An unsent, deeply self-recriminatory letter penned two years ago by Uber founder and former CEO Travis Kalanick has surfaced online.
The 2,000-word missive – which Kalanick had intended to share with Uber staff, but then shelved – was made available to tech journal Gizmodo  by New York Times reporter Mike Isaac: author of a newly published account of the ride-hailing firm’s meteoric rise and leadership traumas, Super Pumped: The Battle for Uber.
Written towards the end of Kalanick’s reign at the firm – when it was mired in business difficulties, lawsuits and a cultural implosion – the letter is piercingly honest about all the areas in which he thinks he went wrong as leader, amounting to a laundry list of ‘if onlys’ about the way he set up and ran the brand.
“When Uber took off,” Kalanick writes, for the first time in my life I was leading an organisation that wasn’t on the brink of failure each day. In just the last three and a half years, our service and our company has grown at an unprecedented rate … [however, as] we grew, I held on to too many things that helped me survive and build a great company, but at scale became ever-increasing liabilities.”
For example, he notes: “I put growing our business ahead of properly scaling our internal culture and organisation. I approached decisions as transactions, instead of opportunities to build relationships with our drivers, riders, communities and [the] cities we serve. I favoured logic over empathy, when sometimes it’s more important to show you care than to prove you’re right. I focused on getting the right individuals to build Uber, without doing enough to ensure we’re building the right kind of teams. I was too focused on making Uber feel like a small company even after we got big.”
He is particularly withering on what he calls an “avalanche of organisational debt” that built up from management misfires, listing six, key failings:
- Too many first-time managers, with 63% of all managers having never managed before;
- Great managers given more responsibility than they were ready for;
- Processes that didn’t scale for the size or complexity of the organisation (procedures for a 400-person company, Kalanick notes, cannot work at a firm of 14,000);
- HR staff and systems that didn’t keep pace with the company’s size and needs;
- Weak coordination of product teams, with each one wanting to communicate with riders and prioritise different features, and
- Loss of empathy and local relationships as small, lightweight driver-support teams transformed into a more centralised support system.
What can leaders – particularly scale-hungry entrepreneurs – take away from Kalanick’s frank and painful confessional?
The Institute of Leadership & Management’s head of research, policy and standards Kate Cooper says: “When you look at those six bullet points, Kalanick isn’t necessarily being as honest about himself as he could be, deflecting issues on to other layers of management or parts of the business. We all know that individuals are promoted to management positions because of their technical track records – and then all too often find that the complexity of managing people, with the myriad relationships it entails, far more challenging than they may have anticipated. In parallel with that, the scrutiny on their performance intensifies, with senior figures watching their every move.
“Also, I don’t think the letter makes enough of the responsibility that workers have to help managers manage them. One of the most challenging aspects of management is that it’s not always a one-way relationship. The power dynamic is fluid – it ebbs and flows, and there’s a lot that employees can do in terms of providing information and ideas to bring their managers up to speed and help them figure out how the business areas they are in charge of work… or should work.”
Cooper notes: “I would question Kalanick’s claim that ‘great’ managers were given too much responsibility. They couldn’t have been great if they didn’t do a good job! They just weren’t ready for the roles they were given. Typically, first-time managers would require valuable insights on all the complexities of leading and managing people. But perhaps what these ‘great’ managers, as Kalanick calls them, need is a greater focus on what some would call the ‘hard skills’: understanding strategy, markets, systems and processes. If you get your relationships and soft skills right first, then there are plenty of books you can learn the hard skills from. But it’s the soft skills where you need to put in lots of groundwork, in terms of learning through experience and developing a collaborative approach.
“As for the challenge Kalanick highlights between centralisation and local autonomy, I don’t think anyone really resolves that, as such: it’s more of an ongoing tension that leaders must monitor and negotiate. The quality of relationships and levels of trust throughout the organisation are absolutely key to mitigating that tension, along with a sense of shared intent: that we’re all working towards the same goals, and we have shared values and a shared vision. Those conditions are very much the result of nurturing great relationships.”
She adds: “What we have here are two threads: the importance of understanding people skills and culture – all those things that drive an organisation and make it what it is – and simultaneously, the need to put in place all the correct systems and processes that will enable a firm to fulfil its commercial objectives. Kalanick’s letter offers some instructive insights on the challenges of managing and leading, the challenges of sustaining growth and the challenges of ensuring that all your employees and divisions are heading at least roughly in the same direction.”
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Image of Travis Kalanick courtesy of JStone, via Shutterstock