Ask The Experts: My Assistant Makes My Life Harder

Isn’t an assistant supposed to, you know, assist you? How can you confront the person hired to help you when they are making work harder?

Ask The Experts: My Assistant Makes My Life Harder
[Photo: Flickr user Dan Foy]

Most busy people (in other words all of us) would breathe a sigh of relief if we were offered the help of an assistant. But what if the person hired to make your work load lighter ends up slowing you down. And what if your new assistant is a friend of your boss?


Leadership coach Lolly Daskal helps a reader sort out this sticky situation.


I have an assistant who is a friend of my boss and who works part time, remotely. She’s incredibly slow and unresponsive, and the little work I give her is apparently too much. It’s difficult to manage her remotely, and I’ve requested that she spend part of her hours in the office, but my request was ignored.

I have tried to be straightforward with my boss about the situation and explain the problems I was having with her, but my boss’ solution is that I check in with her more and monitor her work more closely.

So instead of an assistant that helps me, I have another thing to do.

Any advice would be appreciated!

I can understand, Cat, that this situation is extremely frustrating. And it seems your boss is not much help, so it’s all yours to handle. Here are some things you can do:

Get to know her better. Find out her story, what makes her tick, what she likes and doesn’t like. What does this job mean to her? What does she like best about this work? Doing so will begin to build a better relationship between the two of you—outside of your boss’ involvement.

Give honest feedback. Talk with your assistant about the current situation and what is actually happening. Tell her you have observed certain behaviors. Tell her what does and what does not work for you. Don’t criticize the person, only the behavior. Speak in the terms of I: I have observed … I feel … I see. And then let her tell you what is going on from her perspective. Open the opportunity to learn from each other.

Ask for help. Ask your assistant for help in improving the current situation. Help her generate as many suggestions as possible to help the working relationship. Ask her what options she can suggest that might make things better. Including her in the process makes the relationship less adversarial and more of a partnership.

Make accountability matter. Clarify the steps forward and let her know that she is accountable for acting on her suggestions. Tell her you will be checking in with her for feedback and conversation to see if she needs any assistance in reaching her goals. Let her know the consequences for these choices and the path to the best outcomes.


Review and revisit. Structure an ongoing process of review and evaluation to help your assistant stay on course. The best that you can offer her is to review her work and provide feedback. Do not take over her responsibilities; make her accountable for her work, and see if she steps up to the plate. I would try this for six months and document all your conversations and progress. If in six months there is no change, you have a fair case against her performance and work ethic.

Keep it moving forward. If the first six months go well, keep checking in. Are the actions moving you toward the outcome you desire? What would success look like when the results are achieved?

Everyone has a different way of working and it might not be the way we want them to work—we have to teach, coach, mentor and guide others so they can learn to excel.

Everything worthwhile takes hard work. If you work on this relationship, it might just turn out to be a beneficial partnership.

To your success,
Lolly Daskal

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About the author

Lolly Daskal is a Leadership Development and CEO coach and consultant and founder of Lead From Within. Follow @LollyDaskal.