A CEO once described to me how isolated they felt, “trapped somewhere between my Board and investors looking down at me, and my team looking up.” It wasn’t an issue of authenticity, they just couldn’t be as completely candid with their Board or team as they could be with me, their executive coach. There are lots of reasons that people decide they want to work with an executive coach, but what exactly is the role of an executive coach, and how should you find and choose the right one for you?
15 of the best articles about leadership for a startup CEO
As an executive coach, I help startup founders, and founding teams, navigate their transition to leadership. If you are a startup CEO or other early member of the leadership team, you often find yourself thrust into the spotlight of leadership without much prior experience or training.
As part of my Scaling Leadership coaching programme, I curate a reading list of leadership articles for clients to read and reflect on. From the thought provoking to the practical, here are 15 of the best articles to help you transition from founder to startup CEO or other member of the leadership team.
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 that they might contain.
Continue reading15 of the best books about executive coaching
Are you a manager or leader who wants to develop your coaching skills, to use with your employees? Are you already an executive coach investing in your personal and professional development? Here is a list of the best books about executive coaching.
Continue readingAdopt these 3 habits of mind to become a better leader in a complex world
Jennifer Garvey Berger is an expert on adult development theory as it relates to leadership. In her book Changing on the Job: Developing Leaders for a Complex World (Amazon UK, US) she identifies a four-stage path to growth that an individual might take to develop a more complex form of mind. She also identifies three specific habits of mind that a leader should cultivate to allow them to better navigate a world of increasing complexity and ambiguity.
Changing on the Job is written for people who really want to understand the shape and features of adult growth so they can either support their own growth and development or support the growth and development of others. Being a book about complexity, not simplicity, it avoids the temptation to provide a prescription for achieving a self-transformed form of mind. Instead, it really gets under the hood of what it takes to be a true leader with developed forms and habits mind.
Read on to learn more about adult development theory and to discover how asking different questions, taking multiple perspectives & seeing the system will help you become a more effective leader.
Continue readingDo 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 coaching 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.
Continue readingCan 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.”
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.
Continue readingWhat is the impact of technology on babies and 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. If you’re interested in how technology affects you, check out my previous post about how your smartphone impacts your brain.
Continue readingHow 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 UK, US). 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.
Continue readingWith 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.
Ray Dalio identifies the 11 characteristics of visionary leaders
Ray Dalio’s book Principles: Life & Work (Amazon UK, US) begins with a brief autobiography before quickly moving on to identify his organically grown set of principles (fundamental truths that serve as the foundations for behaviour that gets you what you want) for building a successful life and business. As the founder of Bridgewater Associates, one of largest hedge funds in the world with approximately $160 billion of Assets Under Management, Dalio’s ideas are worth listening to. Although Bridgewater itself has been criticised by some for being cult-like (its culture built on the foundations of Radical Truth and Radical Transparency), that Dalio began the company in his two bedroom apartment in New York in 1975, makes him not just one of the world’s greatest investors but also one of the world’s greatest entrepreneurs and leadership visionaries.
You should read Dalio’s book to learn about his principles and consider your own – “because we all have our own goals and our own natures, each of us most choose our own principles to match them”. This post will focus on the fascinating research that Dalio himself undertook into what he calls shapers.
Continue reading15 books that will make you a wiser person
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 more informed 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, all in the hope that they would me become wiser. Two years of radiotherapy, chemotherapy and several operations means you have a lot of time on your hands. The following books influenced me most.
Victor Frankl on 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 the meaning of human existence 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.
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 are. 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.
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 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 make predictions and become a superforecaster.
Continue readingHoward Marks & Nassim Taleb on the role of luck & randomness
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 UK, US). A highly successful investor, and multi-billionaire in his own right, Marks is clear that luck has played a key role. I explore his perceptions of luck in this post.
Continue readingHoward Marks on second level thinking & being a contrarian
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 if you want 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.
Continue readingPaul Kalanithi teaches us why technical excellence is not enough
Paul Kalanithi, M.D., was a neurosurgeon and writer. He graduated from Stanford University in 2000 with a B.A. and M.A. in English Literature and a B.A. in Human Biology. He earned an M.Phil in History and Philosophy of Science and Medicine from the University of Cambridge before attending medical school. In 2007, Paul graduated cum laude from the Yale School of Medicine. He returned to Stanford for residency training in Neurological Surgery and a postdoctoral fellowship in neuroscience. In 2013 he was diagnosed with stage IV lung cancer, though continued to work, completing his neurosurgery residency in 2014. He also authored the book When Breath Becomes Air, which detailed his journey through treatment and eventually his death in March 2015. He is survived by his wife Lucy and their daughter Cady.
Although I’d heard of this book before, I first stumbled across it in a charity shop about one month after I’d finished 5 months of chemotherapy for colorectal cancer. I cried my way through much of the book, but I had to read about Paul’s journey and his exploration of life and death. Continue reading
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.
Continue readingDaniel 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.
Continue readingThe best 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.
Continue readingYuval Harari explains the Capitalist Creed
Yuval Harari’s book Sapiens: A Brief History of Humankind 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. Continue reading
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.
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
Advice for startups: do one thing really well
The June 2015 edition of Wired magazine leads with “41 lessons from Uber’s success”. Leading industry commentators shared their opinions, but it was Josh Elman from Greylock Partners that hit it out the park. Reflecting on Uber, his advice is to: “Do one thing really well – then figure out what the second leap is”. You can say what you like about Travis Kalanick, but that’s some of the best startup advice you will ever hear.
The most successful companies did this. Elman cites Facebook’s beginnings as a private social network at colleges, before the company realized that the news feed could help propel the site into a massive multi-billion-user, multi-billion-dollar company. Uber, he says, was the same thing: Continue reading
Do management consultants add value?
Sam Altman is the President of Y-Combinator, an American seed fund with investments in over 840 companies including Dropbox, Airbnb, Stripe, Reddit, Zenefits, Instacart and Weebly. Sam sent a Tweet out the other week expressing the view that consultants get paid the most money whilst delivering the least value. Sam is of course entitled to his perspective but I’m not comfortable with it.
Continue readingWhat is the definition of focus?
An inspiring idea and early validation of your business model are just the start of the entrepreneurial journey. When it comes to scaling, there are a thousand and one things that you could do, but you must focus on the one hundred and one things that you can actually do with limited available cash, resources and time. In Tren Griffin’s blog A Dozen Things I’ve Learned from Steve Jobs about Business, he references one of my favourite quotes from the great man, and a second that I’ve not heard before.
10 of the best posts about startup Boards
Startup Boards can be a contentious subject. Do you even need a Board in the early stages? When the time comes to introduce more effective governance arrangements, how do you go about attracting the right Board members and developing a high-performance Board culture? There’s no magic wand that you can wave at your governance challenges, and you will find lots of different answers to the same governance questions.
Here’s my list of 10 articles on the subject of startup Boards that I’d really recommend reading. Continue reading
Why you should always begin with the end in mind
I picked up my copy of The 7 Habits of Highly Effective People by Stephen Covey the other day. I remembered that one of Covey’s principles was to begin with the end in mind and I’ve been doing some detailed thinking recently about what my own end is, so to speak. It struck me that there’s some useful lessons in the book about how to grow a business in 2015.
Covey says that beginning with the end in mind is based on the principle that all things are created twice. First a mental creation, then a physical creation. He uses the example of building a house: “you create it in every detail before you ever hammer the first nail in place” he says. Continue reading