Previously on 2020 – Worklife Edition: Surprise! You’re getting a new boss!
I can’t really blame CoolBoss for leaving.
As one of the founding members of the design org at Large Financial Institution, she should have been on track to make real headway in how the organization approached design. Unfortunately, her Bohemian style and lack of organization all but ensured she would never be effective.
CoolBoss believed in flat management structures. Large Financial Institution most manifestly does not.
CoolBoss was not a strategic thinker, which is what is required for success in a place that functions on politics and relationships. Large Financial Institution runs on relationships and hallway meetings.
What she had going for her is she trusted her people, her senior people anyway. She gave us the freedom to work at home at will primarily because we made our deadlines and impressed our partners. Watching her learn that her junior people, who took that same freedom and ran with it, was an education I couldn’t have paid enough for.
She advocated for me hard during my conversion from contractor to full-time employee. So hard, in fact, that as she was leaving she told me that the year I converted I made more money in salary than she did.
CoolBoss wasn’t perfect. In fact, she was only good-adjacent.
Sure, she trusted her senior people. And we never got more than even the vaguest direction about the politics and the rumblings among the titans (aka: senior managers).
That meant we were constantly walking into project meetings with partners thinking that the things that had been decided in the last meeting were still the things. We didn’t know those partners had told her different things in meetings we were excluded from. She was so disorganized we got information too late to avoid looking like fools.
It was super fun being constantly out of the loop on a year-long, multi-million dollar project with 14 executive stakeholders.
She also expected us to figure these kinds of things out on our own.
In a hierarchical organization that functions in silos and on relationships, being expected to figure stuff out on your own, even as a senior practitioner, is a bit like being given the parts in an assemble your own car kit and a manual where 42% of the pages are missing.
Given that our team seemed to get the dregs of projects – which was a combination of poor positioning on her part and lack of understanding of our capacity on our Vice President’s – I really can’t blame her for leaving for a Chief Design Officer position at an agency. She wanted the chance to be a design rock star.
Even with all her flaws, being with CoolBoss had the advantage of being a known quantity and type of chaos. This the logic that causes people to vote for the incumbent even if that person isn’t serving their needs.

We got 15 minutes to process before the rest of the team learned we were getting a new boss. Some of us got a little more because EmpireBuilder Boss was, conveniently, out on vacation.
That gave the 60% of us going to her team time to:
- have real-talk conversations with folks already on her team (Hint: perception is everything. Nothing in that “real-talk” proved true for us)
- obsess over whether we were getting “real-talk” (ibid; or maybe that was just me)
- try to position ourselves to present in the best light once she was finally back in the office (definitely not just me)
My first big clue it was all for naught was when she got back to the office on Wednesday the following week and blithely went through her previously scheduled meetings.
She didn’t even bother to clear 15 minutes to meet with us as a group so she could reassure us that yes, she understood this was sudden, and yes, she knew there would be an adjustment period.
No, she just had her regularly scheduled meetings. For three days.
Then she left to go to a conference in San Francisco, which got cancelled while she was on the flight there because of COVID-19 concerns. Then she got trapped in the hotel because Large Financial Institution, like so many other corporations, makes you buy the cheapest possible travel tickets which usually don’t allow for changes.
By the time she came back to the office on March 9th, sick, and we had a first team meeting, I was already checking the Johns Hopkins University COVID tracking map hourly in much the same way, and for many of the same reasons, people are constantly refreshing the electoral college tracking maps as I write this.
I had my first 1:1 meeting with EmpireBuilder Boss on March 12th and the micromanagement was already in the wind.
We had already been talking about COVID, hand washing, and social distancing in my circles. It doesn’t hurt that I have some really smart friends, one of whom once had a grant from the WHO to study hand washing techniques in rural societies.
That 1:1 meeting was an exercise in boundary setting. My informal agreement with CoolBoss was I would work at home two days a week during curling season (October-April) and one day a week the rest of the year.
She pushed back, of course. Did I have a formal work arrangement filed with HR? Had she met CoolBoss, I asked back.
Then I told her that based on the JHU map, the trends, and my family situation that starting the next Monday I would be working remotely for at least two weeks. She was smart enough to agree to that without much of a fuss.
Later that afternoon, we got an all-staff email saying that to prep for possibly having to work at remotely for an extended period Large Financial Institution would do a phased systems test.
All employees in our DC-metro and regional offices would work at remotely on March 13th. On March 15th, the following Monday, all employees in our Texas office would work remotely.
By 1pm on March 13th they told us they were closing all offices effective immediately and everyone would be working full-time at home until further notice.
While it had the advantage of protecting me from getting COVID-19, going home to work meant that all my interactions with EmpireBuilder Boss now happened via video call.
It’s hard to read body language when someone refuses to turn on their camera, or turns on their camera but walks away from the computer while treating it like a speaker phone.
And I was uniquely positioned to be a difficult employee for EmpireBuilder Boss.
I am one of two people in my group who do what I do. I’ve spent that last two years building up a subject matter practice inside this design group. Socializing what I and the other SME do, why it matters, and what value we can add to the design process.
I’ve essentially been in sales mode for two fucking years.
And since I am not a people manager but a senior individual contributor, something EmpireBuilder Boss “doesn’t believe in,” she excluded me from all her senior leads meetings while simultaneously expecting me to know and react to things said in those meetings.
As the other SME and I started having meetings with EmpireBuilder Boss, the cracks started to show.
She had zero interest in the subject matter area my colleague and I specialize in.
We laid out the year-long plan we’d made for the community of practice we run and she immediately began to make changes as if she knew better what we do and what the designers we’d already been working with needed.
We had project update meetings during which she talked about my colleague instead of to her while she was literally on the call.
Instead of trusting us to turn in good work we’d get impossibly short deadlines, no responses to requests for feedback, and then she’d just change stuff back to the way it was ignoring best practices.
After two years of making progress with getting visually oriented people to understand that the words in the things the design matter to the user experience, I found myself having to justify my existence all over again. Every day.
In retrospect, I’m surprised it took me until April to realize there was no way I could work for this woman and stay sane.
And since I am an introvert, a bit reserved, and largely a private person, the idea of trying to sell myself and my colleague to another Boss inside the organization or, even worse, look for another job in the middle of a pandemic made me want to vomit.
I used the data instead.
I took a hard look at the projects my co-worker and I were on and realized that 85% of the work we were doing was for another team.
And this is how I ended up with Nerd Boss.
Nerd Boss saw this and ended up exactly where I wanted him to go: It made more sense for me and my colleague to be on his team than to be on EmpireBuilder Boss’ team.
Nerd Boss is not a dream. To refer to conversations with him as “word salad” is all too often accurate. He sometimes gives vague, confusing directions expecting us to find our own way through the thicket of expectations.
But Nerd Boss respects his team. He sees the value in what I and my colleague bring to the team.
He lets the people in his group make mistakes. It’s okay to ask questions, to be genuine, uncertain, and need help.
He absolutely wants us to do the work and he sees his team as a team. I think he really believes we can do good things if we all row the metaphorical boat in the same direction.
Not to mention that on our Friday huddles, funny hats are the dress of the day.
My colleague and I moved over to Nerd Boss in June. And because I am not a people manger, she got her third manager in 6 months. Everything was great.
In September my entire group got moved into the Marketing & Communications roll-up.
Next time on 2020 – Worklife Edition: I don’t think that word means what you think it means
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