Dear Madeleine, I have a great job that I love, with a terrific company. I kind of stumbled into it and felt really lucky to find a job that suits me, with people I respect and like. I recently had a performance review and my boss made it clear to me that the sky is…
Dear Madeleine, I am an EVP of sales in an organization that is growing insanely fast. I have a brand new Chief Sales Officer and my regional counterpart just quit—so I have gone from four direct reports leading 300 people to seven direct reports leading 700 people. I would have thought my number one job…
Dear Madeleine, I’ve been managing a couple of teams located around the globe. Recently, our business has exploded, and I find that I am losing control of things. My question is: how do I help my people clarify when they need to include me in big decisions and when they don’t? I’ve never had this…
Dear Madeleine, It still will be months until my company invites us all back to work in the office, so until then, we are all WFH. I miss my work friends and the hallway conversations that helped us deal with situations on the fly. I definitely don’t miss the commute or having to make myself…
Dear Madeleine, Ever since the beginning of this work-from-home situation, our entire department feels like it is on hold. The reason? Our seriously old school boss is not at all comfortable with meeting via phone or web conferencing. He was always a stickler for meeting in person, and has just kind of fallen apart. I…
Dear Madeleine, I am the GM for a small brewery that has been shut down during the COVID-19 crisis as non-essential. However, the owner believes it is still worthwhile to stay open to serve take-out customers, which is allowed according to the shutdown rules. Because I am the GM, I have been designated as the…
How do people who are comfortable with finite games like football or chess learn to flourish in a world that operates with an infinite mindset? In his latest book, The Infinite Game, Simon Sinek explains how leaders must learn to operate with the understanding that business isn’t about winning or losing—it’s about being ahead or…
Dear Madeleine, I am what’s called a “people leader”—I lead individual contributors at a global software giant. I am also a technical contributor as a subject matter expert in a specific application. I don’t love managing people. I am quite reserved and I find it tiring—but it is the only way to get ahead in…
Dear Madeleine, I am a regional VP for a global services company. I get excellent performance reviews, have been promoted regularly, and have had some employees tell me I’m the best boss they’ve ever had. I am ambitious and on track to be a senior leader in the company. Five directors report to me. Our…
Dear Madeleine, About three months ago, I was promoted to COO in my organization. I wasn’t expecting it—a lot of changes happened at once. A large group of people were fired and the next thing I knew I was COO. I have no real senior leadership experience, but here is the crazy thing: I’m pretty…