When Your Boss Won’t Delegate

When your boss won’t delegate, how can you move to the next step? But how can you grow your own skills when working with this person? When I got this question from Reader E a while ago, I knew just the woman to ask: Jodi Glickman, the author of Great on the Job: What to Say, How to Say It. The Secrets of Getting Ahead. (both book and blog), and a fellow Northwestern alumna. I hope you all enjoy her guest post today! – Kat

Multiple Choice, originally uploaded to Flickr by CoreForceHere’s Reader E’s question:

Can you do a feature on how to deal with a boss that is not good at delegating work, does not “have the time to teach” and believes it is easier to handle the matter herself, has issues letting go of important matters or bringing in the associates to work on such matters and etc. when one has been at the firm already for a good amount of time? Would love to hear the feedback you and the readers have other than the obvious answer of switching firms.

The reason your boss won’t (or can’t delegate) is that she’s too busy to think about putting you to work and she’s convinced it will take more time to get you up to speed than to do the work herself.  So, you’ve got to prove her wrong by showing that you can indeed add value and that you bring real skills to the table. (Multiple Choice, originally uploaded to Flickr by CoreForce.)

Before you think about walking out the door, consider using the multiple-choice strategy when you offer to help.  Instead of simply asking: “how can I help?” try offering to help out with two (or more) specific tasks:

Jane—I know we’ve got a lot to prepare for next week’s meeting- I’d be happy to draft an agenda or prepare a briefing memo in advance—which would you like me to start on?

The multiple choice strategy makes it harder for her to say no—if it’s clear that there’s a lot to be done and you demonstrate that you’re ready and willing to take on specific tasks, she’ll be more likely to give you the go-ahead.   This approach also shows that you’re in the loop—you have a sense of what’s going on around you and you’re aware of the challenges that lie ahead.

If this strategy still doesn’t work—then think in advance about how you’d actually help with those two or three specific tasks and go to your boss with your plan of action.  For example, when you offer to put the agenda together, have a sketch in hand of what you think the agenda should look like.  Or, give her your preliminary thoughts on what the briefing memo should include.  By doing some initial work, you’ll give her a sense of your thought process and demonstrate that you’re smart and you’ve got good judgment—both of which should go a long way in helping her to start offloading more meaningful and challenging for you.

Finally, once you do start getting some meaningful work, be sure to show her the continued benefits.  Let her know that you’re working hard to make her life easier (or better) and continue to challenge yourself.  Also, be sure to acknowledge that you appreciate her guidance and support.  If and when you need additional help or guidance with new tasks, state clearly that you expect the benefits to far outweigh the costs.  For example, you can say,

I’d appreciate sitting down and taking up ten minutes of your time to review the memo—I know once we make sure I’m moving in the right direction it will save us both considerable time and energy on the backend.  I want to be as efficient and effective as possible.”


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  1. “The reason your boss won’t (or can’t delegate) is that she’s too busy to think about putting you to work and she’s convinced it will take more time to get you up to speed than to do the work herself.”

    Not necessarily. A lot of lawyers just hoard work (and clients). It might be overly optimistic for a would-be delegee to think (s)he could change that.

    • Like having 100 cats, only different :

      True that. If you are in a turf-conscious environment and/or with insecure individuals, you may never get more work simply because of hoarding. Wait, is there an A&E hoarding show for that problem? Because I would totally watch that…oh, wait, no, no, I wouldn’t…

      • It’s all about turf!

        Power dynamics.

        Insecure managers protecting their territory, afraid of the smart, up-and-comers.

    • karenpadi :

      Work hoarders (and micro-managers), the previous bane of my existence. If that’s the situation, start planning a job hunt. You won’t make your hours and the hoarder will blame you for not taking “initiative.”

      Kat’s advice was right on. I’d also suggest offering to do projects based on what you’ve done for other attorneys. I love when my interns say something like “I just wrote a continuation application with Mike. Do you have any I could do?”

      • FYI only: it’s not Kat’s advice. This is a guest poster, with info outlined at the top of the page.

    • Exactly. I had a boss like that and it was not about not wanting to delegate as much as wanting to hoard work and clients.

    • And in a less cynical comment, I should add:

      Junior associates: be coachable. This is not as easy as it might sound.

      When I cut down on delegating or mentoring a junior colleague, it’s often because I find it’s not worth the effort anymore. Adapt. Listen. Take instruction. Implement constructive criticism when it’s offered. Don’t allow yourself to think you’re too good or too smart for a particular assignment.

      • This. There is nothing more aggravating than a junior colleague who thinks they know everything and/or are too good for the job. We know you don’t, and aren’t. My wonderful mentor taught me that humility is one of the best attributes you can have in a high-powered work environment. You can learn much more by quashing your pride and just listening.

    • This!

    • Diana Barry :

      Yes. This has been a problem in every job I’ve ever had. Doesn’t matter if the partners are swamped and the associates twiddling their thumbs….delegation wouldn’t happen until it was the last minute.

  2. Very early threadjack, but Gilt has Tumi luggage on sale, at great prices, plus you get another $15 off your order. I just became a very happy owner of a pretty orange carry-on!

    • What the hell are you talking about? That’s not a thread hijack, that’s a plug for Gilt.

  3. An overworked boss :

    “The reason your boss won’t (or can’t delegate) is that she’s too busy to think about putting you to work and she’s convinced it will take more time to get you up to speed than to do the work herself.”

    Yes! This is exactly why I don’t delegate as well as I should. My huband keeps asking “is your staff as busy as you are?” If I think about it honestly, no, they probably aren’t. That’s my fault. I hired these people because they’re talented and want to learn. Managing others is not wussy, and does take time. Letting go is the hard part, and if someone can self-assuredly take things off my plate, that is fantastic.

    • Yes…ditto….this is especially hard with anyone who is also a student!

  4. Divaliscious11 :

    In my experience, bosses don’t pass down work for two resins. One being the above, and two being they don’t trust your work product, and if they have to review your work with a significant level of review, they may as well do it themselves. So in addition to the above advice, do some self reflecting, ask for some qualitative feedback from your boss or other senior associates you work for or with. Be extra diligent in the work you do turn in. If is reason one, then show some initiative. What is the project, is there a project plan, what can you own off your bosses desk etc.. Also, if your boss mentions a problem, take it on as your own responsibility.

  5. anon for this :

    I’m a big law junior associate and I work very closely with a partner who doesn’t delegate, mostly because he’s a perfectionist (and admits to it). he cannot delegate because others would not comply with his standards the caliber of work has to be equal to that he would do himself. i see where he’s coming from, because his work is immpecable.

    i’ve been working with him for two years and, have been trying to work with the situation and increasingly, he has let go of the reigns, sometimes it’s a little scary for me because i’m not sure i can meet those high standards–but the fact that he let’s me go ahead and do a filing without a final check or let’s me correspond and speak with clients without butting in is serious progress and shows that he is developing some confidence in me.

    my strategy has been to do everything that is assigned to me as perfectly as possible:

    – impeccable presentation/formatting/etc. -i’m talking marketing-department level of professionalism (sometimes it helps make up for not-so-perfect work product that needs editting because he sees that my eye is on getting it right and it’s not that i’m just being sloppy or inattentive)

    – foreseeing what might be useful in the future and getting it started (for example, if he has a big meeting coming up, i start getting binders of materials i expect he will need ready–so when i go ask him what he needs, i can show him what i have and ask if that’s what he had in mind. usually he likes the direction i’m headed in and let’s me run with it, or makes some tweaks. either way, i’m in charge beginning to end because i got started before he thought of it)

    – handling criticism very well (if he’s giving me constructive feedback, it’s something i can implement in the future- nothing to get in a tizzy about)

    – making the most of minimal directions (chances are if you are working with someone like this, they aren’t very good at giving instructions because they of course avoid giving instructions). if i’m asked to draft a letter and i have no idea what it should look like, i search our system for samples (by him of course) to death and try to have something 90% decent before i go back to him and say, “is this right?” if i were to instead ask for detailed instructions up front, chances are he would not waste his time (his midset, not mine) on delegating something again in the future because it’s too much effort. i’m seeing this same partner struggle with a mid-level associate on this–that mid-level comes back and asks too many questions upfront and it just frustrates the partner, he would prefer to critique work product once something exists.

    i realize that none of these strategies are ideal for all circusmstances with all partners, but it works for this particular situation. during my annual reviews i’ve been told that it’s particularly impressive that i’m working so well with this partner because he has a history of difficulty working with associates. after two years, i really have not have an ounce of difficulty with him, we get along well, he is giving me more and more work, and i learn a ton.

    • This sounds fantastic, and is exactly how I learned when I was a junior. Will you come work for me? :-)

    • Sounds like you are a dream employee!!

    • Same idea as Nonny – you are a great example of what I strive to be with my management and what I wish my resources would do. Kudos to you!

    • anon for this :

      you all are too sweet! i’m far from perfect, but i’m definitely trying. this partner isn’t too forthcoming with feedback (if he’s giving me more work with more responsibility, i assume i must have done something right), so i’m glad to hear i’m headed in the right direction.

    • I have to confess that I am this boss (I know, I know…) and your advice is spot-on.
      The drawback for employees is that I don’t hand out a ton of responsibility early on (and probably need to do more of that), but employees that meet my exacting standards eventually end up getting enormous amounts of responsibility and I’ll help them out professionally years after they’ve moved on to other jobs. One flawless project (even if you have to be a little aggressive to get it from me) leads to another project and then another one… And the rare few that have that impeccable attention to detail, think of needs before I ask, handle critique well and don’t require a lot of instruction become indispensable.
      In thinking about it, one of my very first bosses was this way and I think I learned it from her – but I have enormous respect for her and felt tremendous pride in eventually earning her trust.

  6. Am I the only one with the opposite problem? I feel like everyone tries to delegate work to me. I work in government so there is no real benefit to taking on tons of extra work. I think I work a lot like anon for this in terms of doing well with minimal direction. If I get given a project I’ve never done before, it’s a given that I can seek out samples and do a passable job the first time around.

    • anon for this :

      the situation i described above is only with one partner, with everyone else—they just dump the work and, quite frankly, pay very little attention to quality and usually blame the junior associates if something goes wrong.

    • An unfortunate reality of practicing law in the U.S. is that the reward for work well done is more work.

      It’s not just you.

  7. I’m about to cry right now. My boss just sent me my review document before our discussion tomorrow. It’s horrible. He actually made stuff up. I just don’t know what to do.

    This is our mid-year review. In July, he asked us to write our own reviews. Now he’s addressing them. All of the nasty stuff and the things he cites have occurred since July. I feel like I need to address them, but at the same I think I should take advice from the No A$$hole Rule book and just not care.

    • Always a NYer :

      So sorry your boss is continuing to be a d!ck. While I’m usually the one to say don’t waste your time with this, but if he’s put in writing a negative, false review then you need to address them ASAP. Be diplomatic about it and go about it as clarification and wanting to clear up any discrepencies. Make sure you do this in an email as well and try to bcc someone you trust who knows about your situation, preferably someone who is higher up than your boss. *hugs*

    • AnonInfinity :

      Is it just you and A-hole Boss in the review?

      I’m so sorry you’re having so many problems with him. From your posts, he sounds so horrible that he belongs in a movie. Sending good luck and coping vibes to you for your review tomorrow.

      • Yes. Per my mother’s advice, I sent him a message saying I was going to update my list of accomplishments, etc since July. He responded stating that those should be included in my year-end review. All of his examples are post-July!!!

        • Respond to his email then and tell him that his examples should be removed since they’re post-July.

    • OK, this is a step too far. I think you seriously have to talk to a higher-up now. Take it to your boss’s boss. This is not something you should put up with.

      • I agree. I can’t remember your exact situation, but isn’t there someone you can speak with about him?

    • I’m not sure if I understand your situation exactly. But, could you play dumb and say something like, “Hey, Boss. I think my name somehow inadvertently was inserted on someone else’s review. I notice that it says, “X,” but I know that never happened/isn’t accurate/etc. If you’d like, I could update the review you had me write in July.”

    • I had a similar experience. After almost 20 years of glowing, beautiful reviews from various employers, an out-to-get-me interim CEO wrote pages of fiction and actually suggested a pay cut (he probably would have suggested firing me but knew he couldn’t get away with it). I spent about 40 hours of my own time over the next 2 weeks carefully refuting, point by point, his entire review of me. Because the review was written documentation, I felt the only way to address it was in written form. I did not give him the satisfaction of arguing with him or the opportunity to twist my words. I sat through the humiliating “review,” with him essentially reading me the review document over the phone (I was in a satellite office) and I recorded the conversation. WHile I didn’t have to use the recording, I did confide in a couple key people who had control over his future with the organization, and, coupled with my written rebuttal, freaked out the interim CEO, HR (they thought I might sue), and key board members. He did not get the real CEO position despite serving as interim for 9 months and I like to think I had something to do with that. I held on for another year (family stuff) and then made an exit on my terms. Bottom line: document – in writing- any issues you have with the review, take the high road, make sure at least SOMEONE else knows the real story and then GET OUT OF THERE!

    • So sorry you have to deal with this, Bunkster. :(

    • I agree you should document. And I really like the advice not to pick fights with him in person during the meeting; just do it in writing.

      But unless your process is very unusual, you don’t need to do it before the meeting tomorrow. If you can, make it through the meeting tomorrow: (1) without crying, and (2) on “receive only, no transmitting” mode. In other words, just listen to what he says. Treat it like an expert deposition: make sure whatever he has to say, he gets it out so you hear everything. Then say something simple like, “My memory differs from yours. I will be submitting my comments in writing.”

      Our company has a rule that anything the employee submits has to be “stapled” (back when everything was paper, don’t know today’s verb) to the official evaluation and whenever the official evaluation is handed out, the employee’s submission must be, too.

      If you can put off doing your writing until after the meeting, it will allow you to rebut anything he adds in person and it gives you more time to methodically rebut and then sleep on it before re-writing.

      Good luck!

      • Breathe PS :

        And take a tip from KS: leave on your own terms. You will find something great. I know you will.

    • Have you spoken to HR yet? If not, why not? I’m going to take advantage of my “anon” status here to be more blunt than I would be in real life: I’ve seen you complaining about this boss (who seems like a real jerk) for weeks, but I haven’t seen you take any real steps to improve your situation. You’re on the verge of quitting without a job, so what do you have to lose by asking HR for help?

    • I really hope you are looking for other jobs. I worked for a similarly d0uch3y boss, and I managed to stick it out until I got a better offer. (I now work part time with almost no cut in pay and my coworkers are awesome and I love the work I do.)

      I’d be careful about going to HR or higher ups about your boss, honestly. I knew it would do no good to complain because a) everyone knew my boss was a jerk, even clients and others in the industry and b) he was in a “boss’ nephew” type of situation in that he would not be fired for his actions. Only you know what your company is like in this regard.

      I had a similarly crappy review where I was blindsided by things that were either untrue or exaggerated and were never mentioned to me previously. I decided it wasn’t worth it to refute, and just took it as “constructive criticism”. If you do plan to refute, the previous advice is amazing.

  8. Threadjack – Some of us in NYC are trying to schedule a meetup. Email me at [email protected] if you’d like to be added to the list!

  9. Job search threadjack:

    Any advice as to how to manage upcoming performance reviews and references that are often required in job applications when you anticipate a likely decrease in your new supervisor’s opinion of you? FWIW, it relates in part to the supervisor making an office culture change from a strict to relaxed environment.

    • This may sound dumb, but is there any way to avoid a predicted decrease in opinion? Are you saying that you are unwilling/unable to adapt to the new situation? I’m honestly a bit confused.

      Usually, when one is looking for a job while currently employed, you can mention that you don’t want your current boss to be contacted. I can’t think of any employer that would not understand/respect that. Even for government jobs, the application has a box you can check if you don’t want your current boss contacted.

  10. Sadly, I think this article is incorrect in saying the boss is too busy. It’s more related to a personality trait, not understanding their role and ultimately the need for control. In doing this they make the organisation less effective, make your skills redundant and alienate workers from a positive psychological contract.

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