Category Archives: Decision Making

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

You’ve heard it already, we live in Volatile, Uncertain, Complex and Ambiguous (VUCA) world. But what does that mean for you as a leader? We’ll explore how traditional horizontal approaches to leadership, which focus on understanding the job to be done and the capabilities required to do it, fall short. In a VUCA world, we need to expand our capacity for leadership. To do so requires the development of vertical skills, to help make sense of the complexity that surrounds us and construct meaning within that complexity.

Drawing on the book Upgrade: Building your capacity for complexity, by Richard Boston and Karen Ellis, we’ll link VUCA with the four leadership capacities they identify that underpin vertical skills:

  1. 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.
  2. 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.
  3. Self-relating – Observing, understanding, regulating and transforming yourself e.g. making sense of your own reactions, thoughts and feelings.
  4. 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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How Cynefin can help you 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 sensemaking tool.

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Stop telling entrepreneurs what to do. Start helping them think

Everyone has an opinion, advice is everywhere. It’s what to do with it that’s hard. If we really want to help entrepreneurs grow into the best CEOs, then we should stop telling them what to do and start helping them think. Because, in a VUCA world, it won’t necessarily be the entrepreneurs who have more information who will be leading the most successful businesses of the future, it will be those who develop their ability to think and act in more complex ways.

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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’ve reached 30, 50, maybe even 150 people. The opportunity is still enormous, but your growth rate is slowing and your early agility is showing signs of strain. Scaling laws are taking hold. 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 high growth technology leadership teams, this article identifies the factors that commonly cause team dysfunction, conflict and other problems. I offer up some advice about how to avoid them based on my experience helping senior management and executive teams navigate 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, the latest leadership thinking, and my own experience working at Her Majesty’s Treasury during the Great Financial Crisis and navigating the uncertainty of cancer.

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How Vertical Development helps new leaders transform

There are many core skills that leaders must acquire, if they are to stand any chance of building a successful business. But to develop truly effective leaders we need to move beyond providing them 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.

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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 (Amazon UK, US) 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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Do these 2 things to get better at coaching your employees

The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever (Amazon UK, US) 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 (Amazon UKUS) 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

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. These are often ordinary people who have an extraordinary ability to make predictions with a degree of accuracy significantly greater than the average. In his book Superforecasting: The Art & Science of Prediction (Amazon UK, US), co-authored with Dan Gardner, Tetlock identifies how you can improve your ability to predict the future and become a superforecaster.

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What is second-level thinking?

Howard Marks is the Chairman and cofounder of Oaktree Capital Management and author of The Most Important Thing: Uncommon Sense for the Thoughtful Investor (Amazon UK, US). In the book, Marks explains why second-level thinking (sometimes referred to as second-order thinking) and being a contrarian is so important, particularly if you are an investor who wants to beat the market.

Howard Marks himself is, according to the book’s sleeve, renowned for his insightful assessments of market opportunity and risk. He is sought out by the world’s leading investors, and his client memos brim with astute commentary and time tested fundamental philosophy. A value investor at heart, his broad thinking and eloquent expression is pertinent to anyone with investment and business interests both 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 (Amazon UK, US) 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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