Feel Like You’ve Been Set Up to Fail? Ask Madeleine

Dear Madeleine,

I have just started a job at a well regarded local firm. I have many years of office experience, but this is the largest firm I have ever worked for.

My job is as an admin to a senior employee—he is not quite a VP, but that is his general level of authority. Since starting, I have been told he goes through admins at a rate of one every six months. After meeting with him, I know why. He is HUGELY disorganized, but resistant to any suggestions of how to fix the problem. His unspoken message to me seems to be “I need you to fix me but I don’t want to change anything.”

I have made several suggestions of new ways to file/organize/process work items, but his responses have been negative. I asked him what he would like to do and was basically told, “You’re supposed to come up with a solution.” Okay—but if he won’t accept my suggestions and won’t offer alternatives, what solution is there?

If I can’t help/satisfy him, the company will apparently find me a job in a different department, but I would rather try to make a success of this position.

Set Up to Fail?

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Dear Set Up to Fail,

This is such a fun question! I always check in with my executive clients about how they work with their EA’s, because once executives have reached a certain level of seniority they are really only as good as their EA. Since I am usually looking at this issue from the other side, I went to a couple of executive assistants in my own organization for their input—ones who I know for a fact have had success with some impossible people! They gave me some excellent ideas and I am really glad I asked.

First, it sounds like you are starting from a place of feeling overwhelmed and discouraged. Could it be because you are allowing yourself to be influenced by others’ opinions of your boss.? It is easy to judge him as a loser going in—he is simply measuring up to the idea you have already formed of him. He is probably used to being judged and is feeling defensive about it. So instead of assuming the others are correct about him, try giving him the benefit of the doubt. Take his less-than-great reputation as a personal challenge. Remember, you are not there to try to change him or, god forbid, fix him. You are there to make his life easier and to help him achieve his goals by doing the tasks he cannot and should not do. You can tell him as much, too. That might be a breath of fresh air for him.

Of course, I wouldn’t be me if I didn’t suggest that you have a candid conversation. Try something like: “I was hired to assist you so let me assist you. I am here to be your partner, and this will only work if you are willing to partner with me.” Do whatever you can to get to know your guy. What are his goals, personally and professionally? What makes him happy, what annoys him, what makes him laugh, what is he interested in? The more you can get a sense of who he is, the more you can use language that resonates with him and propose solutions that make sense to him. Ask about times he has felt most successful at work. Ask him to give you examples of the perfect assistant—what has worked and what hasn’t. This will provide you with needed insight and build trust and chemistry between you.

If he really has no ideas, maybe you can suggest he do things your way for two weeks and then meet to tweak. Be clear and firm and, of course, kind and respectful, and keep your sense of humor. Be open to feedback, of course. Don’t take anything personally and don’t give up! After this approach, if you really can’t get it to work at least you will be able to leave knowing you did your best.

It is good that you have an escape valve. Perhaps you could decide on a time frame that you are willing to try—and if you are really suffering at your deadline, allow yourself to bail. Give it your best shot. You clearly have the will to find a way.

Love, Madeleine (with a little help from my friends)

About the author

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. 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.

Got a question for Madeleine? Email Madeleine and look for your response here next week!