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 who was brought in from another tech company that does not have a great reputation. She immediately challenged me to diversify my team. She said I did not have enough men, because “most of our customers are men, and men prefer to work with men.” Let me be clear here that we have never, ever rec ..read more

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 put people on the defensive. What is your advice on what to do when someone asks a why question? I was recently asked one by a manager who works for me, who also went through the training and should know better. I find myself not wanting to answer the question for fear I will appear defensive by even answe ..read more

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 number of good applicants—some young people who clearly want to grow and some middle-aged folks who seem happy to get into a swim lane and stay in it. My boss is advocating for me to focus on the younger, ambitious ones, but I think that is just setting people up for frustration. I think it makes more sen ..read more

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 reported to someone else.  Since then, we have restructured and now she is going to report to me. When I worked with her ten years ago, she was senior to me. She is at least fifteen years older and I was just getting started. She has remained at the same level. I know this ..read more

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 question is: how much of a problem it this for you? And how do you know? You say you usually realize you have done it after the fact.  How?  Is it that you remember the look on some ..read more

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 of the critical tasks that weren’t getting done. I had to replace a few key managers who weren’t enthusiastic about being held accountable. All of the processes and systems are now up and running, and things are smooth enough that I have devoted some time to doing skip-level meetings with people who report to my executive ..read more

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 at the beginning of January. I believed taking that step would put a lot of things in motion—ready or not—based on my past experience. And that is exactly what has happened. I have some really interesting interviews coming up for GC roles that present considerable gaps for me (regarding technical knowledge, n ..read more

Dear Madeleine, My organization instituted a mentoring program a few years ago. We have a cool online system so that prospective mentees can review bios and request people who have signed up to be mentors. I have been chosen by a few people and have really enjoyed being a mentor.  Our system provides some guidelines to mentors but it isn’t a lot of information, and I have some questions. Our HR person didn’t have many answers for me so I thought I should ask you.  I notice that you are a coach and I am wondering: what do you think the difference is between coaching and mentoring? Wh ..read more

Dear Madeleine, I work for a bioengineering company that was a successful startup. It is now well into its seventh year and we still have our founding CEO. As the fairly new COO, I report directly to him and he is driving me insane. Every time he and the other leaders in the organization meet, we have new conversations but never follow up on past conversations. The agenda for these meetings is never clear, much less sent out in advance so that we can prepare. I knew working for a founding CEO was going to be a challenge, but I just don’t see how anything is going to get done the way we are op ..read more

Dear Madeleine, I have risen through the ranks of my organization very quickly. Last year I took on a lot of new responsibilities with almost no direction, did a good job, and got a raise and a promotion. My boss, the president of the company, has told me several times that he sees me as partner material. One of my superpowers is figuring things out—but I fear I have reached my limit in one area. I keep asking my boss for more clarity on what is expected of me to be able to reach partner. And he keeps saying I need to become “more comfortable with ambiguity.” It is maddening. If I knew what I ..read more