May 21

UpSkill Digital’s 2019 reading list, curated by our network of transformation experts

We’d love to share our 2019 reading list, curated by our network of transformation experts. 

Business and leadership

  1. Trillion Dollar Coach: The Leadership Handbook of Silicon Valley’s Bill Campbell by Eric Schmidt, Jonathan Rosenberg and Alan Eagle.  
  2. Start with Why: How Great Leaders Inspire Everyone to Take Action (Hardcover) by Simon Sinek
  3. Hooked: How to Build Habit-Forming Products by Air Eyal
  4. Inside the Nudge Unit: How small changes can make a big difference by David Halpern  – explains how to consider behavioural science to nudge and encourage positive behaviours from inside the UK’s Behavioural Insights Team unit.
  5. Leaders Eat Last: Why Some Teams Pull Together and Others Don’t  30 Jan 2014 by Simon Sinek –  a good read, with case studies, especially as we lead new generations entering the workforce with different needs from the workplace, at the same time as we have 5 generations working side by side.

Understanding ourselves and our workforce

  1. Elastic: Flexible Thinking in a Constantly Changing World by Leonard Mlodinow – how the human mind deals with change, very timely for the world we live and work in.
  2. Drive: The Surprising Truth About What Motivates Us Daniel H. Pink – covering high performance and satisfaction in today’s world.
  3. Flow: Living at the Peak of Your Abilities Mihaly Csikszentmihalyi PhD – a 30-year-old seminal work on a state of being that involves working at your full potential.
  4. Thinking, Fast and Slow Paperback by Daniel Kahneman – “A tour de force is a must-read for anyone interested in either human behaviour or investing.” ―Larry Swedroe, CBS News.

The Future of work

  1. The 100-Year Life: Living and Working in an Age of Longevity by Lynda Gratton – this reframes how we associate age and work-life stage, and how we must reframe the 3 stage life model of education, work, retirement – future of work, named business book of the year 2016.
  2. Reinventing Organizations: A Guide to Creating Organizations Inspired by the Next Stage in Human Consciousness by Frederic Laloux – this book shows that every time humanity has shifted to a new stage of consciousness in the past, it has invented a whole new way to structure and run organisations, each time bringing extraordinary breakthroughs in collaboration.

Food for thought – the world, the future, ourselves

  1. Skin in the Game: Hidden Asymmetries in Daily Life Nassim Nicholas Taleb – this has practical elements and plenty of examples of the concept as Taleb says, “The symmetry of skin in the game is a simple rule that’s necessary for fairness and justice and the ultimate BS-buster,” and “Never trust anyone who doesn’t have skin in the game. Without it, fools and crooks will benefit, and their mistakes will never come back to haunt them.”
  2. The Black Swan: The Impact of the Highly Improbable Nassim Nicholas Taleb – the impact of unpredictable events, with examples, such as 9/11.
  3. Antifragile: Things that Gain from Disorder by Nassim Nicholas Taleb – ideally read after The Black Swan, this explains how we need to be in a complex and VUCA.
  4. Sapiens Yuval Noah Harari – the history of humankind.
  5. Bullshit Jobs: A Theory  – 15 May 2018 by David Graeber – based on the essay “On the Phenomenon of Bullshit Jobs.” which went viral. After a million online views in seventeen different languages, people all over the world are still debating the answer.

Transformation and the impact technology

  1. Technology vs. Humanity: The coming clash between man and machine (FutureScapes) Leonhard, Gerd – about the exponentially growing and pervasive impact of technology on humanity.
  2. A Whole New Mind: Why Right-Brainers Will Rule the Future – 17 Apr 2008 by Daniel H. Pink – The future belongs to a different kind of person with a different kind of mind: artists, inventors, storytellers-creative and holistic “right-brain” thinkers whose abilities mark the fault line between who gets ahead and who doesn’t.


  1. Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days by Jake Knapp , John Zeratsky , Brad Kowitz – process, practical, new ways of working, reframing risk, this is a step by step guide for running a sprint to solve big challenges- trust us, this method REALLY works.