A while ago, i had a discussion with a coworker about their boss. My coworker was venting a bit about a number of patterns that i recognized from my experience with various managers.

First off, let me say that i’m not a manager. i was a manager for a while and was terrible at it, so not being one to want to repeat mistakes, i haven’t pursued being one since. Being a good manager is incredibly difficult and requires a number of talents that are not included in WSJ Productive Resource Engagement books or whatever the current trend is.

What i do have a lot of experience in is managing my manager. Each manager has their own quirks, but there are certain types of managers that i’ve learned how to train and deal with.

Let me talk a bit about Process Managers.

Process Managers are folk that are in love with the process of management. These are folks smitten by things like JIRA, AGILE, SCRUM, and all the other things that either add or remove things from various checklists that they fetish over. These are people who “want to see progress” and expect their reports to have complete, analytical breakdowns of tasks done within minutes of being assigned. These folk do not do well with things like “discussion” or “revision”, since that requires them to alter the carefully crafted charts and diagrams that they spent all week putting together to impress their own manager.

Some folk might feel that these sorts of managers like to micro-manage, and a number do, but mostly, they’re looking for the dopamine hit of “number goes up” (or down, but basically not “stayed the same” so that they can show “the process works!”).

As a software engineer, we know full well that Life Does Not Work That Way. Asking how long a given task might take is like asking “how long will it take to carve this statue?” You have a rough idea, and can show progress, but as an artist, you have no idea what’s actually in the stone and if you it something unexpected, you have to deal with that. Sometimes you need to alter the design a bit. Sometimes you have to start over. It’s the nature of the art, and that is completely incomprehensible to the Process Manager.

So, how do you manage a Process Manager? You feed them the dopamine they’re looking for. Give them short updates where you specify the work that’s been done and the very short scale work that lies ahead. Give them little things that they can check off of a list. If you need to alter a design or the scale of something changed, give them a new checklist of things to tick off. Track Everything via the ticketing system of choice (Jira, bugzilla, Postit notes on the cube wall, whatever). They’ll grouse, but you gave them delicious mental candy, so they won’t stay mad for long.

Play the game they want to play and they stay happy.

On the other side, realize that they are not invested in your growth and career unless it maps to some form of progress they can chart. So, if you want to go to a conference or learn about something, you need to absolutely qualify it with all the bells and whistles they want to see. Put together an Impact Assessment that highlights what percentage points of improvement you expect to deliver or whatever.

(bit of a side note: Process managers tend to think of reports as ‘resources’. You know, like the copy machine or coffee maker. Mind you, when the coffee maker has a bad day, i replace it, because coffee makers very seldomly self correct. A coffee machine doesn’t perform poorly because it’s kid was up until 3 AM, or because a parent just got a cancer diagnosis. People do, and they’re not going to tell their manager or coworker about that for lots of reasons. People have off days and weeks, and a good manager knows and works with that. The coffee machine also doesn’t angle to get the copy machine’s job, but that’s a different matter.)

i kinda spelled all that out for my co-worker, with the added point that “all of this is temporary”, none of it is actually personal, particularly since the senior engineer on the project has zero complaints, and frankly the stuff the Process Manager is complaining about is stuff like “too much discussion in PRs”. Uhm, you want discussion in PRs. That’s documentation. It also means that folk aren’t just rubber-stamping future bugs into the code. i’d rather there be good conversation in a PR than a bunch of issues being re-opened.

i also gave a bunch of other tips for how to deal with a Process Manager, and maybe i’ll write those up sometime.

A key aspect of a good engineer’s life is dealing with non-technical issues like these. A key aspect of a senior engineer’s life is giving junior folk the insights needed to become a good engineer. Dealing with iffy managers definitely falls into that category.

So, a bit of personal news. i got promoted.

i’m happy about that, and i expect that little will actually change, since i’ve been doing the stuff at this level for a while, but i did want to underscore a few things i learned.

1) Your manager is your ally (or foe).
My current manager is amazing. People management is an art and a skill that not everyone has. It is more than just juggling tasks and filling out paperwork. There’s a lot of other skills that good managers have including marketing (basically, promotions are making a marketing plea on behalf of their reports), mentoring, coaching, and dozens of other “soft” skills you don’t just magically get when you have people assigned to you.

This was absolutely highlighted to me when i read his promotion proposal letter. Not only did it make a concise case built off of what i had been doing, but it included anonymous “pull quotes” that he had collected from peers and team members. It also included a critique section that, summed up the reasons in two pages of well balanced advice for how i can improve.

2) Promotions are proactively retroactive.
There’s a statement in the company’s Leveling Guidance document that basically says “You’re not promoted for past work, you’re promoted for work you’re going to be doing.” i can’t help but smile a bit at that because there’s a built in contradiction.

You’re not going to be given new responsibility unless you’ve demonstrated you’re responsible. Your prior work absolutely sets the stage for any promotion you’re going to get, and that’s why i spent the past eight months or so working on demonstrating the stuff i can do. i kept a record of the tasks i did. i spoke up more. i made sure that others had a clear path to do more. It wasn’t hard for me to do any of that, because it’s what i normally do, but i made sure that i wasn’t as quiet about it.

Granted, that part i hated, and i may back off the drum beat a wee bit for a while.

Still, the one driving thing is that other people have clearly failed to develop the sort of mind-reading omniscience that i also lack and making sure that folks find out about things turns out to be a good idea. Who’da thunk?

3) Timing
i’ll admit, i’m also taking advantage of some interesting timing that is clearly in my favor. Right now, the company i work for is very concerned about attrition. With tech, folks tend to change jobs fairly frequently, and with the pandemic and general burnout, that churn is a good deal higher than normal. So, folks at the top are very interested in keeping folk. i have some fairly big cards to play, and i absolutely played them this round. Had the market be flush with folk wanting to work here or had the company been struggling financially, i would have lost my shot and had to try again in a few years.

4) Improve the ladder
One of the things that drives me nuts is when i see someone “pull up the ladder behind them”. They do stuff to get ahead, then once they’re in a position of more authority, they sabotage others from following them. i have no idea why they do this because real success comes when you do the opposite.

Think of it this way: If more people succeed, the team (and company) succeed, right? That means that there’s more resources available, and the company is going to invest those resource where there’s clear success. If you’re the person that’s seen as the success facilitator, why wouldn’t you be considered key?

Should i have done a lot of this work earlier? Yes. i was under the assumption that “If you keep your head down and do good work you’ll be rewarded.” That’s not strictly true. You probably won’t get fired or laid off. You might get a bonus or two, but anything longer termed requires effort and focus on your part.

Humans are amazing pattern recognition engines.

Here’s a lovely example:

1, 2, …
A, B, …
Red, Green, …
Apple, Boy, …

i’m going to go ahead and guess that you responded with 3, C, Blue, and Cat (or some other simple word that begins with “C” that you probably remembered from a primary school reader).

You didn’t reply with 12, Abacus, Yellow, and Orangutan.

i’m also going to bet that you absolutely would not have answered Orangutan for any of those even if you worked out the other pattern i was using, because orangutan doesn’t fit any pattern. (i’ll note that one of the keystones of comedy is pattern breaking so it’s ok if you giggled at that one.)

So, why, when we are setting aside time to plan our work are we setting out to sabotage ourselves?

Think about it. Every 6 months, we’re asked to come up with a set of goals. The first set are company focused goals, where we plan what objectives we’re going to try and make and what challenges we’re setting up to deliver. We’re going to be judged and evaluated on those, and if we don’t meet those self designated marks, we will not be fiscally rewarded. That means that we have to assess our skills and capabilities, then craft a message that can be presented to Those That Write Checks in a way that can sound more challenging than it probably really is.

This is absolutely human nature. No one willingly sets themselves up for failure unless that failure is actually a success in disguise. (i actively tried to get myself fired from a company once because i realized that if i left, i wouldn’t get a generous severance package. Guess what the winning strategy was in that case?)

So, after all that careful, and borderline Machiavellian planning, we then turn and ask “How do you want to improve?”

Your brain will absolutely scream “OH NO! SAY SOMETHING THAT WON’T GET YOU FIRED!”

You’ll come up with yet another modest goal that will be achievable with great show that your boss will rubber stamp because they’ve got a dozen reports. If you do manage to pull off something impressive, it’s probably going to be by surprise, and you might add it to the goals list next time. Well, unless you got your name in the papers or headlined a conference or something, then you’re kinda screwed and you’ll just add that to your resume.

Instead, let’s break the Personal Goals from the Corporate ones. Like REALLY break them, not just put them in a different section on the same page. Give folks a clear and separate workspace to log how they want to improve (or what they want to improve) and how they’re going about doing that. It should be a log, not a report card, so folks can note the disappointments and setbacks that are crucial. It should be something they’re willing to share not only with management, but peers and even outside folk. This is how you get folks to expand and how you get them to recognize what they can do.

A LARGE number of people do not have a high opinion of themselves. That’s the main reason that Impostor Syndrome is prevalent. i will note that i am not a fan of myself, and haven’t been for pretty much my entire life. i am acutely aware of my shortcomings, failures, and areas of ignorance. We are all hard wired to remember the awful and dismiss the good.

It is really, really hard to see progress, particularly personal progress, because of the head full of a**holes that constantly remind me of the terrible. Heck, my personal goals have been crap and dismiss-able because of that as well. It was only after i made a concerted effort to address that problem that i got anywhere.

Now i just need to convince HR.

Apparently continuing to journal my personal career epiphany.

Every six months, we are asked what we’d like to do to grow our career. For some, this may not be an obvious answer, and i’m hoping that i can help explain to those like me. 

Let me explain how i was wrong 

i was raised not to speak well of myself. Bragging was frowned upon. Folks that sent Christmas Family Updates filled with accomplishments and awards were quietly mocked. Family members who managed to rise through the ranks without drawing attention to themselves were heralded as heroes.

When i began my first career, that was true in the workplace. “Keep your head down and do a good job and you’ll go far!” was the silent mantra. Bonuses were handed out in private. As one prior manager said “It’s like we do these things like drug deals”, and they were pretty accurate. 

If you had said to me that i had to have an active hand in my career growth, it would be like saying i had to steer the continent. It would seem like an alien, impossible concept, particularly since that obligation belonged to my manager, right?

Well, no.

It turns out that your manager is also a person. Depending on the organization they may have too many reports, plus their own task set, and far more meetings and paperwork than you can possibly imagine. If you’re also a “pure engineer”, they may be doing things that feel like dabbling in arcane arts, with terms that sound like gibberish. The good thing is that it may also be mutual. They may have no idea what you do aside from whatever mutually agreed metrics you’ve presented. “Has JR done the four items he listed three or six months ago? Check. 4% cost of living it is, then. Oh, he also single handedly refactored the CriticalSystem? Huh, forgot he did that. Ok, let me see if i can budget out an additional 1%.” 

Add in that many organizations tend to reshuffle fairly regularly, meaning that you, or your team, get a fresh, new scorecard with every change to the management chain. More than likely, they’re new person with little experience with your team. If i’m lucky they may be able to distinguish me from a rock, provided how empty the field was. 

This is not a slam against managers. As i said, they’re people who are also overworked and generally doing more than their fair share. They do a job that i recognize that i cannot do. It’s a very specific set of skills and empathy that not a lot of people have, and when you get a good manager, you should enjoy the great opportunity you have and realize that nothing is permanent. Managers get promotions too.

Positioning Save Points

If you play platformer games, you probably know about save points. Well, if you’re as terrible at video games as i am, you’re thankful that save point keep you from starting over from the beginning when you die every five minutes. 

It’s not a bad idea to think of ranking up as kind of a career “save point”, but instead of getting eaten by a grue while you were getting coffee, the “save point” kicks in during a reorg. Like i noted, bosses are people. People are neurologically hard-wired to take short cuts. When a person gets a new team, they get the brief overview of the members and do a quick assessment. They may see two people at level 2 and one at level 3, and in their minds they see them at about 50% of their respective levels. 

Mind you, one of those people may have been working way beyond their level, but doing so quietly, so all that effort is lost to the winds. Or at least put in the same mythical Permanent Record that your elementary school teacher threatened you with. 

By the way, this is why it’s absolutely CRITICAL to keep a personal, detailed log of your weekly accomplishments. This document should be something that you control (although you should share it with your boss), that logs the high and low points for yourself. It’s amazing what you’ll forget if you don’t and it’s absolutely vital when it comes to self-review times.

But why might you want to go beyond what you’re doing now? Well, it kind of depends. If you’re absolutely comfortable with what you do, that’s fine. But if you find yourself doing more than what’s in your job description, you might want to consider leveling up.

In fact, it’s a really good idea to do an honest self assessment.

What grade of houseplant could replace me?

Ok, that’s a bit facetious, i admit, but like i’ve said, i have a pretty low opinion of myself. Don’t be like me, in that respect.

Instead, try to abstract “you” from what you do. Could you be replaced by someone else for less money or experience? And be fair. Include all the additional stuff you do that’s not part of the strict job description. Let’s say that your job is to keep the widget server running. You do that, but you also provide the QA teams tools to test the widget server, fill in missing documentation on how to use the widget server, teach classes on effective use of the widget server, and answer customer emails about bugs and issues. Yeah, all those are around the widget server, but if you were eaten by a grue (sorry), could someone just promoted to your position do the same, or even think about that sort of thing?

Likewise, it can be VERY hard to recognize your level of influence. “i was just answering a bunch of questions.” can be easily dismissed, but can carry a huge amount of impact. Eventually, you’re seen as an expert, and you may well be. Your gaining, and more importantly sharing, experience which makes things easier and others more productive. 

If it helps, take “you” out of it. Make up a person like “Pat” or “Chris” who happens to be a lot like you and talk about them as if you’re trying to get them promoted. Point out the things they do that go the extra kilometer. 

Extending your reach

Remember how i said that people are neurologically hard wired to take short cuts? They really are. When you go up the ranks, folks tend to change how they interact with you. (i’ll even add that you will change how you interact with yourself.)

There’s an old adage called the Peter Principle which says that folks will advance up the ranks to the level of their incompetence. i tend to also think about what i like to call the Inverse Peter Principle, that says people are held back by their levels of competence. If you’re particularly good at your job, there may be little reason to move you out of it because, well, why would any sane person willingly break something that cheap and functional? 

But, going up a rank broadens the number of folks that you can reach. That has a real impact. It gives your voice more leverage that you can hopefully use for good. Because of your higher rank, more folks will listen to you. You have a smaller, more focused peer set that you can connect to, and they also have wide audiences that you may not be connected to. Working with them you can cause real change and progress. 

If you’re like me, you know that what matters in life is how often you reach down to help folks go up. It’s a lot easier to do that when you’re higher up yourself. 

Plotting your goals

Goals are hard. i get it.

We use OKRs. Those can be tricky as hell because you specify them six months out, they need to be aligned with the company, group, division, and team objectives. Be actionable, accountable, with clear success markers, and you’re graded on them at the end. That grade gets reflected into your possible raise and bonus potential. 

Clearly, the incentive here is to be fairly conservative about what goals you set for yourself, or at least, vague-ish enough about them that when future fudging the results, you still come out better than average. 

That’s terrible for a number of reasons, but i won’t go into all of those right now. Instead, i’ll note that after that exercise, you’re then asked what personal goals you want to achieve. 

There’s a funny trick you can pull on some folks, where you ask them “What does Y-E-S spell?” They’ll respond “yes”, because of course yes is the answer. Anyone who has greater than a 3rd grade education would absolutely say that Y-E-S spells “yes”. 

Then you ask them what “e-Y-E-S” spells. 

Some will tell you that it’s not a word, Others might say it’s “ee yes” or something. 

Again, neurology is hard and shortcuts are easy. 

After playing mental chess and filling out the OKRs, you get that one thrown at you, and you’re probably still going to play mental chess. “What answer can i give that will give me the best chance of not getting fired/laid off/paid more?” and you say you’re going to do something like learn a new programming language or study machine learning or something. 

That’s also probably a terrible answer. i mean, it may not be, depending on what your personal end goals actually are, but if you’re just writing that without any sort of long term plan, then it’s not a good answer. 

Instead, you should be asking yourself “what would i like to change?” or “how can i improve things around X”. If you’ve been working somewhere long enough, you probably  know the sore spots and sticking points. You do have the ability to change them, you just need leverage. If you need more leverage perhaps you should consider levelling up? 

Likewise, if there’s a graph or chart that shows all the things that someone the next grade up should do, and you’re already doing all of those things, why aren’t you getting the proper recognition? 

A work in progress

i’ll note that all of this is pure speculation on my part. i’ve been at the same grade for about 20 years, through multiple companies (See: “Let me explain how i was wrong”). i’m currently working to try and address that, and i fully understand that it’s not going to happen overnight, nor am i going to be greeted by banners and balloons. 

Still, my gross legacy of mistakes and near-sightedness should not be yours, and there are ways and approaches you can take to this to make it far less uncomfortable.

i mean, it’s never going to be super comfy, but at least it won’t be something you dread doing as much anymore.

i am, and i need to make sure i’m very clear here, an idiot.

i’ve been working for my current employer for just over 10 years. i am still pretty much at the same position i started with. It’s not a huge deal in my life, since i make good money, working with good people on interesting things and am able to both tell people what i do, and sleep at night knowing i am not screwing them over. Heck, it’s an open source company, so it’s possible to audit everything we do, and frankly, that’s pretty unique.

Still, it’d be nice to get a kudo every so often or at least some sign of progress. Part of the problem comes because every so often we have a reorg, and i get a new manager, and i basically have to start all over again. Myself and someone i’ve worked with even created a “New Manager On-boarding Document” that lists various things to do (like, make sure your github credentials are in order, here’s some groups to join, here’s the slack channels and calendars we use, etc.). It’s mostly pre-emptive because then we minimize the disruption that occurs whenever there’s a new boss. New boss arrives, and mentally classifies me with my various peers, and starts to either question all the things i currently work on or “help optimize” things which usually results in me continuing to do them because stuff breaks otherwise.

i tend to work on some fairly long lived, highly critical, but not super showy projects. That means less “Hey, we launched Shiny New Thing in three months then forgot about it!” and more “here’s a system that people have relied on / will rely on for years, can you make it better?” Not super glitzy, but solid work. Sometimes, it’s even the less shiny, less new Thing that got thrown over the wall and now it’s my problem. So, after a regime change, we’ve got a new reporting structure, and either old boss goes on to new things, or i get re-assigned to new boss and things get reset across the board and i have to spend time mitigating the impacts of the change.

Because of that, i’ve actually gotten fairly OK at understanding larger corporate psychology. i’ve tried to consider how folks at each level tend to think and operate and why they may make the sorts of weird decisions they do. Re-orgs, for instance, often have less to do with fluffy corporate goals, and more with just plain workload. Your move to some tangentially related org is probably due to Current Boss being overloaded and New Boss having room. This is true up the chain, so things get all sorts of screwy at times. Bosses who have more than 6 or so direct reports have a HUGE amount of work just on dealing with having that many reports. Think of the review process alone. All bosses will find as many short cuts as possible, and frankly that’s encouraged. The “self assessment” isn’t for you, it’s for them. It’s a cheat sheet you hand them to determine why you should continue to be employed, and usually it’s cut and pasted into their review, with maybe a few additional “points to work on” to justify why they spent more of their raise budget on someone else.

This is something i’ve told peers for literally decades now. It’s why i keep a document outlining all the things i’ve done over the year, so that i have a reference when doing my “Self Review”. i forget all sorts of crap and there’s zero expectation that my boss would even remember a fraction of it.

Ah, right, the “idiot” part. i’m getting to that.

So, like i said, your boss is mostly your boss for organizational reasons, and while there’s a notation about “career growth” unless it’s something that’s fairly low bar (like signing off on a conference ticket or picking between two programming languages), they probably don’t have a lot to offer.

So why the hell was i expecting them to figure out i’m ready for a promotion?

Yeah, like i said, i am an idiot.

i was recently reminded of this fact by someone far smarter than i, when he noted that he had to put together his own doc talking about why he qualified for a change from IC3 to IC4. It was like being hit by the back hand of Captain Obvious. Of course, being introverted, talking about myself is a bit like riding porcupines bareback, so not something i willingly want to ever do, but it’s something i absolutely need to do for any form of career growth.

i sat, feeling both dumb and dumbstruck at that revelation. Mind you, i am also a HUGE advocate of stating things that seem obvious to you because there’s always someone to which it’s not. i am the lucky someone in this instance. So, yeah, make sure you do that if you don’t already. If nothing else, keep a longer list of the accomplishments you’ve done over your career at X so that when you’re ready to put together that document detailing your accomplishments, you have them at hand.

Because, yeah, i didn’t do that.

Because i’m an idiot.