Category Archives: Entrepreneurship

A Deliberately Developmental Experiment

When the founders at Upside approached me to develop a business-wide coaching programme, they were clear they wanted to do something different. It felt appropriate that a scaling company that puts talent and the development of talent 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).

This article unpacks how we developed a deliberately developmental coaching programme for Upside, and what we’ve learnt so far along the way. If you’re a leader in a high-growth startup who wants to know how to embed a deliberately developmental culture in your business, or if you’re interested in DDOs generally and would like to learn more about them through a real life example, then join us on this journey of discovery.

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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:

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.
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.
Self-relating – Observing, understanding, regulating and transforming yourself e.g. making sense of your own reactions, thoughts and feelings.
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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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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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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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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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: 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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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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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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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.

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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, 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.

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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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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 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.

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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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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 →

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 →

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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