The Corner: Avoiding Ready, Aim... Ready, Aim... What intangible of leadership have you found most difficult to convey or prepare for?

  • Chesky: The expectation that our senior leadership team and every member of our team not fear failure. The financial institution vertical is undergoing enormous stress and disruption – working in this vertical demands leadership that drives innovation, disruption and reengineering. A team cannot accomplish these objectives without understanding that failure will be a constant companion to these efforts. I work tirelessly to remind our entire team that we will celebrate failures with the same intensity we do our successes – for if we have not encountered failure we have not taken the risks required to drive innovation. Are you a fan of a management book or books? If not, why not. If so, which have resonated with you and why?

  • Chesky: I fly a lot, so during flights I try to read at least one management book a week. I am particularly an avid fan of management consultant Verne Harnish. Subscribe to his e-mails and several times a month you’ll get links to thought-provoking articles and recommendations on new books on management and leadership. I also subscribe to John Spence – another great thought leader on management and leadership. There are three books I have read over the last year that I keep rereading – their insights are fascinating to me; Digital Disruption by James McQuivey, Escape Velocity by Geoffrey Moore, and Antifragile by Nissim Taleb. Innovation: four syllables getting all the attention. Deservedly so? If so, can you really drive innovation? Or is it coming at the cost of implementation and delivery?

  • Chesky: We believe that innovation requires eventual deployment and measured impacts – so innovation and delivery go hand in hand. Many companies drive for innovation but never set an implementation and delivery objective at the back-end, we describe it as the syndrome of innovate…ready…aim…innovate…ready…aim… The FIRE never happens, or if there is a deployment or implementation event, no one is measuring outcomes. One of the most important management issues we tackle is following through on an innovation with delivery, testing, modification and retesting. It is easy to get caught in the “innovation” cycle where your team is always looking for the next great idea and forgetting the importance of deployment. Which school is ultimately more valuable: Business School or The School of Hard Knocks? Why?

  • Chesky: They are both invaluable. I am a product of the school of hard knocks, and am now watching my 24-year-old son apply to Business school for his MBA after two years on the job with me. I think the question you’re asking leaves out the third alternative – investing in working and learning. Some of our greatest leaders take sabbaticals regularly – to recharge – study – and question. I am forever promising myself that “next year” I’ll take a month off to attend a class and get some perspective. That is a big mistake. I think boards of directors should insist that their CEO take time for class work, collaboration and discussion outside of the industry – and not for a week – but for 4-6 weeks… really recharge and reinvigorate. We all imagine that our companies can’t survive a week without us – frankly, what does that say about our leadership. If you could go back and talk to You On The First Day On The Job, what advice do you share?

  • Chesky: Take quiet time to think about what your day-to-day goals are for your job. Job descriptions and performance reviews are stitched into the fabric of today’s business environment, but I wish someone told me to take some time to think about what my objectives were in my job each and every day. We are always driven by aspirations, next steps, political positioning and gamesmanship. I wish someone had said to me, “Focus on what will you do today, in this moment, that will make you a valued employee and important contributor to the day’s work.” We all work hard – but can easily forget that our actions in the moment can have significant consequences for us and our customers and co-workers. We have pioneered a unique process to remind ourselves of what our “jobs” are at the moment. Every customer we interact with is sent an e-mail, and given a chance to rank their experience with us on a scale of 1-10 (The Net Promoter Survey). What we do that is unique is EVERY customer response pops up on EVERY employee desktop, real-time, each and every day. Most survey methods are post mortems – imagine every employee knowing all day every day that their customer is going to communicate their experience to all of your peers. Helps to answer the question – what is my job today?

 Mr. Chesky can be reached at

Section: Standard
Word Count: 1062
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Copyright Year: 2019
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