Gut check: tell my "cool boss" I'm looking for other work?

Title. Should I give my boss a heads-up? I feel like I owe a lot of my career to her "taking a chance on me" and mentoring me. I would say she is a good friend outside of work.

I am on a small corp finance team (4 people) for a megacap tech company, and I am right-hand man for Big Finance Boss Lady. We are the only finance team for $6B division, handling all financial reporting, forecasting, strategy, and plenty of sales ops bullshit. Workload is roughly 70-80 hours per week, with greater loads during crunch time.

We had a gap in our team for 4 months and it was hell for everyone. I slept in office several times. It was worse for Big Boss Lady. We've since hired a junior analyst and stabilized at 70-80hrs, but my departure as an associate will be even more catastrophic. Hiring is slow here and takes 3+ months from identifying opening to filling the position.

Common sense says there is only downside to telling my boss. But I keep fighting a "guy feeling" to "do the right thing" so that my team can get the ball rolling on hiring/finding my replacement. Can you talk me down from the cliff?

 
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I think most people will advise you not to tell your boss and that is definitely the safe approach. I’ve had a similar relationship with my first boss/mentor and decided to let them know, but only after I had interviewed and was close to receiving an offer. On 2 different occasions, they actually talked me out of taking new jobs and gave very insightful guidance about the trajectory of those opportunities and why I should think twice about them. I was disgruntled in my current role and obviously suspicious of their bias to keep me around, but looking back it was the best possible guidance I could have received.  Later, when I finally got an offer that I was excited about, they validated my excitement and encouraged me to take it.  Taking it a step further, when they left that company and went to a new company years later, they recruited me to join and we're back working together.
 

Point is, if you’re fortunate enough to have the kind of relationship that weights more heavily towards mentor/mentee vs. boss/underling, you should take advantage of that and look to preserve it. Only you will be able to make that judgement but I can't overstate how important having a really strong relationship with a mentor has been for me in my career.

 

Everybody here will probably tell you not to inform her and emphasize the downside of potentially pissing her off. I think the optimal approach here depends on how intimate your relationship with this person really is.  

I'd encourage you to reflect on whether this person is someone you truly consider a 'mentor', or if it's just someone senior who you have a good relationship with - that's a really important distinction and i think too many people confuse the two. 

If they're really a mentor, your best approach is to sit down with them and discuss why you're thinking about exploring other options, framing this as more of a 'i'd love to get your feedback and advice' type discussion and less of a 'I don't think i like it here anymore so i'm trying to move on' declaration. Worst case scenario she's aware you want to leave (which you'll have to bring up at some point either way), best case scenario you get extra respect from her for being transparent and trying to help out the team (which can go a huge way over the longer term of your career). 

 

I’d be straight up with her if you’re seriously looking and work with her to plan for the departure, set the new team up.

Being straight up with her does 2 things:

  • Preserves your relationship, hopefully also a good reference
  • Runs possibility for you to maybe get an uplift in pay and / or responsibility (if that’s possible) should you stay

If she’s truly been good to you then give her that level of respect back. Don’t be a prick

 

OP again. Thanks everyone for the guidance. Really appreciate the level-headed responses. One commenter suggested I reflect on the relationship--whether she is truly a mentor or just a good colleague--and they are right. This is worth reconsidering.

I am still in the early stages of the job hunt (within my org as well as elsewhere), so I don't see any point in bringing it up now. But as more specific and meaningful opportunities arise, I will reevaluate.

I'll update the thread later on.

 

I hope you are getting paid bank. I would need some ridiculous $$$s to make it through 70-80 hours worth corp fin work

As for telling your boss? Not until you have something secured. You don't want them to walk you out the door and then you're left with nothing. That being said, if you're trying to leverage into a promotion/raise then the story changes considerably.

 

Makes sense, I have no real leverage right now.

About comp--haha nope, I am expecting 83k all-in in NYC metro. I am waiting to hit the golden 2Y mark then will jump ship, hence the thread.

Comp package is weighted towards "performance incentives", but I was an idiot when I signed and didn't ask about the bonus structure. Turns out my team's comp is heavily impacted by market share and sales performance KPI's... in a down market. All my bonuses have literally been less than standard paychecks. 70+ hours for pennies 🔥🔥🔥

 

What's your comp split and how many YoE? 83k all-in in NYC is pretty low. I left IB after 1 year and 2 years total of experience since grad and am at 130k all-in. Also have a great manager and work very little (mostly 40hrs if that) but still think I could've aimed a bit higher in comp.  

 

Commented on this thread already but after seeing you're getting all-in comp of $83k for a job requiring 70-80 hours a week...hard to believe you're not being taken advantage of and as such, if you do decide to solicit advice, keep in mind she has pretty strong incentives to try and convince you to stay no matter what.

I've had a similar experience with a very senior colleague that said all the right things and made me think they cared about my longer term career but once i became aware that this wasn't the case it was clear as day to me that they just couldn't care less about the implications of manipulating / lying to underlings if it meant making their lives marginally easier. Worst part is I cant even tell if it was fully intentional or if they were so sociopathic that they actually believed their own bullshit. 

 

Do not tell your boss that you're looking for a new job. Instead, tell any companies that you interview with that you'd like to give your current employer 1 to 2 months notice and mention the reasons why. They'll respect you for being thoughtful and professional about your current employer and setting the right expectations for your new employer. This way you avoid the downside/risk of telling your boss that you're trying to leave and lessen the disruption caused due to your departure.

 

I'd just indicate something like "I'd likely want to give notice a little earlier to help ensure there's enough time to transition" and leave it ambiguous, at least early on.

From a process standpoint, saying 1 month+ notice could cause some recruiters/interviewers, especially early on in the process, to just put you in the no pile. It's fine to defer the details of your notice/start time until a little later in the process when they're a little more interested or engaged with you. This is more of an issue at more junior levels, as companies are more likely to be willing to wait it out for the right senior person.

 

I know exactly what you're feeling, and have had my own brushes with heavy guilt over leaving bosses that previously stuck their neck out for me.

And the solution others have offered is predictable: "you have to put yourself first."  I don't find that argument convincing at all.

What I have found convincing is that as I get older, I increasingly feel that management mistakes are incredibly destructive and must be punished, and other considerations (like kindness and loyalty) aren't more important than that.  

Clearly there are reasons you want to leave, so something is wrong.  Even if it feels out of your boss's control (maybe you fell in love with a new career) ultimately I'm sure your boss had more than 0% control over your desire to leave.  Look at the damage done by that . . dramatically affects your life, no doubt affects your teammates and boss's life . . affects everyone's families to some degree.  And we haven't even gotten to all the little ways the business and its millions of customers & investors might be ever so slightly better off if things are managed better.

And yet we are very forgiving of management errors, because we don't associate them with poor character.  My view is, we can't just decide a mistake is forgivable because it lacks a moral component.  It's still incredibly destructive.  So kudos to your boss for the good things she does.  She seems like a good person, maybe even a good overall manager.  But she needs to face the music for whatever mistakes are contributing to your desire to leave.  And part of facing the music is, she's not going to get advance notice from you.

 

You may tell her, but only after you’ve secured another position and know you’re leaving or a situation/conversation arises where you realize you’re comfortable talking about it. Ideally, time your leave and new start date so that it gives them enough time to prepare and work through the transition without throwing them under the bus. Do what you can to preserve the relationship, but absolutely do not give them any chance to walk you out.

 

70-80 hour weeks for what sounds pretty much like a standard divisional FP&A role is certainly not standard. This is a corporate environment, not IB. If "big boss finance lady" were such a big boss and a good manager, she would make sure that her team is appropriately resourced. It seems like she is either disinterested in the WLB of her team, or lacks organizational clout.

Recruiting taking 4 months for a junior analyst role in the current job market? Doesn't sound reasonable. And sleeping in the office? At $83k???

Bottom line: You owe absolutely nothing to her.

 

kamel123:

70-80 hour weeks for what sounds pretty much like a standard divisional FP&A role is certainly not standard. This is a corporate environment, not IB. If "big boss finance lady" were such a big boss and a good manager, she would make sure that her team is appropriately resourced. It seems like she is either disinterested in the WLB of her team, or lacks organizational clout.

Recruiting taking 4 months for a junior analyst role in the current job market? Doesn't sound reasonable. And sleeping in the office? At $83k???

Bottom line: You owe absolutely nothing to her.

Exactly my thoughts

 

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