Dear Madeleine, I am an EVP of sales for a US-based fitness and weight loss website that is in hypergrowth. I started with the company about eight years ago and rose through the ranks, figuring things out as I went. About 18 months ago, my regional counterpart (I was East, he was West) quit suddenly…
Dear Madeleine, If relationships fail and one decides to pivot away from a toxic organization or situation, what is the best way to tell that story in a job interview? For example, I may be asked “Why did you leave that company?” My true feeling is it was all about the toxic culture. The objective truth…
Dear Madeleine, I am a veteran employee of a large, very healthy organization. I like the company and my co-workers. I’ve had plenty of advancement opportunities and I think my comp package is fair. I have been managing people for a long time and feel that I am skilled. I am not just tooting my…
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 work for a scrappy startup that offers a system for weight loss and coaching. It’s for folks who need extra help losing and maintaining their weight and who want a healthier lifestyle. All of the interaction is over text, with some notes being automated to offer specific messages at different points in…
Dear Madeleine, I am sixty years old and really love my work. I have had a long and varied career and had hoped to get another decade in before retiring. The institution I worked for closed down for good last year because of COVID. Since then, I have sent out 72 cover letters and resumes.…
Dear Madeleine, I am a client services manager at a new cancer center in Lagos, Nigeria. I have just had my six-month appraisal with the CEO. Along with my responsibilities, I have been helping my CEO with her calendar and all other duties. During the appraisal, she said she wants me to be her executive…
Dear Madeleine, I just started what is probably the last decade of my career. I am settling into a new role after being promoted to an EVP spot that reports directly to the CEO. Sometimes I sit in my office at home—although at some point it will be a nice office on the executive floor—and…
Dear Madeleine, I am a director in a small company. My boss (a boomer) keeps mentioning that I need to develop my brand. I really don’t understand what she means. The more I learn about personal branding, the more it feels like something that can limit me. It also feels like kind of an old,…
Dear Madeleine, I manage a small team in a fast-growing area of a giant information security company. There is so much opportunity for my industry right now (have you seen the stuff about “Zoom-bombing” in the news? We stop that kind of thing). I have always been ambitious—and right now, during this crisis, I am…