wisdom, and Wiles: Harness the trifecta of associative knowledge, deep insight, and cunning strategy.

Intellectual Honesty and Thought Leadership: Craft and contribute to the ideas that shape the future.

Narrative Strategy and Mythopoetics: Weave compelling stories with a poetic acuity to the meta-patterns of myth.

Meaningful Progress: Establish qualitative rituals and contextual beacons to guide the unfurling development of your organisation.

Bullshit Artistry: Learn how to spot and appreciate artful bullshit (an indifference to truth)—and yield this insight to do intellectual honesty better.

Metamodern Wizardry: Embrace the generative paradoxes metamodernism—the emergent philosophy of The Internet.

Decentralised Leadership: Discover how to govern and coordinate effectively—amidst scale—without relying upon centralised authority.

Fellowship and Scenius: Learn how to tend to the mycelium that brings about collective genius and collaborative brilliance.

Sensemaking amidst Complexity: Become connoisseurs of thoughts, and develop your affinity for warm data and transcontextual information.

Presentation Glammourie: Learn how to distil complex ideas into compelling presentations—without dumbing things down.

Motivation Design: Know when to wield incentives, and how to create the conditions for work to be inherently rewarding, in and of itself.

Keystone Behaviours: Understand where it makes sense to establish specific and reliable behaviours, and how to do so.

Metacognition and Reflection: Learn to develop introspection to identify allergies and unhelpful patterns before they become an issue.

Developing Metarationality and Metasystemic thinking: Learn to work at higher orders of complexity, and to find the ‘fractal simplicities’ that hold true across contexts and scales.

The Metacrisis: Develop a response to a time of systems transformation and collapse. This is the most important element of the whole program—something we must ‘level-up’ to, in order to effectively confront.

The curriculum itself is alive, and evolves with each cohort. This is just a sample.

The Everquest Leadership Program is not for everyone. It requires sponsorship from mature senior executives. Folks with influence, authority, budget—and the wit, wisdom and wiles to realise that the thinking that got us here won’t get us to where we need to go. If that’s you, and if you suspect folks within your organisation are ready to begin developing the capabilities necessary for the world of tomorrow (not yesterday)—do reach out and let’s begin to explore what might be possible.

4. Enteprising Quest Leadership

& Wizardly Sparring

Much of my work as an advisor to questing teams is commercially sensitive and thus wrapped up in non-disclosure agreements. These assignments are usually formed after having worked closely with executive leadership teams, and span a minimum of two years. I cannot talk to you of the endeavours that have resulted in the genesis of multi-million dollar companies, genius restructuring, and the development of breakthrough intellectual property. But I can offer an alternative: wizardly sparring.

This is effectively like executive coaching—but more within the domain of questing. Sometimes, it pays to have a thinking partner to work through complex challenges with. For this, I can be your wizard. All such affairs begin with a one-hour consulation.

Shall we?

If you suspect a quest beckons, but don’t know where to begin—simply get in touch and mayhaps we can book a discovery call to see what might be possible.

For all bookings and enquiries, please email my partner and business manager kim@drjasonfox.com

Or—if you prefer—feel free to use this contact form.

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