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How to Lead a Quest: A Guidebook for Pioneering Leaders

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Unlock progress through doubt and uncertainty The biggest threat facing modern business is the sheer complexity of an uncertain future. That, and the fact that everyone is busy. Too busy for progress.

Workplace cultures have become cursed with efficiency. And so when it comes to developing strategy, we default to our defaults.We favour quick fixes, easy templates and familiar approaches, developing 'robust plans' that do little to mitigate strategic risk or generate new value. The result? The future comes, and businesses die.

But no longer! *cue trumpets* How to Lead a Quest is a book for pioneering leaders - folks who know that enterprise strategy is far too important to condemn to 'smart goals', 'a clear vision for the future' and other such rubbish. Within this book, you'll discover how to:


liberate enterprise leadership and workplace cultures from the curse of efficiency, default thinking and the delusion of progress explore complex and uncertain futures to find profound insights that mitigate strategic risks and ensure your business model remains viable create new value and enduring relevance by pioneering into unchartered and unprecedented territory embed new structures and rituals into your enterprise to build for the future, while still delivering operational excellence today. Not for the faint of heart or short-of-wit, this uniquely refreshing book bravely tackles the paradox that is pioneering leadership. You'll discover how to lead meaningful progress - even if you don't know what the goal or destination looks like.

304 pages, Kindle Edition

First published March 4, 2016

39 people are currently reading
284 people want to read

About the author

Jason Fox

4 books6 followers

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Displaying 1 - 14 of 14 reviews
Profile Image for Dominick Quartuccio.
11 reviews15 followers
November 25, 2016
Well, Dr Fox absolutely nailed the challenges faced by large, established organizations. He described my former employer of 15 years (Prudential Retirement) as if he'd sat alongside me for that decade and a half.

This is a must read for any leader of a large organization.

He offers up brilliant cautionary quotes:

"Large organizations die from a series of reasonable decisions."
"Few leaders are aware of their information diet."
"When a sense of progress eludes you, you tend to your inbox or micromanage small tasks because it feels like progress."

Fox navigates us through the discomfort of NOT holding rigidly to a specific future so we can "lead a quest," that will keep our businesses relevant and thriving in the future.

And he has some fun in doing it. With plenty of sidebars, jokes and whimsical interludes throughout, this book reads almost like business and fairy tale have had a baby.
Profile Image for Vernon Stinebaker.
34 reviews1 follower
April 15, 2021
Good book, with a density of information that makes me want to read it a second time later in the year. One element that stood out to me were references to other books I've also read and found useful and interesting (which has me wondering if I'm reading too much in an echo chamber -- I've tried to select some other books to expand).
Profile Image for Paula.
157 reviews5 followers
November 1, 2023
I thought this book was okay, although it did have a bit of a third grade vibe going on. He calls himself Dr. Jason Fox but we don't really know what his degree is in and I am skeptical of his credentials. People with PhDs, usually state it after their name and do not call themselves Dr. unless they are an actual medical practitioner. Some chapters I didn't find anything particularly informative so did not take down any notes. They are for my personal reference and may be underlined. Below are the points that I thought were interesting.

Part I - Default Thinking and the Kraken of Doom: Why lead a quest?
Chapter 1 - The Anatomy of Default Thinking: Cognitive shortcuts & the virtue of laziness
Pg 11. Templates and systems serve our default thinking. They provide instructions and guideposts when we're uncertain about what to do. Reverting to the default saves you time, thereby enhancing your productivity and efficiency but it costs you accuracy, empathy, relevance, and meaningful progress.

My comment: I think there is value in having a process and system that you follow, especially if it's something you've put together yourself. The author probably isn't saying templates and systems are useless but it sure does sound like it. If anything, I find that having a system and following rules gives you a chance to be creative because constraints can spur on creative thought. So I think it can go either way. A system can be something that helps us grow.

Chapter 2 - The Curse of Efficiency: A Delusion of Progress & the bane of strategy
Pg 16. Someone has a brilliant idea, and begins to promote said idea to their colleagues, only to be met with stiff resistance or general indifference. New ideas pose a real threat to people's time, especially when everyone is so busy being efficient.

Pg 17. Author says in previous book, "The Game Changer" there was a study by Professors Teresa Amabile and Steven Kramer where they asked 600 managers, "What makes employees enthusiastic about work?" They thought being recognized for good work was the most powerful factor in influencing motivation. The number one thing that was most important to the employees was actually what the managers ranked dead last - a clear sense of progress. The more we sense that our effort is contributing to progress, the more likely we are to stay motivated to invest effort. Later on page 19, he does say progress needs to be meaningful which I think is true.

Chapter 3 - A Rainbow of Growth and Despair: A default growth arc & the Inevitable Kraken of Doom

Part II - A Quest Beckons: What makes up a quest?
Chapter 4 - An Alternative Option: A call to adventure & the hidden benefits of doubt
Pg 43. Author references the concept of the hero's journey. Basically I think he is trying to compare creating organizational change to that of being on a hero's journey. He calls it a call to adventure so I think it's helpful to have that type of attitude rather than having an attitude of drudgery.

Pg 55. Intrapreneur is like an entrepreneur and that an intrapreneur is someone who seeks to create new value within an organization.

My comment: I never heard of this word before so I think it's an interesting idea, although I'm sure there are already existing terms to identify wanting to create new values within an organization.

Chapter 5 - Quest Augmented Strategy: A call to adventure & the hidden benefits of doubt
Chapter 6 - Here be Dragons: Dissociated metacognition & the siren call of self-sabotage

Part III - Cultivating Options: How do we find alternative pathways?
Chapter 7 - An Intuitive Reckoning: A nagging hunch & the hint of strategic advantage
Pg 76. What is the right size for a team? Author suggests 7 +/- 2 so a team with 5-9 people. According to Jeff Bezos, if a team can't be fed with 2 pizzas, it's too big. 

Part IV - Crafting Experiments: How do we validate alternative pathways?
Chapter 10 - It's Not About Ideas: The many virtues of a science-based approach
Pg 130. I'd have to say the comment his makes here is probably his dumbest. He writes "science doesn't seek to prove things - rather, it seeks to disprove."

I knew this wasn't true. The following link says the following:
"Science neither proves nor disproves. It accepts or rejects ideas based on supporting and refuting evidence, but may revise those conclusions if warranted by new evidence or perspectives."

Link: https://undsci.berkeley.edu/understan...

I really hate when people make arguments out of false definitions. That's just dumb. No. Stop.

Chapter 11 - Planning to Fail: Navigating the nine layers of Fell
Pg 143-152. Author uses Dante's 9 layers/circle of Hell as a metaphor of Failure-Hell which he shortens to Fell. I personally do not like that he called it Fell. Like it's Failure Hell. Let's call it that or something else. Fell is not really describing what's going on. I like this concept and include a link to the diagram.

Author includes an interesting visualization of this concept which I posted at:
https://imgur.com/a/UpL4t7Z

The 9 layers of Failure Hell are broken up into 3 levels. They are:
'Celebrate' This
1. Imperfection
2. Considered Quitting
3. Failed Experiments

Change This
1. Lack of Ability
2. Process Inadequacy
3. Distraction

Don't Celebrate This
1. Pessimism & Willful Ignorance (Oddly the author using the British spelling of "Willful" which is "Wilful." Was that on purpose? 🤔)
2. Apathy
3. Corruption & Deviance

My comment: I liked this because based on reading I've done on self-compassion and productivity, we do need to show compassion towards ourselves and that means embracing what the author lists under Celebrate This. I mean sometimes you have to deal with negative feelings if you want to keep moving towards your goal. Life isn't always going to go as you planned but we don't move forward if we don't acknowledge what we feel and what our experience is.

Chapter 12 - Viable Alternative Options: Packaged intelligence & a path to follow

Part V - Augmenting Strategy: How do we lead better strategy?
Chapter 14 - Choosing to Choose: Mapping options & dodging cognitive bias
Pg 180-186. Outlines some key biases. He lists 25 altogether and says these are the main ones to watch out for in the context of strategic decision-making. There's a lot out there and some he referenced so I will list the ones he highlighted.
1. Ambiguity effect
2. Anchoring bias
3. Availability heuristic
4. The bandwagon effect
5. Base rate fallacy
6. Bias blind spot. Partly related to the introspection illusion
7. Confirmation bias
8. Conservatism bias
9. The curse of knowledge
10. False-consensus bias
11. The framing effect
12. Hindsight bias
13. Hyperbolic discounting
14. Illusionary truth bias
15. Information bias
16. Normality bias
17. Omission bias
18. Optimism bias
19. The ostrich effect
20. Outcome bias
21. Pessimism bias
22. Planning fallacy
23. Social comparison bias
24. Sunk-cost fallacy
25. Worst-case thinking bias

Chapter 15 - Strategy for Breakfast: The networked enterprise & a responsive hydra

Part VI - Making Progress: How do we create meaningful progress?
Chapter 16 - Bimodal Beginnings: Planting seeds & growing new ways of working
Chapter 17 - Meaningful Progress: Finding progress amongst a sea of vagueness
Chapter 18 - Mission Impossible: Projects with imperative & a few caveats

Part VII - Pioneering Culture: How do we embed pioneering leadership into work culture?
Chapter 19 - Lost in Translation: Finding the behaviours that make strategy happen
Chapter 20 - Structures, Artefacts, and Rituals: Getting deliberate about the vibe
Chapter 21 - Contextual Momentum: A map of rituals to get you moving
Profile Image for Harry Vinh.
47 reviews12 followers
August 5, 2017
This book dramatically changed my mindset about the perception of change in the business landscape.
What it preaches is that the very fundamental mission of a company, regardless of being too big to fail or a newly-founded start-up is to stay relevant by adapting to changes as fast as possible, instead of sticking with what has worked all along rigidly.
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This book will guide you through 4 steps to constantly adapt to changes:
1. Imagining alternative possible future scenarios.
2. Testing those hypotheses and devise new strategies accordingly.
3. Smooth integration of the new strategies.
4. Fostering the culture of thorough thinking to stay relevant.
This entire review has been hidden because of spoilers.
Profile Image for Ricky.
51 reviews
April 16, 2019
Good guidebook

I like the way the author describe the purpose of venturing into pioneering work is to make meaningful progress to keep the business relevant in possible future context. It is unarguable fact that future is not certain, nobody can predict how exactly the future would be. But there are signs, trends and patterns that we can observe today that can help guide us to prepare ourselves to stay relevant all the time before it is too late.
Profile Image for Mykel Dixon.
Author 2 books5 followers
January 8, 2020
Wow. This guy has really found a way to make big business topics hilarious, engaging and easy to understand, without reducing or diluting them to 3 key takeaways or top 10 tips.

This was a thoroughly entertaining read. It's written in a unique format that perfectly captures the author's style and vibe in real life (I've seen him speak live before and he's equally hilarious and insightful on stage). And left me with a big bag of better questions, not just a barrage of razor-sharp answers.
Profile Image for Scott.
263 reviews12 followers
September 27, 2017
This book provides a fantastic strategic mindset to take to your leadership role and across the organisation.

Dr Jason Fox provides a charismatic style to his writing, that allows the reader to enjoy being challenged by his approach.

Throughly recommend this book.
Profile Image for Cliff Hazell.
65 reviews14 followers
January 17, 2019
If you’re just starting out with the topics of leadership and innovation, this book will be great. If you’re more expenses the book will lack depth.

I greatly enjoyed his sense of humor, and his metaphor of “default thinking”.
Profile Image for Glenn.
1,733 reviews8 followers
March 4, 2021
I found this book full of good insights and practical examples. Very helpful for people who work in large organisations and want to change and challenge the way things are done. Now to apply the learnings...
Profile Image for Joseph.
233 reviews
August 5, 2019
Inspiring; but not terribly practical. Its a bit of a paradox, unfortunately.
Profile Image for Daniel Taylor.
Author 4 books95 followers
October 27, 2016
The temptation with this book is to overlook its flaws because the ideas are fresh and well written. Aimed at business leaders, none of the books ideas relates to the core purpose of any business: making a profit. Much more useful business books are anything by Dan S. Kennedy or Verne Harnish, starting with the latter's Mastering the Rockefeller Habits: What You Must Do to Increase the Value of Your Growing Firm.
Profile Image for Patrick Hollingworth.
Author 4 books1 follower
August 16, 2016
In a world of business and consulting blandness, there are only a few who truly stand out for all of the right reasons. Dr Jason Fox is undoubtedly one of them. How to Lead a Quest is a must read for any business executive or head of HR. Interesting to see how all of the supposed global 'thought leaders' in this space are starting to talk about pioneering leadership and experimentation... a year after this book came out. Read it.
Profile Image for Jonathan.
5 reviews
Read
May 26, 2016
This is probably the best book I've read on innovation.

The style invites reflection and makes a good argument for why organisations need to do more than improve on what they already do - since the world is far more dynamic than that. And with this in mind, the author elaborates on why innovation efforts typically go south, and how to not let this happen.
Profile Image for Alison Goss.
200 reviews2 followers
July 30, 2016
Dr. Fox challenges some of the conservative approaches on how to create a business strategy. Highly accessible, refreshing ideas, practical tools. All thrown together with a pinch of good fun, and the odd bit of self-deprecation. Great reading for those who desire to achieve great things.
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