my favorite managers

disclaimer: the opinions and views expressed here are entirely my own and do not express the opinions nor views of my employer.

when friends are looking for a new job and are about to sign an offer, i find myself routinely dispensing the same advice: interview your future manager before you commit.

i remember when one of my managers announced he had too many reports and would be sweeping me under some other manager who’d never managed anyone before. “any concerns?”

young and naive 23-year-old me shrugged, “i don’t really know what would be changing or how it affects me, so… nope! seems reasonable.” 

new manager turned out to be my worst. manager. ever. 

welp, lesson learned.

after leaving that team, i miraculously landed my favorite manager ever. they taught me the importance of working for an excellent manager, and i’ve (unfairly?) held every subsequent manager to their standard.

it recently occurred to me that my experience working for/with a zillion managers is unusual. i’ve run into a buncha folks who don’t really know what a good (or bad) manager looks like because they’re either new grads, have stuck to the same 1-2 managers their entire career, or are typical silicon valley young executives who’ve always been at the top of the food chain and have never been managed by anyone before. 

in the startup world, you don’t need stellar management skills to survive through seed stage and series A. after all, there are very few employees to manage, and company goals are (ideally) very focused. but as the company grows, so, too, does product complexity, and a need for organizational structure/ hierarchy emerges. management skills suddenly become important, as things that weren’t as much of a thing before (like employee retention) suddenly become a thing. 

i’ve worked directly with and been managed by more managers than most people (the result of somewhat frequent job switching and working in support roles for execs (…and sometimes the job switching was motivated by escaping bad managers who showed no signs of improving at an acceptable rate)). i’ve observed what works and what doesn’t work. i’ve played therapist to colleagues who can’t stand their managers. i’ve talked extensively to friends who are unhappy and burned out but are fiercely loyal to their managers. 

so. maybe my observations will be useful to new managers and to people who’ve never experienced being managed by an awesome manager. i tend to skim and roll my eyes at articles that focus on generic traits (“three surprising traits of successful leaderslololol) as i’ve never seen ambiguous actually help anyone change their behavior, so instead i’ll focus on concrete specific examples. whee.

my favorite managers…

were accessible. 

they responded to my IMs and emails within a reasonable timeframe and were always willing to chat in person whenever i needed it (not that i needed it very often). this meant that 1) they never blocked my progress for very long, 2) i always felt supported by them like some sort of psychological security net.

set up regular 1:1s and were happy to chat as long as i needed.

we never used my regular 1:1s to primarily talk strategy or execution — those were scheduled as separate meetings. instead, 1:1s were used to understand the things that can be easily overlooked. am i overworked? do i have any concerns about the team? am i bored? are my projects aligned with my ideal career trajectory? do i have any feedback for them? employee retention is much easier when warning signs are spotted early on and you can have a dialogue about how to get things back on track.

proactively discussed my career development.

they cared from the get go about my career goals. they’d point out where i was doing well and where my work/ behavior differed from their expectations. they’d look ahead to where i wanted to be in 6-12 months and would continuously present or create opportunities to help me get there. 

cared about me as a person.

they convinced me that my health and my happiness genuinely mattered to them and that they wanted the best for me. this started by getting to know me as more than just an employee and investing the time and energy to understand me as a gail as well. who are the important people in my life? what do i like doing outside of work? what values drive my decisions? what would cheer me up after a stressful day?

removed as many obstacles as they could for me.

common obstacles included other higher ups, pending decisions, money, and incomplete knowledge.

always coupled action items with timeframes.

me: i’m blocked on x until you do y.
awesome manager: ah yes, i’ll do y by end of day tomorrow.


awesome manager: i need your help with x. it’s not urgent, so anytime in the next two weeks is fine by me.
me: got it. x will be done within two weeks.

did what they said they’d do when they said they’d do it.

if my awesome manager promised they’d do something by end of day, 90% of the time, i knew i could count on them to do it by end of day. the other 10% of the time, they wouldn’t actually do it, but would at least communicate to me their new timeline by end of day.

okay managers might not have as awesome a ratio as 9:1, but were consistent enough in their behavior to be predictable. if you always complete something in double the time you say you’ll complete it, then i can mentally adjust for your lag in an accurate fashion. in other words, if you say you’ll do something by end of day, i’ll plan around you having it done in two days.

shielded me from politics so i could focus on my work.

for example, if i was assigned a project that another team wasn’t necessarily happy about, my manager would do a few things: reassure me i was working on the right thing, remind me i have their support, and would go deal with the unhappy outsiders who were trying to squash the project.

they’d say things like:

  • “feel free to blame me if they get upset”
  • “point them to me if they have questions about why we’re doing this”
  • “make me the bad guy”

made me feel heard.

they’d practice active listening and could repeat what i’d said in their own words. if i expressed concerns or frustration about something, they’d acknowledge my input and—depending on the situation—would tell me what actions they’d take to address it (even if that action was “i need to think about it more carefully and come up with something”), would explain why things are the way they are, or help me think through how to solve my problem. 

practiced radical candor.

they were direct in their feedback but delivered it in a compassionate way; think brutal honesty, except replace the brutality with tact.

the worst managers would passive aggressively phrase commands as questions without context. “is <stuff> enough?” really meant “i disagree with you and don’t think <stuff> is enough. i have my reasons, but instead of being straightforward about them, i’m instead going to make you think i don’t trust you and test you and see if you know what my reasons are. the right answer i’m looking for is so obvious that only an idiot could miss it: <stuff> is not enough.” 

a much more effective form of communication is to be direct with curiosity and without judgment: “i’m not sure <stuff> is enough. here’s why. if i’m missing something, can you help me understand your reasoning for <stuff> this time?”

left their ego at the door.

great managers have little trouble admitting when they’re wrong or aren’t 100% sure of the right answer. awesome managers do this in a way that doesn’t shake anyone’s confidence in their leadership.

bad managers let their insecurities erode their relationships with their team. they’re preoccupied with their pride and image and don’t understand that people don’t care if you make mistakes (as long as you learn from them). this compromises trust and allows nub-stimulaters (more commonly known as brownnosers) to get ahead.

never asked me to do specific tasks. 

here’s the gist of problem-solving:

  1. identify problem
  2. generate solutions
  3. evaluate solutions and pick one
  4. execute on solution

the bestestestest managers looped me in at step two (generate solutions) and expected me to engage in step one (identify problem) alongside them. they’d present me with problems, ask me to solve them, and then trust me to go and do it. or they’d have me sit in meetings as an extra brain to look out for problems they might’ve missed. this meant i always had the agency to get things done in whatever way i deemed fit so long as i produced a solution that fit the bill. this also meant i always knew why i was doing what i was doing and allowed me to build a better mental model of the kinds of things my manager cared about.

my not-so-favorite managers looped me in at step four (execute on solution). “put the names from this document into this spreadsheet.” no context. just do it. there’s no way i can evaluate whether this task is worth my time because i have no idea why i’m doing it. this is pretty much the definition of micromanagement, but at least if i keep my mouth shut and just do the task, they can’t fault me for obeying their direct order.

the worst managers didn’t know wtf they were doing and would loop me in at step three (evaluate solutions and pick one). this was confusing as fuck. “gail, i want you to do this. or, actually, this other way might work, too. or even this third way. well, whatever you want.” how am i supposed to evaluate the tradeoffs for each solution if you haven’t even given me context on the problem i’m supposed to solve or the goal we’re trying to achieve? these managers expected me to execute on every solution and present them the results for each. if i executed on one solution only, they’d pause and think and ask, “what does it look like if you do it the other way i mentioned?” … cue table flip. don’t make me do more work because you’re not decisive enough to pick a solution and too paranoid to give me full context on the problem.

shared their priorities with me and trusted me to prioritize my own work accordingly.

if i’m working on four projects but can only make progress on two of them this week, then i’m going to work on what i believe are the two most important projects. if my idea of what’s most important doesn’t line up with my team’s or company’s priorities, then that means i’ve prioritized my work incorrectly and have just set my team and company back.

the more visibility i have into my manager’s priorities, the better i can prioritize and plan my own work. the best managers have their shit together: they’ve set their priorities and communicate them to their underlings.

up next: interviewing your potential future manager

(would that be useful?)

new norms

i've been thinking a lot lately about:

  • how often i silently forgive others for being inconsiderate or thoughtless or abrasive because i know it's not their intention
  • whether i should care that people seem to expect a low level of competency from me by default and whether i should do anything about it
  • how i now flinch when i hear the words 'passionate' and 'ambition' and 'impact'

wouldn't it be lovely if we...

  • answered 'what do you do?' with what we love to do instead of what we do to pay the bills?
  • complimented girls by praising their character instead of their looks or their obedience?
  • asked each other 'how are you?' and meant it?
  • were (system 1) impressed by those who are kind and generous instead of those with power and status?
  • defined the success of a relationship by what we learned and how we grew from it rather than whether it ended?
  • humanized those who are different from us by default instead of only when we're called out on it?
  • stopped perpetuating the notion of finding our other halves / finding someone who completes us? (thank you, alanis morissette, for inspiring eleven-year-old me with the lyric: i don't wanna be your other half; i believe that one and one make two.)
  • put as much effort into nurturing our friendships as we do into our careers?
  • had kids because we want to populate the earth with compassionate and loving humans and not because it's a thing we're expected to do?
  • saved the world by improving our interactions with other people rather than enslaving each other to solve problems with much lower impact?

best of the bay area

these are not my favorite places; these are the best places. think i'm wrong? do tell.

best place to make reservations just for french toast
custard french toast / nopa / sf (nopa)

best place to take off your clothes and induce tachycardia
archimedes banya / sf (hunter's point)

best place to become a wowowowow-PANCAKES-zomg person
lemon ricotta pancakes / venus / berkeley

best place to have a sit-down on a bench
ina coolbrith park / sf (russian hill)
honorable mention: on a tree trunk bench, west of morrison hall at uc berkeley

best place to bring cash and yell at each other over drinks outdoors
jones / sf (tendernob)

best place to marvel at pretty, dead things
paxton gate / sf (mission)

best place to eat everything on the menu
cafe de casa (brazilian breakfast) / sf (north beach)

best place to eat just so you can check out their bathroom
kenken ramen / sf (mission)
don't actually eat their ramen (it's not great); go during lunch and eat their curry

best place to put freshly fried sugary bread in your tummy
freshly made glazed doughnuts / king pin donuts / berkeley

best instructor to get you to join a cult
andrew / soulcycle / sf (soma) or san mateo or palo alto

best place to lick the thickest, creamiest, whitest, tastiest froyo ever
italian frozen yogurt / foodhall / sf (mission)

best yakionigiri (oily grilled rice balls)
tanto / sunnyvale

best ramen
shio ramen (hokkaido-style white tonkotsu) / santouka / santa clara
if i had to choose on in sf... tsukemen / waraku / sf (japantown)

best place to listen to people telling personal stories
fireside storytelling / sf (mission/bernal)
honorable mention: bawdy storytelling / sf (potrero)

best place to ice cream
tara's / berkeley
if i had to choose in sf... ici / berkeley
oops, for real, if i had to choose in sf... bi-rite / sf (nopa / western addition)

best place to see a play in someone's house (seriously, it's awesome)
third cloud from the left / sf

best place to stare at the walls while you eat
radio habana (social club) / sf (mission)

best place to enjoy some gold ol' fashioned roller disco
6th ave + kennedy in golden gate park / sf

how (i attempt) to win friends and influence people, part ii: listen.

last time on…

in part i, i talked about how connecting with humans and creating meaningful interactions (where winning friends and influencing people is a not uncommon side effect) is a one-step process in which you shift your attention from yourself to the other person. one way you can do this is by being curious about the other person and making genuine attempts at getting to know them. 

so now that you’re an expert at following your curiosity and you’ve asked some interesting questions, you’ll need to continue fixing your attention on the other person by listening to their response. how can you tell if you're a good listener? good listeners can say ‘i get what you mean’ and the speaker will believe them without suspicion. they do their best to understand the other person's experience. by developing your ability to listen, understand, and relate to someone else, you increase your chances of creating meaningful interactions.

interruptions can actually be a good thing.

some naive advice on good listening suggests that interruptions are bad. interruptions themselves are not inherently bad, but interruptions that occur because you weren’t paying attention are indeed bad. if you interrupt me with a non-sequitur, you’re telling me that connecting with me is a lower priority for you than talking about yourself and your own distractions. 

but when someone interrupts me to ask a clarifying question or to get a better grasp of the situation, it signals that they’re paying attention and are interested in understanding my perspective. when speaking, it’s easy to overlook and leave out minor details. when listening, it’s easy to fill in those gaps with our assumptions that might not actually reflect the reality of the situation. instead of assuming, it’s often better to explicitly spell out your assumption or ask the speaker to clarify. some examples of good interruptions might be:

  • wait, what do you mean by ______?
  • before you continue, when you said _______, i assume you were referring to ____. does that sound right?
  • hang on, when you say _______, are you talking about ______?
  • if what you’re saying is _____, does that mean that ______?

but interruptions, even good ones, are still interruptions. it’s polite to acknowledge that you’ve interrupted and steer the conversation back on course once your questions have been answered.

“sometimes it's better to be kind than right. we don't need a brilliant mind that speaks, but a patient heart who listens.”

it’s extremely common among engineers and researchers and rationalists and other analytical types to interrupt in order to correct each other. this makes a lot of sense when your goal is to seek truth, build accurate models, and solve problems. but if connection is what you seek, it’s often not worth it to interrupt just to tell someone they’re misusing a word or that their feelings aren’t justified or that their experience was a fluke or that they didn’t think through the whole situation. you can still connect with someone even if you disagree with them. remember, the goal of listening is to understand the other person and make them feel heard. 

avoid deadending conversations. 

being quiet isn’t the same as being a good listener. if someone is speaking and i’m nodding and uh huh-ing along the way, presumably i’m internalizing their words and am reacting to it in some way. generally, it’s my curiosity (yes, have you noticed how much i talk about curiosity?) that drives my response, which means my attention is healthily focused on both them and me. asking open-ended what and how follow-up questions shows that i’m still interested in understanding the other person, but it also rewards me by satisfying my curiosity. for those who aren’t as curiosity-driven, i’d be curious :P to hear what kinds of strategies you employ for not deadending conversations.

utilize microacknowledgments and body language.

this is pretty basic/ common advice, but i surprisingly still seem to meet people who are clueless, so here's my obligatory list:

  • nod when you understand what the other person’s saying.
  • sincere use of microacknowledgments (“uh huh” “yeah” “i see” “hmm”) lets the other person know that you’re engaged and not lost in your own thoughts. 
  • look at the other person's face while they speak, even if you’re not sitting directly across from each other. pointing your eyes and your body in their direction says, “hey my attention is focused on you.”
  • people notice when you’re looking at things behind them or around them. even a subtle glance at your watch or your phone can immediately tell the other person that you’re preoccupied with yourself. 

making suggestions can also be a good thing.

other well-meaning but naive advice i’ve heard is to listen and not try to solve the other person’s problems. the problem i have with someone trying to solve my problems is that, in most cases, they haven’t gathered enough of context around the situation or problem in order to provide useful suggestions. that can often leave me feeling frustrated that the other person doesn't get what i'm trying to say.

but if i feel like the other person sufficiently understands what i’m talking about and what i’m feeling, i’ll generally welcome suggestions. to get to that point, you’ll first need to display signs of empathy, channel your curiosity, and ask more clarifying questions. it also doesn’t hurt to preface your suggestions with qualifiers (for example: 'you may have already considered this, but just in case, what about ______?'). you can make suggestions without appearing arrogant by first acknowledging that you may not fully understand the nuances of the situation before dispensing your advice.

side note: when speaking, you can also make things easier for the listener by explicitly stating upfront ‘i’m about to rant about a situation. i don’t need you to fix it. i just want to share how i’m feeling and have you acknowledge my experience.’ might seem somewhat weird at first, but i’ve found it to be super effective. conversely, if you do want someone’s input or advice, ask for it!

stay tuned for part iii on how (i attempt) to win friends and influence people.

how i (attempt to) win friends and influence people, part i: get curious.

or more accurately… how i (attempt to) connect with humans and create meaningful interactions, where winning friends and influencing people are not uncommon side effects. 

i remember being confused the first time someone told me they thought i was a people person. weird. people are scary and complicated. i'm scary and complicated. how can someone so socially anxious be a people person? 

a year or two later, i was shocked that a different person thought i was an extrovert. me? O_o

a couple years after that, i was described as “bubbly” and “outgoing”. i then proceeded to poll my friends to see if they agreed with this latest assessment because i couldn’t believe it. most people seemed to agree on these descriptions... if not both, then at least one or the other. i suspect that their agreement is more telling of the types of people i'm surrounded by (other introverts, science/tech folks all day errday) rather than some objective unbiased unfiltered measure. so, disclaimer: this is what works for me. your mileage may vary.

step one: shift your attention from you to them.

…and that’s about it. there isn’t really a step two. i’m not saying that i pander to people’s narcissism or that i don’t share anything about myself or that i become a doormat and forget about my own values and needs. i’m saying that when we talk to other people, by default, most of us are paying attention to ourselves. we’re often preoccupied by our insecurities, what we’re going to say next, and what we want from the other person. instead, practice shifting your attention toward making the other person feel comfortable, doing your best to understand/ process what they’re trying to communicate, and noticing what they might want.

easy peasy, yeah? i've decided to write this as a series of parts instead of publishing one long mega-post. each part will focus on a different aspect of what i mean by shifting attention away from myself and toward the other person. this is part i. stay tuned for more.

get curious.

despite being a hella introvert (yes, i believe that’s the terminology susan cain uses) who is easily drained by large groups, gets cranky and stressed without alone time, and thinks most effectively when no one’s watching, i can’t help but fill my time with people-oriented activities. why? there’s some force that competes for my energy and inexplicably draws me towards other people. i become extremely curious about interesting people (and extremely motivated at the prospect of discovering interesting people). what drives them? how do they make decisions? why do they behave the way they behave? what were they like as a kid? what do they value?

given enough time, the right questions, and a mutual commitment to openness and honesty, i’m able to take some abstract 2d rough draft i have of them in my head and revise it into some model that resembles an actual multidimensional person. and somewhere in that process are meaningful moments of i get youyou get me, some reminder that we’re all human and that we’re all connected in some way. 

those moments of connection are my crack, and crack is the stuff life’s made of. for crackheads, at least. personal crack example: i choked on a gigantic heap of SRSLY when my friend sunil beautifully commented on the question “how are you?” with “what a fucking waste of a perfectly useful phrase, right?”

when talking to someone new, get curious about the parts that are unique to them: what it was like to grow up in a huge family, why they’re enthusiastic about their field, what traits they admire in their role models, whether there's any meaning behind their tattoo. anyone can rattle off the who/ what/ where/ when superficial facts of an everyday event, but discussing the feelings/ reactions/ opinions/ internal monologue that went along with it turns it into an engaging story. if i wanted someone to talk facts at me, i’d take a class or read wikipedia. be curious enough to steer the conversation toward engaging story and away from wikipedia.

as nice as it is to agree on things and feel like 'wowowow we're the same!', it's the differences that pique curiosity. for example, fleet week sf took place a couple weeks ago, which meant the bars were filled with navyfolk. one of my friends pointed out that this is a great opportunity to learn about another person who made such different life choices than the ones we'd made. and she was right! our curiosity led to some interesting conversation where i learned about whether this dude gets lonely on the boat, his immense respect for his colleagues, the brownie badges on his uniform, how he's american yet grew up in yokosuka, japan and speaks mandarin. 

i'd like to believe that all people are interesting, but it's up to us to be curious (and patient) enough to find the interesting bits. don't be afraid to ask questions. seek answers to 'why?' and don't let them get away with one word answers. ask them to expand on things that interest you. if you find yourself getting stuck and being terrible at this, don't panic! practice makes perfect. you can even practice with yourself by role-playing as someone else getting curious about you. what's important to you that you'd be willing to share? what parts of you would you want to be discovered? what kinds of questions would you ask yourself in order to discover those parts? 

stay tuned for part ii on how i (attempt to) win friends and influence people.