Good Bosses, Bad Bosses, + What to Wear to Work.

*Image above via Daphne Wilde featuring Kelly Rutherford wearing their Claiborne dress. Any of her dresses are the perfect pieces to bridge WFH to in-office to school pick-up to dinner out. Wouldn’t hate the Hermes Kelly bag either, ha! You can get the look for less with a Tory Burch Radziwill bag or one of these woven styles!

Have you ever had a bad boss?

One of the insights from my brief stint in the “people tech / HR tech” space was that employees do not quit bad jobs — they quit bad bosses. Now, people management is difficult and requires vast reserves of patience, empathy, and thoughtfulness, not to mention nimbleness in the sense that it is rare that all team members respond to the exact same type of coaching, feedback, and management. There will be team members that perform best with a long leash and others who need much more scaffolding to succeed. Some respond to “tough love” and others need gentler feedback, delivered with a light touch. The best bosses, I think, are flexible in their approach and try new things constantly to get the best out of each individual team member. They also tend to have a rare mix of humility and steeliness: a great manager once told me that a key mindset for people management runs as follows: “All successes belong to the team and all failures belong to the manager.” Let your people claim the victories, but you must take responsibility for the disappointments.

Still, good managers are made, not born, and so it stands to reason that even folks who go on to be incredible leaders have missteps and periods of growth along the way, and it may be that you work for them while they are “in development.” And some people are simply not motivated or fulfilled by the challenges of management. It is far too common an occurrence that high performers are promoted into positions of management without any training or consideration of the dramatic change in responsibilities afoot. Just because someone is a fantastic individual contributor does not mean that she will be a fantastic manager of other individual contributors. In fact, I have had several good friends tell me that they wished they’d never been promoted. One friend told me he felt alienated from the work he’d once loved and from which he had derived a sense of pride and identity and regretted accepting the promotion, pay increase be damned. “I don’t do any actual work,” he complained. “I just tell other people to do it.” I remember gently suggesting that managing people is actual work, just perhaps not what his cup of tea. And that’s OK, too.

It’s strange, perhaps, to be writing about these workplace dynamics as the sole proprietor of a business I run entirely on my own. I sit in an ivory tower, reporting only to myself. (In my previous start-up, prior to hiring any additional staff, there was one morning where a customer called and asked me to “check with my tech people” on some specific question. I acquiesced, put my hand over the phone, and waited in silence for 30 seconds to pass before jumping back on: “OK, we circled up and…” I had been checking with “my tech people”: it was also me.) In some ways, this is easier, because I tend to carry awkwardness and missteps in relationships with other people heavily. The day I had to let my engineer go because we had decided to shut down the business was one of the most difficult days of my life. I did not sleep for several nights prior and had rehearsed what I was going to say in the mirror at least a dozen times. I remember pacing around our kitchen working up the courage to call and then working hard to avoid crying. That’s an extreme example, and one worthy of the hand-wringing that accompanied it because — my God! How horrible to be responsible for such an enormous upheaval in someone’s personal and professional life? — but I also regularly spent hours and hours of my work week thinking through how to respond to team members in various circumstances, worrying about how my words might have been perceived, fretting over the tone of email, etc. So to be honest, I don’t necessarily miss the emotional toll of managing other people. But it can also be lonely, navigating decisions on my own, and accepting that all successes and failures sit squarely on my own shoulders. And it is fun and exhilarating to build beautiful things with other motivated people, a lesson I learned while collaborating with some of the smartest people I have ever met in my past life in the non-profit world.

All in, “experience is a tough but effective teacher,” as one Magpie wrote on a post years and years ago. (Elsewhere, this quote is often written as: “experience is a hard teacher: it gives you the test first and the lesson after.”) Both ill-equipped bosses and mistakes as an inexperienced boss myself have shaped me for the better. I had a boss call me an idiot and throw papers in my face. That person also routinely forgot my name and referred to me instead as “the sidekick.” Those things were so egregiously and cartoonishly unkind that I almost had to laugh at them. Worse still: I had a boss who would ask me to do all kinds of things that were not in my J.D., none of which were fair or compensated, and some of which were honestly inappropriate for an individual in my position, like firing team members, writing up legal documents, and preparing speeches whose content I had not the faintest of authority to be commenting on, all on top of the ambitious stack of responsibilities I had signed up for. But you know? Those experiences earned me the grit and grace that have seen me through many hairy situations. Beyond that, even while I was young and mildly terrorized by those interactions with “authority,” I saw that it was all a tradeoff: I also had the rare and unlikely good fortune to be put in positions of leadership at a young age, and so I was determined to take the good with the bad. OK, tough boss, but I’m getting so much experience that I frankly have no right to claim! Harder to bear, though: my own failures as a manager, whether hurting someone’s feelings, shutting someone down, or — my most common foible — micromanaging. (Ugh! I was the worst at micromanagement! I know I have several former employees who read this blog and who can attest this, and I am sorry.) Still, though I regret the experiences of the individuals who worked for me while I was learning on the job, I believe I did improve with time and considered myself a competent manager by the end of my run. Experience truly has been a tough teacher.

What has your experience been with bosses, or as a boss yourself? Any lessons to share?

Post-Scripts: What to Wear to Work + Other Work Gear.

+Some great pieces for your return to the office (or next Zoom):

ADORE THIS FLORAL SHIRTDRESS

BEAUTIFUL TOILE SKIRT

TWEED JACKET — ALSO LOVE THIS!

GORGEOUS MIDI DRESS

THIS EASY SKIRT WITH A CREWNECK AND A BIG NECKLACE

A PRETTY BLOUSE LIKE THIS, THIS, OR THIS, DEPENDING ON HOW CONSERVATIVE YOUR OFFICE IS…

THE WORLD’S MOST PERFECT WORK FLAT – GOES WITH EVERYTHING, SO CLASSY

A GREAT WORK TOTE — ELEGANT BUT DISCREET, BEAUTIFULLY MADE BUT DOES NOT COST A FORTUNE, AND FITS A COMPUTER

THIS BUTTON DOWN IN THE STRIPES

ALWAYS LOVE A CHUNKY PEARL NECKLACE TO LAYER OVER A SIMPLE CREWNECK

DAISY SHIRT DRESS

THIS PLEATED SKIRT

A TIMELESS WHITE SILK BLOUSE — THIS BRAND IS THE BEST

ANYTHING FROM DAPHNE WILDE

+Every woman, regardless of where she works, needs a “desk cardigan,” a term recently discovered via Nell Diamond of Hill House, who will be launching an ultra-cute desk sweater today at noon that is perfect for layering over nap dresses — or anything! It is often SO cold in office buildings, and you never know when a cool front might catch you unaware. A few favorites, in varying levels of formality…

THIS CHUNKY ALEX MILL

THIS PERFECT J. CREW (LOVE THE BLUE)

I HAVE BEEN LUSTING AFTER THIS KHAITE EVER SINCE I SAW IT ON KATIE HOLMES IN THE BRA-AND-CARDIGAN LOOK THAT BROKE THE INTERNET

J. CREW’S JACKIE IS PERFECT WHEN YOU WANT TO CUT A SLIM SILHOUETTE

TOTALLY IN LOVE WITH THIS RIBBON-TRIM KULE

KILTE MAURA CARDI

THIS CARDIGAN WITH PEARL BUTTONS

THIS DONNI

+Or, just go with a cashmere wrap. (Great gift — every woman loves these!). Bloomie’s also often has cashmere wraps at a discount — PSA!

+A laptop sleeve with shadow lettering, a laptop sleeve for a true grown up (so elegant!), a laptop case with great prints and monogram options!.

+This shop has the greatest AirPods cases — monogrammed, floral, and much more…

+Simple, sophisticated letterpress business cards.

+Such an elegant notebook, though I have been using soft-covered leuchtterms or Moleskine cahiers for awhile now.

+As a leftie, I also love notepads without binding to contend with — I just ordered this pad with my initials in shadow lettering and have this pad with our family name on the top in my cart. I also love having a stack of these unmarked white pads at my disposal for lists, sketches, doodles, notes.

+Structured notepads like these are also handy from time to time. I go back and forth from liking the structure to wanting white space.

+On that note, I have gone back and forth on my Day Designer. It is enormous — like a huge brick — which is not so much a big deal for me since I WFH permanently and don’t schlep it anywhere, but it is a little bit hard to write on at the bottom of the page because it is so thick. I also go back and forth on the structured format. There are periods of my life where I love the prompts and boxes to fill out when I’m feeling organized, and other periods I just want a blank page with the date at the top to configure as I’d like.

+My favorite pens forever and ever.

+I’m ordering this desk chair for myself in our new home! I will officially have my own office!!!

+Another key element of my workday: coffee. Coffee gear (including mugs!) for fellow java enthusiasts.

+An oldie but a goodie: the dotted lines between work and home life.