Like everyone, I have endured many challenging professional experiences and had to work closely with individuals that would not have been on my list of favourite people. Some would say “that’s why we get paid the big-bucks”. Regardless, the key question for me is what to do with the multitude of learnings I have acquired over more than 25 years as a health executive. Recently I was privileged to have the opportunity to provide leadership coaching to a bright young enthusiastic woman who had been promoted to the position of Executive Director. Our conversations primarily related to the challenges she was facing. While the specifics were unique to her and her organization, every one of her conundrums were ones which I had dealt with myself. What a delight it was to have someone else derive some benefit from my own experiences, failures and successes, all with the benefit of hindsight and reflection.