This is a guest post by Cassie Boorn. She works with me at Quistic. That’s a photo of Cassie and her son. And here’s another guest post she wrote, before we started working together. 

A few years ago I targeted Penelope as someone I want to work with. Then I spent a lot of time and energy getting her to hire me. You can probably tell from reading this blog that Penelope would be a difficult boss. I work hard figuring out how to make her like working with me. This is called managing up. And these are rules for managing up that I’ve learned from working with Penelope:

1. Show how you can improve the bottom line.
When I’m first getting to know Penelope I tell her she could make money if she did an online course. She says no and it would be too much work.

It takes two months to convince her to do a course, one week to convince her to publish the course on her blog, and one hour for her to realize this was the best idea ever and she is going to make so much money.

The way that I convinced her to do the course was by offering to handle all of the details. But I can’t. Penelope fires me 30 hours before the course starts. But she makes a lot of money, so she sends me a thank you note.

2. Don’t ask for favors. Earn them.
I have spent twelve months traveling back and forth to New York, and my life is falling apart. Penelope thinks I should move out of Peoria. I think my son will miss his father too much. I tell her I am staying in Peoria. She tells me to find a new job.

I call Penelope every day to tell her how much job-hunting makes me want to die. She tells me how it’s a good experience for me. I tell her how amazing my resume is, and she tells me that I am not special. She reminds me that while I have a well-written resume because she wrote it; I don’t actually have any skills.

I am standing in a hotel room the first time Penelope suggests we do a startup together. I am so happy that I dance around the room, but only in my mind. I appear calm because if I give her even one sign that I want to do a company she might take it back.

3. Push back on your boss when it’s really important.
I could spend my entire day thinking about ideas. Penelope tells me I can have any job I want, but whatever job I choose must have deliverables. We end up screaming at each other about how I don’t want deliverables and she reminds me that we are in a startup, so everyone has to do stuff they hate.

We decide I will do sales because I am good at coming up with ideas about what we could sell.

When Penelope hired me, she thought I was an ENTJ, like her. Had Penelope realized I was an ENTP, I wouldn’t have a job.

She says, “Did you see how much more money ENTJ’s make than everyone else?”

I say, “Yeah. I sent you that link.”

Penelope reminds me on a daily basis that she will never hire another ENTP.

I tell her that hurts my feelings.

She says it shouldn’t. She says I’m lucky she takes all this time to argue with me. She only does it with people she cares about.

4. If your boss gives you work you hate, hire someone to do it.
I tell her I am bad at details so we need to hire  someone to help me with details.

She says that I was terrible at managing the freelance designer, and the copywriter I was managing quit, so I can’t manage anyone else.

So, I hire my friend Katie to do all the details of my job. Now my career feels like my own little business. I tell Penelope that companies aren’t hiring lower level employees, so maybe this will be the new model. Instead of professionals hiring house cleaners or nannies to run their house, they will hire people to do the parts of their work they hate. Maybe this is how millennials do work/life balance.

Penelope tells me I’m a genius.

5. Pick a boss who treats people how you want to be treated.
I am sitting in Penelope’s hotel room while her son practices cello.

She sits on the floor in front of him. I have never seen her focus on anything so hard. She catches every move, and yells reminders at him: eyes on the bow, better bowing, remember to end with your bow down. I wonder if Penelope played cello. I wonder if she could play from the memory of watching her son.

He finishes the song, and she asks him to play the end again. The song ends with the bow down, but he had ended with the bow up. I wonder how she could remember all of the terms. He thinks the song ends with the bow up, so they get the sheet music out to find the answer. He’s not frustrated, but I would have thrown the cello at my mom twenty minutes ago.

After studying the music they conclude that the song ends with the bow down. He is happy she caught his mistake. Penelope sings the notes she wants him to play, “ba ba baba ba.” She has the song memorized.

He sits down to play and Penelope settles down to watch. I have never known someone so invested in the success of other people.

This is a guest post by Cassie Boorn