Dear Madeleine, I am a senior leader in a highly specialized digital publishing organization and I have about 14 direct reports. Organizationally, I’m third in seniority. My plan is, by the end of 2025, to transition out of this role and into my own coaching and consulting business. I’d be working with some clients, but…
Dear Madeleine, I have owned a boutique specialty consulting firm for over twenty-five years. My founding partner died a few years ago and left me her share of the business, so I am the sole owner. I am working with a broker to find the right buyer for the business. I don’t expect to get…
Hello Madeleine, I have read your articles, and I wanted to reach out to you. I have an equal business partner with whom I have successfully run a restaurant for six years. While I have 30 years of experience in the industry, my business partner had no previous knowledge about restaurant operations. I have used…
Dear Madeleine, I have been managing people for decades. With the advent of Covid, I put a lot of focus on getting better at managing hybrid teams. (This blog really helped me.) I have some people who come to the office and about half the group works remotely. I go in four days a week.…
Dear Madeleine, I work for a giant real estate company and have been selling houses in a big metropolitan city for a long time. Over the years, I’ve been heavily recruited and this is my third company. I never wanted to be in management as I really like working with clients. I’ve had terrible managers,…
Dear Madeleine, I am the COO for a medium sized, mostly US-based specialty product business. Our CEO was always the idea guy and I was execution. Our business used to be straightforward, but we recently expanded with services and a couple of storefronts—against my recommendation. Our CEO is a visionary and expects his executive team…
Dear Madeleine, I am a regional president for a global financial services company. About five years ago, I hired a whiz kid to inject some creativity and innovation into our use of technology and how we approach our regional customer acquisition. He is technically a genius in terms of IQ, and he excels at grasping…
Dear Madeleine, I am an HR generalist working at a REIT (Real Estate Investment Trust). Our CEO started the company about eight years ago, and I have been his right hand since the beginning. He is a genius in many ways—high IQ, a deep intuitive understanding of the real estate markets, a complete whiz with…
Dear Madeleine, I work in a large global organisation. The president for EMEA (UK and all of Western Europe) is my boss’s boss. I recently hired his son into my team. He gave a good interview and seemed totally committed to the role. Since then, I find him very challenging. He mimics his father, who…
Dear Madeleine, I read your article “Celebrating Women at Work” with interest and it prompted this question. I am a female senior manager in a fast-moving tech company. I run a high-level customer success team made up of mostly older women. About a year ago, my old boss retired. I got a new female boss…