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My investment banking mentor was a sociopath

I'm a student in my final year at university and I want to warn other students about a bad encounter I had with a managing director at a leading Wall Street bank in New York who volunteered to be my mentor.

I am a diversity candidate and I met her at a diversity event in my first year. Although she's well over a decade older than me and incredibly successful in her banking career, while I'm just a student trying to get in, we got on incredibly well.  This was pre-COVID, and she'd stand close behind me and lean over my shoulder to look at my screen while I worked. There was a connection: we both come from non-banking backgrounds and have both had to work hard for what we want. She said she'd mentor me and help me in my career.

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We started meeting on a bi-weekly basis, sometimes in person and sometimes on Zoom. She'd give me advice about everything, from my appearance to my posture. She advised me how to talk, what to wear, what to eat, what to read and what to watch. She said that she could change me for the better. I loved the attention, and she appeared to love giving it to me.

I gave her my phone number, and we messaged on WhatsApp. She viewed all my statuses, and would send me heart emojis at the end of her communications.

When it came to applying for internships she wanted me to join her team. I wasn't sure: she's an MD in the front office, but I wasn't completely sold on her area of the bank - I think it relies too much on personality over ability and is open to automation. Despite my doubts, I let her persuade me. I applied for and got the job, and spent last summer on a virtual internship in her division working out of the office in NYC. She messaged me throughout and said she hoped I'd join her team. 

I still wasn't sure though. Eventually, I explained to HR that I just wasn't convinced it was the right area for me. She immediately found this out. She called me shouted at me, telling me that I wanted to work in her division but didn't understand it yet. I tried to explain that I didn't but that I hoped we could still be friends, but she then cut me off entirely. HR did the same: they stopped responding to my emails, even though I'd hoped to be introduced to a different division. She told HR that I was some kind of stalker, and they then emailed me and asked me never to contact her again. The diversity organization I worked with was also contacted, and cut me off too. But I had done nothing wrong: she had asked to be my mentor and had actively set the tone of our relationship. 

Clearly, I don't contact her anymore, but the entire experience has been very stressful and confusing. I still want to work in banking, but not if it contains other people like this. I feel like I was manipulated by someone who pretended to have my best interests at heart but actually just wanted a vulnerable student to control and dominate. Has anyone else had this kind of experience? Let me know in the comments below.

Oba Shadare is a pseudonym 

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AUTHOROba Shadare Insider Comment
  • Jo
    John le Carre
    7 November 2023

    Your experience is very interesting and I believe you can learn a lot from it.


    The banking industry is known for having difficult personalities, and these tend to get worse as you move up the corporate ladder. I know this because my mother was a managing director at a large bank. She worked her way up from being a graduate and was consistently told that she was one of the best from her cohort. Although this may sound like the dream to many, it came with negatives. Unfortunately, the type of people (probably not all) that dominate this industry tend to possess undesirable qualities. Firstly, they tend to be very transactional. With my mother I learned very quickly that when she was being nice or doing something kind for you, it was because she needed something or wanted you to do something in return. If you refused to do what she wanted, she would get offended and even shun you. It was surreal and absurd. Secondly, these people usually have massive egos. I imagine this stems from being told that they are better and smarter than everyone else. They even have the position of authority to firmly cement these beliefs in their heads. I saw with my mother how this affected her behaviour. To her, her opinion was always the best opinion and her advice was always the best advice. Anytime, I decided to not do things her way and take things in a different direction, she would feel offended. It injured her pride. It was almost like she was thinking to herself: “Who even are you and what do you know?” However, I had the luxury of doing that because I wasn’t her subordinate at work and she couldn’t force me into doing what she wanted.

    Since her retirement from banking, she has definitely changed. Some of those traits are still there, but they aren’t as intense. I would say she has actually become a better person. This led me to believe that the environment that a lot of these people work in tends to breed and accentuate negative qualities. It’s an ultra-competitive, dog eat dog world,

    and can cause people to become self obsessed and manipulative without even realising it. They want you to do what they want and they want you to do it now. If not, you are useless to them.


    From my perspective, it seems like there are several ways to deal with people like this. One way is simply to become like them, although I wouldn’t recommend this. I learned how to deal with people like this by realising that the world isn’t all sunshine and roses. These people and the corporations they represent do not care about you at all. Even with diversity and inclusion initiatives, for some firms it may exist solely to earn social credits. I believe that navigating this and perhaps all industries is almost like playing the floor is lava, I learned (and am still learning) to read the room, to understand the type of people I’m working with and act accordingly. I learned firsthand that complaining about individuals like your former MD and my mother gets you nowhere. They are often manipulative and may spin the situation to make it seem like you are the problem. Moreover, I learned not to become quickly attached to people, as this can affect your objective assessment of them. Often times, people like this will seemingly do nice things for you, but there are almost always strings attached. Again, this doesn’t apply to everyone.

    At the end of the day, it seems like if you are determined to work in this industry, then you simply have to learn how to play game. You need to be sharp and keep your wits about, otherwise you

    could get run over - metaphorically. I would consider winning the game to be getting the good stuff like high pay, without absorbing the negatives (damaging influences on your morality and personality) of the industry.

  • An
    AnonMe
    6 November 2023

    This is just bad behavior on the part of the "mentor." Who, in a leadership position, sends messages with heart emojis in professional communications? That alone is a huge red flag. This mentee is obviously young and inexperienced, and sounds like she was treated very harshly. And of course HR...well...they are what they are. NEVER count on them. They work for the company - not you. There is a lot of bad behavior in financial services. You either form a thick skin or you don't. And then you make a choice.

  • an
    anonymer worker
    3 November 2023

    I think the way you have been treated by your mentor was highly unprofessional and sounds like it could have legal implications.


    Leaving a team without burning bridges/angering people is always a difficult thing to do. It does happen that managers completely cut you off after you tell them that you resign. It helps to remind oneself that these are not your friends but business relationships. Some rare and very experienced managers at banks would be mature enough to handle a rejection in a professional manner but most are not and will take it very personal. Telling HR that you do not want to work for her, instead of telling her directly was probably a major shock to her. Speaking to her directly might have worked better. 'What I will tell you will shock you. You might get very angry. You might think I am stupid for turning down this role and the opportunity of working with you.'-type of way. Speaking out negative emotions the other person might have helps to diffuse situations like this.


    There are alot of difficult personalities in finance, and being able to handle them well is unfortunately part of the unofficial job description.


    Most people dont know what is a good fit for them unless they try it - so you feeling that this wont work for you very early on is a huge advantage. Getting introduced into another division is the job of the HR of the bank - not the one of your mentor, and they are expected to be discrete about it. If other divisions are hiring they should have done that. Not sure if you told them that your mentor misrepresented what has happened between the two of you.

  • Ri
    Richard Hayes
    22 December 2020

    I must say I was first shocked by the story but then even more shocked by the answers you got from most of the community. It’s ok to be advised an warned on a professional basis and I do think the advises you’ve been provides about Banking are true and actually really good as most interns need to learn this by hard but, once again, I am incredibly astonished none has cheered for your gut feeling. If you felt it wasn’t the right place or choice, very likely it wasn’t. Feel proud of yourself for listening and hearing your gut feelings, they are your allies! And this won’t be the first time you’ll experience such irrational behaviour from people but I can assure that the quality of your decisions will impact in the same way your future. Congratulations, your decision was of such quality. Learn to listen and understand yourself and keep on learning from new experiences so you can later advice others! Best wishes for 2021

  • C-
    C-Jay
    24 November 2020

    Sound like a messy breakup. In my personal opinion diversity should be grounded in equal opportunity not preferential opportunity.

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