Thank You, Next — What My Ex Bosses Taught Me
Our culture is rife with the meme of people hating their bosses; badmouthing them, complaining about them, wishing they’d go away.
It’s true that if a core relationship dynamic doesn’t work, it becomes the bane of your existence. (just as with spouses or housemates)
But when core relationships work, then for me they’ve been without a doubt some of the happiest and most rewarding parts of my life.
In my last job, I had the privilege to be managed by people I still respect and admire, despite (or perhaps because of) our tumultuous pasts.They taught me skills and techniques about life, relationships, and work that I’ll remember and use for the rest of my life.
Here I enshrine their lessons in writing for all!
“Act like you’re the CEO of your domain”
“I’ll mute for 5 minutes and listen to you talk.”
“Don’t tell me about problems. Tell me about the problems with your solutions.”
Daily 1:1s Are Probably Unnecessary
People Don’t Leave Jobs. People Leave Managers.
Trust, but Verify
Get Pirate Funding, Bring Back Treasure, Repeat
Be a Botanist Sideways And a Weedwhacker Upwards
Tailor the Medium to the Person
Manager 1: The Hands Off CEO
“Act like you’re the CEO of your domain”
Our CEO would always say this, which is odd as it is empirically false, but I eventually understood the subtext.
One may think the CEO’s job is to tell others what to do, but the best CEOs turn everyone in the company into a mini-CEO. That is: everyone is acting like an owner rather than an operator; challenging others’ opinions, thinking strategically about their domain, and constantly trying to abstract themselves out of the recipe for success.
Once inhabited, this mindset of ‘what would I do if I was the CEO here?’ for every decision in your corner of the company is both empowering and overwhelming. It forces you to think long term, about how decisions affect others, and to make smart trade offs. It’s definitely another level of cognitive load, but if you care about the company (and if you have equity, you should), this is self evident.
It’s also a good question to ask myself in my personal life. Since I am the only person who knows everything Corey knows and has to deal with the outcomes of my decisions, I am truly the CEO of my life.
So, what would the CEO of your life do?
“I’ll mute for 5 minutes and listen to you talk.”
This management hack is a surefire way to illuminate all the brambles in a direct report’s domain that wouldn’t be mentioned otherwise. Tell them you’re going to be on mute for X minutes, and ask them to simply babble about their stream of consciousness with no prompt.
This manager used it on me to find the things I was thinking about, how I thought about them, how work intersected with my personal life, and on and on. I used it on my direct reports to get them to open up to me when I knew the reason for their failures laid on a conversational dimension that wasn’t coming to light otherwise.
It’s amazing what kinds of things come up when you’re forced to just keep talking. You end up talking about what you’re really thinking about, your fears, your worries, your entire perspective architecture.
It’s like meditation out loud — and everyone loves talking about themselves!
The beautiful thing is you don’t need someone else to do this exercise — journalling or talking to yourself does the same thing. The difference is that solo, you have to act on the information that comes up, whereas with a manger they can coach, guide, or escalate.
“Don’t tell me about problems. Tell me about the problems with your solutions.”
In other words, the only valuable skill for a report is self-management. When I reported to my managers, I used to tell them about problems.
Your manager doesn’t want to hear about your problems. They want to hear about the solutions that you already implemented, and what issues are cropping up with them.
This is alluded too in the levels of delegation, where you trust someone to do something with many or little guardrails. Which was another favorite axiom of this guy — “Always delegate to those with more information than you.” Good managers don’t want to micromanage you — they want you to do the thing yourself, and loop them in for visibility or guidance only when you need help.
A report who does everything they need to do and only involves the manager when absolutely necessary is a favored report. What’s more, it’s a report who’s empowered to act and solve the company’s problems on their own.
Manager 2: The Senior VP of Marketing
Daily 1:1s Are Probably Unnecessary
I already knew that in a 1:1 meeting, the onus is on the report to come prepared and ‘give’ the meeting to the manager for them to respond. But I never though to question the frequency with which they were scheduled. After all, I was the subordinate!
After multiple daily syncs with little new to report, we move to three times a week. That was novel for me — to think of the meeting as an equal hassle for the manager to receive, as it was for the report to give.
This depends on the job and the task, but for most work, daily 1:1s are probably spending too much time on coordination rather than execution. What’s important is to look at the content of the past meetings and decide a frequency and format that works for both parties.
One minimal manager 1:1 agenda template I like is: “What are you doing? Where are you stuck? How can I help?”
People Don’t Leave Jobs. People Leave Managers.
I’ve long believed this axiom, but this was the first time I experienced the inverse directly. This manager wasn’t afraid to get real with me and poke at the underlying reasons why something wasn’t happening. He was the most motivating manager I ever had because I wanted to do right by him.
When I messed up, it wasn’t about being the CEO or doing some abstract thing good for the business. When I messed up, I was letting him down, and I didn’t want to let him down.
I daresay that is the best way to turn operators into owners. Pair them in manager/report combos where both respect and admire each other. That way they are motivated to do well because of very real human reasons, rather than abstract capitalistic ones.
My hardworking friend at Facebook once told me something similar — he worked hard because everyone else was working hard and he didn’t want to fall behind, not because he thought he needed to work hard necessarily. (which is probably not as healthy, to be fair).
Manager 3: The Junior VP of Growth
Trust, but Verify
If you ask a report to do something, the balls in their court, but the manager still holds responsibility for ensuring it happens. How does one remain responsible for something they don’t do themselves?
The answer is to trust, but verify. That means setting them up to do the thing, and then independently checking to see if they’re hitting the milestones along the way.
The simplest version of that is setting deadlines they agree to, then checking in on those deadlines. They know what you’re expecting from them and when it’s due, and they know that you’re there to support them if need be. If they didn’t get the thing done, time for the manager to get more involved, and maybe mute brain dump in a 1:1 (as above) to learn the blocks.
Get Pirate Funding, Bring Back Treasure, Repeat
The core of political power is the ability to manipulate people’s wants to align with your own.
A good way to do this is the Spanish conquistador model: Ask the royal crown to finance an expedition, get treasure from said expedition, then do it again.
You want to be the person whose name inspires memories of success and accountability for your superiors. If the last 3 things you recommended or spearheaded on ended well, then it makes sense they’re going to support your next endeavor. But if your name is associated with failure and stagnation, they’re not going to follow your advice.
In essence, this is managing your personal brand with everyone in the company that is more powerful than you. Be consciously aware of what others think of you, and then tailor it to be what you want it to be.
I suppose my caveat here would be to ensure it’s still an authentic picture. Airbrush out the blemishes, rather than creating an entirely new and false Instagram reality — otherwise it’s worse for all parties.
Be a Botanist Sideways And a Weedwhacker Upwards
Another way to think of this is to be a botanist on your team, but a weedwhacker upwards.
You have to be a botanist to identify weeds correctly and know which ones to whack and which ones to grow. But bosses don’t want to know all those details, unless the thing is going poorly. (see above point) Instead they just want to know which weeds got whacked, when the next ones are gonna be whacked, and why they’re not all whacked yet.
In short, simplify anything you report upwards, and dig into the complexities with your team colleagues. Below is the template we worked out to capture the perfect engagement with the manager of your manager, along these lines.
“Thanks for highlighting that issue, PERSON.
I’ve already addressed it myself and here’s the plan that’s running.
X because Y and Z etc. (display confidence and assurance through the plan)I corroborated this with DOMAINEXPERT and he is in sync.
MANAGER and I also covered it together and they are on the same page.If you have questions with the above, happy to call you.”
Tailor the Medium to the Person
One manager and I had what we called ‘our dance’ in which he’d call and chase, I’d email and analyze, and neither party would be happy.
I admit that my tendency to write big emails mapping out the entire problem space didn’t always help. But I’ll also say that his tendency to throw many minds into a meeting and lecture at them didn’t either.
The lesson here for both of us is that of tailoring the medium to a person. Just like everyone has their favorite messaging app, they also have their favorite figures of speech, styles of delegation, and so on. If you use your own style on everyone, chances are it won’t stick. It pays to learn their style.
I learned quickly to call this manager if I wanted something from him, and to use his own figures of speech for added legibility. Often I would write out the problem space first (using my method), come to a conclusion, then call the responsible parties and hold em to it (using his method).
