How to talk so a somewhat sensitive supervisor will listen?

My immediate manager is nice. She is interesting. We agree on many issues, political and otherwise. She has said (paraphrasing), “Please don’t be afraid to tell me if I’m doing things that you don’t like.” But in practice, that statement appears to run up against a need to be liked that is so strong as to discourage anything that could be construed at all as criticism.

For example, I discovered today that I was charged to call into a meeting for which I thought there would be no charge. Use of this online conferencing system was proposed by my manager. I don’t want her to feel as though I’m attacking her if I explain the issue and ask if there’s a way to get around using the phone number that is not toll-free.

I always try to be considerate (well, almost always) but the walking-on-eggshells feelings I’ve developed around this person are a little wearing.

Any ideas? Thanks.

On this one, simply submit an expense report.

On others, be careful to talk about processes, not about her, and it often helps if you can use “I” statements rather than “you” ones. Be constructive. “I feel really overwhelmed when I
have 10 things to do at once because I want to do a good job and meet the team’s expectations. It would help me if we could prioritize my to-do list and clarify deadlines. If I set up a standing meeting every day with you at 9:30, could we review what’s on my plate and make sure I’m using my time in the best way possible for the team?”

This is about your problem, the help you need, and how it’s for the common good. Never mind that the list was a result of your boss dumping on you with no context!

And keep the focus on what you like about her and how you get along. These prickly people issues are easier to work through if you can feel positive about the other person. Once you start focusing on what bugs you, it gets much harder.

Thank you! These are great suggestions.

Yes to expense reports. Keep submitting them. When she sees the numbers on paper, she might change the provider for that conference service.

Be positive and don’t sound like a whiner. Ask for her input as to the solution to your work issues. Call them issues, not problems - the terminology matters. Good luck!

Can you find another alternative system that doesn’t charge? Then you could say: “I used the conferencing system, and apparently they charge for it, but I found another option that doesn’t. Maybe we could see how Option B works?”

Not to be unsympathetic, but I thought you’d be describing a more contentious issue. But I guess that is the idea - if unexpected phone charges are hard to discuss then other issues that arise will be a bigger problem with this person.

Oh, there are definitely more contentious issues. Last year, when this person started at my workplace, I was training her in some job duties and when I corrected something in a document she had worked on, she came to my desk with daggers in her eyes. She was really angry.

If it had been almost any other coworker, I would have spoken to the person already (about the phone bill issue) and I think the interaction would have been straightforward and without contention.

Unfortunately supervisors often say one thing and do another, the infamous “my door is always open” often translates into “my door is always open, but I don’t want anyone coming through that”, the manager who tells you they welcome feedback are often the most sensitive, etc.

A lot of the time it comes down to your approach, someone who is sensitive to criticism or in feeling like they are being attacked have to be handled in certain ways. For example, if you say to this person “You asked me to dial into this meeting, and calling that number costs me money” it sounds like a personal attack, but if you submit an expense report for the calls, and then point out that using that number will cost the company money, as someone else said, and suggest maybe finding a conference that has local access or an 800 number might be more cost effective, it becomes about process. One thing to note, if the number involved is in the US, most people these days have plans with unlimited local and long distance calling, whether through VOIP or through landline or cell service, so they might not even think that a call would cost anything extra.

Likewise, when it comes to correcting a document, some people get upsets if you correct the words in the document and give it back to them. A better way may be “Hey, I looked over the document you sent me, and I had some thoughts on how it might be improved if you would like”, it turns from being (in their head) “You screwed these sections up” to being a colleague suggesting improvements.

Unfortunately there are always difficult people in the workplace you have to deal with, what seems trivial to you might be a big deal to them, have had to deal with that with both bosses and people reporting to me over the years, and it can be hard and frustrating how to avoid the minefields, and often with people like that the big thing is finding a way to criticize or give feedback without seeming to. One rule I learned (from a book on being the parent of a sport kid, written by Cal Ripken, Jr) is to sandwich feedback’/criticism in between compliments, so say something “Hey, X, I think that document you sent to me was really clear and well written. I do have a couple of suggestions that I think may help improve it, but overall I think it really got the job done”.

When coaching children, it is often advised to use a “praise sandwich” when conveying correction. In addition to the other excellent techniques mentioned above, it might help.

In other words, roughly:

Praise: I really like this kind of phone in conference that you created.
Correction: But I found out that the current service is charging us to do so. Do you want me to just expense it, or could we use a different service?
Praise: These conferences are really valuable, great idea on your part, and I hope we can keep having them.

ETA: Oops, just noticed the prior post mentions the same concept!

I know it’s frustrating to feel like you’re walking on eggshells. But can you imagine being approached by employees complaining about stuff and essentially blaming you? It can feel like that sometimes. I have thick skin and I prefer people just being direct, but I know over the years I’ve had overly sensitive people managing - which is great if you want sympathy and encouragement, not great if you just want to communicate an issue. My husband is very direct, and I have to laugh when some women will invariably ask - is he always like that? You mean walk in, tell you what he needs, ask if you know how to do it and then just say thanks? Yes, he never means more than that and literally just means exactly what he says with no deeper meaning.