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Book Review: How to Lead a Quest - and reframing the conversation of failure

Through this book review in support of our #FailureWins series, TCB editor Luke Webb explores Dr. Jason Fox’s book on How to Lead a Quest and how it can help Air Force build better language and mental concepts around failure. If Air Force truly wants to seek the edge, it needs to have an appetite for the right kind of failure – but this doesn’t mean tolerating every kind of failure, something that’s already in the blood of aviation professionals.

Failure in the context of aviation sounds like blasphemy. The idea that ‘failure’ could be permitted in mission- & safety-critical contexts rightfully can be on the nose, and hearing how ‘failure is part of success’ (or some other digital philosophical epithet) can cause the boiling of AVTUR-blood.


I’d contend that it’s the lack of nuance around the word failure that is so unhelpful. The cult-like sentiment around pursuing failure as a means to grasping success is popular in the tech-media scene. Here failure means you have to apologise to a group of vapid teens because of a change to an app’s feature. To extrapolate that implied meaning to the world of airpower seems insulting.


In aviation, failure can mean a devastating conversation with the loved ones of colleagues and friends who were lost because of a split-second mistake. In the military, it can change the entire course of a campaign – even the moral imperative to fight.


And yet, if Air Force is desirous of maintaining “the edge”, it must be on the forefront of trying new things. Of innovating. Of, at times, failing. But it’s not an easy gambit for an organisation that has matured (perhaps corporate-speak for atrophied?) in several aspects of its business.


In the context of #FailureWins, I felt compelled to review one of my favourite books on the topic – How to Lead a Quest by Melbourne academic Dr. Jason Fox. It’s not an airpower piece, but I’ve found it one of the most accessible, implementable, and entertaining business books I’ve read that deals with untangling the realm of complexity faced by pioneering leaders.





Fox offers it as a ‘handbook for pioneering executives’, and provides a series of practical actions, frameworks, and rituals to apply in a variety of workplace settings (including my favourite “Beacon Words”, where he gives an example of his word for the year being pirate). He also offers several concepts to help pioneering leaders in their work, particularly around ‘quest-augmented strategy’ - where corporate experimentation is central to organisational learning, which in turn drives intelligible work that’s future-focused. Another is around crafting experiments: since reading his work, I’ve recast my own language around innovation and new pursuits as ‘experiments’ as a way of removing cultural cringes to ‘innovation’ and ‘learning from failure’.


His work is vast but efficient at unpacking the complicated, visceral pulses that so often trigger our grimace-face when we experience failure (especially in an organisational setting). Rather than approach the topic from a growth or benefits perspective, Fox looks at innovation from the lens of organisational atrophy and death - the inevitable consequence of group human endeavour of an organisation that fails to keep pace. Not just from a product or service perspective, but how organisations have a tendency to default to rote decision making slowly but surely. Where justifications and rationalisations based in past thinking become a quiet, but powerful corporate gospel.


Innovation – grounded in a practice of crafted corporate experimentation – is vital for ensuring the core of an organisation doesn’t succumb to entropy. Fox has much to say about innovation, framed as pioneering leadership (hence the title How to lead a Quest). But perhaps some of the more exigent insights he offers are around failure. He has mixed views about it:


“Another extreme has also crept into the vernacular – that of celebrating failure. It’s certainly preferable to the alternative, in which failure is shameful, but celebrating failure might be taking things a bit too far. The real thing to celebrate is learning.”


The Layers of Fell

In the context of leading a quest against organisational irrelevance, “one thing that is consistent” with this nonlinear new way of working is failure. But, in the same breath, he asserts that failure is a spectrum, and expresses a model which he refers to as the Nine Layers of Fell (“failure + Hell = Fell” … he is a bit of a wordsmith). The deeper layers are forms of failure that should not be celebrated; the mid-layers are forms that should be the focus of change, and the upper layers are matters that should be ‘celebrated’ (or, at least, learned from). They’re a spectrum of organisational failure modes that can emerge from undertaking the messy, experimental work of quest-augmented strategy; however, they’re also instructive to safety- and mission-critical organisations that need to differentiate between hazardous operational failures, and ‘just’ embarrassing corporate failures.





Ninth layer – Corruption & deviance: This isn’t about deviance from SOPs; it’s the deliberate violation of values, and actions that put the whole organisation at risk for personal gain. Fox says this “demands immediate inquisition – into not just why and how an individual or team did this, but also why and how they were able to”.


Eight layer – Apathy: Fox defines apathy as the non-participation in meaningful progress and where people simply go through ‘the default motions.’ It’s characterised by ‘not rocking the boat’ or ‘computer says no’ and is “perhaps the most insidious and common failure among enterprises”.


Seventh layer – Pessimism and wilful ignorance: “Pessimism is where people prejudge something before collecting or reviewing the evidence”. Fox sees this form of failure as only slightly better than apathy, but also draws a distinction with scepticism where judgement is reserved until the evidence is reviewed. Scepticism is engaged in the process by “leveraging doubt effectively” through asking questions, but not blocking progress.


Sixth layer – Distraction: In this form of failure, “people are busy doing the work…it’s just they’re focused on the wrong things”. Fox highlights that one of the causes of such failure can be performance measures that are skewed towards business-as-usual activities, rather than incorporating work designed to advance the organisation’s capability. Fox refers to this as the Delusion of Progress.


Fifth layer – Process inadequacy: Where there is an active intent to pursue both BAU and meaningful work to adapt to the future, existing processes can be a letdown. It’s where people are frustrated with current systems and processes and can lead to using workarounds (itself another potential source of failure in some contexts).


Fourth layer – Lack of ability: This is where Air Force mostly excels owing to its approach to training and education. However, it’s worth considering that “the world is changing fast, and we are required to learn faster than ever before”. Whilst a robust training program ensures BAU activities are catered for, how well is the whole learning ecosystem – training, education, integration of strategic intelligence and lessons learned (or just recorded?) into the intellectual life of the organisation - keeping up with new technology, new applications of these technologies, and the nature of the tactical and operational threat? It’s a challenge that’s found in several of AFSTRAT’s lines of effort.


Third layer – Failed experiments: As Fox frames corporate innovation through the lens of experimentation, it follows that experimentation will lead to many failures. That’s the point of experiments – find what works (and why) and find what doesn’t (and why). But it’s not an open slather invitation to be sloppy; such experiments must be subject to analysis and feedback to pinpoint flawed methodologies or biases. It’s celebrating what’s learned from failures that’s crucial.


Second layer – Considered quitting: Part of our cultural avoidance of failure is the sunk-cost fallacy of ‘quitting is never an option’. But sometimes it’s worth actually celebrating the ending of a particular endeavour when the evidence-base points to it being no longer relevant. Fox points out that it’s not “about stopping – it’s about letting go so that you can progress”. Placing cultural currency on the courage to invest resources into other meaningful pursuits is “something definitely worth celebrating”.


First layer – A lack of perfectionism: This is perhaps one that will be most difficult to accept in an aviation world, at least on the surface. Operational excellence and adherence to detailed procedures are hallmarks of safety-critical professionals. However, as any safety system specialist will agree, mistakes will happen, and it’s the learning from errors and incidents that builds safety capability. And there is space for celebrating this level of failure in recognising and encouraging the learning from mistakes. A facet of the US space program that potentially saved years during the space race was Werner von Braun’s focus on encouraging the reporting of failure and mistakes.





So what?

In a nation where tall poppies are ripe for the cultural plucking, failure is like crack cocaine for talking heads and copy editors. This cripples our public sector organisations from taking already uncomfortable experimental steps towards a more relevant form. Air Force is subject to the same dynamics.

But being able to unpack the variety of meanings that sit behind ‘failure’ can:

  • Establish a class of leadership styles that can be recognised within the Air Force organisation as pioneering leaders – in addition to formulaic/operational executing leaders

  • Empower Air Force’s pioneering leaders to make the case – with compelling language – to engage in systematic activity without a known outcome. E.g., an experiment.

  • Enable Air Force as an organisation to build narratives that deflect criticism of failures because they’re engaged in experiments. Plan Jericho is a vehicle that uses narratives of exploration and development to carve-out experimental space. Potentially the next wave of this approach is Jericho-like constructs at the Group, Wing & Squadron levels – led by pioneering leaders.

The more we discuss the many shades of failure, the more we can remove the cultural sting that sits behind the word. In an era of developments such as grey-zone aggressions, Air Force needs to build an appetite for the right kinds of failure – ultimately, to avoid the truly fatal failure forms.


Luke Webb is a Melbourne-based aerospace engineer, casual academic & science communicator. He is the Chair of the Melbourne Branch of the Royal Aeronautical Society, and one of the editors of The Central Blue.

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