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Leadership Challenges

Afraid Your New Leader Is Running the Company Into the Ground? Ask Madeleine

Dear Madeleine, I work for a mid-sized global accessories brand. I was head of PR for many years but wanted to scale back when I had a kids. Now I serve as brand ambassador and influencer. The organization has been growing rapidly. About a year ago, it was sold and a new president was hired.…

September 13, 2025 in Cost of Doing Nothing, Leadership Challenges.

Not Sure How to Get Someone in Their Mid-40s to Stop Behaving Like a Child? Ask Madeleine

Dear Madeleine, I run a commercial retail real estate firm in a big city in the Midwest. We have some seasoned senior brokers, all of whom have done well working with junior brokers, training them while also benefiting from their help. The model has worked really well, except in the case of one senior broker.…

December 21, 2024 in Accountability, Leadership Challenges.

Need Help with Possible Layoffs? Ask Madeleine

Dear Madeleine, I am a talent acquisition leader with a midsize tech company. I built my team from scratch in the past year. We are a high performing team that is greatly appreciated by our stakeholders. Like many companies out there, ours is seeing the impact of inflation and economic downturn. Many organizations are putting…

July 2, 2022 in Downsizing, Leadership Challenges.

People Aren’t Stepping Up? Ask Madeleine

Dear Madeleine, I lead a team of seasoned, expert professionals in a fast-growing global company. My boss has told me in no uncertain terms that my biggest priority in the next year is to develop my team and groom a successor. My biggest obstacle is, although every one of my team members is very good…

December 18, 2021 in Leadership Challenges.

“Mean Girls” Team Running Amok?  Ask Madeleine

Dear Madeleine, I manage a small group of what we call WMS professionals—Website Marketing Specialists. They all work remotely, and the group has developed into an extremely effective team. I am very proud of our work; together we have found a way to really add value to sales and to the company. Taken individually, each…

October 9, 2021 in Leadership Challenges.

Latest Team Member Causing Chaos? Ask Madeleine

Dear Madeleine, I am a cofounder of a retail swimsuit company that is really taking off. We were lucky the pandemic hit just as we were about to sign leases on some actual stores, so we really dodged a problem that could have tanked us. About nine months ago, we hired a full-time marketing person.…

May 22, 2021 in Leadership Challenges.

Stepping into a Big Mess as a New Manager? Ask Madeleine

Dear Madeleine, I started a new job as a senior leader for a large manufacturing firm about four months ago—and I still haven’t gotten to the bottom of the disaster I’ve walked into. All I heard about when I first came on was how much everyone loved my predecessor, how smart he was, how much…

June 15, 2019 in Leadership Challenges.

Concerned about a Difficult Employee? Ask Madeleine

Dear Madeleine, I have an employee who hates me. I have been supervising and managing people for 25 years and this has never happened to me before. I’ve been to training classes, attended webinars, read books on managing, and worked hard to hone my leadership skills over the years. I am generally a likeable person,…

June 8, 2019 in Leadership Challenges.

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