Category Archives: Decision Making

Mental Models & Mastery: Forging a Theory >>

There’s no playbook for business, leadership and life. There’s no single archetype to embody. The journey to mastery that I help take my coaching clients on is a journey of unfolding and becoming in accordance with their own values, principles, morals, beliefs and experience.

But how can you speed up that journey? As a coach, how can I work with someone who already has a good level of business experience and help them accelerate the rate at which they become an even better executive?

It turns out the authors of a fascinating book called Accelerated Expertise: Training for High Proficency in a Complex World were asking themselves similar questions and forging their own theory about this, on behalf of the US Department of Defense. The DoD was trying to wrap its head around the changing nature of warfare. They recognised that speed in acquiring the knowledge and skills to perform tasks is crucial, “yet it ordinarily takes many years to achieve high proficiency in countless jobs and professions in government, business, industry, and throughout the private sector”. Wouldn’t there be great advantages if regimens of training could be established that could accelerate the achievement of high levels of proficiency?

The Theory behind Models & Mastery

Business is not warfare but the military serves as a helpful metaphor, and there is a universal applicability of the book’s core theories and ideas as they relate to the acceleration of executive proficiency. It asks questions that will sound familiar to any business executive, like:

“How can we train for adaptivity and the need to cope with the ever-changing workplace and changing and challenging activities?”

“How can we train for resilience in the face of increasing complexity and unexpected events stretching resources and capabilities?”

Whether you are in the military, or a startup founder, CEO, other executive or professional, there’s a theoretical underpinning that supports anyone’s journey to mastery. By understanding it, you can speed it up.

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The Mental Models Paradox >>

Ever since word of Charlie Munger’s worldly wisdom built upon a latticework of mental models got out, people have become obsessed with what mental models they can use to make them smarter. If we take these mental models and conceptual frameworks and run our reality through them, then we’ll become better thinkers, make better decisions (and investments), and achieve Munger-level wisdom (and wealth). Or will we?

Here’s the paradox:

Good mental models, and other conceptual frameworks, make us smarter but only up to a point, after which they can actually constrain our thinking.

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A fresh look at executive presence, for technology leaders

There comes a point on your leadership journey when you have largely mastered the technical aspects of your craft. You’re now a senior executive, or well on your way to becoming one. It’s not just what you think, say and do, it’s how you think, say and do it. At this stage, transitional startup founders, experienced CEOs and other senior technology executives come to me to help them work on their executive presence to support their next leadership leap.

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The Duck-Rabbit & the Polarities of Leadership

A polarity is a paradoxical situation in which two interdependent and seemingly contradictory states must be maintained for success over time. In business, leadership and life, we find ourselves presented by polarities all the time, often without even realising.

As leaders, we’re told that we must be great problem solvers. That’s true, but a polarity is not the same thing as a problem, for which a definitive solution can be reached at a given point in time. That’s why the ability to recognise when we are facing a polarity – otherwise known as a paradox, duality, dichotomy, tension, or wicked problem – can be a developmental leap for leaders. Embracing the polarites we face with a both/and mindset, as opposed to trying to solve them as problems with an either/or approach, opens up whole new ways forward.

In this article, we’ll meet a number of leaders who are facing polarities at work. We’ll focus on Shrupti, the founder and CEO of a crypto analytics business. We’ll unpack how she identified and navigated a polarity that was holding her leadership and business back. With these practical examples, you too will gain a greater understanding of how you can identify and work more effectively with polarities.

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Executive coaching: a complete guide to finding the right coach for you

We know that the most important predictor of coaching success comes down to the relationship between the coach and the coachee. So it’s critical that you find the right coach for you. Whether you’re a leader looking to find a coach personally, or a people lead exploring coaching for your leadership team, this complete guide to executive coaching will tell you what you need to know. Click on the links below to jump to a section.

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8 Time Management Techniques for Leaders (based on real CEO coaching conversations)

Time management is one of the most common themes in my coaching conversations with CEOs and other leaders. There’s just not enough time in their calendar to get everything done. It’s a challenge for any leader but it’s particularly acute for executives in the high-growth businesses that I work with, as they realise that they can’t scale themselves at the same rate as their business.

Born out of real coaching experience with CEOs and other C-Suite executives, here’s 8 proven time management techniques that will help you manage and leverage your time better. Experimenting with these time management techniques will, at the same time, reveal some deeper, psychological truths about what drives you and your behaviour.

Time Management

Click to jump to each time management technique:

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4 Vertical leadership skills to help you thrive in a VUCA world

We live in Volatile, Uncertain, Complex and Ambiguous (VUCA) world. But what does that mean for you as a leader? Let’s explore how traditional horizontal approaches to leadership fall short and double down on the Vertical skills that leaders need to develop in order to make sense of and thrive in a VUCA world.

The book Upgrade: Building your capacity for complexity links VUCA with four capacities that underpin Vertical leadership skills:

Sensemaking – Observing, understanding and processing the complexity of a situation e.g. getting your head around all the different interconnected topics, data, issues or causal relationships.
Perspective-shifting – ‘Zooming out’ to benefit from a more realistic and multifaceted understanding of a situation or relationship e.g. understanding the perspectives and agendas of the various stakeholders.
Self-relating – Observing, understanding, regulating and transforming yourself e.g. making sense of your own reactions, thoughts and feelings.
Opposable Thinking – Responding to the dilemmas and conflicting ideas that can create tensions within us and / or between us and other people e.g. working with opposing views.

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Using the Cynefin framework to become a better leader in a complex world

There’s no shortage of “how to” advice, playbooks, formulas and even secrets and guarantees for success (at least that’s what the gurus will have you believe). This can work well in complicated situations. But high-growth technology businesses are not complicated, they’re complex. That requires a different approach to leadership, explored here through the lens of the Cynefin framework.

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Learning to think for yourself (aka. the problem with ‘how to’ advice)

Advice is everywhere, everyone has an opinion. It’s what to do with it that’s hard. If we really want to become our best selves, then we should stop listening to what everyone else tells us and start learning to think for ourselves. Let’s explore what that means, including the problem with “how to” advice and the benefits of becoming an independent thinker in a complex world.

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5 challenges startup leadership teams face & how to avoid them

Your startup exploded out the blocks. Your metrics rose impressively. You bootstrapped your way to growth, or super-charged it with external funding. You’re growing fast… 15, 50, 150 people. The opportunity is still enormous, but your early agility is showing signs of strain. There’s challenges all around you. People are stressed. True team leadership is now needed, but it’s at this point that it so often fails.

Startup growth is never linear, it’s a rollercoaster, but similar challenges are observable on the ride. Written for CEOs and other leaders building their startup leadership team, this article identifies 5 common factors that cause problems for a team. I offer up some advice about how to navigate these challenges based on my experience helping leadership teams through this critical stage of growth.

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Beware the Illusion of Certainty

We like to think that our lives are ordered, predictable and subject to a great deal of control. The past is finite; we see only one outcome. We attach causality and narrative to it so that it makes sense. We roll our ability to make sense of the past over into the future, which is infinite; there are many outcomes, as yet unknown and unknowable. Randomness, chance, and luck influence us far more than we realize. Certainty is an illusion. Uncertainty is everywhere.

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How can leadership team coaching help your technology business scale?

In his 2017 TED Talk Want to get great at something? Get a coach, surgeon, author and CEO Atul Gawande tells the story of the Harvard and Yale American-rules football teams: “In 1875 Harvard and Yale played their first game. Yale hired a coach Harvard did not. The results, over the next three decades Harvard won just four times. Harvard hired a coach”. Every high performing sports team has a coach, why doesn’t every leadership team?

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A leader’s guide to decision making under uncertainty

Uncertainty is normal for leaders of any business, but the Coronavirus pandemic has taken this to another level. Asked by clients for advice on how to navigate this crisis, I’ve pulled together thoughts and key resources into this decision making guide. It draws upon evidence from behavioural and decision making psychology, my experience coaching leaders through high-stress situations, my own time working at Her Majesty’s Treasury during the Great Financial Crisis and navigating the uncertainty of cancer.

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What is Vertical Development & how can it help leaders transform?

To develop truly effective leaders we need to move beyond providing people with more information – telling them what to do and how to do it, to helping them improve how they think, make decisions, and make sense of the world. This is the distinction between horizontal development, which focuses on what you know, and Vertical Development, which concerns how you think:

Traditional horizontal development focuses on the acquisition of further knowledge, skills and development of specific personal qualities to become more proficient and experienced in a given aspect of leadership. By contrast, Vertical Development transforms the underlying capacity of the leader to make sense of and respond to situations, working directly on their internal ‘meaning making’, rather than just behaviours or actions.
Vertical Development: building leadership capabilities for the future

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8 books all new leaders should read

“Why is it that when I ask for a pair of hands, a brain comes attached?” Henry Ford once asked. The capitalist economy of the last few centuries was built upon the work of men and machines. Men (and it was almost exclusively men) were paid to do, not to think. Command and control approaches to leadership prevailed, but these traditional approaches are outdated and ineffective. The way that businesses are built and led, and the future of work is changing: the world is more complex than it used to be and the best leaders are learning to adapt. To survive and grow in today’s volatile, uncertain, complex, and ambiguous (VUCA) environment, leaders need skills and organisational capabilities that are different from those that helped businesses succeed in the past.

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Trillion Dollar Coach – Summary

Trillion Dollar Coach: The Leadership Handbook of Silicon Valley’s Bill Campbell is a book about a man who helped build some of America’s greatest companies, including Apple and Google. A former college football player and coach, Bill didn’t enter the business world until he was thirty nine. Moving quickly though through executive roles, he went on to coach the likes of Steve Jobs, Larry Page, Eric Schmidt, Ben Horowitz and Bill Gurley, to name just a few. He passed away in 2016, leaving a legacy of growing companies, successful people and an enormous amount of respect. The book is essential reading for any manager or leader operating in a fast-moving, high growth business.

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2 powerful ways to get better at coaching your employees

The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever is one of the best books I’ve read for managers and leaders who want to use a coach approach with their employees but don’t have the time or inclination for formal training. It’s short on theory but long on practical tools and techniques that are a shot to the heart of great coaching.

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Victor Frankl on finding meaning & happiness

Man’s Search for Meaning by Victor Frankl is essential reading for anybody interested in happiness, personal growth, the psychology of suffering and mental health. It chronicles the author’s time as an inmate in the Auschwitz concentration camp during World War II. The early chapters do not make for easy reading but the book opens up into one of the deepest and most eloquent explorations of finding meaning and man’s search for meaning and happiness.

Striving to find a meaning in one’s life is the primary motivational force in man… This meaning is unique and specific in that it must and can only be fulfilled by him alone; only then does it achieve a significance which will satisfy his own will to meaning.

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Superforecasting: The Art & Science of Prediction – Summary

Superforecasting: The Art and Science of Prediction is a book about how to become a superforecaster, an often ordinary person who has an extraordinary ability to make predictions about the future with a degree of accuracy significantly greater than the average.

In a landmark study undertaken between 1984 and 2004, Wharton Professor Philip Tetlock showed that the average expert’s ability to make accurate predictions about the future was only slightly better than a layperson using random guesswork. His latest project, which began in 2011, has since shown that there are some people with real, demonstrable predicting foresight. In his book, co-authored with Dan Gardner, Tetlock identifies how you can become a superforecaster too. Read on for a summery of how.

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What is second-level thinking, according to Howard Marks?

Howard Marks is the Chairman and cofounder of Oaktree Capital Management and author of The Most Important Thing: Uncommon Sense for the Thoughtful Investor. In the book, Marks explains why second-level thinking (sometimes referred to as second-order thinking) and being a contrarian is so important.

Let’s take a look at what second level-thinking really is and why mastering it is so important to anyone with investment and business interests, professional and personal.

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The strategic genius of John Boyd: “The Fighter Pilot Who Changed the Art of War”

Robert Coram, author of Boyd: The Fighter Pilot Who Changed the Art of War describes John Boyd as “first, last and always a fighter pilot – a loud talking, cigar-smoking, bigger-than-life fighter pilot”. But also as more than that: “he was that rarest of creatures – a thinking fighter pilot.” Boyd is widely considered to be one of the world’s greatest military strategists, despite the fact that it’s unlikely you have ever heard of him. Over his career he bought the Air Force its Aerial Attack Study, invented Energy-Maneuverability (E-M) Theory, was the father of the F-15 and F-16 fighter jets and created a decision making framework called the OODA loop. His thinking about strategy spread across the US armed forces: his Patterns of Conflict briefing provided the basis for the US military’s strategy in the first Gulf War, leading to their 100 hour victory. It still underpins US Marine Corps fighting doctrine to this day.

John Boyd was an endearing eccentric and strategic genius who is brought wonderfully to life by author Robert Coram in his meticulously researched book. Coram demonstrates what one man, surrounded by a few devoted and loyal Acolytes, can do to change the world. Maneuverability, as it relates to military (and business) strategy, we learn is key.

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ANOTHER post about what’s WRONG with The Lean Startup

The Lean Startup, by Eric Ries, was first published in 2011 and has since become the bible for startup entrepreneurs around the world. More recently, the approach outlined in The Lean Startup has received criticism, but is that fair? In this post I argue that it is not, because that is all it is, an approach, albeit a very good one.

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Risk management for startups

It’s a general perception, but startups and early-stage growth businesses don’t really do risk management. It’s not a concept that’s on their radar and anyway, there’s just too much other stuff going on. But managing risk within a startup business is important because, as the saying goes, “shit happens”.

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