How to Handle Team Members Who Push Boundaries

Dear L.A.,

It’s so hard in our industry to “benchmark” things like comp, benefits and work-from-home philosophies, because if you show me 15 teams or firms, I’ll show you 15 different ways to answer these questions. I know the WFH question is a big one, and many teams are struggling with it. Here in Boston, where I live, Fidelity went to five days in-office and The Boston Globe has had a field day with experts opining on whether that’s a good thing or a bad thing.

For many teams, the collaboration and in-office ability to connect easily is more important than giving team members the chance to have at-home time. For others, however, in order to attract great talent in their area, they have to be flexible on WFH policies.

All of this said, ultimately the leaders of a team or firm must decide what’s best for their staff. I try to refrain from being judgmental, but in your case I will use the word “pushy” to describe your team members’ behavior around this topic. 25 days seems more than fair to me — over a month of work-days off. Your team members could be asking for WFH Fridays where they are working the full day so they are not eating into PTO at all. It seems there are variations where you could meet in the middle if you wanted to accommodate their request.

This decision really rests on what you want your culture to be. When you are pushed so far you use a word like “appalling,” I’m not sure it is the right thing for you to capitulate to the demands completely. I don’t have an opinion about which choice is right. However, I think you will end up regretting it, and it could cause problems with your younger team members over time.

Perhaps this is an opportunity to sit down and talk about the view from above, in leadership, and coach them on how to present a meaningful idea in the future. Feeling pushed and being appalled by team member’s behavior is not good for anyone. See if you can use this as a chance to collaborate and guide them for future discussions and requests.

Dear Bev,

We are having an issue with our head of operations, “Mary,” who is dealing with a sick parent. Mary had told me two months ago her mother was very sick and they weren’t sure how much time she had left. My partners and I agreed Mary could work a reduced schedule while she cared for her mother. Mary has been with us for 19 years, and we do whatever we can to support our team members.

It’s now over two months, and Mary and her mother are buying a condo together and going on a vacation. It could be these are end-of-life decisions, but Mary has stopped sharing information with us about the status of her mother and what’s happening. One of my partners is very suspicious and is suggesting we hire a detective to investigate whether Mary is on the up and up. My other partner and I are uncomfortable with this, because it obviously would show we don’t trust Mary right now, after almost 20 years of commitment to the firm.

Have you had situations where advisors have used investigative resources to spy on team members? I know we do background checks in our industry, and it’s not uncommon with higher level jobs to do an extensive one. That said, this feels intrusive for a director of operations.

Anonymous

Dear Anonymous,

My first response is “yikes!” It sounds a bit intrusive for any level, any role and any situation. Mary has been with you for almost 20 years. I understand there is suspicion around her behavior, but maybe before hiring a detective to investigate, one of you sits down with her to have a heart-to-heart discussion. You don’t say if Mary has taken leave and is not coming to the office at all or whether she is still working this reduced schedule, so you could do this one of two way:

1. You reach out and schedule a Zoom with her, or ask her to come into the office to check in on a few things both personally and professionally; or
2. When she is next in the office, you ask her to allocate an hour of time to sit down and clarify a few things.

You need to address this with her directly before you take any other steps and let her share her view of what’s happening. Importantly, you can’t be accusatory in your approach. You actually don’t know what Mary is doing and why. She could have very valid reasons for her actions. It’s best to broach the subject with a Socratic approach, asking open-ended questions and listening to her answers. You can share your observations of her behavior and let her know how you are perceiving the actions she is taking. She might not realize how things look there internally.

I think if you don’t do this before hiring an investigator, should anyone in your firm — not just Mary — discover what you’re doing, you could destroy trust that has taken decades to build. While I understand your questions and your frustration, always trust first — then verify.

Beverly Flaxington co-founded The Collaborative, a consulting firm devoted to business building for the financial services industry, in 1995. The firm also founded and manages the Advisors Sales Academy. The firm has won the Wealthbriefing WealthTech award for Best Training Solution for 2022, 2023, 2024, 2025 and 2026. Beverly is currently an adjunct professor at Suffolk University teaching Executive MBA students Leadership and Managing Teams. She is a Certified Professional Behavioral Analyst (CPBA) and Certified Professional Values Analyst (CPVA).

She has spent over 25 years in the investment industry and has been featured in Selling Power Magazine and quoted in hundreds of media outlets, including The Wall Street Journal, MSNBC.com, Investment News and Solutions Magazine for the FPA. She speaks frequently at investment industry conferences and is a speaker for the CFA Institute.

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