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Difficult Conversations

Struggling to Salvage a Relationship with a Direct Report? Ask Madeleine

Dear Madeleine, I am an American working overseas. A few years ago I took a break from adventure travel to make some cash by accepting an entry level job in IT operations. I was surprised to find that I liked it. Never in a million years did I think I would be happy or successful…

November 1, 2025 in Difficult Conversations.

CEO Is Derailing Your Communication Plan for a Change Initiative? Ask Madeleine

Dear Madeleine, I work in communications in a multi-national, publicly owned company. I report to our CHRO with a dotted line to marketing. My job is to make sure our messaging is consistent across all our countries. Our CEO and his executive team recently rolled out a complex strategic vision for the next five years,…

February 1, 2025 in Difficult Conversations, Managing up.

Direct Report Has a Chip on Their Shoulder? Ask Madeleine

Dear Madeleine, I manage a large team of accounting professionals for a company of about 4800 employees. I have worked very hard to create a great team, and I have excellent, dedicated people. My problem is our payroll manager (PM). He is generally very easy-going and a hard worker. He is a whiz at working…

October 19, 2024 in Difficult Conversations, Engaging Employees.

Concerned about a Teammate’s Commitment to Work? Ask Madeleine

Dear Madeleine, I manage a fully remote team and have one member who is wonderful—when he is able to focus on work. His contribution is valuable, he is easy to get along with, and other team members depend on his experience and wisdom. But he is always dealing with some kind of personal crisis. He…

September 30, 2023 in Difficult Conversations, Emotional Intelligence (EQ).

Boss Is Having a Hard Time Letting Go of the Details? Ask Madeleine

Dear Madeleine, I am the director of ecommerce marketing for a fairly new and innovative global digital logistics company. The marketing team is huge; there are three other directors for other kinds of marketing and we are all very busy. My problem is with my boss, our CMO. She is brilliant, she does a great…

August 19, 2023 in Difficult Conversations, Managing up.

Work Colleague Said Things at a Party She Shouldn’t Have? Ask Madeleine

Dear Madeleine, I am a partner in a medium-sized professional services organization headquartered in a large metropolitan city. I was recently at a private social function that some employees of my company also attended. It was quite a party, and pretty much everyone had way too much to drink, including me. One employee, a person…

August 12, 2023 in Difficult Conversations, Human Resource Issues.

Direct Report Going Too Far with Unlimited PTO? Ask Madeleine

Dear Madeleine, I manage a team in a large company that recently went to an Unlimited PTO policy. I am glad, because tracking and trying to get people to take their PTO was a pain. So far, it has worked pretty well. The policy is that people need to request holiday time in advance, mainly…

November 12, 2022 in Difficult Conversations.

Talking to An Employee about Body Odor? Ask Madeleine

Dear Madeleine, I am a branch manager for a regional bank. We are a small crew, and everyone reports into me. Things run smoothly for the most part. I have one team member—an older woman—who has terrible body odor. It is so off putting that I lose focus each time she comes near my desk.…

January 16, 2021 in Difficult Conversations.

One of Your Direct Reports Is Lying? Ask Madeleine

Dear Madeleine, It has recently become apparent that one of my newer direct reports is lying. In one instance, he told me a presentation was proofed and ready to go and I found out it wasn’t when I went into the document on our shared drive to make a change. In another instance, I learned…

June 13, 2020 in Difficult Conversations.

Direct Report Seems to Be Overdoing it with Health Excuses? Ask Madeleine

Dear Madeleine, I run a very lean team and one of my people is a hypochondriac. Every week there is a new reason he needs to go to the doctor. Any cold that comes through he gets, and it is worse for him than for anybody else. He gets the flu every year. It is…

October 5, 2019 in Difficult Conversations.

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