Dealing with a Disorganized Boss? Ask Madeleine

Dear Madeleine,

My boss is driving me nuts. I work in corporate communications at a complicated global corporation with a fast-paced, high-pressure environment. I am often given assignments with tight deadlines on top of my regular day-to-day work.

My boss will send me emails with assignments, using a request format that I thought was smart when I started. If only my boss would pay more attention when she fills it out.

The request calls for details about the audience, key messages, preferred tone, urgency level, and timing. I make the effort to weave in the company values and I put a lot of thought into each draft.

Lately, my boss has had an issue with every single piece I’ve written—but it is always because she left out something critical. Her comments contain some variation of “Oops, I forgot to mention such and such; could you redo this and weave that in?”

This throws off my schedule for the day and creates a last-minute fire drill. I feel like (1) she must have forgotten how much I have on my plate; (2) she doesn’t care enough to put thought into the original request; or, on my worst days, (3) she is trying to sabotage me.

I like the company and my co-workers, but I now dread my boss’s feedback. I have completely lost faith in her. I don’t really want to try to find another job, but I find myself fantasizing about doing just that.

How can I get her to cut it out?

Just So Annoyed

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Dear Just So Annoyed,

I hear your frustration, and I can relate—but you aren’t going to like this, so put on your seat belt.

My experience is that people who quit their job to escape an unresolved communication issue will encounter a new version of the exact same problem in their next job. You can certainly choose to jump ship, but this won’t be the last time you have to deal with an imperfect, distracted boss so you might as well use this opportunity to learn how to deal with it.

The question, as I understand it, is: how can you get your boss to give you all the information you need the first time so that you can deliver exactly what is needed?

First, it might help you to find a bit a grace for your boss by putting yourself in her shoes. I suspect this is a recent problem, as you noted that this behavior has shown up “lately.” It is possible that she also has too much on her plate, or perhaps she is wrangling with some personal problems. Regardless, the more she feels your judgment and annoyance, the higher the chance that she will make errors when working on a brief for you and eventually will start assigning the tasks to someone more easy-going so she can avoid your ire. That is a career-limiting eventuality that you probably want to avoid because, if you do decide to leave your position, you want to make sure you do it in good standing.

Once you make the choice to help your boss give you what you need in a timely manner, the next step is to figure out how to do that. One idea is to schedule a quick chat, which will give her the mental space she needs to capture all of the details before you start the work. Repeat what has been requested, and simply ask “What else?” or “Is there anything missing?” Many people think out loud, and when they become accustomed to working with someone super competent, they can start to believe (or at least hope) that you can read their minds.

If you can’t get fifteen minutes on her calendar, you might change your work style and spend less time making the first draft perfect, knowing it will need a second pass. If you go with this option be sure to mention that, in light of the recent need for revisions, you are switching up your approach and will polish the piece once you are sure that all points are captured.

Finally, I recently read somewhere that anyone who isn’t using AI in their work is almost certainly going to be replaced by someone who is. I’d like to think that isn’t true, but I suspect it is. The kind of work you are doing is exactly the kind of thing AI can help you with—so I highly recommend that you learn how to leverage it. Of course, you should check your company’s policy and use only the AI the company allows. I have spoken to many people who have avoided AI because they feel threatened by it, but that is also a career-limiting attitude.

Instead of getting mad at your boss, try a collaborative approach. Experiment with how you can help her give you what you need to do the best possible job you can. Helping her to help you will build trust—and it won’t go unnoticed. Change your work protocols to accommodate your boss’s absent-mindedness, and leverage technology to take time and effort out of your tasks. The world is only spinning faster, so anything you can do to make things go more smoothly for yourself, your teammates, and your boss will serve you well.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services as well as a key facilitator of Blanchard’s Leadership Coach Certification course. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

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