Ask a Boss: I’m Doing My Boss’s Job For Him!

Dear Boss,

To put it bluntly, I need some help figuring out how much of my boss’s job I should do for him.

I work as one of two staff that run a particular program, within a larger department at a nonprofit. We also work with two administrative assistants who provide support to all of our department’s programs and several consultants who provide some of our direct services. My boss is the director of the program; I have a variety of responsibilities that could be summarized as outreach.

My boss is great at some parts of his job, but fundamentally lacks management skills — both in terms of managing his own to-do list (he has, and I’m not kidding, 10,000+ unread emails in his inbox, going back over five years) and managing his staff. He just … doesn’t do things that are basic parts of his job: short-term to-dos like responding to requests from other departments who need information about our program or writing thank-you notes to donors, but also bigger-picture things like signing off on a fundraising strategy or managing a problematic relationship between two other staff members.

Because he just doesn’t do this stuff, the responsibility for getting it done falls to me (or, I suppose, I could let it just not get done, but that would be a road to ruin for the program). On the day-to-day to-dos, he seems to have an unstated expectation that it’s my responsibility to catch the balls he drops. On the bigger-picture issues, I bring him proposals for how to handle the situation (sometimes he asks for this, sometimes I just do it as a strategy to get something moving when I know it’s off track).

I am not his assistant and it is not my job (unless it is, and he just hasn’t formalized that) to track his workload and help make sure that he’s getting done the things he needs to get done. I am also explicitly not responsible for overall program management (were I classified as a program manager, I would be paid significantly more).

I’m increasingly frustrated with all of this. So my question is this: Do I need to recalibrate my understanding of the kind of support I should be providing my boss? Or, if my boss is acting unreasonably, what other actions should I take?

Well, it’s hard to say for sure from the outside, but it sounds likely both are true — that you do need to readjust your expectations of what you should handle versus what your boss should handle, and that your boss is failing on at least a few fronts.

First things first: It’s very, very common for the logistical work of running a program to fall to staff members who are below director-level. It would be pretty normal for you to be the one who handles things like responding to information requests from other departments or sending thank-you notes to donors. In fact, in most cases, that should be you, since that’s work that doesn’t generally require a director to handle it.

That’s actually the principle that good managers use for figuring out what should and shouldn’t be delegated: If someone more junior is able to handle the work reasonably well, it usually makes sense for that lower-level person to do it, so that the manager’s time is freed up for things that only he can do. It sounds like a lot of the tasks you’re wondering about are ones that it likely does make sense to delegate to you.

But not all of them. Unless you’re in a pretty senior role, your boss should probably be the one signing off on big strategic decisions. And he should certainly be the one handling actual people-management issues, like intervening in a problematic relationship between two employees.

So it sounds like you’ve got a boss who’s hands-off to the point of negligence, at least in some areas. (His 10,000 unread emails fit that pattern, too.)

And what’s happening to you sounds like a thing that happens very often when you’re working in a job with some dysfunction: You start not being able to tell what’s normal and what isn’t, and you can end up overreacting to things that aren’t that big of a deal or even things that are fairly standard. You can also end up under-reacting to things that are a huge deal, because your norms are all thrown off. This is one of the biggest long-term problems with working for a bad boss, and it can make things tough when you move to a more functional employer and are still calibrated for the dysfunctional one.

But there also can be a real advantage to working for a negligent boss who lets significant pieces of his job fall to you: It can give you the opportunity to do the type of higher-level work that you otherwise wouldn’t have access to, and which you eventually can parlay into a better job with a better boss. For example, in order to keep things moving, you bring your boss proposals for the bigger-picture strategy work that would normally fall to him. That can go on your résumé as “created and pitched proposal to do X, which resulted in Y and Z successes.” That’s a big deal when it lets you significantly raise the level of work that you can show you’ve done, and done well. There’s probably a lot more like that that you can use to pitch yourself in the future, like “kept the day-to-day workflow of a busy department running smoothly” and “became the go-to staff person for information about X and Y” (if those things are true).

In fact, there might even be an opportunity to formalize those responsibilities, if you want them. It’s possible that you could pitch yourself to your boss as a sort of deputy director for the department, pointing out the things that you’re already doing and asking that your title — and your salary — be updated to reflect what your role has evolved into. (And note that “what the role has evolved into” is the way to frame it to him, even though you secretly mean “I’m cleaning up after you.”)

Of course, you might not want that. You might want to focus on the job that you were hired for, and not have to pick up extra responsibilities just because your boss is letting them drop. If that’s the case, one option is to see what happens if you go back to just doing your own job and leave your boss to deal with the consequences of, say, not coming up with a fundraising strategy for the year. It’s possible that this approach will either (a) make him realize he needs to get his act together, because suddenly his safety net (you) is gone, or (b) make his negligence more visible to his own boss, something that probably isn’t the case now because you’ve been stepping in. (Note that if you take this approach, you’d want to make sure that it’s not going to look like you’re the one who’s dropping balls; you don’t say how long you’ve been covering for your boss, but if it’s been a while, he may now believe those things are actually your responsibilities, not his. So think carefully about how you’d navigate that.)

But if you’re a certain kind of person, you might be constitutionally unable to do that. When you’re highly conscientious, it can be really hard to sit on your hands and watch things fail, especially when it’s work that you care about. If that’s the case for you, and if you won’t be happy taking this stuff on as a launch pad to something better down the road, then it might be time to start thinking about an exit plan for the job.

But there really is an opportunity here if you want it.

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