Ask a Boss: Am I Too Needy With My New Boss?

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Dear Boss,

I’m a few months into a new position that I’m not entirely sure I’m qualified for. This new role would more typically be filled by someone with a strong tech background: an understanding of network protocols, some basic programming skills, and probably a few years of sysadmin experience. My background is in something completely different — I’ve got a graduate degree in a social science and nearly 15 years of work experience in very academic nonprofits that directly relate to that degree. Due to a combination of factors, I ended up moving from several states away and taking an entry-level customer service position at my current company. I saw a need for someone to be fluent with a particular tool, taught myself to use it, and used it to build some new tools to help coworkers be faster and more accurate. The work I did impressed a few different people, and now I’m working directly for one of them.

My new boss and I have talked about what I do and don’t bring to the table. He says that I’m good with analyzing data, that I have shown I learn quickly, and that my background helps me translate between my new team and some of the less technical teams. On a day-to-day basis, though, I often feel like I’m not pulling my weight, and I end up asking my teammates to explain really, really basic stuff (I have some wonderful, patient people on my new team), or end up taking five or six times longer on a simple task because I need to google most of the words. To make things worse, I’m based in a different office (and in a different time zone) than the rest of my team. We’ve got a pretty good team chat going, but there are a million different subtle, team-culture things that I feel like I’m just not sure about, and the uncertainty can get paralyzing sometimes.

My boss is great, and makes an effort to check in with me specifically every few weeks. I always ask how I’m doing, and what I can do better. The last few conversations, though, I’m getting the sense that it’s perhaps starting to annoy him — but again, I’m all the way over here, so maybe he was just having a bad day? He says that I’m exceeding expectations, and he’ll let me know if I ever get down to just meeting them. That doesn’t seem like it can be true, though, and I’m driving myself to distraction trying to figure out how to become competent at this job. 

Am I asking for too much feedback? How do you get more constructive feedback when all you ever hear is that you’re doing great? Or am I in fact doing great, and it’s just that my expectations for myself are way off? And if my expectations are what need adjusting, how do I let go of those expectations and trust that my boss is right and I’m doing a good job?

Well, you’re only a few months into a job that’s a real change for you — of course you’re feeling overwhelmed. That’s very, very normal. In fact, even in jobs that aren’t entirely new areas of work, I’m fairly sure that it takes somewhere around six months in most professional jobs to start feeling like you really know what you’re doing, and sometimes longer. Often, too, it’s because of exactly the factors you described: not yet having a basic foundation in the subject matter and having to stop to look up things that everyone else already knows, and simultaneously having to learn a whole new office culture while you do it.

That can be really unsettling if you’ve never experienced it before, and it can drive you to do things like ask your boss if you’re doing okay every time you talk to him. But I’d resist that impulse. It does sound like you’re asking a lot, if you’re asking for broad, how-am-I-doing feedback every time he checks in with you. And if he’s telling you that you’re exceeding expectations, the most likely explanation is … that you’re exceeding expectations. Unless he is a truly terrible manager, he wouldn’t tell you that if you were actually disappointing him in significant ways. This might become more intuitive if you put yourself in his shoes: If you had serious concerns about a new employee, would you tell her that she was exceeding expectations? Not “You’re doing okay” or, “Well, you’re still new and learning,” but exceeding expectations? You would not, and he almost certainly isn’t either.

I mean, I’ve certainly been guilty of waiting too long to have a difficult feedback conversation with someone — show me a manager who isn’t a jerk and who hasn’t dragged their feet on that at some point — but you know who gets candid feedback the fastest? People who make it really easy for the manager to broach the subject. By regularly asking how you’re doing, you’ve been making it as easy as possible for your boss to say, “Actually, this isn’t going quite as I had hoped,” and he is not saying that. So, yes, believe him.

This doesn’t mean, though, that you can’t request feedback at all. It just means that you should pull back on the frequent requests for general “am I doing okay?” feedback. But what you can do instead, and what I suspect he’d be more receptive to, is ask more specific questions. Tell him about an obstacle in a project you’re working on and ask for his advice about how to approach it. Or ask to debrief a recent project and tell him how you think it went at some point — the good parts and the could-have-been-better parts — and the lessons you’re taking away from it. Ask if that sounds right to him. This is the kind of thing that can’t be answered with “You’re doing great”; it’s going to get you into a much more nuanced (and probably useful) conversation about the actual details of your work.

Dear Boss,

I am a young, female lawyer, with an assistant I share with one other lawyer.   

My assistant is great at her job, but very high-strung and sensitive, and we have been through a steep learning curve together around management skills (mine) and being calm and less emotional at work (her). She is valuable and I want her to feel that, and I want her to be happy and fulfilled in her job because I’m a decent human being. However, I don’t want to be friends. 

The problem: She buys me presents. Christmas, my wedding, my birthday, even chocolates on Valentine’s Day, etc. It’s very sweet, but 1) I feel very uncomfortable with my assistant buying me gifts, and 2) it’s not a culture I want to participate in. I get my assistant flowers for Administrative Professionals Day and on other appropriate occasions, as well as a gift at Christmas (which is expected here).  I want to end the arms race, but I don’t want her to feel bad. 


Gifts are such a fraught thing at work, largely because work is a place that’s full of power dynamics and obligations. On the employee side of things, it’s easy to start wondering if giving gifts is sometimes obligatory (although more often at times like Christmas than on Valentine’s Day!) Lots of ickiness arises from people feeling pressured to buy gifts for their managers, especially if other people around them are doing it. You shouldn’t have to give gifts to the person who controls your income, but it still can feel really awkward to be the one person who didn’t give the boss a birthday gift.

Complicating matters further, sometimes gifts are truly just genuine expressions of goodwill, so it’s tough to say to someone, essentially, “Cut out these lovely expressions of kindness.”

But it’s entirely reasonable for you to do that as a manager — both because it’s making the relationship something you don’t want it to be, and because it’s a reasonable stance for managers to take in general (see power dynamics above).

The trick, of course, is in how to say it without making her feel bad. I’d say it this way: “It’s so kind of you to think of me on these occasions. You have great taste and I constantly use the beautiful blue vase you gave me for my birthday. But I would never want you to feel obligated to give me a gift — and while you might not feel that way now, it could feel like an obligation someday. With me being your manager, that can be a sticky dynamic. So because of that, I’m going to ask you not to continue with the gifts. I really appreciate that you’re a thoughtful and generous person, but in this case, just continuing to do the great job you always do is all the gift I need.”

The language complimenting her taste and a particular gift is intended to lower the chances that she’ll feel embarrassed and start wondering if this whole time you hated the things she was giving you. This framing makes it more about you looking out for her and the relationship in general, and that should be easier to swallow. She may still be a little embarrassed, but it should ease some of the sting.

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Ask a Boss: Am I Too Needy With My New Boss?