15 of the best articles about startup leadership

As an executive coach, I help startup founders, and founding teams, navigate their transition to leadership. If you are a startup CEO, CTO, COO 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.

1. The First Rule of Leadership

Ben Horowitz is a former CEO and a founding partners at Andreessen Horowitz, one of the world’s leading venture capital firms. He emphasises the importance of individuality and self-determination.

In order to be a great leader, you must be yourself. If you try to be someone else, not only will you not be able to lead, but you’ll be ashamed to have people emulate you.

2. What a CEO does

This short but classic post from Fred Wilson will help you think about your most important responsibilities as you transition to CEO.

A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.

3. Notes on Leadership

Another post by Ben Horowitz on the a16z blog. He says that leadership is the single most important attribute required to be a successful founding CEO. Horowitz identifies and explains the three key traits that he looks for in a CEO.

1. The ability to articulate the vision
2. The right kind of ambition
3. The ability to achieve the vision

4. How to Scale: Do Less Lead More

Ed Batista is an executive coach based in San Francisco. Based on his years of experience working with startup and early-stage entrepreneurs, he explains how to transition from a hands-on leader who personally gets things done to someone who leads in a different way in order to be more effective as the organization scales.

The challenge is that throughout our education and in most, if not all, of our early professional roles, we’re rewarded for our effectiveness as doers, and when we achieve a more senior position we often assume that our effectiveness as leaders will rely upon the same skills and characteristics that have fueled our success up to that point.But this can result in the illusion of effectiveness as a leader. We may believe that by working longer, harder, smarter–pick your superlative–than our team on a given set of tasks, we’ll inspire by example. We just need to keep doing what we’ve been doing, albeit at a higher level.

5. How Your Leadership Has to Change as Your Startup Scales

Many startup CEOs adopt [a] “visionary entrepreneur” leadership style. They set out a broad vision, provide lofty goals, and model an ambitious work ethic. And at this stage in a company’s growth, it generally works. Just being close to the founders — working alongside them, being in meetings where there is a personal connection — tends to motivate and inspire young staff. Early employees feel that they belong to a special “club.” Yet keeping enthusiasm up as the company grows is difficult, especially as the direct link between founders and employees becomes less tangible or less possible (when opening remote offices, for example). As a result, many startups that experience zero turnover during the first year or two suddenly find themselves dealing with as much as 40% turnover in year three.

In this article, executive coach and professor of leadership at NYU Jeffrey W. Hull identifiers four things leaders and their organizations can do to move from startup mode to scale-up mode and transition as a leader.

6. In Praise of the Incomplete Leader

A seminal leadership article from the Harvard Business Review for new and emerging leaders on a transition to mastery.

Have you ever feigned confidence to superiors or reports? Hidden the fact you were confused by the latest business results or blindsided by a competitor’s move? If so, you’ve bought into the myth of the complete leader: the flawless being at the top who’s got it all figured out. It’s an alluring myth. But in today’s world of increasingly complex problems, no human being can meet this standard. Leaders who try only exhaust themselves, endangering their organizations. [The authors] suggest a better way to lead: Accept that you’re human, with strengths and weaknesses.

7. What Makes a Leader?

Emotional intelligence (EQ) needs no introduction by now. In this article, Daniel Goleman, explains the five skills that enable the best leaders to maximize their own and their followers’ performance.

1. Self-awareness – knowing one’s strengths, weaknesses, drives, values, and impact on others

2. Self-regulation – controlling or redirecting disruptive impulses and moods.

3. Motivation – relishing achievement for its own sake.

4. Empathy – understanding other people’s emotional makeup.

5. Social skill—building rapport with others to move them in desired directions.

8. How Humble Leadership Really Works

Servant leadership has gained traction in recent years as styles have switched from that of command and control to something that accepts that the world is inherently uncertain and unknowable. Businesses are also increasingly staffed by individuals who may have higher IQs and technical skills than the leadership team but they still need to be led.

Servant-leaders have the humility, courage, and insight to admit that they can benefit from the expertise of others who have less power than them. They actively seek the ideas and unique contributions of the employees that they serve. This is how servant leaders create a culture of learning, and an atmosphere that encourages followers to become the very best they can.

9. How to be a better leader in a complex world

This is my own post, in which I draw on leadership expert Jennifer Garvey Berger’s application of adult development theory to complexity and leadership.

The best way to develop and grow your form of mind is through adopting transformational habits of mind. Cultivating these three habits of mind will lead to lasting change: asking different questions, taking multiple perspectives and seeing the system. As we develop these habits, we grow.

10. Carol Dweck: A Summary of The Two Mindsets And The Power of Believing That You Can Improve

Carol Dweck is a psychology professor at Stanford. She studies human motivation. She is most famous for her work on fixed and growth mindsets. People with a fixed mindset believe talent is everything. If they’re not gifted with the ability to do something, they think they’re doomed to be a failure. Their skills seem to be written down in their genes, just like their looks, which is why they never try to improve in something they’re not good at. People with a growth mindset, however, believe that whatever they want to achieve is theirs for the taking, as long as they work hard for it, dedicate themselves to their goal and practice as much as they can.

It’s very helpful to have a growth mindset as an entrepreneur, and as a leader. Understanding Dweck’s work will help you grow in both disciplines. 

11. The Psychological Price of Entrepreneurship

Like a growth mindset, optimism is a virtue. But founding and building a business is one of the toughest things anyone can do. It’s important to remember and embrace that as you undergo your transition.

Successful entrepreneurs achieve hero status in our culture. We idolize the Mark Zuckerbergs and the Elon Musks. And we celebrate blazingly fast growth. But many of those entrepreneurs harbor secret demons: Before they made it big, they struggled through moments of near-debilitating anxiety and despair–times when it seemed everything might crumble.

12. Imposter Syndrome – The dark side of leadership

I am afraid I will be found out for being a fraud.

Google ‘imposter syndrome’ and you will find lots of helpful articles onthe subject. It is one of the most common conversations that I have as a coach. I chose this article because it highlights the affliction in the context of leadership, shows that people suffer from it at all levels of leadership and explains the science behind it.

13. Getting Beyond the BS of Leadership Literature

“All models are wrong but some are useful” said the British statistician George Box. Many leadership models exist. I encourage my clients to explore them and think about what they mean for their own style rather than become attached to any particular one. In this Mckinsey article Stanford Professor Jeffrey Pfeffer explains:

This consuming interest in leadership and how to make it better has spawned a plethora of books, blogs, TED talks, and commentary. Unfortunately, these materials are often wonderfully disconnected from organizational reality and, as a consequence, useless for sparking improvement.

The thought provoking article sets the tone for thinking about you frame your own leadership style. It also has some excellent suggestions for alternative books on the subject of leadership beyond the usual literature and commentary.

14. The Leadership Framework: Do Management Bestsellers provide Applicable Insights for CEOs?

Steven Dunne, of Frog Capital, makes a similar point:

The framework is a core selling point of many management books and having a structured is undoubtedly useful. However, the issue remains that there is no strong evidence proving causation between use of the methods proposed and success – despite the certainty that the authors imply… Don’t take management books as gospel. Instead, take the academic approach and read with a critical eye.

15. Solitude & Leadership

An inspirational final read on how to avoid being an “excellent sheep”, being “able to think independently, creatively, flexibly” so that you can “deploy a whole range of skills in a fluid and complex situation” and “have the confidence, the courage, to argue for ideas even when they aren’t popular.”

Solitude is the very essence of leadership. The position of the leader is ultimately an intensely solitary, even intensely lonely one. However many people you may consult, you are the one who has to make the hard decisions. And at such moments, all you really have is yourself.

If you enjoyed this, you might like:

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Ray Dalio is the founder of Bridgewater Associates, one of largest hedge funds in the world with approximately $160 billion of Assets Under Management. In this post I summarise the 11 characteristics of visionary leaders that he identifies in his book Principles: Life & Work (Amazon UKUS) .