Posted by Ask a Manager
https://www.askamanager.org/2025/11/am-i-too-long-winded-employee-leans-on-me-for-help-with-everything-and-more.html
https://www.askamanager.org/?p=34352
It’s five answers to five questions. Here we go…
1. Do I need to be less long-winded?
How can I be less long-winded? I’m a senior manager, so I have to talk frequently: laying out project goals and plans, providing directions to team members, clarifying roles, explaining my feedback or why I disagree with a recommendation, explaining a complex situation/problem we need to solve, etc.
I feel like when I’m talking, I might be going on too long because people often interrupt me because they think I’m done talking, but I’m not. I often have a detail to add that I think is important because it adds nuance to what I just said, or it sums up the explanation I just gave. Earlier in my career, I felt like I was not talking or explaining enough, because I would say my piece and get blank stares back, or people would gloss over what I said, only to circle back later and realize that what I had said was spot on/helpful/important. Now I wonder if I’ve overcorrected in the other direction. Maybe I’m over explaining, maybe people get the point the first time I make it, maybe I just drone on. I’m not sure. How would I know? What can I do to be more concise and still get my point across?
It could be any of those possibilities, or it could be that you work around a bunch of fast talkers / fast processors who are jumping in too soon or it could be that you’re pausing longer than you realize (or otherwise giving off cues that you’re done) and so people don’t realize that you weren’t finished. The best way to figure out what’s going on is to ask someone you trust to be honest and who has opportunities to see you in action! Tell them you want the unvarnished truth; you can’t fix it without knowing exactly what’s happening.
It’s also possible that your points weren’t given the same attention earlier in your career because you didn’t have the standing that you have now (because of your current position) and that it had nothing to do with your communication style back then. So you could also experiment with assuming that you don’t need to explain as much as you’ve been doing and see what happens if you limit yourself to, say, two-thirds of how much you’d normally talk now. Do your points still seem to land or are people not following what you’re saying? That would be interesting data as you sort through this, too.
2. Coworker refuses to consider any candidate who opens their application with “Dear Ms. ___”
Recently I met a man with a name that is often coded as female (think Ashley). He told me that it makes first round hiring easier, because he just automatically discards anyone who addresses their application “Dear Ms. ___.”
While I take his point that it speaks to a lack of research and preparation from the candidate, this also seemed extreme to me. I have a name that is very feminine and even still I occasionally get addressed as Sir/Mr. in emails (I assume this is because the role of hiring manager is still coded as masculine for many). It’s useful information, but I just make sure to include my pronouns in any replies.
It seemed to me a bit of a privileged stance to say, “Of course you should be able to address me correctly,” when women have to deal with this on a far greater level. I’m sure women named Max would have a very small candidate pool if they discarded every applicant who misgendered them. Or am I overreacting and, gender aside, he’s right that candidates who don’t check the genders of the hiring managers when applying deserve to not be interviewed?
Yeah, that’s bad hiring. It sucks that we live in a world where people make incorrect assumptions about gender based on names, but that’s what happens … and I am really skeptical that he himself always successfully avoids misgendering people when their name is the only thing he knows about them.
It doesn’t reveal a ton about those candidates’ mindsets (as opposed to the way “dear sirs” does reveal an assumption that in business, maleness is the default). It just reveals that they were taught to associate many names with gender and that Ashleys are usually women (and also that the person isn’t a Gone With the Wind fan).
If he thinks they should be doing more research to determine he’s a man, I’d be interested to know if he’s also automatically rejecting everyone who opens their letters with “dear hiring manager” (I bet he’s not, nor should he be). If I managed him, I’d be very concerned about his hiring processes if he was automatically rejecting good candidates over either of those things.
3. My employee leans on me for help with everything
I am struggling with an employee who, at best, has a confidence problem and, at worst, is letting herself off the hook on executing things because she’s always waiting around for my feedback. This employee has a need to run EVERYthing by me, including emails she’s drafted to individual people. She is very kind, but struggles to really complete tasks in general and this added layer of needing my approval on everything she does has become a real issue.
I have tried the kind way, trying to build her confidence by reassuring her that I trust her judgement (I do!) and that she is very intelligent and capable, but it has not helped and the issue seems to be getting worse. I am worried I’m being too harsh, but I have my own very long list of tasks to complete, and having to constantly hold her hand has been completely draining to me and makes me not love my work in the way that I used to. I am rarely critical of her in any real meaningful way and do my best to really praise her work when it does occasionally get done, but at this point I’m at a loss.
It sounds like the problem is that you haven’t been clear enough with her. This shouldn’t just be, “I trust your judgment so you don’t need to run things by me.” It needs to be, “I need you to make decisions about things like XYZ on your own without waiting for my feedback.” The first version is too soft and leaves the door open for her to think that continuing to lean on you so much is still an option; the second version tells her clearly she needs to change what she is doing. If you’ve already done that, then it’s time to escalate in seriousness to something more like, “Making decisions independently on things like XYZ is a really important requirement of this position, and I need to see you doing that in order to keep you in the job.”
That isn’t too harsh! It’s actually kind to spell out what you need from someone who isn’t picking up on it, and to tell her now, while there’s still an opportunity for her to change what she’s doing, rather than waiting until the issue has festered so long that the situation is unfixable.
Related:
how can I stop softening the message in tough conversations with my staff?
4. The yoga studio where I teach hasn’t been paying me on time
I’ve been teaching yoga for about four years now and was hired for my first job at this small group training facility. I teach once a week and often sub for one of the two other instructors. I previously got paid monthly. I have a full-time job and this is my side gig. So, it’s money I use for things like gifts, or save up for vacations.
Over the last two years, my monthly payment stretched to being paid every two months. This past year, it’s stretched out to being paid every four or five months. I’ve asked the owners several times to leave a check for me for next week. I’ve also asked if there is an easier way for them to pay me, such as Venmo or direct deposit.
I’m at the point now where I’m owed for over 21 classes ($40 per class). Enrollment in the small training groups seems to have dropped as I’m seeing new members less. People do join for the yoga-only package to come to the yoga classes. What’s the best way to ask to be paid and let them know I can’t/shouldn’t have to wait longer than two months for payment? I’m at the point now where I want to say that I won’t teach until I get paid, but that isn’t really my vibe.
Well, wait, saying that you won’t teach until you get paid should be your vibe! That’s a very reasonable and justifiable stance to take. If there are any wrong vibes here, it’s “we hire you for your labor and then don’t pay you when promised.”
I’m guessing you’re worried about coming across as confrontational with people you’re on good terms with … but where is their worry about coming across badly to you?
In any case, it doesn’t need to be adversarial. You can simply say, “I’m currently owed for 21 classes and I’ve tried to extend as much grace as I can, but I really do need to be paid. There’s so much owed now that I can’t teach any additional classes until we get this squared away, because I don’t want the outstanding amount to grow larger. Can you let me know when I can pick up the check?”
But also: once you’re paid, consider whether you can safely continue teaching at this studio, because it sounds like the payment issues may continue. At a minimum, you could consider requesting that monthly payment be made before you teach for the following month … because otherwise you’re risking that at some point payment will never arrive and you’ll have been working for free.
5. Skipping a holiday party while grieving
I experienced the death of my child this year, and though I seem okay at work, I’m struggling with my grief. My therapist and I have been working on preparing for the holidays, which can be a fraught time for grievers, and we’ve agreed that I should minimize my participation in holiday events and parties.
How can I explain this to my boss? We all get the time out of the office to attend our daytime holiday party, so it’s not like I can say I need to stay at the office for staffing reasons. Am I just unexpectedly “sick” on that day? I don’t want to seem like a Scrooge or like I’m not a team player, but I really do need to take a big step back from the holidays this year for my own mental health. What do you suggest?
I’m so sorry! Any manager who is even a 10% decent person would understand if you explain that you’re not up to attending a party this year. I would say it this way: “It’s been such a hard year for me and my family that I’m not in a place to attend a holiday party yet. I can remain at the office during the event or head home once everyone leaves for it, whichever you prefer.”
The post am I too long-winded, employee leans on me for help with everything, and more appeared first on Ask a Manager.
https://www.askamanager.org/2025/11/am-i-too-long-winded-employee-leans-on-me-for-help-with-everything-and-more.html
https://www.askamanager.org/?p=34352