Questionable Advice: The Trap of The Premature Senior

I’ve been at my current job for three years, and I am suddenly, accidentally, the most senior engineer on the team. I spend my days handling things like bootcamps, mentoring, architecture, and helping other engineers carve off meaningful work. This has taken a huge toll on the kind of work I want to do as an IC. I still enjoy writing and shipping features, and I am not a manager, but now I feel like I spend my days conducting meetings, interviewing, and unblocking others constantly instead of writing code myself.

What should I do? How can I deal with this situation in an effective manner? How can I keep from getting burned out on zoom? How can I reclaim more of my time to write code for myself, without sacrificing my influence? Should I get a new job? I have thought about going out and getting a new job, but I really like having a say at a high level. Here I get looped into all of the most important decisions and meetings. If I get a new job, how can I avoid starting over at the bottom of the heap and just taking assignments from other people? P.S., this is my first job.

 

Get a new job.

Yes, you will reset your seniority and have to earn it all over again. Yes, it will be uncomfortable and your ego will be cranky over it. Yes, you will be at the bottom of the heap and take assignments from other people for a while. Yes, you should do it anyway.

What you are experiencing now is the alluring comfort of premature seniority. You’re the smartest kid in the room, you know every corner of the system inside and out, you win every argument and anticipate every objection and you are part of every decision and you feel so deeply, pleasingly needed by the people around you.

It’s a trap.

Get the fuck out of there.

There is a world of distance between being expert in this system and being an actual expert in your chosen craft. The second is seniority; the first is merely .. familiarity

Deep down I think you know this, and feel a gnawing insecurity over your position; why else would you have emailed me? You were right. Treasure that uneasy feeling in your gut, that discomfort in the face of supreme comfortable-ness. It will lead you to a long and prosperous career as an engineer if you learn to trust it.

Think of every job like an escalator — a 50-foot high escalator that takes about two years to ride to the top. But once you’ve summited, you stall out. You can either stay and wander on that floor, or you can step to the left and pick another escalator and ride it up another 50 feet. And another.

In my mind, someone becomes a real senior engineer after they’ve done this about three times. 2-3 teams, stacks, languages, and roles, over a 5-8 year period, and then they’re solidly baked. There are insights you can derive from having seen problems solved in a few different ways that you can’t with only a single point of reference.

You don’t become a senior engineer at the 50-foot ascent, no matter how thoroughly you know the landscape. You become a senior engineer somewhere well over 100 feet, with a couple of lane changes under your belt.

The act of learning a new language and/or stack is itself an important skill. Experiencing how different orgs ship code in vastly different ways is how you internalize that there’s no one blessed path, only different sets of tradeoffs, and how you learn to reason about those tradeoffs.

And it is good for us to start over with beginner eyes. It’s humbling, it’s clarifying, it’s a cleanse for the soul. If you get too attached to feeling senior, to feeling necessary, you will undervalue the virtues of fresh eyes and questioning, of influence without authority. It is good for you to practice uncertainty and influencing others without the cheat codes of deep familiarity.

Nobody wants to work with seniors who clutch their authority with a white knuckled grip. We want to work with those who wear it lightly, who remember what it was like in our shoes.

Ultimately, this is a strong argument for building our teams behind a Rawlsian veil of ignorance concerning our own place in the pecking order. Starting fresh yourself will help you build teams where it is not miserable to be a beginner, where beginners’ contributions are recognized, where even beginners do not simply “take orders”, as you said. Because literally nobody wants that, including the beginners you are working with on  your teams today.

After you have gotten a new job or two, and proven to yourself that you can level up again and master new stacks and technologies, that fretful inner voice questioning whether you deserve the respect you receive or not will calm down. You will have proven to yourself that your success wasn’t just a one-off, that you can be dropped into any situation, learn the local ropes and succeed. You will be a senior engineer.

Get the fuck out of there. Go. <3

 

 

 

Questionable Advice: The Trap of The Premature Senior

On Call Shouldn’t Suck: A Guide For Managers

There are few engineering topics that provoke as much heated commentary as oncall. Everybody has a strong opinion. So let me say straight up that there are few if any absolutes when it comes to doing this well; context is everything. What’s appropriate for a startup may not suit a larger team. Rules are made to be broken.

That said, I do have some feelings on the matter. Especially when it comes to the compact between engineering and management. Which is simply this:

It is engineering’s responsibility to be on call and own their code. It is management’s responsibility to make sure that on call does not suck. This is a handshake, it goes both ways, and if you do not hold up your end they should quit and leave you.

As for engineers who write code for 24×7 highly available services, it is a core part of their job is to support those services in production. (There are plenty of software jobs that do not involve building highly available services, for those who are offended by this.) Tossing it off to ops after tests pass is nothing but a thinly veiled form of engineering classism, and you can’t build high-performing systems by breaking up your feedback loops this way.

Someone needs to be responsible for your services in the off-hours. This cannot be an afterthought; it should play a prominent role in your hiring, team structure, and compensation decisions from the very start. These are decisions that define who you are and what you value as a team.

Some advice on how to organize your on call efforts, in no particular order.

  • It is easier to keep yourself from falling into an operational pit of doom than it is to claw your way out of one. Make good operational hygiene a priority from the start. Value good, clean, high-level abstractions that allow you to delegate large swaths of your infrastructure and operational burden to third parties who can do it better than you — serverless, AWS, *aaS, etc. Don’t fall into the trap of disrespecting operations engineering labor, it’s the only thing that can save you.
     
  • Invest in good release and deploy tooling. Make this part of your engineering roadmap, not something you find in the couch cushions. Get code into production within minutes after merging, and watch how many of your nightmares melt away or never happen.
     
  • Invest in good instrumentation and observability. Impress upon your engineers that their job is not done when tests pass; it is not done until they have watched users using their code in production. Promote an ownership mentality over the full software life cycle. This is how dev.to did it.
     
  • Construct your feedback loops thoughtfully. Try to alert the person who made the broken change directly. Never send an alert to someone who isn’t fully equipped and empowered to fix it.
     
  • When an engineer is on call, they are not responsible for normal project work — period. That time is sacred and devoted to fixing things, building tooling, and creating guard-rails to protect people from themselves. If nothing is on fire, the engineer can take the opportunity to fix whatever has been annoying them. Allow for plenty of agency and following one’s curiosity, wherever it may lead, and it will be a special treat.
     
  • Closely track how often your team gets alerted. Take ANY out-of-hours-alert seriously, and prioritize the work to fix it. Night time pages are heart attacks, not diabetes.
     
  • Consider joining the on call rotation yourself! If nothing else, generously pinch hit and be an eager and enthusiastic backup on the regular.
     
  • Reliability work and technical debt are not secondary to product work. Budget them into your roadmap, right alongside your features and fixes. Don’t plan so tightly that you have no flex for the unexpected. Don’t be afraid to push back on product and don’t neglect to sell it to your own bosses. People’s lives are in your hands; this is what you get paid to do.
     
  • Consider making after-hours on call fully-elective. Why not? What is keeping you from it? Fix those things. This is how Intercom did it.
     
  • Depending on your stage and available resources, consider compensating for it. This doesn’t have to be cash, it could be a Friday off the week after every on call rotation. The more established and funded a company you are, the more likely you should do this in order to surface the right incentives up the org chart.
     
  • Once you’ve dug yourself out of firefighting mode, invest in SLOs (Service Level Objectives). SLOs and observability are the mature way to get out of reactive mode and plan your engineering work based on tradeoffs and user impact.
     

I believe it is thoroughly possible to construct an on call rotation that is 100% opt-in, a badge of pride and accomplishment, something that brings meaning and mastery to people’s engineering roles and ties them emotionally to their users. I believe that being on call is something that you can genuinely look forward to.

But every single company is a unique complex sociotechnical snowflake. Flipping the script on whether on call is a burden or a blessing will require a unique solution, crafted to meet your specific needs and drawing on your specific history. It will require tinkering. It will take maintenance.

Above all: ✨RAISE YOUR STANDARDS✨ for what you expect from yourselves. Your greatest enemy is how easily you accept the status quo, and then make up excuses for why it is necessarily this way. You can do better. I know you can.

There is lots and lots of prior art out there when it comes to making on call work for you, and you should research it deeply. Watch some talks, read some pieces, talk to some people. But then you’ll have to strike out on your own and try something. Cargo-culting someone else’s solution is always the wrong answer.

Any asshole can write some code; owning and tending complex systems for the long run is the hard part. How you choose to shoulder this burden will be a deep reflection of your values and who you are as a team.

And if your on call experience is mandatory and severely life-impacting, and if you don’t take this dead seriously and fix it ASAP? I hope your team will leave you, and go find a place that truly values their time and sleep.

 

On Call Shouldn’t Suck: A Guide For Managers

Things to know about engineering levels

This twitter thread seemed to strike a chord with people, rather astonishingly so. I am transcribing parts of it for the sake of longevity and findability.

I keep talking to engineers who are frustrated that they aren’t leveling up faster, aren’t reaching senior levels as quickly as other people they know, feel stuck and don’t know how to get to the next level, etc. And I’ve begun to notice a common blind spot around leveling —

✨ not every opportunity exists ✨
✨ at every company ✨
✨ at every time.✨

Sure, if you’re a junior engineer, you should be able to level up to intermediate pretty much anywhere. But it gets progressively trickier after that. Even the path from intermediate to senior can depend on a number of situational variables:

Is there oxygen?

  • How many other senior engineers do you work with? how many other intermediate engineers around your level? All of these people will be pulling from the same bin of work, looking for promo-worthy, solidly-senior projects.
  • Does your ladder explicitly call for mentorship or leading small teams of lower-leveled engineers? Are there enough of those folks to go around?
  • Have you sufficiently wrapped up your last project well enough to move on? Was it actually completed in a way that demonstrated clear mastery and readiness for bigger and harder work, or did you leave a mess behind you? That may limit people’s appetite to take a risk on you with mission-critical projects.
  • What are the biggest needs of the business right now? Any process that generates projects ought to begin with this question before proceeding on to carve out a chunk that fits your promo desires, not the other way around. 🙃
  • Do you happen to work in a niche or specialty area of engineering, particularly one crammed with super-senior, world-famous highly leveled people? This can be fantastic when it comes to your ability to soak up knowledge from the world’s best, but it may simultaneously delay your ability to level up.

In short, is there oxygen at the next level? Does the company need more of the type of engineer you want to be, vs more of the type of engineer you are now? If they need more people pounding out code and fewer architects, they’re unlikely to want to promote you to a role that involves mostly architecture..

Literally no company can possibly make use of a top-heavy eng org stuffed with senior+ engineers, if all of them are expected to demonstrate company-wide impact or global impact every review period. There’s only so much high-level work to go around for every fifty engineers writing code and features and executing on those systems.

There is only so much oxygen at each level.

Inflation.

Of course, this is all assuming that your company takes leveling seriously. Most … really … don’t.

It’s tough. It’s tough to hold your ground when a valued engineer is complaining and dropping hints they may leave if they don’t get that promotion soon. It’s much easier to give in, make an exception, argue for rounding up.

This may sound good, but it is not ultimately in your best interests as that engineer. Seriously. </3

There is sooo much title inflation in this industry already. People are given the title “senior engineer” in just 3-5 years, need I say more??

If you let a little inflation into your system by making exceptions, it causes more trouble than it’s worth. Always. The only leverage you have when people try to get you to make exceptions is if you can honestly say, “no exceptions.” Give in just once, and your moral authority evaporates.

Leveling up.

I would urge you not to make most, if any, career decisions based on levels or titles that are offered you. But I do understand how frustrating and infuriating it can be to be in a situation that is clearly unfair (usually because a manager got pressured into making an exception… tsk tsk), or if you don’t understand how to move your career forward.

So, here are a few strategic tips for leveling up.

  1. Generalists level up faster than specialists.
     
  2. When evaluating roles, choose ones where your specialty is part of their mission, or at least key to its execution. It has a far lower likelihood of getting outsourced, deprioritized, lacking investment in, or just forgotten about if what you do is core to what they do.
     
  3. Always ask to see the job ladder when interviewing. If they hedge or fumble, don’t take that job.
     
  4. Talk to your manager about the job ladder. Talk to your skip level about levels too! Managers love this shit. They can talk on and on and on about levels, long past your exhaustion point. It can be annoying, but it’s actually a sign of a good manager who cares and thinks about the edge cases in processes, and their impacts on people and teams.
     
  5. That said, don’t take the ladder as a checklist to memorize or thing to be pored over and obsessed over. It’s an incomplete attempt at both shaping and reflecting relative impact. Focus on impact.
     
  6. Is it easier to level up as a manager than as an engineer? Sorta-kinda, I guess so? There are at least two real phenomena at play here.
    1. There are simply more roles to go around in the management track. You need like, what, 1-2 E7/E8 (or principal, or architect?) level engineers per 100-500 engineers, but several managers/directors/etc
    2. Manager effectiveness is grounded in their relationships. It takes managers longer to have impact after they start a new role, but their potential impact grows and grows as their tenure gets longer. So yes, there’s a bit more of an escalator effect if you stay on the manager track at a company for several years. There is no similar escalator on the eng side; you have to be truly exceptional or truly lucky.
    3. But it really depends on the organization.

     

  7. It is much easier to level up quickly at fast-growing companies. When there is far more work than workers, and everyone is getting dropped in the deep end to sink or swim, you level up fast. Don’t underestimate what a stressful and awful experience this can be, though.
     
  8. Many engineers get stuck on the bubble getting to senior because they are impatient and want a map. They just want someone to *tell them what to do*. Which is the very opposite of what a senior engineer does. 🙃  Develop your judgment around what needs to be done, and do it.
     
  9. Your relationship with your manager matters. So does your ability to communicate about the work you are doing, its difficulty, its unexpected challenges and triumphs, etc. This is called “managing up”, and it is an actual skill which I am *terrible* at. So are most of you. 😉
     
  10. TLDR, if leveling matters to you (and it should matter to everyone, to some extent!), then look curiously and critically around for opportunities, and seek to maximize them. Want to become an E6/E7? Probably don’t join a startup that doesn’t have any very high-level work to do, or already has more than enough people functioning at those levels and many more nipping their heels looking for the same opportunity.
     
    This sort of thing is very obvious to us with the manager track (if you want to go from M->Dir, don’t join a startup that already HAS directors and managers who want to level up), but seems less obvious with engineering.

Most reasonable, non-desperate companies with options won’t hire you directly into the next level up which you haven’t done before, on either the manager or the engineer track. (Yellow flag if they do.)

But it is perfectly reasonable to express your career objectives in the interview, and make sure you’re on the same wavelength and seeing the same opportunities. Do you want to become a manager or a tech lead in a few months? Say so.

If it doesn’t exist now, do they think this opportunity may soon open up? Can they see a path forward for you there, if all goes well? Would they be interested in helping you get there? How many people may already be eyeing that same path? Is there enough opportunity for more than one? On what timeframe? Who will decide who gets the role, and how?

Engineers tend to find these conversations uncomfortable, and so they tend to avoid them because they don’t want to make the hiring manager uncomfortable by being pushy.

Relax. Managers don’t find this uncomfortable at all, it’s their bread and butter. (And even fi they do find it uncomfortable, tough beans.. it’s their job.) Ask away. ☺️

Misc notes on leveling.

P.S. Engineers seem to have a very sparse mental model of how leveling works, so here are a few more notes on how levels work at Honeycomb, which is adapted from conventions at Facebook/Google.

  • Each level after senior engineer (E5 for us) gets approx an order of magnitude harder to achieve, and an order of magnitude fewer engineers hold that title.
  • E5 is considered a “terminal level”, which sounds scary, but just means “you do not have to advance beyond this level.” If you never get promoted again, you won’t get fired either.
  • Whereas if you do not advance from E3-> E4 within 2 years, and E4->E5 within 3 years, you are automatically put on a performance improvement plan (at Facebook, I mean, not Honeycomb).
  • We (Honeycomb) hire into E5 as our highest level to start at, both because a) our interview process is not designed to let us parse differences between senior vs super-senior or super-duper senior, and b) we figure nobody is really able to come in the door with >E5 impact for the first 6 months anyway. So we can level them up quickly after they join and we get a feel for their work.

<3 charity.

Things to know about engineering levels

If Management Isn’t A Promotion, Then Engineering Isn’t A Demotion

I wrote a piece this week about what motivates people to become managers (tldr mostly org dysfunction), and Julian Dunn replied with some typically insightful tweets:

(I originally titled this article “Julian Dunn and the Case of the Bad Manager”, lol)

God, YES. This is something that has been on my queue of “topics to write about” for so long, and I haven’t because it’s just too big (and sometimes I tell myself, optimistically, it’s just too obvious?).

Julian’s point is that the reason so many bad managers persist is because it’s perceived as a promotion. Which means going back to engineering after managing is, ipso facto, a demotion. Which is really fucking hard to swallow. For anyone.

I touched on this briefly in an earlier post, the Pendulum or the Ladder, when I wrote,

“If management isn’t a promotion, then returning to hands-on work isn’t a demotion, either.  Right?”

There are a few separate points here which are worth unfurling separately.

  1. Management is widely seen as a promotion
  2. Management really does grant you some formal powers over your peers, which contributes to perceived hierarchy
  3. Humans are hierarchical mammals, exquisitely sensitive to any loss of status — we hates it
  4. But this is a cultural choice, not destiny. And we can change it.

Management is seen as a promotion

The notion that management is a promotion is deeply ingrained into our culture. It’s in language, pop culture, business books, any and all sources of career advice. If you became a manager and told your mom about it, she probably congratulated you and told you how proud she was. If you go out on a job interview, you’re expected to reach for the same rung or a higher one — or eyebrows will raise.

That’s a lot of cultural baggage to lean against. But I believe this is an idea whose time has come.

Any technical company should work hard to center and celebrate the work being done to build the product and make customers happy. Management is overhead, to be brutally frank about it, and we should not design organizations that would lead any rational, ambitious person to aspire to be overhead, should we?

The surest path to acclaim and glory (and promotions and raises) should be found through contributing. Not managing. Not being overhead.

… Because it mostly is a promotion, honestly

It is absolutely true that when you become a manager, you acquire new powers. As a tool of the org, you are granted certain powers to act on behalf of the organization, in exchange for being held accountable for certain outcomes.

These explicit powers often include hiring and firing decisions, access to privileged information, and making and meeting budgets.

But most of your powers aren’t formal at all. Most of your power comes from people listening more closely to what you say, giving your opinions more weight, and (consciously or subconsciously) just trying to please you, because they know you hold some influence over their career outcomes. It comes from the fact that so much information flows through managers. And finally, it comes from relationships — the strength of your personal relationships and mutual trust with other people throughout the org.

So how is this not a promotion? Well, it is a promotion at most companies, to be perfectly honest. But it does not have to be a promotion, if you acknowledge that these privileges and powers are accepted only by sacrificing other privileges and powers, and if you structurally allocate power to other roles. For example, you should acquire managerial powers only at the expense of technical decision-making powers.

I believe that the healthiest companies are ones where managerial powers are limited, enumerated, and minimal, with robust powers explicitly reserved for technical ICs. (much like the Constitution provides for Congress and the States, respectively.)

But it shouldn’t be. “Management” is a support role

Here are some of the reasons why we should invert the hierarchy and embrace management as a service role, a support position.

  1. Tech is a creative industry. Hierarchical leadership is a relic, a holdover from the days of manual labor. Hierarchy kills creativity, which leads to worse business outcomes.
  2. Bad managers are a huge problem in tech. Just like Julian says, the wrong people are doing the job, for the wrong reasons, because they can’t to take the hit to the ego (and paycheck) of the demotion. This leads to unhappy teams and ultimately loss of talent.
  3. I firmly believe that the engineer-manager pendulum is the way to build great technical leaders. The great line managers are never more than a few years removed from hands on work themselves, the great tech leads have always done a stint or two as a people manager. The promotion myth therefore both starves us of powerful technical leadership.and leaves us saddled with unhappy managers who have dwindling relevant skills, year after year.
  4. The ladder is a trap. There are an order of magnitude fewer jobs for each rung you ascend. Meanwhile, the higher you climb the farther removed you are from the work most find meaningful (building things, making customers happy). The perception that you are a failure if you do anything but climb higher therefore traps a great many people in a cycle of intense anxiety and unhappiness.
  5. Management is only one of many forms leadership can take. Yes, you have formal powers delegated to you on behalf of the org, but formal authority is the weakest form of power, and you should resort to using it rarely. Good leaders lead by influence and persuasion, weak leaders with “because I said so.”

Most engineers become managers to cope with org fuckery

Many people (like me!) become managers because they want access to the powers it gives them. As I argued in my last article, this is usually because they are frustrated with some organizational fuckery and it seems the only plausible way to fix or work around said fuckery is by becoming a manager.

Earlier this year I was having a 1×1 with one of our engineers, Martin Holman, who has been a manager before and had expressed interest in doing it again. So, I asked him, was he still interested?[1]

He thought for a moment, and replied, “You know, I thought I wanted to be a manager again, I really did. But I think what I actually wanted was a seat at the table — to know what was going on, to have a say in what work I do. But I don’t feel out of the loop here. So it turns out I don’t feel any need to become a manager.”

Not only did that warm my heart, it answered a question I didn’t know I had. I think they would be a good manager, and should they change their mind again in the future, I will completely support them changing their mind again (minds change! it’s what they do!) — but I hope it is never because they feel that technical contributors are left out of the loop, or don’t have a say in what they do.

That’s what I’d call organizational fuckery.

A roadmap for changing your company culture

If “management is not a promotion” is a cultural value you would like to embrace at your company, here are some concrete actions you should take.

  1. Make sure the pay bands for engineers and managers are equal, or even pay engineers more than managers of the same rank. (Slack does this, or used to.)
  2. Have IC (individual contributor) levels for engineers that track management levels, all the way up to VP.
  3. Look for ways to give high-level ICs information and opportunities for company impact that are on par with their people-manager counterparts.
  4. Technical contributors should own and be accountable for technical strategy and decision-making, not managers.
  5. Demystify management. Break it down into its constituent skills (giving feedback, running meetings, planning and budgeting, mentoring, running programs) and encourage everyone to develop those leadership skills.
  6. Offer any management roles that may open up to internal transfers before considering external candidates.
  7. Offer training and support for first-time managers who are undergoing that first career change. Offer engineers the same leadership coaching opportunities as managers.
  8. Explicitly encourage managers to swing back to IC roles after two or three years. Support them through a generous grace period while refreshing their technical skills.
  9. Watch your language. Loaded terms are everywhere, whether hierarchical (referring to people as being “above” others), or authoritarian (talking about bosses, managers). While it’s impossible to strip it from our vocabulary, it’s worth being thoughtful in how you represent reality, and using neutral phrases like “I support two teams” whenever possible.
  10. Be explicit; repeat yourself. Say over and over that management is not a promotion, it is a change of career. Say it internally and externally, in your interview processes and recruiting messages. Educate your recruiting staff too (and be stern about it).

This isn’t a thing you can do once and be done with it; it’s an ongoing effort you must commit to. Managers tend to accrue power over time, like a gravitational force. In order to counterbalance this drift, managers need to consciously push power out to others. They must use their role as “information router” to inform and empower people to own decisions, instead of hoarding it for themselves.

“Management is not a promotion” is my favorite bat signal

“Management is not a promotion, it’s a change of career.” I say this over and over again, even though it’s more aspirational than accurate.

Yet I say it anyway, because it’s a bat signal. It’s how the people I want to work with can find their way to me. And it repels the people I don’t want to work with just as efficiently.

When we recently posted our first-ever job req for an engineering manager, I included this under the list of optional skills:

  • You have worked as an engineering director or higher before, and decided to return to line management. Why? Because we value people who don’t blindly climb hierarchies just because they’re there. We value people who know themselves and what they find fulfilling in work and in life, and who can handle the hit to the ego that it takes to move “down” in pursuit of that fulfillment. Also, it would be interesting to talk about how you have solved org problems at other companies.

I cannot tell you how many amazing candidates zeroed in on that paragraph and came running. People who had been VPs before, been CTO, been director. People who were not only interested in becoming a line manager again, but were hungry to go back, to be closer to the people doing the work.

Something I heard them say again and again was, “People look at me like I’m crazy for wanting this,” “I have never had anyone see this as a strength.”

These were candidates who were acutely attuned to power dynamics, had exceptional self-knowledge, and who had seen and done so much to make organizations successful at multiple levels. What a set of superpowers!

Humans HAAAAAATE losing status.

We hate it. We hate it so bad. Even when we tell ourselves it’s what we wanted, even when we know it’s best for us, even when all the stars align. Something inside of us kicks and screams and feels excruciatingly attuned to the ripple effects of any status loss for a long time.

Like all such powerful irrational feelings, it’s evolution’s fault. Once upon a time it helped us survive and procreate. Now it’s just a nuisance, something to be worked around and minimized.

Where someone sits on the org chart should not determine that person’s ability to drive change, nor should their preference for tech problems or people problems. We need to see the work that engineers, managers, directors, VPs, and CxOs do as equally valuable and equally capable of prestige. We need to flip the org chart upside down, and treat “management” roles like the support systems they should be.

The work done by a database engineer is different from the work done by a VP marketing, or a director of database engineering. It is not inherently better or worse, easier or harder, more or less deserving of praise and admiration. It is simply different.[2]

And we will have the best chance finding the work that brings the most meaning and joy to our lives if we can drain the hierarchical residue out of our perception of these roles, by flattening pay structures, equalizing power dynamics, and making sure everyone has the tools they need to do their job with as little hierarchical bullshit as possible.

charity.

[1] Martin said I could tell this story and use his name. I actually try to avoid talking about people, conversations, or anecdotes from Honeycomb as a more or less blanket rule, because I don’t want people to be perpetually on edge wondering if I am talking about them. (So if you’re wondering if I’m talking about you: I’m not. Unless I asked first.)

[2] Raise your hand if you’ve worked at a company where a DB engineer had a far greater impact on the bottom line some quarters than any of the VPs did. ✋

If Management Isn’t A Promotion, Then Engineering Isn’t A Demotion

Questionable Advice: War Rooms? Really?!?

My company has recently begun pushing for us to build and staff out what I can only describe as “command centers”. They’re picturing graphs, dashboards…people sitting around watching their monitors all day just to find out which apps or teams are having issues. With your experience in monitoring and observability, and your opinions on teams supporting their own applications…do you think this sounds like a bad idea? What are things to watch out for, or some ways this might all go sideways?

— Anonymous

Jesus motherfucking Christ on a stick. Is it 1995 where you work? That’s the only way I can try and read this plan like it makes sense.

It’s a giant waste of money and no, it won’t work. This path leads into a death spiral where alarms are going off constantly (yet somehow never actually catching the real problems), people getting burned out, and anyone competent will either a) leave or b) refuse to be on call. Sideways enough for you yet?

Snark aside, there are two foundational flaws with this plan.

1) watching graphs is pointless. You can automate that shit, remember?  ✨skillsComputers!✨ Furthermore, this whole monitoring-based approach will only ever help you find the known unknowns, the problems you already know to look for. But most of your actual problems will be unknown unknowns, the ones you don’t know about yet.

2) those people watching the graphs… When something goes wrong, what exactly can they do about it? The answer, unfortunately, is “not much”. The only people who can swiftly diagnose and fix complex systems issues are the people who build and maintain those systems, and those people are busy building and maintaining, not watching graphs.

That extra human layer is worse than useless; it is actively harmful. By insulating developers from the consequences of their actions, you are concealing from them the information they need to understand the consequences of their actions. You are interfering with the most basic of feedback loops and causing it to malfunction.

The best time to find a bug is as soon as possible after writing it, while it’s all fresh in your head. If you let it fester for days, weeks, or months, it will be exponentially more challenging to find and solve. And the best people to find those bugs are the people who wrote them

Helpful? Hope so. Good luck. And if they implement this anyway — leave. You deserve to work for a company that won’t waste your fucking time.

with love, charity.

selfie - 4

Questionable Advice: War Rooms? Really?!?

The Official, Authorized List Of Legitimate Reasons For Deciding to Become a Manager

“Why did you decide to become a manager?”

It’s a question that gets asked a lot, in job interviews, 1x1s, and plain old casual conversation. I ask this question a lot, and I am often frustrated (or bored) by the answers I hear back.

Most of them can be bucketed in one of three ways:

  1. The pious. “I just really, really love helping other people achieve their goals.”
  2. The pleasers. the ones who answer, then pause uncertainly: “Is that what you’re looking for?”
  3. The sheepish. “I probably shouldn’t say this, but..” (followed by something very close to real honesty)

People are rarely inclined to divulge the range and depth of their reasons for going into management. And why should they? We are constantly being lectured about what the RIGHT reasons for going into management are, with aspersions cast upon anyone who dares enter the profession for any reasons that are not completely selfless.

“I LOVE mentoring.” “I wanted to protect my team.” “I’m motivated by people problems.” “I just really love helping people grow.”

Okay.

I’m not saying that everybody who says these words is lying, but I would be surprised if it was the entire story. People make career moves for a complex mix of altruism and self-interest.

It’s socially acceptable to cop to the selfless reasons. But what about the rest? Like “I wanted more money”? “I wanted career progression and couldn’t get any as an IC”? What about “I couldn’t get a seat at the table as an engineer”, “I was tired of being left out of important decisions”, or “My reporting chain was opaque and kept fucking up, and I figured I couldn’t do any worse than those bozos”?

Now we’re talking.

Most people become managers to compensate for org fuckery.

In my experience, most engineers become managers primarily due to organizational dysfunction. When you become a manager you acquire certain institutional powers, and you can use those powers to change the thing that makes you miserable.

It’s a hack. A gnarly one. And like most hacks, it kinda works.

For example, say it pisses you off to be left out of decisions. So you become a manager, and then you can either a) use your power and access to push for including engineers in the decision-making process, or at very least b) you personally will no longer left out.

In a healthy org, I would argue that most of these reasons should not exist. You should not have to become a manager to have career progression, pay equity, access to information, to be included in the decision-making process, even to set company strategy (to an extent congruent with your level, impact, role, tenure, etc)..

Everybody can’t weigh in on everything, obviously, but technical leaders are the best people to make technical decisions, not managers. In healthy orgs, managers work to push those powers outwards to the people closest to the work rather than hoarding it for themselves.

Legitimate reasons for being interested in management.

If you claw away all the org fuckery that forces so many people who care deeply about their work and coworkers into management, there is only one honest reason left for why anyone should try management.

✨Because you feel like it.✨

Because you’re curious. Because there’s an opportunity, maybe, or it seems interesting. Because why not? It’s as good a reason as any. Why do you learn a new framework, a new language, why do you write about your work, why do you pick up any new skill or new role? Why do any of it?

We are not rational beings. First comes emotional urge (“I want that”), then comes rationalization (“because, uh, I love people?”). That’s just how our brains work. You don’t really have to defend or justify it any further.

In reality …

I have observed that many people (especially early-career) are semi-obsessed with getting in to management.

There are many reasons for this. In most places, it is still regarded as a promotion, not a support role / change of career. With high achievers, all you have to do is plunk a ladder next to them to make them want to climb it. Many people feel a lack of agency and lack of autonomy in their role, and they think becoming a manager will solve all their problems.

The swiftest cure for this delusion is  … actually becoming a manager.

Management is a role where you are granted certain institutional powers, at the expense of other powers, freedoms and benefits. Many people who try management figure out pretty quickly that it’s not for them. Formal powers are, in many ways, the weakest powers of them all.

Which is why I think anybody who is interested in management should get a shot at it. Let’s demystify the role, strip it of its mystique and glamour, and make it what it should be: a role of service to others not dominance over others; staffed by people who genuinely take joy in that people side of sociotechnical problem solving.

 

charity

bed - 13 (1)

 

The Official, Authorized List Of Legitimate Reasons For Deciding to Become a Manager

Questionable Advice: Can Engineering Productivity Be Measured?

I follow you on Twitter and read your blog.  I particularly enjoy this post: https://charity.wtf/2019/05/01/friday-deploy-freezes-are-exactly-like-murdering-puppies/ I’m reaching out looking for some guidance.

I work as an engineering manager for a company whose non-technology leadership insists there has to be a way to measure the individual productivity of a software engineer. I have the opposite belief. I don’t believe you can measure the productivity of “professional” careers, or thought workers (ex: how do measure productivity of a doctor, lawyer, or chemist?).

For software engineering in particular, I feel that metrics can be gamed, don’t tell the whole story, or in some cases, are completely arbitrary. Do you measure individual developer productivity? If so, what do you measure, and why do you feel it’s valuable? If you don’t and share similar feelings as mine, how would you recommend I justify that position to non-technology leadership?

Thanks for your time.

Anonymous Engineering Manager

Dear Anon,

Once upon a time I had a job as a sysadmin, 100% remote, where all work was tracked using RT tasks. I soon realized that the owner didn’t have a lot of independent technical judgment, and his main barometer for the caliber of our contributions was the number of tasks we closed each day.

I became a ticket-closing machine. I’d snap up the quick and easy tasks within seconds. I’d pattern match and close in bulk when I found a solution for a group of tasks. I dove deep into the list of stale tickets looking for ones I could close as “did not respond” or “waiting for response”, especially once I realized there was no penalty for closing the same ticket over and over.

My boss worshiped me. I was bored as fuck. Sigh.

I guess what I’m trying to say is, I am fully in your camp. I don’t think you can measure the “productivity” of a creative professional by assigning metrics to their behaviors or process markers, and I think that attempting to derive or inflict such metrics can inflict a lot of damage.

In fact, I would say that to the extent you can reduce a job to a set of metrics, that job can be automated away. Metrics are for easy problems — discrete, self-contained, well-understood problems. The more challenging and novel a problem, the less reliable these metrics will be.

Your execs should fucking well know this: how would THEY like to be evaluated based on, like, how many emails they send in a day? Do they believe that would be good for the business? Or would they object that they are tasked with the holistic success of the org, and that their roles are too complex to reduce to a set of metrics without context?

This actually makes my blood boil. It is condescending as fuck for leadership to treat engineers like task-crunching interchangeable cogs. It reveals a deep misunderstanding of how sociotechnical systems are developed and sustained (plus authoritarian tendencies, and usually a big dollop of personal insecurity).

But what is the alternative?

In my experience, the “right” answer, i.e. the best way to run consistently high-performing teams, involves some combination of the following:

  • Outcome-based management that practices focusing on impact, plus
  • Team level health metrics, combined with
  • Engineering ladder and regular lightweight reviews, and
  • Managers who are well calibrated across the org, and encouraged to interrogate their own biases openly & with curiosity.

The right way to look at performance is at the team level. Individual engineers don’t own or maintain code; teams do. The team is the irreducible unit of ownership. So you need to incentivize people to think about work and spending their time cooperatively, optimizing for what is best for the team.

Some of the hardest and most impactful engineering work will be all but invisible on any set of individual metrics. You want people to trust that their manager will have their backs and value their contributions appropriately at review time, if they simply act in the team’s best interest. You do not want them to waste time gaming the metrics or courting personal political favor.

This is one of the reasons that managers need to be technical — so they can cultivate their own independent judgment, instead of basing reviews on hearsay. Because some resources (i.e. your budget for individual bonuses) are unfortunately zero-sum, and you are always going to rely on the good judgment of your engineering leaders when it comes to evaluating the relative impact of individual contributions.

This also is why it’s important for leaders to model the act of openly exploring whether they might be biased in some way:

“I would say that Joe’s contribution this quarter had greater impact than Jane’s. But is that really true? Jane did a LOT of mentoring and other “glue” work, which tends to be under-acknowledged as leadership work, so I just want to make sure I am evaluating this fairly … Does anyone else have a perspective on this? What might I be missing?” — a manager keeping themselves honest in calibrations

I do think every team should be tracking the 4 DORA metrics — time elapsed between merge and deploy, frequency of deploy, time to recover from outages, duration of outages — as well as how often someone is paged outside of business hours. These track pretty closely to engineering productivity and efficiency.

But leadership should do its best to be outcome oriented. The harder the problem, the more senior the contributor, the less business anyone has dictating the details of how or why. Make your agreements, then focus on impact.

This is harder on managers, for sure — it’s easier to count the hours someone spends at their desk or how many lines of code they commit than to develop a nuanced understanding of the quality and timbre of an engineer’s contributions to the product, team and the company over time. It is easier to micromanage the details than to negotiate a mutual understanding of what actually matters, commit to doing your part … and then step away, trusting them to fill in the gaps.

But we should expect this; it’s worth it. It is in those gaps where we feel trusted to act that we find joy and autonomy in our labor, where we do our best work as skilled artisans.

p.s. someone just shared this link with me, OF COURSE martin fowler has already said this 

Questionable Advice: Can Engineering Productivity Be Measured?

Trolley Problems as a Service

Consider:

  • Is it ethical to discriminate in whom you will sell to as a business?  What would you do if you found out that the work you do every day was being used to target and kill migrants at the border? 
  • Is it ethical or defensible to pay two people doing the same job different salaries if they live in different locations and have a different cost of living?  What if paying everyone the same rate means you are outcompeted by those who peg salaries to local rates, because they can vastly out-hire you?
  • You’re at the crowded hotel bar after a company-sponsored event, and one of your most valued customers begins loudly venting opinions about minorities in tech that you find alarming and abhorrent.  What responsibility do you have, if any?  How should you react?
  • If we were close to running out of money in the hypothetical future, should we do layoffs or offer pay cuts?

It’s not getting any simpler to live in this world, is it?  💔

Ethical problems are hard.  Even the ones that seem straightforward on the face of them get stickier the closer you look at them.  There are more stakeholders, more caveats, more cautionary tales, more unintended consequences than you can generally see at face value. It’s like fractal hardness, and anyone who thinks it’s easy is fooling themselves.

We’ve been running an experiment at Honeycomb for the past 6 months, where we talk through hypothetical ethical questions like these once a month. Sometimes they are ripped from the headlines, sometimes they are whatever I can invent the night before. I try to send them around in advance. The entire company is invited.**

Honeycomb is not a democracy, nor do I think that would be an effective way to run a company, any more than I think we should design our SDKs by committee or give everyone an equal vote on design mocks.

But I do think that we have a responsibility to act in the best interests of our stakeholders, to the best of our abilities, and to represent our employees. And that means we need to know where the team stands.

That’s one reason. Another is that people make the worst possible decisions when they’re taken off guard, when they are in an unfamiliar situation (and often panicking). Talking through a bunch of nightmare scenarios is a way for us to exercise these decision-making muscles while the stakes are low. We all get to experience what it’s like to hear a problem, have a kneejerk reaction .. then peeling back the onion to reveal layer after layer of dismaying complexities that muddy our snap certainties.

Honeycomb is a pretty transparent company; we believe that companies are created every day by the people who show up to labor together, so those people have a right to know most things. But it’s not always possible or ethically desirable to share all the gritty details that factor into a decision. My hope is that these practice runs help amplify employees’ voices, help them understand the way we approach big decisions, and help everyone make better decisions — and trust each other’s decisions — when things move fast and times get hard.

(Plus, these ethical puzzles are astonishingly fun to work through together. I highly recommend you borrow this idea and try it out at your own company.)

cheers, and please let me know if you do try it ☺️

charity

** We used to limit attendance to the first 6 people to show up, to try and keep the discussion more authentic and less performative. We recently relaxed this rule since it doesn’t seem to matter, peacocking hasn’t really been an issue.

Trolley Problems as a Service

Good Days, Bad Days, Impossible Days

Last night I was talking with Mark Ferlatte about the advice we have given our respective companies in this pandemic era.  He shared with me this link, on how to salvage a disastrous day.  It’s a good link: you should read it.

My favorite part: “Your feelings will follow your actions.  Just do it.”

The hardest part for me is, “Book-end your day.  Don’t push it into the midnight hours.”  Ugh.  I really, really struggle with this because my brain takes a long long time to settle in and get started on a task to the point where I feel like I’m on a roll with it, and once I’m on a roll I do not want to stop until I’m done.  Because god knows how long it will be — days? weeks?? — until I can catch this wave again, feel inspired again.  But it’s true, if I stay up all night working I’m just setting myself up for a fuzzy, blundery tomorrow.

The advice we gave Honeycombers was differently shaped, though similar in spirit.  I’ve had a few people ask me to share it, so here it is.

We formally request …

First, we would like to point out that what you are all being asked to do right now is impossible.  Parenting, homeschooling, working, caregiving, correcting misinformed neighbors, being an engaged citizen … it is fifteen people’s worth of work.  It is literally impossible.

But hey, it has always been impossible.  We have never been able to do everything we want to do — there isn’t enough time.  There was never enough time!  We succeed as a company not by doing everything on our list, but by saying no to the right things; by NOT-doing enough most things so we can focus on the few things we have identified that matter most.  That was true before COVID, it’s just truer now.

So: let’s all focus hard on our top priority.  Shed as much of the other stuff as you have to.  Shed more.  Ask your manager for help figuring out what to shed, until you are down to an amount you can probably manage.

And speaking of focus:

You aren’t operating at full capacity.  We all get that right now: none of us are.  And nobody expects you to.  So please spend zero energy on performing like you’re doing work, or acting extra-responsive, or keeping up a front like things are normal and you’re doing fine.  That performance costs you precious energy,  while doing nothing to get us closer to our goals.

What we need from you is not performance or busy-busy-ness but your engaged creative self  — your active, curious mind engaging with our top problem.  I would rather have 30 minutes of your creative energy applied to our biggest problem today than five hours of your distracted split-brain, juggling, trying to keep up with chat and seem like you’re as available per usual today.

So when you’re figuring out your schedule, please optimize for that — focused time on our biggest problem — and then communicate your availability to your team.  If you’re a parent and you can only really work three days a week, calendar that.  (If you’re not a parent, remember that you too are allowed to feel overwhelmed and underwater.  Just because some have it even harder, doesn’t invalidate what you’re going through.)

In Summary,

Take care of yourself
Take care of your loved ones
Say no to as much as you possibly can
Focus on impact
No performative normalcy
Remember: this is temporary 🖤

We are incredibly fortunate — to be here, to have these resources, to have each other.  It’s okay to have bad days; this is why we have teams, to carry each other through the hardest spots.  Do your best.  Everything is going to be okay, more or less.

 

Good Days, Bad Days, Impossible Days

Questionable Advice #2: How Do I Get My Team Into Observability?

Welcome to the second installment of my advice column! Last time we talked about the emotional impact of going back to engineering after a stint in management. If you have a question you’d like to ask, please email me or DM it to me on twitter.

Hi Charity! I hope it’s ok to just ask you this… 

I’m trying to get our company more aware of observability and I’m finding it difficult to convince people to look more into it. We currently don’t have the kind of systems that would require it much – but we will in future and I want us to be ahead of the game. 

If you have any tips about how to explain this to developers (who are aware that quality is important but don’t always advocate for it / do it as much as I’d prefer), or have concrete examples of “here’s a situation that we needed observability to solve – and here’s how we solved it”, I’d be super grateful. 

If this is too much to ask, let me know too 🙂 

I’ve been talking to Abby Bangser a lot recently – and I’m “classifying” observability as “exploring in production” in my mental map – if you have philosophical thoughts on that, I’d also love to hear them 🙂

alex_schl

Dear Alex,

Everyone’s systems are broken. Not just yours!

Yay, what a GREAT note!  I feel like I get asked some subset or variation of these questions several times a week, and I am delighted for the opportunity to both write up a response for you and post it for others to read.  I bet there are orders of magnitude more people out there with the same questions who *don’t* ask, so I really appreciate those who do. <3

I want to talk about the nuts and bolts of pitching to engineering teams and shepherding technical decisions like this, and I promise I will offer you some links to examples and other materials. But first I want to examine some of the assumptions in your note, because they elegantly illuminate a couple of common myths and misconceptions.

Myth #1: you don’t need observability til you have problems of scale

First of all, there’s this misconception that observability is something you only need when you have really super duper hard problems, or that it’s only justified when you have microservices and large distributed systems or crazy scaling problems.  No, no no nononono. 

There may come a point where you are ABSOLUTELY FUCKED if you don’t have observability, but it is ALWAYS better to develop with it.  It is never not better to be able to see what the fuck you are doing!  The image in my head is of a hiker with one of those little headlamps on that lets them see where they’re putting their feet down.  Most teams are out there shipping opaque, poorly understood code blindly — shipping it out to systems which are themselves crap snowballs of opaque, poorly understood code. This is costly, dangerous, and extremely wasteful of engineering time.

Observability is like a headlamp for your code.

Ever seen an engineering team of 200, and struggled to understand how the product could possibly need more than one or two teams of engineers? They’re all fighting with the crap snowball.

Developing software with observability is better at ANY scale.  It’s better for monoliths, it’s better for tiny one-person teams, it’s better for pre-production services, it’s better for literally everyone always.  The sooner and earlier you adopt it, the more compounding value you will reap over time, and the more of your engineers’ time will be devoted to forward progress and creating value.

Myth #2: observability is harder and more technically advanced than monitoring

Actually, it’s the opposite — it’s much easier.  If you sat a new grad down and asked them to instrument their code and debug a small problem, it would be fairly straightforward with observability. Observability speaks the native language of variables, functions and API endpoints, the mental model maps cleanly to the request path, and you can straightforwardly ask any question you can come up with. (A key tenet of observability is that it gives an engineer the ability to ask any question, without having had to anticipate it in advance.)

With metrics and logging libraries, on the other hand, it’s far more complicated.you have to make a bunch of awkward decisions about where to emit various types of statistics, and it is terrifyingly easy to make poor choices (with terminal performance implications for your code and/or the remote data source).  When asking questions, you are locked in to asking only the questions that you chose to ask a long time ago. You spend a lot of time translating the relationships between code and lowlevel systems resources, and since you can’t break down by users/apps you are blocked from asking the most straightforward and useful questions entirely!  

Doing it the old way Is. Fucking. Hard.  Doing it the newer way is actually much easier, save for the fact that it is, well, newer — and thus harder to google examples for copy-pasta. But if you’re saturated in decades of old school ops tooling, you may have some unlearning to do before observability seems obvious to you.

Myth #3: observability is a purely technical solution

To be clear, you can just add an observability tool to your stack and go on about your business — same old things, same old way, but now with high cardinality!

You can, but you shouldn’t.  

These are sociotechnical systems and they are best improved with sociotechnical solutions.  Tools are an absolutely necessary and inextricable part of it.  But so are on call rotations and the fundamental virtuous feedback loop of you build it, you run it.  So are code reviews, monitoring checks, alerts, escalations, and a blameless culture.  So are managers who allocate enough time away from the product roadmap to truly fix deep technical rifts and explosions, even when it’s inconvenient, so the engineers aren’t in constant monkeypatch mode.

I believe that observability is a prerequisite for any major effort to have saner systems, simply because it’s so powerful being able to see the impact of what you’ve done.  In the hands of a creative, dedicated team, simply wearing a headlamp can be transformational.

Observability is your five senses for production.

You’re right on the money when you ask if it’s about exploring production, but you could also use words that are even more basic, like “understanding” or “inspecting”.  Observability is to software systems as a debugger is to software code.  It shines a light on the black box.  It allows you to move much faster, with more confidence, and catch bugs much sooner in the lifecycle — before users have even noticed.  It rewards you for writing code that is easy to illuminate and understand in production.

So why isn’t everyone already doing it?  Well, making the leap isn’t frictionless.  There’s a minimal amount of instrumentation to learn (easier than people expect, but it’s nonzero) and then you need to learn to see your code through the lens of your own instrumentation.  You might need to refactor your use of older tools, such as metrics libraries, monitoring checks and log lines.  You’ll need to learn another query interface and how it behaves on your systems.  You might find yourself amending your code review and deploy processes a bit.  

Nothing too terrible, but it’s all new.  We hate changing our tool kits until absolutely fucking necessary.  Back at Parse/Facebook, I actually clung to my sed/awk/shell wizardry until I was professionally shamed into learning new ways when others began debugging shit faster than I could.  (I was used to being the debugger of last resort, so this really pissed me off.)  So I super get it!  So let’s talk about how to get your team aligned and hungry for change.

Okay okay okay already, how do I get my team on board?

If we were on the phone right now, I would be peppering you with a bunch of questions about your organization.  Who owns production?  Who is on call?  Who runs the software that devs write?  What is your deploy process, and how often does it get updated, and by who?  Does it have an owner?  What are the personalities of your senior folks, who made the decisions to invest in the current tools (and what are they), what motivates them, who are your most persuasive internal voices?  Etc.  Every team is different.  <3

There’s a virtuous feedback loop you need to hook up and kickstart and tweak here, where the people with the original intent in their heads (software engineers) are also informed and motivated, i.e. empowered to make the changes and personally impacted when things are broken. I recommend starting by putting your software engineers on call for production (if you haven’t).  This has a way of convincing even the toughest cases that they have a strong personal interest in quality and understandability. 

Pay attention to your feedback loop and the alignment of incentives, and make sure your teams are given enough time to actually fix the broken things, and motivation usually isn’t a problem.  (If it is, then perhaps another feedback loop is lacking: your engineers feeling sufficiently aligned with your users and their pain.  But that’s another post.)

Technical ownership over technical outcomes

I appreciate that you want your team to own the technical decisions.  I believe very strongly that this is the right way to go.  But it doesn’t mean you can’t have influence or impact, and particularly in times like this. 

It is literally your job to have your head up, scanning the horizon for opportunities and relevant threats.  It’s their job to be heads down, focusing on creating and delivering excellent work.  So it is absolutely appropriate for you to flag something like observability as both an opportunity and a potential threat, if ignored.

If I were in your situation and wanted my team to check out some technical concept, I might send around a great talk or two and ask folks to watch it, and then maybe schedule a lunchtime discussion.  Or I might invite a tech luminary in to talk with the team, give a presentation and answer their questions.  Or schedule a hack week to apply the concept to a current top problem, or something else of that nature.

But if I really wanted them to take it fucking seriously, I would put my thumb on the scale.  I would find myself a champion, load them up with context, and give them ample time and space to skill up, prototype, and eventually present to the team a set of recommendations.  (And I would stay in close contact with them throughout that period, to make sure they didn’t veer too far off course or lose sight of my goals.)

  1. Get a champion.

    Ideally you want to turn the person who is most invested in the old way of doing things — the person who owns the ELK cluster, say, or who was responsible for selecting the previous monitoring toolkit, or the goto person for ops questions — from your greatest obstacle into your proxy warrior.  This only works if you know that person is open-minded and secure enough to give it a fair shot & publicly change course, has sufficiently good technical judgment to evaluate and project into the future, and has the necessary clout with their peers.  If they don’t, or if they’re too afraid to buck consensus: pick someone else.

  2. Give them context.  

    Take them for a long walk.  Pour your heart and soul out to them.  Tell them what you’ve learned, what you’ve heard, what you hope it can do for you, what you fear will happen if you don’t.  It’s okay to get personal and to admit your uncertainties.  The more context they have, the better the chance they will come out with an outcome you are happy with.  Get them worried about the same things that worry you, get them excited about the same possibilities that excite you.  Give them a sense of the stakes. 

    And don’t forget to tell them why you are picking them — because they are listened to by their peers, because they are already expert in the problem area, because you trust their technical judgment and their ability to evaluate new things — all the reasons for picking them will translate well into the best kind of flattery — the true kind.  

  3. Give them a deadline.

    A week or two should be plenty.  Most likely, the decision is not going to be unilaterally theirs (this also gives you a bit of wiggle room should they come back going “ah no ELK is great forever and ever”), but their recommendations should carry serious weight with the team and technical leadership.  Make it clear what sort of outcome you would be very pleased with (e.g. a trial period for a new service) and what reasons you would find compelling for declining to pursue the project (i.e. your tech is unsupported, cost prohibitive, etc).  Ideally they should use this time to get real production data into the services they are testing out, so they can actually experience and weigh the benefits, not just read the marketing copy.

As a rule of thumb, I always assume that managers can’t convince engineers to do things: only other engineers can.  But what you can do instead is set up an engineer to be your champion.  And then just sit quietly in the corner, nodding, with an interested look on your face.

The nuclear option

if you <3 prod,
prod will <3 you back

You have one final option.  If there is no appropriate champion to be found, or insufficient time, or if you have sufficient trust with the team that you judge it the right thing to do: you can simply order them to do something your way.  This can feel squicky. It’s not a good habit to get into.  It usually results in things being done a bit slower, more reluctantly, more half-assedly. And you sacrifice some of your power every time you lean on your authority to get your team to do something.

But it’s just as bad for a leader to take it off the table entirely.

Sometimes you will see things they can’t.  If you cannot wield your power when circumstances call for it, then you don’t fucking have real power — you have unilaterally disarmed yourself, to the detriment of your org.  You can get away with this maybe twice a year, tops. 

But here’s the thing: if you order something to be done, and it turns out in the end that you were right?  You earn back all the power you expended on it plus interest.  If you were right, unquestionably right in the eyes of the team, they will respect you more for having laid down the law and made sure they did the right thing.

xo

charity

Some useful resources:

Questionable Advice #2: How Do I Get My Team Into Observability?