How Do I Work With Someone I Don’t Like?

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Dear Bev,

What happens when you simply don’t like a colleague but you need to work side-by-side with them every single day? I know everyone has their preferences and their ways of doing things, but I have to deal with someone with whom it could not be more difficult to work, communicate or talk to about work-related issues.

More importantly, this person (I will call “TP”) makes frequent mistakes – not small mistakes, but big mistakes. And these mistakes leave me in the role of cleaning up messes and fixing things on behalf of clients.

Yes, I have talked about my frustrations with TP directly. Yes, I have gone to my manager to talk about how many times I have had to fix things. Yes, I have tried managing my expectations and responses.

Nothing works.

At what point do I stop fixing the messes? At what point do I say I can’t work with TP anymore? At what point do I consider walking out of here because of what I am being asked to do?

A.F.

Dear A.F.,

I hear your frustration, and I understand what you are going through has been difficult. I can’t tell someone when it is time to stop fixing things for clients or when to leave altogether. I can’t know when you have reached your personal limit of tolerance. While I do like to give insights and ideas, I try to refrain from telling people what they should do. I’m not in your shoes and I don’t want to make a bad decision on your behalf!

But I will do what I typically do, which is to ask you to consider some things you might not have thought about before you do anything.

1. I acknowledge this is a business where “right” matters. Consider first, if your colleague is making mistakes on behalf of clients, what the consequences are. Is it possible to let something drop because TP didn’t do it right so that the alarm bells could go off within the firm about what’s happening? You are essentially covering for TP, and that’s not always the best thing.

Of course, if there would be severe outcomes such as clients losing money or reputational risk for the firm, don’t do this. However, if it is something like an address change that didn’t get done – just let it drop. Somehow you have to let others know TP isn’t pulling the necessary weight. The firm is paying someone who isn’t doing their job!

2. What has been your style of confronting your colleague? Consider whether you have been passive-aggressive, aggressive, too passive, or anything in between. We often think we have been clear and addressed something, but you always must consider style. If your colleague’s style is different from yours, TP might just shut down or not hear what you are saying.

We may think the person is choosing to ignore or not respond, but more often it is a style difference at play. How could you modify your approach to tell TP, “No more!” You want to be able to say you are no longer going to hide the mistakes and fix things. Do this in an objective and clear way. Then actually do it. Don’t take on fixing whatever it is. Give notice, but then don’t back away from your commitment (to yourself!).

3. Consider asking your senior leaders to talk with TP about whether they are in the right role. Sometimes, the firm has a need and someone gets tasked with filling it. But it may not fit with their natural abilities and they might not have been trained. A client I worked with always talked about it as “skill versus will.” Does TP drop the ball because of lack of knowledge or because of lack of interest? It’s not your role to explore this, but if you have brought these behaviors up to your manager, perhaps they might be willing to investigate a bit more.

I’m not going to tell you to leave your job. The number one reason people leave jobs is because of the boss or leadership, not usually because of their colleagues. Colleagues come and go, and TP might very well figure out at some point this isn’t the right role and move on. Don’t let this behavior push you out if you otherwise like your job, your manager and your firm.

Dear Bev,

How do you stop a colleague from crying every single time there is a whiff of conflict? I am partnering with another advisor to work on a couple of really large client accounts. There are opportunities to extend the relationships with these clients. Our firm pushes certain products and services more than others.

My colleague, call her “Sue,” has been avoiding discussions on some topics where we really need to present certain ideas. Every single time I bring this up (or, quite frankly, anything else) Sue’s eyes well up and she starts sniffling. Once in a while she breaks out into full-on crying.

Of course, I stop speaking and feel I cannot push any further. However, it is getting nauseating to deal with. I have never cried at work in 12 years despite having had many clients yell at me and being frustrated with what’s happening in our office. It’s not appropriate, and I believe it is controlling.

But how do you address someone who won’t let you address anything?

V.E.

Dear V.E.,

Ah yes, there is almost nothing more difficult to deal with than someone who gets emotional, in a sad way, when you are trying to address something that needs to be discussed. You can deal with anger, you can deal with apathy and you can deal with ignorance of the issue. But when someone starts to cry, all bets are off!

The saying “Don’t let them ever see you cry” is a good one. It is really based on the belief that someone looks weak when they cry, but in reality, when a colleague cries it is almost impossible to know how to respond or what to do next. The natural reaction is to want the crying to stop and the person to stop being upset, so you stop doing whatever triggered the tears.

You have two main options here:

1. Take away the need for Sue to be the one to address things she might not be comfortable with. If your firm is pushing you to do something, and Sue is uncomfortable doing it in these joint client situations, then take it away and be the one to address the issues. You don’t have to ask permission, as Sue and you both know the firm is asking you to do this. A wise person once told me that when someone doesn’t want to pick up a ball and it needs to be thrown, maybe you are the person who needs to pick it up and throw it.

2. Your second option is to do your best to address this with Sue in an objective, non-threatening way. Perhaps you could ask her out to lunch – somewhere that crying is less likely to occur. Let her know you care about her and you want to have a good working relationship, but you are prevented from having an open dialogue by her responses. Ask her how the two of you could interact and communicate differently. I doubt she will open up and give you ideas, but it is always worth a try.

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 and 2024. Beverly is currently an adjunct professor at Suffolk University teaching undergraduate and graduate students Entrepreneurship and Leading 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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