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?)