A long time ago I had to work with a very frustrating administrative assistant. I was a relatively new consultant and as far as she was concerned, it was way below her dignity for her to provide support to the likes of me. One day she said to me, “I am corporate and you are small business.” She was an expert at playing passive-aggressive games, like preparing documents for me at the very last minute before I had to go into a meeting. 

Frankly, she drove me crazy. I used to lie awake nights trying to figure out how to deal with her. I mean, for goodness sake, I’m a psychologist! And I’m generally regarded as pretty easy to work for. Surely I could fix this problem.

Well, I never did, and on the day when I left that job, one real source of satisfaction was the thought that I would never have to work with her again.

I’m telling you this story to illustrate that I know how difficult it is to work with a subordinate who undermines what you are doing. So my initial reaction was sympathy when I read an article in the Chicago Tribune about Mayor Lightfoot’s tussle with one of her team members. Apparently, in January the mayor sent her scheduler an email explaining that she needed more “office time” (unstructured time) booked into her calendar. 

So far so good. A senior executive like Mayor Lightfoot absolutely needs time to think and write. I coach executives all the time about building this time into their calendars. 

But here’s the problem. By the time she sent the email, the mayor was livid, and the email made that very clear:

  • “I need office time everyday!” — repeated 16 times in a row
  • “Not just once a week or some days, everyday!” — repeated 10 times
  • “Breaks or transition times between meetings are not office time” — repeated seven times
  • “If this doesn’t change immediately, I will just start unilaterally cancelling things every day” — repeated five times
  • “Have I made myself clear, finally?!” — repeated 13 times.

Whew, I guess she was pretty mad!

How Mayor Lightfoot could’ve handled that email (hint: don’t use email)

To her credit, she did not call her scheduler names or resort to vulgarity. She did not threaten to fire the  person. But she did make mistakes in how she handled the communication. So although she has not asked me, here’s my advice to Mayor Lightfoot and other executives about how to deliver fierce negative feedback:

  • Don’t wait too long. I don’t know what led up to this outburst. In the email, the mayor said she had expressed her preferences before. But she allowed her frustration to build up to the point where she had a hissy fit. Pay attention to your level of anger and deal with the situation firmly before you reach your boiling point.
  • Don’t use repetition to emphasize your point. It just annoys the other person and makes you look out of control.
  • Don’t use email. There are four reasons this is a bad idea:
    1. Email is a treacherous medium. We often come across too harsh.
    2. It’s easy to get mean on email because you don’t have to see the other person’s reaction.
    3. Email is too easy to send before you’ve had a chance to reflect.
    4. Email is not private. The mayor actually copied several other people on this email. But even if she hadn’t, do you think for one second that the scheduler wouldn’t share this extraordinary missive? Especially when you are a public figure, this kind of display damages your leadership brand.

So what should Mayor Lightfoot have done instead? Here’s my 5-step guide to delivering tough feedback:

  1. Give yourself time to calm your physical response and sort out your thoughts. 
  2. Figure out your goal. What do you want the other person to do differently? Are you trying to maintain or improve the relationship, or do you want to demolish the other person?
  3. Plan out how to speak to the person so that they can hear what you’re saying and will do what you want. A very useful tool is to say, “I’m confused” and describe what the other person did and why it didn’t make sense to you. Confusion is not threatening – it invites conversation and clarification.
  4. Rehearse. Think about the person’s possible responses and how you will react.
  5. Have the conversation in person if possible. Video is second best, and email is the worst because of the likelihood of misunderstanding.

Not all performance issues are solvable. I never did figure out how to get what I wanted from my problem assistant. That scheduler is no longer working for Mayor Lightfoot. But the framework above gives you a fighting chance to address the problem and get the working relationship on track.

Gail Golden, MBA, Ph.D., is the Principal of Gail Golden Consulting, LLC. As a psychologist and consultant for over 25 years, she has developed deep expertise in helping businesses to build better leaders. Get in touch if Gail Golden Consulting can help you achieve your goals.

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