When to cc boss’s boss?

Assistant PM in CorpStrat

Hi all. First time poster, here.

I have a been in a job for about a year now, and I've had some serious trouble getting "in-sync" with my boss's working style over that period, despite some significant effort and direct conversation with them. Since I started, they have belittled my contributions, disparaged my character, not giving me proper training and left me out of key meetings/calls that I need to be a part of to be an effective member of the team. I'm frustrated.

My role involves analysis on new business opportunities. My boss's role is finding those new business opportunities. To be blunt, they have not found those opportunities the whole time they have been in their role, which is about 2 years. I've repeatedly asked if I can help source new business, and they have basically said I can't help. I know I can bring in new business.

This all came to a head when we had an all hands meeting last week discussing our shift in how we would find new business. In that meeting, the team that covers a different geography from us lead said that all teams members are in charge of finding new business. When my boss was prompted for their response, they sheepishly agreed to this approach in front of everyone. This made me feel vindicated, but I suspect they did it to appease their boss, and everyone else on the call.

I had planned to send a follow up "confirmation" email to my boss, cc'ing my boss's boss, to asked if I can start finding new business. I think this accomplishes two things: 1.) it signals to my boss's boss that I want to grow, and contribute more to the business dev side of things, and 2.) it puts in writing the agreement that my boss made on that call, in front of their boss. The email is respectfully written, and asks for permission to drum up new biz.

The drawbacks are that I know, because of my boss's personality, that this would really rub them the wrong way, but I'm tired of being treated like I don't matter on this team.

TLDR; when is it appropriate to cc my boss's boss on an email?

Comments (35)

May 18, 2020

That would never end well for you, how old are you, 22?

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  • Associate 2 in RE - Res
May 18, 2020

Any suggestions of how to address this, then? I've tried ad nauseum having conversations with them about it, to no avail.

May 18, 2020

You don't address it. Never go over your boss, management will always take your boss's side over your side.

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May 18, 2020

You don't address it. You just do it. The order is coming from above. If your boss wants to give you shit then stand your ground and simply inform him that you are following management's new mandate.

Or, find a new job. Guy sounds toxic.

  • Associate 2 in RE - Res
May 18, 2020

Thanks. Had considered this, but don't want to be seen as "stepping on toes" and this, insubordinate.

Most Helpful
May 18, 2020

Absolutely do not do that.

You have a couple of options here and none of them involve email:

  1. Find a new job. It sounds like your boss sucks, or at least that you two don't mesh well. That happens in life. Sometimes you just have to move on.
  2. Sit down with your boss and discuss your interest in supporting him finding new business. The key here is to not come at him like you're going to do his job better than him - you're here to make him better by being good in the first place. Explain what you are offering, your interest in mentoring under him (even though you think he sucks), and the benefits and free time you can give him by sharing the workload. If he refuses, refer to Option 1.
  3. Keep our mouth shut and find new business in your spare time. Your boss's boss seems to support that idea, and a company turning down business seems unlikely, so you could end up being a hero here without any confrontation. Still, you're in a much stronger position with the business to say "I can go get new business" as opposed to arguing for the possibility of doing so. Maybe your boss steals credit for your new business. If that's the case, refer to Option 1.
  4. Finally, and this is a "risk it all while burning the bridge behind you" move, if you're ever going to go above your boss, you do so in-person like an adult. You get a meeting with your boss's boss, you speak directly and cite evidence, and you remove all emotion out of it like "disparaged my character." You should fully expect to get reprimanded for this 95%-99% of the time, if not let go or frankly, completely ignored. Know that going in - but it could work. Make sure you have Option 1 or Option 0 - a trust fund - ready though before you even go down this route.

CC'ing your boss and your boss's boss on an email is so passive aggressive that even if your argument is 100% correct, your method will make your boss's boss think you're a little shit. Not only will it devalue your argument in the first place, but it will make your boss look better by comparison.

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  • Associate 2 in RE - Res
May 18, 2020

Good point about the perception of my boss's boss on the email. You're probably right that despite the arguments merits it would be perceived as a political move trying to make them look bad.

May 19, 2020

I would strongly recommend this advice. OP should read "the 48 laws of power". Guess what is #1? "Never Outshine the Master".

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May 19, 2020

The man, the myth, the legend.

Incredibly well written! Love the writeups and support, CRE!

  • Analyst 1 in RE - Comm
May 18, 2020

Well isn't it implied that you have the green light to bring in business since it was discussed on the call with everyone present? I don't see a reason to send a confirmation email in writing - it seems awkward and makes it look like you are trying to throw your boss under the bus in front of management, which is what you are effectively doing. Not a good look.

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  • Associate 2 in RE - Res
May 18, 2020

Yes it is implied. I didn't mention in the main post that my boss talks out of both sides of their mouth. There is a lot more nuance in this situation that the post suggests. Anyway-- point is that what they said on the call likely won't be the way that it practically plays out.

Funniest
May 18, 2020

So confusing when you keep saying 'they'. Is your boss Taylor Mason?

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May 18, 2020

If you are so confident that you can find a deal then go find one.

Do not send the email. Doing so will create a world of problems for you.

Frankly you saying "I am confident I can find a deal" rubs me the wrong way and I am just an internet stranger (if you have never sourced a deal why are you so confident that you can bring one in?) I assume you are only a year or two out of school and if so please stop saying this. If you have experience sourcing deals then ignore what I said above.

You may have innocently said this around the office and and rubbed your boss the wrong way.

Office politics suck and not meshing with your boss sucks big time. Go find a deal and cure all, or play the game long enough to leverage this job in to something better.

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  • Associate 2 in RE - Res
May 18, 2020

I get that. There's a lot of nuance to this situation, but I appreciate your offering that I could be rubbing them the wrong way.

I have found deals with a previous employer. I have relationships to leverage.

I brought two deals to this boss in the first couple of months on the job, which were killed on site without further discussion.

I don't pretend to be a rainmaker, but I also don't accept that I'm purely an excel jockey. Again, I'm not trying to be a bull in a china shop but I'm tempted to push the envelope now because we haven't closed a deal in 24 months, 12 of which I've been on the team...

May 18, 2020

Totally disregard my advice above then. I thought maybe you were inexperienced in finding deals.

If they are killing deals you are bringing in that is very worrisome (as long as they fit your investment criteria and you are confident they can pass your IC).

Hopefully the older guys can give you a better course of action. Best of luck!

May 18, 2020

Did the deals you brought in fit your firm's investment strategy? Did they have the appropriate levers to pull to add value and bring in returns worth your firm's time, and that they could push through your IC?

If yes to the above and your boss is killing deals just because you're the one bringing them in, there's two options:

  1. He's an overprotective dickhead and afraid to let other's advance in their careers - get a new job.
  2. He specifically does not like you for some reason (maybe you've rubbed him the wrong way - no offense but based off this thread I could see that happening) - again, get a new job.

If you guys actually haven't closed a single deal in the last 24 months, you really should be looking for a new job already anyways...

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May 18, 2020

I have to agree with EVERYONE on this thread. Do not do it.

Also, not to belittle you, you are fucking 22 years old. The only 'value' you can add is by kissing butt and grinding it out in excel.

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  • Associate 2 in RE - Res
May 18, 2020

Not 22. But thanks.

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May 18, 2020

Ok 23, same thing. Haha trolling you here but you get the point. Follow the politics.

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May 18, 2020

Bring in a deal first and then send that kind of email. I always wanted to bring in deals (when I wasn't "supossed" to) in junior roles. I took a shoot first ask last approach in 2 jobs / 2 phases of my career it worked both times.

Successfully, bring in a deal first and then ask for permission. You will never get into trouble for making them more money and it will give you leverage becasue you're a proven sourcer at that point. If you ask now it's all just conceptual.

I'm sure you're a killer but everyone thinks they can source business. The numbers show that only about 10% of us can and do so consistently to be top performers.

You need a proof point. Find a deal first and then ask.

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May 19, 2020

Never, ever, ever - maybe I should keep saying that - do this in an email. You have a few options, however I'd encourage you to do something first. Audit the last year. Look over meeting notes, look at work product, talk to your colleagues (if you have any) in your group - and really understand what is being said to you.

A sidenote - I used to think my boss was leaving me out of a bunch of things in our group on purpose. Either he didn't value my input, didn't care what I think or simply didn't respect my 'contributions' on those projects. Eventually, I'm in his office and ask him 'hey, what's the deal' (in a much nicer way, of course). That's when he clarified what his expectations, and perception, of my role and where he thought I could add the most value on specific projects - rather than pull me into things he felt would suck up a lot of time, with little impact.

My second sidenote - I was in a similar situation where I was petulant brat about sourcing new business for our firm. Sign me up for sales, I said. I can do better than these idiots we have, I said. Eventually I got the opportunity and, I discovered, that it's quite a bit more challenging than it seems. It's a different skill set and just because I was great at identifying opportunities didn't mean I could do anything with executing them. Again - know yourself.

I say that because msot likely your boss is under pressure to source deals, drive the business and needs you, in your role, to support that effort. Slow yourself down - consider his position - talk to others in your group - and really think about what you are doing.

My other assorted thoughts are below:

  1. Source new business. Want to do it? Prove it This could be doing the legwork on some prospects you think have been overlooked, analyzing a market that people may have not considered, etc. I don't know your business - you say you can source new stuff - do it.
  2. Understand your role and have your boss articulate what your key projects are. If you aren't happy with it - talk to your boss. Be direct. Be clear. But most importantly DO NOT challenge him to say - hey, you don't do shit - i can do it better than you. In most cases this is an issue of either communcation or priortization - probably both.
  3. Do not be that person who tries to get 'agreements in writing' based on conversations, meetings, etc. It does not matter if you are 'correct' and he did say that - you will be toast. Burnt. Toast. The number one rule is to never embarass your boss, ever, in front of his boss. You exist to support him until someone thinks you can do his job, especially in this case.

I cannot stress number 3 enough here. The moment you do that - your boss's boss goes 'hey jackass, what's going on in your group? Who is this guy, why can't you manage him, what's the deal...' That may sound like a good outcome to you considering you are frustrated - it's not. It's a death sentence for you. You've burned any human capital you have with your current boss - and it's not a good look regardless, and won't lead to the outcome you want.

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May 19, 2020

This is great advice. I'd add that #3 extends beyond interactions with your boss. Don't be Paper Trail Guy. Nobody likes Paper Trail Guy.

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May 19, 2020

Don't take things so personally. I have a feeling you're thinking about this even outside of work..

Assuming you're a good performer, I have a feeling you have no opportunity for growth in your role. I would start job hunting. If you keep on asking your boss about finding deals he's gonna get annoyed and potentially can you. Having a job and being healthy in this environment is a blessing. Smile, grind it out, and then get the fuck out! :)

Array

  • Associate 2 in RE - Res
May 19, 2020

First off, thanks to everyone who provided constructive feedback. This situation sucks, but after reading through the comments I was definitely being hasty.

That said, a few of you alluded to me "rubbing the wrong way." Curious, was it the tone of my description? Or, my assertion that I can find a deal and my boss can't? Something else?

Thanks again for the feedback.

May 19, 2020

Definitely don't go over their head. Maybe try to get on their good side. Like send them your leads or essentially drum up business for your boss to take credit for. Best way to look good is to make your boss look good.

xx,

Twizzzz

May 19, 2020

Here is how you do it.

1) you do the research and go find new business leads, and do your analysis also...fast as you can
2) you write an email to your boss in summary style, starting with a statement to the tune of "in the spirit of the recent meeting where it was suggested that all team members are in charge of finding new business, i've done some research and found these top 3-4 leads"

(here is where you only present your best ideas)

Keep each lead as a short summary, like a resume, with short bullet point for each with potential realistic revenue from each

cc'boss's boss.

If you have the time, include your more detailed analysis as a separate attachment to this email (again, to prove that you are a rockstar).

This way, you are not undermining your boss...you are doing exactly what you have been asked to do. cc'ing the boss's boss just ensure that your boss doesn't take credit for your work (because that definitely happens)

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May 19, 2020

A wise MD once said "It's the analyst's job to make the associate look good, it's the associate's job to make the VP look good and it's the VP's job to make me look good." As the analyst don't piss off your boss unless you're sure you can destroy them, because if you strike at the king you must kill them.

The best option if your boss sucks is to do great work and look for an opportunity to move on. Network with other groups internally or externally and commit to making tracks.

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May 19, 2020

Agree with general thoughts above and adding a few things -
1. Just keep your head down and job search. Your situation doesn't sound terrible as far as corporate BS goes.
2. Don't outshine the master unless necessary for your survival, in which case you have to go for the kill.
3. If you want to bring in business just go for it and ask later

Also, if your perception of the situation is accurate, then your company fucking sucks. The manager has been failing completely at his individual goals for years as well as suppressing talent/ambition from you, and he's still there? There are broader problems at your company and you should try to get out.

May 19, 2020

whatever you do, just don't be like this guy

https://www.reddit.com/r/AmItheAsshole/comments/g6...

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May 20, 2020

never. Unless your boss tells you.

May 20, 2020
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May 21, 2020