Giving a damn: Five must-read books to lead your team to success

As this strange year draws to a close, I’ve been reflecting on my experience as COO of Riverlane. I had never worked at a tech start-up before joining Riverlane and I threw myself headlong into the experience, learning on the job and reading everything I could get my hands on about how to expand and empower teams in a fertile entrepreneurial habitat. However, after 18 months, a towering pile of management and start-up books threatens to overshadow my desk.

I’ve highlighted hundreds of sentences in over 30 books but I’m afraid that much of my reading has blurred into one fluorescent-pink mess. It’s been hard to know where to start (and when to stop!). In truth, there were only a few stand-out books – ones that have stayed with me and proved useful on my start-up journey – and they were easy to pull out of the pile on my desk.

So, to save others time, I’m sharing those books here (I’ve also posted these thoughts on Linkedin). Written from the perspective of a generalist COO and aimed at managers joining a high-growth start-up, here are my top five books:

Scaling up

First up is Tech Nation’s book ‘Upscale’ written by James Silver. I read this in my first month at Riverlane and it’s a book I’ve come back to time and again. Based on interviews with the UK’s top technology entrepreneurs and investors, 26 digestible chapters focus on the major themes that arise when you move from ‘start-up’ to ‘scale-up’. The book offers practical advice on everything from building a talent pipeline to the importance of brand and the thorny question of when to set up an international office.

Everything mentioned in the book has come to pass, in one way or another, as we’ve grown from 6 to 24 team members at Riverlane over the past year. And I know it will help us as we scale even more quickly in 2021! This is my top start-up book recommendation.

Being candid

The second book I’d recommend is ‘Radical Candor’ by Kim Scott. I first read this book when it was published in 2017 and I’ve read it every year since. While it draws heavily on tech company examples, it’s basically a clear and practical navigation tool for anyone who manages a team. The first half outlines Kim’s management philosophy on giving praise vs criticism, and how to do both well. The second half provides a step-by-step approach for building ‘radically candid’ relationships with your direct reports, with the ultimate aim of guiding and inspiring your team to achieve top results.

I love the book because it speaks to my core beliefs about being a manager: about giving a damn, about sharing more than just my work self, and about caring about everyone who works for me. As someone who has tended towards ‘ruinous empathy’ in the past, Radical Candor also inspires me to ‘challenge directly’ and ‘care personally’. Just as importantly, the book is also hugely practical. Its tips and tricks have helped me navigate communication challenges in both my working and my personal life. A must-read for all line managers!

Navigating venture capital

Do you know your ‘pre’ from your ‘post’ money? Can you navigate a ‘term sheet’? And do you understand why investors keep mentioning LPs? I thought I knew quite a bit about fundraising before joining Riverlane, but it turns out that venture capital is a completely different ball game to research grants and philanthropic fundraising.

There are loads of great articles about ‘venture capital and how to get it’, but I recommend you save yourself the time and start with the bible: the ‘Secrets of Sand Hill Road’ by Scott Kupor. Everything you need to know in one place, from pitching to choosing investors to navigating that all-important term sheet. It’s US-centric, and the detail gets heavy at times, but it delivers practical takeaways on VCs that every entrepreneur needs to know.

Leading with vulnerability

My fourth recommendation is ‘Dare to Lead’ by Brené Brown. My best friend brought this for my 40th birthday earlier in the year, and it’s one of those books I wish I had written myself. Brené writes about courage, vulnerability, shame and empathy in relation to leadership. She reminds us that we’re all ‘emotional beings’, whether we like it or not. Her work has helped me navigate the start-up world, where emotions can often run high, and has also proved useful in these covid times. Current favourite quote:

“In the midst of uncertainty and fear, leaders have an ethical responsibility to hold their people in discomfort – to acknowledge the tumult but not fan it, to share information and not inflate or fake it. Daring leaders acknowledge, name, and normalise discord and difference without fueling divisiveness or benefitting from it.”

Un-learning

My final book recommendation is ‘Survival to Thrival’ by Bob Tinker and Tae Hea Nahm. This book focuses on people – the CEO, the leadership team, the wider team and the board – and how their role changes as a start-up evolves. It uses comic-book and action-movie analogies to guide you through their thinking.

The book reaffirms something I have always believed – that ego is the enemy of leadership – but also, more radically, that you have to be able to constantly re-conceptualise your role as a company grows. The authors normalise the challenge of ‘change or be changed’ – an ever-present tension in a start-up – and argue that the key to success is unlearning as your company scales. This thought would have scared me when I was younger, but it now feels freeing and exciting.

Riverlane is currently at the “Captain America / Avengers” phase of the start-up lifecycle. I’ve no idea what my role will look like when we move into the “Professor X / X-Men” phase, but I’m looking forward to finding out! Herein lies both the beauty and challenge of working for a start-up; embracing and harnessing the uncertainty of the journey while driving an ever-expanding vehicle for changing the world.

Conclusion

Going through my top five management and start-up books was an insightful exercise. By taking the time to step back, I’ve gained some perspective on my start-up journey. So, what are my key takeaways?

  • While every start-up is unique, it’s a well-trodden path from the box-room to the boardroom and managers face the same types of problem on their journey. There’s no need to go it alone – get reading and start building connections.
  • Start-ups are all about people: recruiting them, retaining them, supporting them, and inspiring them. This takes work to do well and managers need to be brave and bold, whilst acknowledging that they are vulnerable and don’t have all the answers.
  • Being a manager at a start-up is a tremendous amount of fun and enormously hard work. Shoving your ego to the side is a helpful first step. Then get ready for a profound growth experience: “a deeply personal mixture of learning and unlearning about what it means to be a leader” (Survival to Thrival).

 

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