How do I manage up with a manager who is a people pleaser?
March 20, 2017 5:10 PM   Subscribe

My boss is a people pleaser, and true to form, she does not want to tell her boss anything they don't want to hear. My team has been bleeding people (one person has left each year I've been there) and is overloaded with work, but the grandboss is not responsive. Any tips on dealing with my boss in an ethical manner while still showing her that there is no real way to get everything requested completed?
posted by knitcrazybooknut to Work & Money (5 answers total) 6 users marked this as a favorite
If she's a people-pleaser, she wants to please you, too, despite the fact that you are subordinate. Go talk to her and tell her you're unsatisfied with how she's getting a lot of work put on the department, and therefore you (everything you say has to come down to the human level, ultimately) are working at or beyond capacity as the staff level drops.

Walk her through how her actions to heedlessly accept work from grandboss are affecting you directly, and how it's necessary to draw the line somewhere if she wants to keep the current staff. I would strongly avoid hinting that you're about to leave...unless you are, but it's probably okay to point out the attrition rate and the fact that things can't improve with fewer staff doing more and more.

People pleasing (and I speak as such a person) is about doing the pleasing thing in the moment and then puzzling out the consequences later. Hard talk avoided, hard work embraced. So it's easy for her to say "yes, I agree, I'll make changes" and then do nothing w/r/t grandboss. So maybe you could suggest a 3-way meeting after you pitch these ideas to your boss; when the 3-way conversation gets difficult, you can take the lead. The important thing is that you can acknowledge that everyone's trying to do right by their respective bosses, but your group has limits. It's okay to acknowledge the feelings and political acts, but they must be tempered every time with a concrete reminder that it's not enough that everyone feels good about the meeting, but that action is needed and you can't leave without some concession from grandboss. Hopefully grandboss will read the tea leaves and not drop it all on your boss...but if grandboss does, you should be ready to call it out.
posted by Sunburnt at 5:27 PM on March 20 [2 favorites]

The most effective method I've found is to say something like " I'm currently working on x, y, and z. How would you like me to prioritize New Task in with those? ". If you can give specific feedback on deadlines, or effects on schedules for existing tasks in order to help prioritize, thats a bonus. This way, you're not put in the position of telling Boss or Grand Boss "no", but let them know the impact that the new work has on existing work, and remind them of what's already on your plate.
posted by nalyd at 5:29 PM on March 20 [13 favorites]

Keep in mind that Grandboss probably knows Boss is a people-pleaser, and that may be a big part of the reason Boss was put there. For Grandboss, that's a feature, not a bug. It's not clear how many people your dept has lost, but if your bosses were that concerned about bleeding people and willing/able to do something about it, they would have done so. One or more people in charge are happy with or at least apathetic to the situation as it currently exists. That's probably not going to change.

As a result, trying to tackle the problem head-on won't work. Boss wants to please you, yes, but probably wants to please Grandboss (and other people above her in the heirarchy) more. Your job here is not to fix the department or to teach Boss how to manage her boss. Your job is to make the situation as sustainable for yourself as possible.

The biggest problem I've had with people-pleasing bosses is they will agree to one thing in person, but the moment Grandboss expresses a different preference, Boss not only changes their mind, but pretends the new plan was the agreement all along. To that end, I'm nthing nalyd's approach, and adding that you should get that information in writing (e.g. ask for it via email). For example:

-- If you can't get priorities or deadlines from Boss by email, make it happen after the fact. Have a conversation with Boss in person, then follow up with an email that says something like "Thanks for helping me prioritize these tasks! My understanding from our conversation is [A,B,C]. Do I have that correct?"
-- If your boss refuses to give you specific priorities / goals at all, follow up with an email that says "Thanks for talking with me today! When you have an opportunity to provide me some guidance on prioritizing [X,Y,Z], I'd really appreciate it." (Do that one even if she didn't indicate she would provide you with any guidance.)
-- If she gives you specifics but later they change: "Thanks for clarifying the deadlines! The new ones are now [1,2,3], do I have that correct?"

You may also want to spend a little time in the archives of Ask A Manager. Based on how long the overload has been happening, this advice might not be relevant, but here's an article from 2015 that could be a place to start. For the record, AAM is one of the few sites where I DO recommend reading the comments.
posted by zebra at 6:18 PM on March 20 [5 favorites]

I still run into this sometimes, but the best success I've had with this issue was to focus less on the underlying cause (boss is a people pleaser) and more on a specific problem that comes as a result (project overload, not being included in the workflow, etc.).

It can be easier to frame a meeting around a specific, concrete issue to resolve rather than an environmental or overarching problem because then you can work on creating specific, concrete solutions to the issue that is causing you problems, which means you might actually be able to affect some change, even if it's not perfect.
posted by helloimjennsco at 12:45 PM on March 21 [1 favorite]

If you generally have a good and trusting relationship built up over time--despite the, say, managerial deficiencies--consider being super blunt. Serious voice, interrupt if necessary to get this out: "No, I am asking for help. I can't juggle things around anymore. Things are breaking. My team is stretched too thin for too long and this is now a crisis and I need you to X." Even if X is only "understand this"--she will stop pleasing grandboss if things collapse.

I have used this successfully, to convince my boss to get out of "general advice mode." There are horror stories of people doing this and getting "Oh, so you're saying you can't handle the job, let me know if I should be looking for your replacement" in response, so know your situation.
posted by mark k at 6:32 PM on March 21 [1 favorite]

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