Category Archives: Advising

Charlie Munger was a complexity thinker

I’ve read a lot about Charlie and his work. Peter Bevelin’s book Seeking Wisdom: From Darwin to Munger is in my top ten. I’ve a signed copy of his Almanack (I figured he’d respect me for that, as I suspect it will make a good financial as well as phenomenal personal investment). His reading list has strongly influenced my own. I’ve written articles that explore his wisdom, as it relates to mental models.

Charlie Munger has had a big influence on me. But despite everything that I’ve learnt, it wasn’t until Cedric Chin emailed me with a speech by him from 2003 – Academic Economics: Strengths and Faults After Considering Interdisciplinary Needs – that I finally grokked that Charlie and I share a similar worldview around a central concept:

Charlie Munger was a complexity thinker.

This is a piece that I’ve been meaning to write for a long time. The announcement of Charlie Munger’s death yesterday (28th November 2023) committed me to writing it. I’ve pulled it together quickly, so excuse any omissions and my brevity.

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

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 executive 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.

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8 Executive Time Management Techniques (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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A Deliberately Developmental Experiment

When the founders at Future Arc approached me to develop a business-wide coaching programme, they were clear they wanted to do something different. It felt right that a disruptive company that puts talent development at the heart of its organisation should embrace a new approach to developing its people. Fascinated by how we can build organisations and develop individuals for the future, and already drawing on Robert Kegan and colleagues’ work on adult development in my coaching practice, I introduced them to the concept of the Deliberately Developmental Organization (DDO).

A DDO is organized around the deceptively simple but radical conviction that organizations will best prosper when they are deeply aligned with people’s strongest motive, which is to grow. Deep alignment, it turns out, requires something more than making “a big commitment to our people’s growth,” admirable as that may be, even when such a commitment is followed up with significant investments in people’s ongoing learning on the job. It means something more than consigning “people development” to punctuated moments outside the flow of day-to-day work, such as standapart trainings, high-potential leadership development programs, executive coaching, corporate universities, or once-a-year retreats. Deep alignment with people’s motive to grow means fashioning an organizational culture in which support to people’s ongoing development is woven into the daily fabric of working life, visible in the company’s regular operations, day to-day routines, and conversations.

The Deliberately Developmental Organization
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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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How Women Rise: Break the 12 Habits Holding You Back – Summary

How Women Rise: Break the 12 Habits Holding You Back identifies 12 habits that commonly hold women leaders back as they endeavour to rise to the top of their chosen career. The book concludes with a practical section on how to put identified changes in habits in to action. This article provides a summary of the 12 habits that the authors, Sally Helgesen and Marshall Goldsmith, identify and adds some powerful questions you can ask yourself to unpack your own habits and unleash your full leadership potential.

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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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Why entrepreneurs need a coach, mentor & therapist

Like any high-performing individual, leaders need to wrap a professional support team around them if they are to give themselves the best chance of success. That team must be trustworthy, objective, and acting always in the leader’s best interests. This post unpacks the difference between a coach, mentor and therapist and explains why, together, they can make up a such a cohesive support team.

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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:

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How to develop a leadership culture in your startup

The internet is awash with articles about the importance of developing a positive company culture. What’s less commonly discussed is the importance of developing a positive leadership culture. In this post I explore what leadership culture is and how you can develop it in your business by: having focused executive leadership team conversations, engaging the whole business in leadership conversations, owning leadership culture from the top, and investing in leadership development.

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Leading on the job: five pieces of advice for new leaders

Not long ago you were part of a small team of people with a big idea that you thought could change the world. Now you are responsible for a rapidly growing team who are looking at you for direction. Your burden of responsibility has increased dramatically and you need to learn to lead quickly. Having coached a lot of new leaders in this situation, I’ve turned that experience into five pieces of advice for new leaders.

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4 questions to improve your leadership self-awareness

Self-awareness is considered to be one of the most fundamental issues in psychology, from both a developmental and an evolutionary perspective. As an executive coach, helping my clients develop their self-awareness is therefore one of the most important aspects of my job. Here’s four self-reflection questions that I ask clients, and which you can ask yourself too, to improve your leadership self-awareness.

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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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How to avoid being duped by survivorship bias

It’s easy to see, and pay attention to, only successful individuals and businesses, not the failures that fall by the wayside. This phenomenon is called survivorship bias: “the logical error of concentrating on the people or things that made it past some selection process and overlooking those that did not, typically because of their lack of visibility.” (Wikipedia). This article explains, with examples, what survivorship bias is and how to avoid being duped by it.

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12 of the best executive coaching books

Are you a manager or leader who wants to develop your coaching skills? Maybe you’re already a coach who wants to continue to develop personally and professionally? Here’s my list of books about executive coaching that have most influenced me.

More about me: I spent ten years at Deloitte Consulting and as a civil servant at HM Treasury. I moved into the technology sector in 2013 and became an executive coach shortly after. I work with founders, CEOs & executives in high-growth technology businesses & the investment industry.

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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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What is the difference between coaching & mentoring?

The words coaching and mentoring are often used interchangeably, though there are in fact important differences. In his book Coaching for Performance the late Sir John Whitmore, explains what the difference between coaching and mentoring is. Whitmore is the founder of the coaching movement in the UK. The book is widely considered to be the industry gold standard for performance based coaching.

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The role of luck & randomness in life & business

Howard Marks is one of Wall Street’s wisest investors. He co-Chairs Oaktree Capital Management which has approximately $100 billion in Assets Under Management. He’s also the author of  The Most Important Thing: Uncommon Sense for the Thoughtful Investor. A highly successful investor, and multi-billionaire in his own right, Marks is clear that luck and randomness has played a key role.

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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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