Purpose – This interview with Michael Watkins is on the occasion of the tenth anniversary edition of his best-selling book The First 90 Days (Harvard Business Press, 2013). The book has helped a generation of executives identify and strategically analyze the opportunities and risks posed by a career move. Design/methodology/approach – The book offers a set of tools and techniques executives can use to accelerate learning and then methodically diagnose the situation to develop the right strategy. Findings – Watkin's approach is designed to speed up the rate at which executive are able to accurately diagnose situations, make good decisions and add value to their firms. Practical implications – Executives considering taking on a new job should learn to think like a historian. It's critical to understand how the organization got to the state that it is in. If serious problems were not addressed early enough to avoid a crisis, why did that happen? What does this say about the culture and politics of the company? About the competence and courage of the leadership? Originality/value – Watkins' approach can help all managers more clearly identify the specific challenges of the type of transition they are experiencing – for example promotion vs. joining a new company vs moving between functions – and adjust their tactics accordingly.