Five Leadership ‘Books’ That Have Shaped the Way I Work, by Growth Stage Investor Serena Dayal

I’m Serena Dayal, a growth-stage investor, currently based in Silicon Valley. 

I was asked to share my favourite leadership books with the GBX membership and I’ll confess, I’ve taken a liberal interpretation to the assignment. While I’m an avid reader, I find many business books would be better served in summarised bullet points and delivered via memo. So, not all of these suggestions are in traditional book format. I’ve included an ongoing newsletter, a video ed-tech series and a diary among my recommendations. I, like many of you, live and work in the U.S. but I’ve made sure to include some Brits in the line-up too!

All of these are relevant to anyone leading a team, building a business or engaging in high-level, strategic decision-making. These are all pieces I’ve leaned on at various junctures in my career, first as an investment banker and private equity investor on Wall Street and now in my roles as a growth investor, board member and manager of a team.

Some are analytically rigorous; some are inspiring. I’ve come back to each repeatedly. And, I hope you’ll notice that they all place emphasis on the ‘how.’ 

Happy leading!

 

1. The Art of Negotiation, Chris Voss on Masterclass

Most things in life, and certainly in business, can be viewed as a negotiation. Chris Voss, a former lead international hostage negotiator for the FBI, walks through the ‘why’ and the ‘how’ of successfully negotiating in this 18-part video series. With role-play and real life examples, Voss teaches the strategic application of emotional intelligence and dissects how collaboration and tactical empathy can lead to meaningful trust-based influence. He’s also written a book, Never Split the Difference.

Invaluable for: negotiating your next enterprise contract, term-sheet or compensation discussion.

 

2. Invisible Women by Caroline Criado Perez

Much of the big data underlying our most ubiquitous systems is subject to gender-bias. We rely on this biased data to make many critical decisions, leading to often hidden sources of gender inequality. Criado Perez explores how the impact of this data is felt across industries, from medicine to consumer products to voice recognition and computer vision software. She also highlights how this inaccurate data leads to inaccurate predictions and can even affect human rights. 

Invaluable for: anyone investing in or building product with a meaningful application of AI.

 

3. Wes Kao’s Newsletter on Substack

Wes Kao is a marketing executive, entrepreneur and co-founder of Maven, an ed-tech platform. Her Wednesday newsletter is packed with accessible marketing and management advice, starting at the strategic and drilling down to the tactical. It is targeted towards those executing within fast-moving organisations. Some of her most popular posts cover negative inception (how to not incept negative ideas—something we all do—into our pitches and work conversations), inspiring your team to think rigorously and providing ‘super-specific’ feedback.

Invaluable for: Marketers, product-people and leaders in tech; anyone working in a start-up org.

 

4. The Vanity Fair Diaries by Tina Brown, CBE

On the face of it this might seem like an insight into power-brokering in the 1980s—and it is, but it’s also so much more. Tina Brown, British ex-pat and Editor-in-Chief of Tatler, Vanity Fair and The New Yorker, recounts her day by day blocking and tackling as she turned around Vanity Fair for Conde Nast in New York between 1983 and 1992. You can read it chronologically or slip in an out of it as I do. Any given diary entry is a real-time cataloguing of CEO-level decision-making, providing remarkably detailed insight into how to execute on a vision to build a successful and long-lasting business.

Invaluable for: Anyone leading an organisation or a team who must grapple with strategic and tactical decisions on a daily basis.

 

5. It Was All a Dream by Raheem Sterling

You may be familiar with this personal essay from 2018, published in The Player’s Tribune. Sterling charts the course of his early life, from moving to England from Jamaica at 2 years old, to learning to play football, to making the England Squad. Central to this essay are the people who got him to where he is, the importance of grit, and the lesson that with perseverance and hard work, you can overcome great odds. 

Invaluable for: anyone trying to build something meaningful who’s currently in the thick of it.