What could Kobe Bryant have taught you about being a better CEO? What can you learn from Bill Belichick about driving your team’s performance? With their shared focus on performance and winning, and because our brains are wired to think in analogies and metaphors, it’s quick and easy to draw comparisons between sport and business leadership. But it can also be lazy and problematic.
Continue readingCategory Archives: Entrepreneurship
8 ways to boost your Executive Presence in the C-Suite
Congratulations, you’re now a member of the C-suite, 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 founders, experienced CEOs and other senior executives come to me to help them work on their executive presence to support the next stage of their leadership development.
Continue readingThe 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 polarities 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.
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 back. With these practical examples, you’ll gain a greater understanding of how to identify and work more effectively with polarities.
Continue reading8 Executive Time Management Techniques for CEOs
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.
Continue readingA 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).
Continue readingA 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
Cynefin: a decision making framework for leaders
There’s no shortage of “how to” advice, playbooks, formulas and even secrets and guarantees for business 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 growing and leading a business, explored here through the lens of the Cynefin framework.
Continue readingLearning to think for yourself
Advice is everywhere, everyone has an opinion. It’s what to do with it that’s hard. If you want want to be your best self, then need to stop listening to what everyone else tells you and learn to think for yourself. 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.
Continue readingHow can leadership team coaching help your technology business scale?
In his 2017 TED Talk Want to get great at something? Get a coach, 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?
Continue readingWhy 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.
Continue readingHow 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.
Continue readingTrillion 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.
Continue readingHow 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, a cognitive error that occurs when we focus on the people or things that have “survived” a particular process while overlooking those that did not, which leads us to incorrect conclusions about a situation or phenomenon.

Table of Contents
A collection of the best articles 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 and startup specific founder 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 which will help you grow and succeed in a new leadership role.
Ray Dalio identifies the 11 characteristics of visionary leaders
Ray Dalio’s book Principles: Life & Work 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, Jack Dorsey and Elon Musk, he identified the characteristics of visionary leaders. This post summarises his findings, with a particular focus on ‘shapers’, as Dalio refers to them.
Continue readingSecond-level thinking & how to get better at it
Second-level thinking is a deep and complex approach to decision-making that goes beyond superficial analysis. Second-level thinkers ask probing questions and consider multiple perspectives to gain a more comprehensive understanding of a situation. They examine a range of potential outcomes, assess probabilities and compare their views to the consensus. They uncover insights that others may overlook, allowing them to make more informed decisions and achieve superior results. By thinking unconventionally and holding well-reasoned, non-consensus views, second-level thinkers position themselves to succeed in investing, business and life.
But how do they do it? Howard Marks is the Chairman and cofounder of Oaktree Capital Management and one of the finest purveyors of second-level thinking (sometimes referred to as second-order thinking). In his book The Most Important Thing: Uncommon Sense for the Thoughtful Investor, Marks explains why second-level thinking is so important and how you can get better at it.
Continue readingDaniel Kahneman on the cognitive biases of entrepreneurs
Thinking Fast and Slow is a book about biases of intuition. It’s ideas are so potent that they won it’s author Danuel Kahneman 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 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 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 readingCancer & 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
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
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.
Continue readingRisk 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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