Over the past weekend in Bermuda, the subject of bad bosses came up quite a bit, and we exchanged some workplace horror stories. On the lighter (but weirder) end of the spectrum, one friend shared that his boss routinely brushes his teeth at his desk in the middle of a meeting, gargling with perrier water and then spitting into his trash can. Can you imagine?! I’ve had some strange encounters with managers in my time, too. When I interviewed for one of my jobs, my future boss arrived at the restaurant, slid into the booth, and ignored me for a full ten minutes, engrossed with his phone. I don’t think he even said hello. I’d rehearsed an entire introduction, and he didn’t look up once. (I did not matter to him; message received.) I eventually stopped trying and just sat there in nervous silence, waiting for him to finish. When he finally did, he asked me a few distracted questions, and said: “OK, you’ll do,” at the end. Yikes! This should have been a red flag but I was young, inexperienced, and desperate for the promised salary. I tend to view everything as an opportunity anyway (if you win, you win; if you lose, you learn); his gruff dismissiveness helped me develop a thicker skin and understand that I could do my job well even without praise or acknowledgment. Funny to think that “best boss” and “boss you learned the most from” might not be the same person, you know? Because he also made me realize that the world is full of all kinds of kinds. We won’t change them; we can only control how we behave in response to them. I don’t think I’ve ever interacted with someone like him in my entire life — I couldn’t have written him out of the depths of my blue imagination if I’d tried! (I later wondered if he might be on the autistic spectrum, and felt a bit more empathy for the cold welcome, but — who knows.)
A lot of the conversations in Bermuda coalesced around reflections on the makings of a good boss. Many of my friends are now executives or tenured, senior professionals with staff reporting into them, and have spent significant time reflecting on this point. What makes for a good boss? How do you live out those values in your own profession, especially if you are in a workplace without many solid models to look up to? I do want to note that management is objectively hard, and that few of us are trained in it. Many of us work our way up the ladder by being excellent individual contributors, but just because we’re proficient at the work doesn’t mean we have the skills to direct other people to do it. And then there’s the human element. People are sensitive and often unpredictable! This can make for chaotic management dynamics. Mr. Magpie once told me about this “negative feedback principle” in which you need something like seven pieces of positive feedback in order to neutralize one piece of critical feedback. What he meant: people will mainly hear and focus on the negative feedback even if it’s balanced by a piece of positive feedback. They need a lot more sun than you think.
I have been lucky to have a couple of incredible interactions with great bosses. A few of the things these people had in common:
+They used “team speak,” even and especially in moments of personal challenge or failure. For example, I remember one time I was nervous to let my boss know that a particular pilot had been pretty unsuccessful. We’d not seen the engagement we’d expected; the numbers were poor. Instead of expressing disappointment or anger, he said: “What can we learn from this? What can we do differently next time?” I’ll never be able to express how relieved I felt that he said “we,” instead of “you.” (The conversation here also beautifully modeled a growth mindset!).
+They were liberal with recognition and praise, especially in the presence of fellow staff.
+They took a specific interest in my own goals and strengths. One of them hired me a speech coach, which (frankly) I needed badly, but was a surprising and generous expense he was willing to incur to help me develop professionally.
+They did not micromanage. This was always one of the hardest things for me to avoid when I was managing a team; I had to work assiduously on this front, as I often wanted to get my hands dirty in the details. (I am such a “specifics” person!) But having been on the other side of the table, I know that there is nothing better for an organization than empowering employees to own their work streams, and fully. A mentor once told me that if someone else can do something 70% as well as you can, you need to delegate it and forget about it. I’ve tried to honor that threshold since!
What do you think? What makes a good boss? Who have been the models in your own professional life, and why? How do you adapt their paradigm to your own team now?
Post Scripts.
+What does your job say about you?
+Things we love about our homes.
+If you could go back to school tomorrow, what would you study?
Shopping Break.
+I absolutely love this SoldOut NYC dress I spotlit last week. Elegant and elevated, but as comfortable as a tank top. You can get the look for a little less with this or a lot less with this or this.
+I love the way those simple solid-colored dresses look with a bit of bling — a Dorsey Riviere (look for less here — use code shoop20 for an extra 20% off) and/or paracord — and then a simple, clean-lines-only sandal.
+My MIL has one of these iconic Tiffany cuffs and I’ve always admired it. I found two looks for less that I’m contemplating: this (less of a replica) and this (more on-the-nose).
+Only a few left of one of my all-time favorite totes in a great black leather trim version (mine is confetti with brown leather). I keep coming back to Altuzarra’s current season knotted tote though. I think I need it, but I’m eyeing it in the suede brown trim.
+Combining all of the items above into one chic look:
MADEWELL DRESS // DORSEY RIVIERE (LOOK FOR LESS HERE) // DORSEY PARACORD // MEJURI DOME BRACELET // LOEFFLER SANDALS // ALTUZARRA TOTE
+LOVE these striped pants. Remind me of La Veste but less expensive!
+Sleek and chic soap pump for the kitchen.
+A very cute statement cocktail dress. Love the rainbow colored threading at the trim — pair with a bold colored purse!
+For my expecting mamas — how CUTE is this $59 maternity dress?!
+Where the Wild Things Are jammies!
+These colorful suede crossbodies are so fun! Perfect size for phone and card case. Pair with a fun crossbody strap like this. (Paracord summer — more of this trend here!)
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This is something I think about a LOT. I’ve been blessed with a lot of great bosses- none perfect, but each taught me something valuable. My first boss was never blame-y: if I made a mistake, she never wasted time assigning blame or making me feel bad. She just focused on solutions for fixing the problem instead. A later boss provided just the right amount of emotional support without crossing boundaries or making me feel like I had to share more than I was comfortable with. I always said that I felt like could talk to him about anything, but that he would never expect me to share or proactively do the asking. My current boss is great with doing internal PR for our team. She has singlehandedly raised the profile and reputation of our team within the org. She taught me that sometimes, just doing good work quietly isn’t enough. Other people need to see it/be aware of it.
GREAT lessons – really sharp and specific. Thank you!