Wednesday, August 18, 2010

Ask Kelli: The Swooping Boss

Kelli Miller writes the Cleveland Park Listserv's Advice Column, Ask Kelli. Questions can be posted here, via the Ask Kelli Facebook group, or on Twitter @askkelli. Your name and email address will be kept confidential.

Dear Kelli,

I'm pretty sure my boss doesn't trust me a whole lot. As a result, she tends to micromanage me and I am very unsure of what she really wants to be involved in and at what level. In the past I have not had this trouble with other bosses. I am currently looking for another job since I've been in the office for more than 7 years in various positions and I'm ready to move on. In the meanwhile, I'd like to have a smoother relationship with my boss. I'm a Fed, so the process of finding a new job could take a while.

She and I have been working together for about three years. In the past she has
gone through cycles where she gets stressed out and overwhelmed with everything
she has to do because she is not a good delegater. The next part of the cycle
is where she tells me that she cannot attend and/or lead meetings related to the
projects I work on because she's not necessary to the project. Then she starts
asking many questions about the projects at inappropriate places (the hallway,
the ladies room, the cafeteria, etc.) and I am not able to answer her questions
intelligently without my notes and/or some preparation. Because of my lack of
ability to update her at a moment's notice in the restroom, she then swoops in
and sort of takes over whatever meeting is coming up next on that project to try
and "rescue" it, or she assigns part of the project to an outside contractor, or
she involves another office from our organization.

This hasn't happened in a year or so, but just today she's sent me a few emails
about not attending meetings. How do I stop this cycle from happening again? I
know I need to talk to her, but she and I don't have fabulous communication with
each other, and I think I inadvertently offend her a lot or make her mad because
I state my opinion, which is not always her opinion. Once she makes a choice I
then support it. But somehow stating something contrary before she makes a
final choice just makes her angry.

I know that if she trusted my judgment more this wouldn't happen, but besides
doing a good job and checking in with her on a very regular basis, I don't know
how else to build that trust. Just today, it wasn't until a coworker echoed my
opinion and rationale for a choice for the look and feel of a new website (a
project she has asked me to lead), that she made that choice. This was after we
asked an editorial board of their opinion and the votes were tied. Things like
this happen all of the time. It's like I'm not using the right words, and when
coworkers use the same words they get a totally different result from the boss.

No More Swooping

Dear No More Swooping,

Yes, it's definitely time for a conversation with your boss. Yes, I know it's
uncomfortable, awkward, and the last thing you want to do, aside from scrubbing
toilets in a prison cell, but it needs to happen. People tend to forget that
bosses are people too. So she probably senses something is off as well. If you
get nervous, remember asking her for this conversation is taking initiative,
being assertive, and being goal-oriented (all great work-related qualities).

Start first, however, by covering your own tush. Write down all the great
things you've done in the last six months. If your department does reviews, get
your last one so you can see where you've improved (and can prove this). Then
brainstorm a few ideas of how you think your relationship with your boss can be
improved (example: your boss attending meetings, setting up specific times with
your boss to talk rather than in the bathroom, etc.).

Then have the sit down. Here's the good news: I believe you get your point
across without admitting the obvious (that you don't feel she trusts you/you
have poor communication). You could something like, "I believe we can improve
our work relationship even more. I had a few ideas but I'd love to get your
feedback as well." Then if she asks for your ideas, be sure to be diplomatic
and spin it in a way that makes you look positive. For example, instead of,
"Boss, it really bothers me when you catch me off guard to talk about the
projects," something more constructive would be: "Boss, it's great that you want
to check in about the projects I'm working on but I'm thinking if we set up a
specific time and place, I could be even better prepared. It helps me to have a
specific time so I can get any questions I have for you ready." And as far as
her attending the meetings, perhaps you could say something like: "And Boss I
know it's hard for you to attend meetings but do you think we could set up a few
that work better in your schedule? I know it definitely helps me when you're
there, and I'm thinking it might be good for the team as well."

Finally, this is a long shot but what about if you asked HR about a trust
building day/departmental outing? That could help your relationship as well.

Good luck,


Dear Kelli,

I'm what you'd call a doormat. I'm afraid of confrontation so I never say what
I really want. I let other people get their way just so I don't have to deal
with the uncomfortableness of speaking out.


Dear Doormat,

Nothing is going to change with other people, if you're behavior doesn't change.
So it's time to stop being a doormat and start being a human being. A human
being is someone who has a variety of wants and needs. And those wants and
needs are going to differ for each person. This is normal and perfectly okay!
Just because you feel differently from someone else doesn't make you mean, rude
or less than someone else. If anything, it makes you interesting and unique!
If you continue to go along with the crowd, not only are not being honest with
your friends, but you are certainly aren't being honest with yourself.

There is a huge difference between being assertive and being aggressive. I'm
wondering if you're confusing the two. Both are asserting your needs but being
assertive is doing it in a nice, calm way, and there is nothing wrong with that.
Think for a moment. Have you ever been truly upset if someone tells you what
they need in a nice, calm way? If anything, you've probably been impressed with
their ability to tell you what they want.

I would suggest role playing your assertiveness with a trusted friend or family
member so you can start feeling a bit more comfortable. It might sound silly at
first but it will help get your feet wet. I'd also write down your fears about
telling people what you want and come up with a counter argument. For example,
Fear: "I'm scared that if I tell people what I want, they won't like me."
Counter argument: "Then they aren't my real friends anyway. Real friends like
me for me--and they don't base friendship on whether or not I disagree with
them." Finally, visualize a person you consider assertive. Think about what
you like and respect about that person. Use that as your model next time you
tell someone what you need.

Good luck,


Dear Kelli

My friend Jackie is always late when we have plans. It drives me CRAZY! What
can I do?

The Punctual One

Dear Punctual One,

Oprah tells the story of how she was always late with her trainer Bob Greene.
One day Bob said something along the lines of: "My time is just as important as
yours. When you're late, you're basically saying your time is more important
than mine." This is absolutely the truth. So if you have enough guts, you
could always say this same message to your friend. Tell her you love being with
her but when she's late, she's not realizing it interferes with your schedule as

The second option is to take the opposite route and just surrender. In other
words, just know that Jackie is just always going to be late. You can be
proactive, though, and schedule things knowing she's always late. For example,
if you want to eat lunch together at 12:30 pm, "tell" her to meet you at 12 pm.

All the best,

Kelli Miller, MSW is a therapist, author, and radio personality. Miller was a featured expert for SIRIUS Satellite Radio Channel 198, the co-host for the TV show Love and Money: The Advice Show, and the advice columnist for Playboy U. She is the author of Professor Kelli's Guide to Finding a Husband, which can be found here, as well as her personal memoir, Joy in Solitude, found here. You can post a question to Ask Kelli here , via the Ask Kelli Facebook group, or on Twitter, There's more about the Listserv's advice column at You can read back issues of her column at, and on the Cleveland Park Listserv.

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