Dear Madeleine, I have been working for a company for a few years now. They moved to an Unlimited PTO policy just as I joined. It was heavily promoted in the recruiting stage. Things went fine the first couple of years. I took the typical PTO breaks—December holiday time, a couple of days in the…
Dear Madeleine, There is a woman on my team who is driving me crazy. I am on the young side and she is nearing the end of her career, but I don’t think it is just about generational differences. In fact, she drives everyone crazy. She always thinks she knows best and assumes I know…
Dear Madeleine, I work in the communications media studio for a large company. I’m kind of entry level here, but I have a lot of experience directing video. I often end up working with very senior people to get short videos made for client work, proposals, stuff for the website, etc. Many high level people…
Dear Madeleine, I have been offered a promotion and need to make a recommendation for the team member who will be promoted into my job. I have one very likely candidate: my most promising employee. She is consistent with her deliverables and has led some projects for the team with great results. She gets along…
Dear Madeleine, I am an executive leader for a giant global organization. Last week, massive layoffs were announced. I have a team of twelve direct reports with hundreds of people reporting up to them. I don’t know every person, but I know a lot of them. Layoffs are going to be devastating for these people.…
Dear Madeleine, This isn’t really a work problem, it is a life problem caused by success at work. I am the CEO of a respected company and have been successful beyond my wildest dreams. I was the first in my family to go to college, let alone get an advanced degree. I am incredibly persistent…
Dear Madeleine, I have an employee who is very dependable and is doing an excellent job. I am certain he will do very well here, long term. He has been with the company about a year, has developed confidence, and often catches errors before it is too late. He is trusted and his peers go…
Dear Madeleine, I was recently promoted to a VP role in my company. It was a bit of a surprise as I thought my boss would never leave—but he did, quite suddenly. I have been in the role now for about five months. My new boss keeps telling me I need to “get out of…
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…
Dear Madeleine, I manage a large regional business unit, and a few years ago all managers went through a coaching class. We learned to ask fewer why questions when coaching, and I have found it to be a helpful tip. I know it’s generally not a good idea to ask why questions, because they can…
Dear Madeleine, I read last week’s column with interest and it sparked a question for me. I am hiring right now for a position that requires someone to simply keep their head down and get the job done. Our company isn’t growing very fast, so there won’t be much room for advancement. I have a…
Dear Madeleine, I recently recommended a former colleague for a job in my company. Months have gone by since then, and our company has restructured. The job she applied for was recently offered to her, and she has accepted. When I made the recommendation, she would have been joining a different department so would have…
Dear Madeleine, I struggle with interrupting people—and I hate doing it. I usually realize it after it is done. What are some ways to help me overcome this habit and make personal improvements? Interrupter ___________________________________________________________________________ Dear Interrupter, I applaud your self-awareness, which is always the first step to any kind of personal improvement. My first…
Dear Madeleine, I lead a business unit for a global manufacturing company and have been in the role for about 18 months. I took over for someone who was completely checked out and it was a bit of a mess. It has taken me this long just to untangle the log jams and uncover all…
Dear Madeleine, I have had a long and varied experience in law. I started as a public prosecutor in corporate law and rose quickly to reporting to the General Counsel. My current boss isn’t going anywhere for a long time, and I feel ready to go for a GC position myself. I put feelers out…
