Dear Madeleine, I think I have a generational disconnect going on. I am a millennial (though I was born in 1981, so many people think I am GenX) and I supervise a lot of young people right out of college—classic GenZ people. I am really struggling with this notion of privilege. When I was a…
Dear Madeleine, I am the founder and CEO of a specialty investment services company, which I started—for fun—after retiring from my first career in investment banking. My executive team is amazing. Since we are so specialized and the field is super technical, I have had to find the best and the brightest. My problem is…
Dear Intern, What do today’s interns want out of a summer internship? My company—like many others—hosts six to eight summer interns every year. I’ve been participating in the program for over fifteen years and during that time I’ve had one, two, or sometimes three interns working for several weeks in our marketing department. It’s been…
Dear Intern, I just got hired as head of sales for a marketing services firm. I’m really excited to drive the future growth of this small and mighty company. My new team includes several very young team members. For some, this is their first professional job. I have always led more senior sales professionals and…
Dear Madeleine, I am a Boomer who is three or four years away from retirement (I hope). Over the last few years I have been working with many people who are much younger than my own children. I went from noticing that I was old enough to be the parent of my direct reports to…
Dear Madeleine, I am a Boomer who is three or four years away from retirement (I hope). Over the last few years I have been working with many people who are much younger than my own children. I went from noticing that I was old enough to be the parent of my direct reports to…
Dear Madeleine, I am a regional president for a global services company. One of my executive team members recently retired, leaving rather suddenly as the result of an unexpected health issue. We interviewed some candidates to replace him but, ultimately, I took his recommendation to go with the person who had been his chief of…
Dear Madeleine, I manage a team of customer support specialists. The job requires in-depth knowledge of our products (outdoor/climbing gear, some of it very technical), so we have provided a lot of training and oversight. In the past year we lost two of our best people, and the executive team refused to let me replace…
Dear Madeleine, I manage a team of mostly young people, all of whom manage internal communications for a global manufacturing company. A few years ago the company went to an unlimited paid time off policy. I have read a lot about the effects of unlimited PTO, and note that the biggest risk is that people…
Dear Madeleine, I manage a small team in a big company. Here is my problem. I start my day at 7 a.m. with a meeting, and then my entire day is back-to-back meetings. Almost every meeting generates work for me to do or to delegate to someone on my team—which requires another meeting. When am…