am I being too needy with my new boss?

Two questions: One from someone worried about being too needy with a new boss, and one from someone wondering how to ask her assistant to stop giving her gifts.

A reader writes:

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 timezone) than the rest of my team. We’ve got a pretty good team chat going, but there’s 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 specifically with me 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 the ones that 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.

Read an update to this letter here.

How can I ask my assistant to stop giving me gifts?

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.

Originally published at New York Magazine.

{ 39 comments… read them below }

  1. Olive*

    Completely off topic – but I love the stock photos that accompany your column there.

    1. Wakeen's Teapots, Ltd.*

      Freaking me out. Like, I had that blouse. :/

      (And the “car phone” in last week’s picture!)

        1. Wakeen's Teapots, Ltd.*

          I have naturally curly hair and you’ll remember BIG perms were in then? So I had the VERY BIG curly hair, with out the perm. Very BIG.

          And that blouse.

          And that monster car phone.

          Thus enters our heroine into the world of work………

  2. Leatherwings*

    Love the new column!

    For LW #2 – I would be sure to get the other lawyer who she works for on board with this too. That will hopefully make it feel less personal and more of a “this is how things are done” convo.

  3. Chameleon*

    I know OP probably doesn’t read here, but for anyone in a similar situation:

    I have always suffered from impostor syndrome like the OP, and have never managed to believe my bosses or mentors when they praised me. In fact, it makes me feel worse most of the time, like “not only am I terrible, I’m sneaky enough to have fooled this person!” (Which, like, I know is ridiculous.)

    The way to deal with this is to remember that this is a person who you presumably think is very smart and competent. On literally any other topic, you believe them and trust their judgement. So, trust their judgement about you, too. If they are able to make good decisions about other things, they probably know what they are talking about regarding your job performance also. So just trust them.

    1. Marillenbaum*

      That’s something I tell myself, too. If I can’t trust my own judgment about whether or not I’m good enough, I can trust the judgment of people I respect, who I know would tell me if I were screwing something up.

    2. OP*

      That’s a great point. It’s hard not to feel like I’ve just somehow managed to fool everyone, and maybe if I am very, very quiet they’ll just not notice the horrible mistake they’ve all made… but you’re right that my boss and my coworkers are the sort of people who very rarely make those sort of mistakes.

      1. Not So NewReader*

        People who have trained a lot of people recognize who will “get it” and who won’t. If you ever do a lot of training you will see the same patterns yourself. What I am saying is trust the people training you to know if you will make it or not.

        I do understand this is hard. But it’s necessary. If you spend too much time dwelling on and asking for feedback, you can unravel/defeat yourself. Yes, sort of a self-fulfilling prophecy type of thing. I can train you to do a task but I cannot train you to believe in yourself. The nature of the work was such that I could train folks how to double check their own work. I found that this greatly reduced the number of “how am I doing?” questions.
        Several suggestions;
        1) Watch your self-talk. Make a commitment to learn the job. When doubt rears its head, which it will every so often, say to yourself, “NO. I am committed to learning this job. I will do what it takes to learn the job.”
        2)If you have to keep a little journal at home of the nice things people say. Make yourself re-read at frequent intervals.
        3) Double check your work. Use little tricks of going over it from the bottom up or whatever you can think of to make yourself use fresh eyes. If you are still having doubts, make yourself triple check the harder parts. Vow to never make the same mistake twice. You know you made a mistake on line 37 yesterday, then check line 37 today. This can drive you nuts for a bit, but after a while you will find that you do not need to do it.
        4)Really. Stop asking how you are doing. You are doing fine. The job is hard and that is what it is. It will not be so hard in a while, you will train your brain to be acclimated to the work. The real question is not what they think of you, it’s what you think of you. Be kind to you. Once you start with kinder self-talk you will find that it is easier to catch on to the job.

        1. Claire*

          On #2, if your workplace is anything like mine, a lot of these little compliments will come via email or IM. Save a copy of them into a dedicated folder in your email so you can access them whenever you’re down at work, and they come in handy for performance evaluations as well. My manager asked me to provide some of the verbatims in my last performance review a few weeks ago, and it was a really nice little boost to my ego to read all the nice things people have written over the past year (especially since I’m feeling a bit dissatisfied and anxious about work at the moment).

      2. TootsNYC*

        One thing to remember–you haven’t fooled anyone. They know exactly how little targeted experience you have, and they know exactly what you don’t know (bcs you’re asking them questions).

        But one think you are overlooking–“bringing your brain with you to work,” investing your creative problem-solving skills, are actually relatively rare. And very valuable.

        There’s also tremendous value sometimes in having someone on your team with a very, very different point of view. Someone who, for example, can imagine USING the software someone else is writing.

        As Not So NewReader points out: there is an ability to learn that some people are better at. I don’t think they’re necessarily born with it–I think it’s an attitude that leads them to develop the skill of learning. You have that.

  4. Natasha*

    I had the same experience, with the same insecurities. It took me 6 months to start to feel adequate, and a year later I finally feel like I’m excelling. In retrospect, I’m grateful for the stretch experience.

    1. KH*

      I had the same challenge as well, made worse by the fact that they switched up my role right at the six months – just as I was starting to feel comfortable, I had to start all over again.

      I’m in the exact opposite position as the OP though: I have the technical background and that is what the team likes about me – they don’t have to explain like I’m 5 – but I didn’t come up through the normal ranks into this position and don’t have the typical background/experience, and so I struggle in different areas.

  5. BadPlanning*

    For the gift giving — would it be helpful to bring up the “gifting down” as an external source? Then it doesn’t sound like you’ve been hating the gifts all this time and not telling her — or that it’s an issue with her gifts — but more of a general workplace standard that you’d like to start. In addition to the suggested language, something like “I was reading about the concept of ‘gifts should generally flow downwards in the workplace’ and thought that was a good policy so employees don’t get stuck in an awkward financial situation.”

    1. NK*

      I like this on top of Alison’s response; referring to it as a general management principle that OP just read about rather than just something that makes her uncomfortable will hopefully help lessen any embarrassment the assistant might feel. I do agree with a PP that the other attorney should ideally be on board with this as well.

  6. SophieChotek*

    I agree, I would hate to feel obligated with giving my boss/superior a gift. But I can also understand where this OP’s assistant might be coming from — especially if one is the type that just loves to give gifts. I have difficulty reigning that in when I see something that reminds me of someone (it doesn’t have to be expensive) that makes me want to buy it for someone…when it is a boss/superior, I understand it might not be appropriate, etc. – but it can/could be hard to resist that impulse

    1. TootsNYC*

      Actually, given that there’s been tension between them, and the assistant has struggled with some of those things, I think this gift-giving is really bad, because it’s almost a form of a bribe: “You can’t discipline me, because I give you gifts!”

  7. Seal*

    #2 is very timely for me. I have an employee who insists on giving everyone in the office, including me, gifts on birthdays and holidays. This is despite the fact that we have very clear (at least to everyone else) understanding in our office that we do NOT exchange gifts on these occasions in favor of quarterly potluck lunches where I provide the pizza. Not so subtle hints from me or her colleagues to knock it off have not deterred this woman; she insists this is something she “loves to do”. Although her gifts are generally small and inexensive, she recently gave me an obviously expensive birthday gift that I am uncomfortable keeping. So now I find myself in the position of not only having to explain to her again that our department doesn’t do gifts. Since this employee has previously demonstrated issues with boundaries at work, I suspect she’s not going to understand why this is a problem.

  8. BRR*

    A lot of #1 applies to me at the moment. The difference being I am a department of 1 and my manager doesn’t know a lot of the technical aspects of what I do, only the outcome. I will admit my preference is on the frequent feedback end of the spectrum but I feel like my boss isn’t hitting the minimum check in requirements. I’ve also had some poor work performance before so it’s hard for me to hear that I’m doing amazing. I think I just don’t like how my organization is most people being siloed while they’re working and I like to collaborate more (we’re even in an open office plan and I’m not collaborating enough *panics*). So you have someone (me) who wants a lot of feedback and a manager/organization that operates with autonomous employees and it’s just not a great fit.

  9. Trout 'Waver*

    For OP #1, google the Dunning–Kruger effect and impostor syndrome and read up on them. Being self-critical is a sign of competence, not incompetence. Just don’t let it actually convince you that you are bad at your job. The experts (your experienced colleagues and your boss) have decided that you are good at your job.

    1. OP*

      I had to go read up on the Dunning-Kruger effect… that’s a fascinating study, and it explains *so* much!

  10. Anonymous Educator*

    I’m in a fairly similar situation to the OP, but I’m a bit further along in getting away from imposter syndrome. I majored in a “useless” humanities major undergrad and have no official training in tech, and yet I do a lot of what it sounds like the OP’s job is (and well, if my boss—like the OP’s—is to be believed). I’ve had a lot of trial-by-fire moments, but I’ve found my footing. The truth is, though, no matter how good you get, technology keeps changing, and you always have to be learning. No one is the eternal master, and everyone who works in tech (whether it’s sys admin’ing, network admin’ing, or tier-1 tech support) has to Google stuff. I’d recommend just toughing it and learning. You’ll do fine!

  11. Former Invoice Girl*

    The timing for this post is perfect. I’ve recently been promoted from Invoice Girl (hence the handle) to Teapot Agent, and I feel like the learning curve is steep; I also often think of how the frequent display of my lack of confidence is annoying. I think the advice to ask more specific questions is great – I’ll use it more often from now on.

    I also love the new column!

    1. HumbleOnion*

      I work with new hires who face a steep learning curve, and I always tell them to think about the kind of questions they’re asking. Are they asking a lot of different questions? That’s great! They’re learning! Or are they asking the same question over & over? That’s not so great. Why aren’t they retaining the information they’ve been given?

      1. Former Invoice Girl*

        That’s something important to consider – thanks for sharing this!

  12. Laura (Needs a New Name)*

    OP1, I had a research assistant like you once. She was really fantastic, but her self-concept was very focused on her inadequacies rather than her strengths. I finally sat her down at lunch and told her “it is my job to give you accurate feedback about your performance, and *it is your job to listen to me.*” This includes listening to the positive feedback!

  13. Junior Dev*

    Hi fellow liberal arts major working in tech! *waves*

    I would believe your managers when they say that being a quick learner is more important than a particular technical skill. I got real angsty during my first programming job because “I’m not doing anything yet! They’ll think I’m lazy!” — while I was taking the time to read about the existing code base and wrap my head around the tools.

    Tech is a years-long process of constantly learning to use more tools. I just finished a temp job as a teaching assistant at a code school, and one thing I try to impress on students is that programming is NOT the same as writing code. I’d say that the most important activity you’ll do is understanding what you’re attempting to do. Second is debugging, although you’ll spend the most time on it. Knowing the syntax and quirks of a particular programming language is a distant third.

    This is counterintuitive, because a lot of beginner programming tutorials focus on syntax–“here’s how you output ‘hello world’ to the console,” “here’s how you write a for loop,” and so on. Learning syntax is to programming as learning to hold a pencil is to writing a novel–a good place to start, but not fundamentally the most important skill.

    You’ve already demonstrated the most important skill, which is intellectual curiosity and a drive and ability to understand the systems you use. It’ll be hard, but I think you’ll do just fine.

      1. Junior Dev*

        You’re welcome!

        If I can give one more piece of advice while I’ve got your attention: try to make friends with other tech people, go to meetups, or at the very least try to read online forums that are beginner friendly, and talk about your struggles. The vast majority of people I have talked to sympathize with how hard the learning process is, but there’s a small minority of jerks who’ll mock you or look at you with disdain for not knowing everything. Stack Overflow has a ton of these come out of the woodwork whenever you ask a question that’s not phrased perfectly by their standards. My first boss was one too. I wouldn’t have gotten through that internship if I hadn’t had friends to reassure me I wasn’t stupid or doing it wrong.

        Sounds like your boss and colleagues are mostly not in the jerk category, which is great. But if you do ever encounter anyone who’s mean to you about not knowing everything they do, remember it says more about them than about you.

        1. AccidentalSysAdmin*

          This is to express my thanks to the OP, BRR and especially the encouragement and advice from Junior Dev. I am currently in a similar situation; long career in social sciences research and education; now in a job without a lot of description which has a LOT of system administration, IT and technical responsibilities coupled with a surprising amount of autonomy. I am reminding myself that technology changes so much that there is really no way to train for this, just to be proactive with others in the field and share knowledge, and appreciate the learning experience.

    1. Leemac*

      Yup, I’ve had a sysadmin career for 18 years, and I still do not have a university degree in computer science, IT, or in fact anything at all.

      Understanding the requirements, defining the objectives, and THEN working out how to do it are the important skills.

      I know that there will always be people better than me in a purely technical sense. I am not and never will be a programmer. But I’m good at research, solving problems, getting things done, borrowing other peoples’ work (openly – why reinvent any wheels?) and so on. I’ve been a valued asset on all of the tech teams I’ve worked in.

    2. TootsNYC*

      It’s like writing.

      It *is* writing.

      The most important thing is knowing what you want to say.
      The next most important thing is being able to edit what you’ve written.
      Last of all is knowing the syntax, grammar, etc.

      I graduated from college in the Mass Communications major w/ a kid who knew the rules of grammar down cold. But his idea of an in-depth feature story about married students was 1.25 pages (double-spaced); he got the statistics on the number of married students from the registrar, spent a paragraph telling about the married-student on-campus housing, got a single quote from the dean of students, and a single quote from a husband.
      I know, because he turned it in to the yearbook as a potential story for us to cover. We tossed it. He didn’t understand why.

      It was well written–not an error in sight. It was well organized. But it was badly written because it had no depth.

      You learn the syntax and grammar to make it easier, but those are not what make you a good writer.
      Having something important to say–that’s first.

  14. Noah*

    Re LW2- She is almost definitely NOT her secretary’s manager. Unless the firm is very small (and likely even then), the secretary has a secretarial manager. That said, in this context, there is nothing wrong with LW saying, “You really don’t need to get me any gifts. I mean it. Do not feel like you have to get me any gifts.” HOWEVER, if it seems like an office culture issue, LW2 should talk to the secretarial manager to address the issue. Actually, a young lawyer at a law firm is better off just following the STFU rule on this issue, but if it’s office culture and she cannot live without it being addressed, then do it through the manager. But be prepared to be viewed by the partners as an associate who makes waves, which is a terrible place for a young associate (and, at most firms, especially a young female associate) to be.

  15. Laura*

    Letter #2 – I’ve found that I am a person who enjoys giving gifts, so I can understand it. Aside from Christmas though, I tend to make it taffy from vacation for the department or something similar. You might try to start something like one department I worked where gifts weren’t expected but snacks/candy were put out by the copier whenever someone went on vacation. In this way, you are redirecting her more than stopping her. Lastly, I had a department where a new manager came in, and he was constantly trying to speak down to people he considered below him. On December 20th, he would announce that as a manager he shouldn’t be getting any gifts but of course then he would take what we had already bought. To the OP, think about what you are saying so it doesn’t come off as demeaning.

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