Ask a Boss: My Work Habits Are Going to Get Me Fired!

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Dear Boss,

I started a new contract two months ago. The projects are exciting, the team is inspiring, and I am doing a terrible job. It takes me two or three times as long as expected to perform simple tasks (like drafting documents that are standard in our field or corresponding with colleagues in order to organize projects). I am generally running behind and disorganized, to the point where I have already missed deadlines and meetings. This is particularly egregious since my responsibilities involve project management. 

My boss has — kindly and diplomatically — warned me that she will need to fire me if the situation doesn’t change soon. I have every reason to think that she will be fair in evaluating me. Her goal really is to make sure that the job gets done: by me if possible or, if not, by someone else.

At this point, I don’t know whether to focus on improving my performance, or on extricating myself in a way that doesn’t destroy my dignity and sense of self, and that doesn’t make life even harder for the team members who depend on my work. And I don’t know how I would go about doing either of those things. 

Some background:

I am naturally disorganized, distracted, and frazzled. Planning, organizing, and setting priorities are all difficult for me, but I have learned to work around those difficulties, and have successfully handled complicated projects before. That said, because it requires a lot of focus and stamina on my part, organization is the first thing to go when I get stressed out. And, yes: I do get stressed out pretty easily! Personal and professional difficulties really throw me off.

I have sought, and follow, medical advice to deal with the anxiety. It helps to some extent, but doesn’t really address the disorganization.

When things are good, I’m a happily anxious overachiever who occasionally shows up to a meeting on time but sweaty, clutching a report that is still hot from the printer. When things are bad, I get lost in a vicious circle of disorganization, poor planning, poor communication, and absurd priority setting. This cost me a job in my 20s. I’m now in my 30s, and precariously employed in a field with relatively few openings. I am terrified.

Have you seen employees who were in my situation turn things around? If so, do you have any sense of how they achieved that? Would it be better to leave now? Are there any steps that I can take to make the situation less awkward and painful for everyone involved?

You should be in a job that you can be great at because it plays to your strengths, not a job where some of the core fundamentals are going to do daily battle with your weaknesses.

And there’s nothing shameful about having this particular set of weaknesses. Lots of people are disorganized; I’ve probably coached more employees on how to get better organized than anything else, and that includes even senior people. It’s not a skill that comes naturally to a lot of people, so you’re not struggling with anything unusual.

But you’re in a job where project management is a big focus, and project management is all about being organized, prioritizing, juggling details and schedules, staying on track, and not letting anything fall through the cracks.

Those are all things you name as difficulties for you, and it sucks to be in a job where your performance relies on the things that are hardest for you. Even if you manage through steely determination to make it work for a while, it’s likely to be exhausting. And it tends to be the kind of thing where the best-case scenario is that you get by, rather than excel.

That said, it’s likely that there are at least some improvements you can make. Generally what I’ve seen work for people in this situation is religious devotion to some sort of work-scheduling system and keeping everything — literally everything — that you need to do recorded in there, even small items like an email you need to follow up on if you haven’t heard back by Friday or your co-worker’s request to stop by her office when you have a free minute. It almost doesn’t matter what the system is, as long as you’re diligent about logging everything in there and checking it multiple times a day so that you see things that otherwise might have slipped your mind. If you’re not doing that already, it’s worth a shot to see how much it helps. (Getting Things Done by David Allen is one good source for help getting started with a system. Lots of formerly disorganized people credit it with reforming them. Inbox Zero is also pretty awesome if you battle with email overload.)

There are other things you could try too, depending on the specifics of where you struggle. For example, if you tend to underestimate how long things will take to complete, it might help to time yourself doing those things the next few times so that you have more realistic estimates to use in the future. Or if you rarely build in buffers when you schedule things (which means that maybe you’ll meet the deadline if absolutely nothing goes wrong and no one is out sick on the day you need them), then you can start building in buffers as a matter of course.

It’s worth giving that sort of thing a try. Maybe it will turn out that there are one or two key changes that would solve the majority of the problems you’re running into! Sometimes that happens. I once watched a chronic deadline-misser completely turn things around by committing to the kind of work-scheduling system I described above. In retrospect, I think she was freaked out enough about the possibility of losing her job that she committed to it with a fervor that she wouldn’t have felt otherwise, but it worked and it stuck. Sometimes that happens.

But if that doesn’t turn out to be the case, then it’s okay to decide that the job just doesn’t match you well. In fact, it’s more than okay. Having a job that’s at odds with your default settings is a hard professional life, and it makes sense to look for work that energizes you at least some of the time rather than draining you daily.

That doesn’t mean, of course, that you should just throw up your hands and say, “I’ll never be organized, so forget it!” and then happily abandon any effort to stay on top of things. Most jobs require at least some degree of organization, so that’s not likely to be workable no matter where you’re working. The issue here, though, is that you’re in a job where it’s central to the work, and that’s the part to change.

To be clear, I’m not suggesting that you should walk into your boss’s office and resign today, but while you try some of the strategies above, it would be smart to actively look around for other roles. And you might also tell your boss that you’re taking her feedback seriously and that you’re actively working to correct the issues she’s identified so that she knows you get what she’s saying.

Meanwhile, though, think about what those other roles might be. What work have you done in the past where you felt like an expert? Have you had jobs or projects that played to what you’re best at? Jobs where you came home feeling great rather than frazzled? Those are the bread crumbs that can lead you toward figuring out how to feel like that more often.

Good luck.

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Ask a Boss: My Work Habits Are Going to Get Me Fired!