Managing Up

Honestly, you don't need to keep suffering under that bad boss of yours. Let me tell you how my colleague Shyrose and I figured out how to manage up, so to speak. Just keep it between us.

It’s unconventional in terms of career advice, but it worked for my team, and we’re a fairly well-known player in our industry. I’m only telling you because I trust you, and I want you to succeed where you are, too. I see myself in you, and I think the conditions are right for you to make a move.

When we finally agreed to do it, we were both drunk. Honestly, I can’t even tell you that we agreed. I can’t say it because we never said it. But we must have agreed, because here I am, telling you about it. 

Maybe it would help for me to tell you a bit about how we worked with Mr. Mercer first. For context. You see, Shyrose was technically my senior, but we were close because both of us spent the same amount of time with Mr. Mercer. We would come into the office at 7:00 sharp and prepare his remarks for the 8:00 stand-up. The stand-up would be held over video, but one or both of us would stay with Mr. Mercer in case he went off script or someone asked a question and he wanted the answer to it. He would stay off camera so no one could see us passing him notes or whispering into his ear.

After that, I would prepare his coffee (nitro cold brew) while Shyrose briefed him on the day’s agenda. By 9:00, I would be on what we called guard dog duty, which means sitting at the desk in front of his office door, and telling potential intruders (employees, clients, our CFO) that Mr. Mercer was unavailable but they could book an appointment through me. In the meantime, Shyrose would review social media and news for mentions of our company, and flag any concerns for our PR department (or on a bad day, legal). 

Mr. Mercer never took morning meetings. I would bring him a fresh coffee or refill his pitcher of water every so often, but during those three hours before lunch, I never saw him do anything other than sit at his desk, usually with his inbox open, sometimes with a pen in his hand, hovering over a legal-sized pad (usually blank). I used to believe that he must be working so hard during the rest of the day that he needed that time to unwind, undisturbed, to better think through the day’s problems. I never asked him about it, but in my first year with the company, he volunteered the information that he spent that time trying to write a novel.

No, I don’t think he ever finished it. I don’t think he started.

At 11:30, I would put in an order for him at one of the restaurants or food courts nearby, pick up the food when it was ready, plate it in the office kitchen, then bring it to him before ten past noon. Any later, and he wouldn’t eat it. Once, he threw it on the floor, and as I cleaned it up, that was when I first felt so angry I could… well, let me get there.

After lunch, things tended to pick up, as Shyrose would brief him on the events of that morning, provide him with his remarks for the midday check-in, and fill him in on his responses to concerns from shareholders, regulators, our client base, and all departments. At that point, I would usually bring him his mail, open the envelopes, and sort them into the wire baskets on his desk. Once the mail was sorted, I would take the contents of the basket marked “high priority” to Shyrose, and “low priority” to my desk. While I responded to the low priority mail, Shyrose would usually accompany Mr. Mercer to meetings throughout the day–increasingly, these were held virtually, meaning that the only time I got to see Shyrose again was in the evening, usually around 7 pm, after the meetings were done and she had the opportunity to respond to any urgent mail items. Mr. Mercer was usually out of the office by 4pm, trusting Shyrose with any late afternoon meetings. 

Around 7, Shyrose and I would usually have dinner together at the office–we’d either order in from somewhere nearby or we’d eat the leftovers from whatever company event had catering that day. After dinner, Shyrose would usually prepare Mr. Mercer’s agenda for the next day and catch up on any reports or department memos that Mr. Mercer needed to be briefed on in the morning. In the meantime, I would print those reports and memos, as well as any slide decks for the next day’s meetings, then shred the ones I left on his desk the previous day. 

Oh yes, we worked on weekends, too. Shyrose usually did some substantive work she didn’t have time for during the week. I usually caught up on filing, and Mr. Mercer told his colleagues that he would always respond to emails within an hour, so that was me on weekends. Then on Sunday evenings, I would print out everything in his email inbox from that week and bind them in cerlox using the comb binding machine in the back room. He was very particular about how this was done: seven volumes (one for each day of the week) with black bindings for weekday emails and white for weekend emails, with a numbered tab separating each email and an index in the front indicating the subject of the email, the sender, the recipient, and a summary of the contents. 

I used to believe that he requested this because Shyrose and I sent all of his emails for him and he wanted to keep records of everything in a format he trusted. But then he told me that he never read the volumes, he just used them to prop up uneven furniture. 

How did I respond? 

Well, I asked him if he was concerned that they would get ripped that way, and he replied that he had them all electronically so I didn’t need to worry about re-printing if they got damaged. No, that's not when I made my move, but it sure made things easier. 

Shyrose and I didn’t have friends or family in the city, so we mostly spent time together when we had time off on the odd Friday evening. I mean, neither of us are problem drinkers, but I like to keep pace with Shyrose and it is hard to really unwind without a few drinks sometimes, especially when the company is getting sued again for… well, let me stay on track.

It was a Friday. We were maybe three drinks in, and we’re not as young as we once were, neither of us. What kicked us off was the yawning. There were twenty-somethings everywhere, live music, it was downtown, the kind of place you’d want to stay up late for. But we were yawning because the lights were dim and because we were old and because we were so tired. 

Shyrose turned to me and asked if I regretted taking this job.

“The pay is alright,” I told her, “but I wish I had three hours a day like Mr. Mercer to write a novel or just daydream, to be honest.” 

Shyrose replied, “If I could just lead meetings without taking the time to brief Mr. Mercer, I swear I’d have the time to hit the gym every day. I’d be a body builder.” 

“I don’t care about body building, but if I had the benefits package I’ve been begging him for, I’d just get the physio my doctor has been nagging me about for the past 6 months.”

“Benefits are the dream. But if I could even take a vacation–even a few unpaid work-free vacation days–I’d go see my niece 2 hours out of town on her birthday. She’s the closest thing to a child I’ll probably ever have and I’ve missed three birthdays in a row!”

“If I had my Sunday evenings back, I would start dating again. Maybe find someone with a hectic schedule like mine and get hitched one day.”

We just went on like that, and kept ordering drinks and talking. We were maybe six drinks in when Shyrose said something like “You know, Mercer sometimes goes three, four weeks without seeing a person other than us two.”

“What about his family?”

“Not a factor. He has his first wife, who hates his guts almost as much as we do. He has his second wife, who is fifty years his junior and probably has a seriously good insurance policy in his name, and he has his stepson, who goes to boarding school and they’ve seen each other maybe four times.”

“He’s lonelier than we are.”

“That’s right,” said Shyrose, “we have each other so we know we’re still human and not just cogs keeping Mercer’s gears in motion. He doesn’t have anyone. He’s at that age, it comes with the territory.”

“I’d be scared to get to his age and have no one, to be surrounded by colleagues who hate you and a family who’s mostly waiting for you to die so they can inherit your wealth.”

“The wealth you’ve been keeping from your increasingly resentful lackeys–that’s us.”

“We’re the resentful lackeys, it’s true.”

“The furious factotums.”

“The hateful hirelings”

“That’s a good one. You’re getting really good with words, you know?”

“Thanks, Shyrose. I learned it from reviewing your meeting minutes.”

“I am good, aren’t I? Always crisp, concise, to the point. Except today.”

“Today?”

“I mean except right now. When you know we’re right there with his wife.” Shyrose smirked as she said it.

“You mean, waiting for him to–”

“I mean, he still has a decade of working life left.” 

At that point, I could still deny where Shyrose was going with the conversation. “Yesterday he told me he loved his job and never wanted to retire.”

“He probably doesn’t want to be alone with his wife at this point.”

“He feels safer with us." I said, "Which is funny because we probably hate him more.”

“Not to mention, you’ve probably brought him his nitro-brew hundreds of times at this point, and he drinks it every day.”

“Lunch too, and I plate it for him.”

“Nitro-brew is so bitter, there could be anything in there and he wouldn’t taste it.”

“Even if he did, he leaves his phone in his briefcase in the mornings. No morning meetings.”

“And people are used to seeing me when he decides to nap through a meeting in the afternoon. No one can deny we get more done without him.”

“I think people at the company would understand if he took a bit of a step back and delegated those meetings to you, Shyrose.”

“That’s a good way to put it. And honestly, it would be good if he would free you up from some of those coffee and lunch-fetching duties. Don’t you have a master’s degree?”

“I do, and my thesis wasn't about pouring nitro-brew.”

“I could probably take a few other things off his plate as well–communication with shareholders, outside parties, clients. I already send things out in his name from time to time. I have signing authority, and I’ve put his signature on documents when he was vacationing in Cabo.”

“I think that would be a huge relief. Honestly, I could draft that email anytime. Tonight, even. Though that would be unusual coming from Mr. Mercer.”

“Monday would probably make the most sense.”

“That would give us the weekend to get ready for that handover.”

“There is a 24-hour drugstore nearby. We could pick something up?”

“For Mr. Mercer?”

“No, for our hangovers tomorrow. But while we’re there, I’m sure we could do worse than pick something up for the pest problem at the office.” She said it with a smile.

So, after Shyrose paid our tab at the bar, I went to the drugstore, and I picked up some hangover remedy and some rat poison. 

I've got to tell you, it all went more smoothly than I ever imagined it would. Mr. Mercer was sick on Monday morning and, after he collapsed onto the carpeted floor of his office, I sent out the email delegating his meetings and other important tasks to Shyrose until further notice. 

After everyone else ended their workday, we hauled Mr. Mercer down to document cold storage, deep in the bowels of our office. No one ever went down there except for us. We didn’t hide him, really–we left him looking like he was taking a little nap amongst some moldy bags of document shreds. We locked the door to the storage room, and dropped the key down the elevator shaft on our way out of the building. 

All that was no problem. Shyrose got her vacation, I got my Sunday evenings back. No one–and I mean no one–has asked to see Mr. Mercer in person over the past sixteen months. For our purposes, he’ll be taking a sabbatical soon and appointing Shyrose as acting CEO. I’m not saying that’s what you have to do, but my advice to you is to keep your options open, especially when you know you’re being taken advantage of. Three words: know your worth.