How Vertical Development helps new leaders truly transform

Have you noticed how awash the internet is with advice from investors and other well-meaning individuals about how to build and lead technology businesses? CEOs and other new leaders need good advice“guidance or recommendations offered with regard to prudent future action” – if they are to stand any chance of building a successful business. There are many core skills that must be acquired, and there is much to be learned from those who have done it before. 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.

In a VUCA world, where information and knowledge is everywhere, it will be individuals and teams who develop their ability to think and act in more complex, systemic, and interdependent ways who will be at the vanguard of leadership and business growth. This post dives into the detail of what Vertical Development is and considers its application to leaders in startup and high growth technology businesses. It ends with three habits of mind that you can develop, as a leader, to help you advance your thinking and leadership capabilities beyond what you know to how you think. This is the place where you truly transform and grow.

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How to develop a leadership culture in your business

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: 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’ve taken on significant investment and 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, in venture capital and private equity-backed businesses, I’ve turned that experience into five pieces of leadership advice.

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8 books that all new leaders should read

Are you a new leader bored by the same old lists of leadership books? Here is a collection of the best books about leadership that will inspire you to think about what it means to lead in a rapidly changing world.

If you would like more book reviews and recommendations, and links to articles and podcasts about leadership, then sign up to my monthly Newsletter.

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4 questions to improve your leadership self-awareness

Many of my coaching clients come to me because they want to understand what type of leader they are now, and identify what they need to do to become a more effective leader in the future. As their executive coach, my job is to act as their guide on this journey of self-discovery and learning, of which improving self-awareness is a key component.

Leadership can be viewed through four principal lenses. Looking at oneself through each lens allows a leader to ‘see’ multiple perspectives and build self-awareness, so forming a more complete picture of their leadership style and presence. The Four Lenses of Leadership mental model asks four questions:

1). How do you see yourself as a leader?

2). How do you think those around you see you as a leader?

3). How do those around you actually see you?

4). How does the literature’s perspective on leadership influence your own?

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The management, leadership & coaching principles of Bill Campbell

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.

This post is a summary of Bill Campbell’s approach towards management, leadership & coaching. For more inspiration, sign up to my monthly Newsletter: a curation of blogs, articles, books and podcasts about the future of business and leadership.

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Survivorship bias, don’t fall for it!

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 what survivorship bias is and how to avoid it.

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A collection of the best articles & books for new leaders

Many of my executive coaching clients are new leaders in startup and high growth technology businesses. They often find themselves thrust into a new leadership role without much previous experience or training to prepare them. The spotlight and responsibility of first-time leadership can be daunting but it is an incredible place to learn. As part of my Executive Coaching and startup specific Founder Coaching services, I curate a reading list of the most insightful leadership articles that I have discovered for clients to read and reflect on. From the thought provoking to the practical, here is a continually updated collection of the best articles and books which will help you grow and succeed in a new startup leadership role.

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The Lindy Effect: a simple heuristic to help you choose your next book

In his book Antifragile: Things That Gain from Disorder (Amazon UK, US), Nassim Taleb provides a simple heuristic, known as the Lindy Effect. The effect simply says: that the expected life of an item is proportional to its past life. You can use this heuristic to help you choose your next book based on the wisdom it might contain.

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How to coach 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.

The author identifies seven questions to ask when taking a coach-approach towards engaging with your team. Rather than spoil the book, I’ll share two challenges that he identifies for anyone seeking to be a better coach-manager or coach-leader.

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Can technology save the American Dream? Lessons from Janesville

Successful businesses today must be technology-enabled and able to compete in a global marketplace. Older businesses must adapt or die. Janesville: An American Story (Amazon UK, US) by Amy Goldstein explores what happens to businesses that don’t adapt and the impact upon the places and individuals that get left behind. An insightful case study of a medical technology company that is incentivised to move to the town, raises the question of whether or not technology can save the American Dream: “the opportunity for prosperity and success, as well as an upward social mobility for the family and children, achieved through hard work in a society with few barriers” (Wikipedia).

Janesville: An American Story tells the story of what happens to an industrial town in the American heartland when its main factory shuts down. The account goes a long way to explaining systemic challenges that are leading to social, economic and political upheaval and broader questions around whether or not technology can save the American Dream.

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What is the impact of technology on babies & young children?

The evidence is irrefutable: the best way to help a baby learn to talk or develop any other cognitive skill is through live interaction with a human being. But what is the impact of technology on young children that are exposed to it? Can an app, an avatar or a 3D cartoon recreate or override human nature? If a child spends too much time being cyber-simulated than connecting with the real world, could it impair other important pre-academic skills such as empathy, social abilities and problem solving? What about a child who spends the bulk of their playtime with an interactive app, in which objects explode, appear, reappear, and don’t play by the rules of the physical world? How does looking at a tablet screen impact an infant’s eyesight?

Cyberpsychologist and author Mary Aiken explores these questions in her book The Cyber Effect (Amazon UK, US). The simple answer to them is that we just don’t know. However, Aiken provides incredible insights into what we do know about child development and how technology could affect it. In the absence of any formal regulatory guidance on technology usage, she shares her own.

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How does your smartphone impact your brain?

The smartphone has become ubiquitous. But what psychological impact does it have on your brain? This is one of the questions that Mary Aiken sets out to explore in her book The Cyber Effect (Amazon UKUS). Aiken is one of the world’s leading experts in cyberpsychology – the study of the impact of emerging technologies on human behaviour.

She is not anti-technology, but does speak with a cautionary tone, identifying potential complications associated with apparently addictive technologies like the smartphone, and urges us to think about what might be done now to mitigate future potential damage before it is too late.

With an intervention [the internet] of this magnitude that had the potential to impact so many aspects of human beings on the deepest and most profound levels – from visual acuity, bonding, and childhood development to identity formation, intimacy and socialisation – I wondered what the blind spots or unforeseen outcomes might be. The unknown unknowns.

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Ray Dalio identifies the 11 characteristics of visionary leaders

Ray Dalio’s book Principles: Life & Work (Amazon UK, US) identifies the author’s organically grown set of principles for building a successful life and business. According to Dalio, principles are fundamental truths that serve as the foundations for behaviour that get you what you want. Dalio also details the personal research he conducted into visionary leadership. Through interviews with the likes of Bill Gates, Reed Hastings and Jack Dorsey, he identified the characteristics of visionary leaders. This post summarises his findings.

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15 books that will make you wiser

My experience with cancer changed my relationship with reading and books. Needing to understand my illness better, I consumed every medical paper I could get my hands on. This knowledge helped me deal with my illness and make wiser decisions as part of my treatment process. If it could help me navigate my illness, could it help me navigate life in general? I transitioned to books about psychology, and then to books about the world around me. Two years of radiotherapy, chemotherapy and several operations means you have a lot of time on your hands. The following books influenced me most.

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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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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 (Amazon UK, US), 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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How to get better at predicting the future

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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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 (Amazon UKUS). 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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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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Daniel Kahneman on the cognitive biases of entrepreneurs

Thinking Fast and Slow (Amazon UK, US) is a book about biases of intuition. It’s ideas are so potent that they won it’s author Danuel Kahnemann a Nobel in economics. Kahneman identifies that the human brain works very well most of the time and our judgments are sound. However, it is prone to engage in a number of fallacies and systematic errors that lead to flawed opinions and adverse decision making, otherwise known as cognitive biases. We assume certain things automatically without having thought them through carefully. Kahneman calls these assumptions heuristics and, for entrepreneurs, they can be deadly. An awareness of them is the first step to countering them.

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The best business & leadership quotes from ‘Shoe Dog’ by Phil Knight

Phil Knight is the founder, former CEO and now Executive Chairman of Nike. In Shoe Dog: A Memoir by the Creator of Nike (Amazon UK, US) he tells his story of taking the business from humble origins, through an IPO in 1980 and onto its current $30 billion market capitalisation.

Nike is still widely regarded to be one of the most innovative companies in the world. Phil Knight started and grew the business out of the back of a van in the early 1970s. A Stanford graduate, avid reader of the Classics and books about military strategy, and a natural introvert, he captures a wonderful story about what he calls his Crazy Idea and the determination and grit it takes to become successful beyond what he’d ever imagined. In Shoe Dog, he also includes some wonderful accounts of the hustle and sometimes downright dirty tactics that it can take to overcome the odds: “you are remembered for the rules you break” is his mantra throughout the book. I’ve captured the best of the rest of his business and leadership wisdom in the quotes from the book below.

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Yuval Harari explains the Capitalist Creed

Yuval Harari’s book Sapiens: A Brief History of Humankind (Amazon UK, US) charts our origins from hunter gatherers 2.5 million years ago on to the rise of Homo Sapiens 200,000 years ago. He takes the reader through the Cognitive Revolution 70,000 years ago, the Agrarian Revolution 10,000 years ago, into the Scientific Revolution in the 1500s, the Industrial Revolution in the late 1700s and on to the present. Harari covers a lot of ground that includes a deep dive into capitalism: “an economic-led system based on private ownership of the means of production and their operation for profit”. He explores how something that began as a theory about how the early economy of the modern age functioned, has grown into much more than an economic doctrine.

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Cancer & Entrepreneurshit

On 13th February 2015 I was diagnosed with Stage 3 colorectal cancer. At the beginning of August this year my treatment was complete. After nearly two years of grappling with a life-threatening illness, whilst at the same time hanging on to the bones of a business that I had set up just eighteen months before diagnosis, it is time to embrace the new normal. This is my story about cancer and entrepreneurshit. Continue reading

How to be a great mentor

What does it take to be a great mentor? Talking at the launch of the Forward Partners mentor network event I shared my thoughts about mentoring entrepreneurs (Forward Partners are a leading London-based early-stage venture capital firm). I talked about the importance of listening and understanding, before giving advice, and suggested some questions that mentors can ask to helpfully open up a mentor conversation.

I started with a quote from Sal Virani’s recently released book Mentor Impact. Based on over 200 mentor interviews and extensive personal experience of working with accelerator programmes across Europe, he launches the book with a quote from one of the best mentors he interviewed (also a founder who had been through an accelerator programme). That person’s advice to other mentors: Continue reading

Cancer & Entrepreneurship

Disillusioned with the corporate world and mesmerised by a whole season living in my campervan in the French Alps, I decided it was time for another change. In September 2013 I resigned from Deloitte Consulting and set up my own business as an entrepreneur coach. After five months spent climbing and skiing consequential lines, my rationale was simple: entrepreneurship was going to push me hard and I might end up penniless, but I’d learn a lot and it couldn’t kill me. On that basis, and with some ideas about how I’d grow my business in mind, the decision was made. Just 18 months into my entrepreneurial journey I was told I had Stage 3 colorectal cancer. That most definitely could kill me and I was petrified.

I don’t want to use my illness to define me but it hit at a very specific time in my life. Given the craziness of the experience, it feels like a missed opportunity not to share it and raise awareness. I didn’t keep a diary, so this is an opportunity for memories and personal reflection. I have also recorded a Podcast with Jerry Colonna and the gang at Reboot, a coaching company that helps people to deal with the internal ups and downs of entrepreneurship.

This is my story of being an entrepreneur with cancer.

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Calling BS on the Startup Cockroach

The startup world loves a buzzword and now we have a new one. Whilst I understand the sentiment behind it, I’m not sure it’s particularly helpful. Posts by Caterina Fake and Adam Draper about the Cockroach caught my positive attention, but on reflection I’m perplexed. A Cockroach is supposedly the name given to startup that makes it through current economic challenges. The origin of the term lies within a Paul Graham post written in October 2008. about why to start a startup in a bad economy. Since then we’ve moved on to the Unicorn phenomenon.  Mark Suster has written about why he Fucking Hates Unicorns. I’ll follow up by saying that I’m not a huge fan of the Cockroach. Continue reading