Outsource Your O11y: Get Aligned With Security (part 2/3)

February 13, 2019February 13, 2019 mipsytipsyaws, engineers, monitoring, operations, outsourcing, security, sre, vendors1 Comment

This is part two of a three-part series of guest posts:

How To Be A Champion, on how to choose a third-party vendor and champion them successfully to your security team. (George Chamales)
Get Aligned With Security, how to work with your security team to find the best possible outcome for all sides (Lilly Ryan)
Now Roll It Out And Keep Them Happy, on how to operationalize your service by rolling out the integration and maintaining it — and the relationship with your security team — over the long run (Andy Isaacson)

All this pain will someday be worth it. 🙏❤️ charity + friends

“Get Aligned With Security”

by Lilly Ryan

If your team has decided on a third-party service to help you gather data and debug product issues, how do you convince an often overeager internal security team to help you adopt it?

When this service is something that provides a pathway for developers to access production data, as analytics tools often do, making the case for access to that data can screech to a halt at the mention of the word “production”. Progressing past that point will take time, empathy, and consideration.

I have been on both sides of the “adopting a new service” fence: as a developer hoping to introduce something new and useful to our stack, and now as a security professional who spends her days trying to bust holes in other people’s setups. I understand both sides of the sometimes-conflicting needs to both ship software and to keep systems safe.

This guide has advice to help you solve the immediate problem of choosing and deploying a third-party service with the approval of your security team. But it also has advice for how to strengthen the working relationship between your security and development teams over the longer term. No two companies are the same, so please adapt these ideas to fit your circumstances.

Understanding the security mindset

The biggest problems in technology are never really about technology, but about people. Seeing your security team as people and understanding where they are coming from will help you to establish empathy with them so that both of you want to help each other get what you want, not block each other.

First, understand where your security team is coming from. Development teams need to build features, improve the product, understand and ship good code. Security teams need to make sure you don’t end up on the cover of the NYT for data breaches, that your business isn’t halted by ransomware, and that you’re not building your product on a vulnerable stack.

This can be an unfamiliar frame of mind for developers. Software development tends to attract positive-minded people who love creating things and are excited about the possibilities of new technology. Software security tends to attract negative thinkers who are skilled at finding all the flaws in a system. These are very different mentalities, and the people who occupy them tend to have very different assumptions, vocabularies, and worldviews.

But if you and your security team can’t share the same worldview, it will be hard to trust each other and come to agreement. This is where practicing empathy can be helpful.

Before approaching your security team with your request to approve a new vendor, you may want to run some practice exercises for putting yourselves in their shoes and forcing yourselves to deliberately cultivate a negative thinking mindset to experience how they may react — not just in terms of the objective risk to the business, or the compliance headaches it might cause, but also what arguments might resonate with them and what emotional reactions they might have.

My favourite exercise for getting teams to think negatively is what I call the Land Astronaut approach.

The “Land Astronaut” Game

Imagine you are an astronaut on the International Space Station. Literally everything you do in space has death as a highly possible outcome. So astronauts spend a lot of time analysing, re-enacting, and optimizing their reactions to events, until it becomes muscle memory. By expecting and training for failure, astronauts use negative thinking to anticipate and mitigate flaws before they happen. It makes their chances of survival greater and their people ready for any crisis.

Your project may not be as high-stakes as a space mission, and your feet will most likely remain on the ground for the duration of your work, but you can bet your security team is regularly indulging in worst-case astronaut-type thinking. You and your team should try it, too.

The Game:

Pick a service for you and your team to game out. Schedule an hour, book a room with a whiteboard, put on your Land Astronaut helmets. Then tell your team to spend half an hour brainstorming about all the terrible things that can happen to that service, or to the rest of your stack when that service is introduced. Negative thoughts only!

Start brainstorming together. Start out by being as outlandish as possible (what happens if their data centre is suddenly overrun by a stampede of elephants?). Eventually you will find that you’ll tire of the extreme worst case scenarios and come to consider more realistic outcomes — some of which which you may not have thought of outside of the structure of the activity.

After half an hour, or whenever you feel like you’re all done brainstorming, take off your Land Astronaut helmets, sift out the most plausible of the worst case scenarios, and try to come up with answers or strategies that will help you counteract them. Which risks are plausible enough that you should mitigate them? Which are you prepared to gamble on never happening? How will this risk calculus change as your company grows and takes on more exposure?

Doing this with your team will allow you all to practice the negative thinking mindset together and get a feel for how your colleagues in the security team might approach this request. (While this may seem similar to threat modelling exercises you might have done in the past, the focus here is on learning to adopt a security mindset and gaining empathy for this thought process, rather than running through a technical checklist of common areas of concern.)

While you still have your helmets within reach, use your negative thinking mindset to fill out the spreadsheet from the first piece in this series. This will help you anticipate most of the reasonable objections security might raise, and may help you include useful detail the security team might not have known to ask for.

Once you have prepared your list of answers to George’s worksheet and held a team Land Astronaut session together, you will have come most of the way to getting on board with the way your security team thinks.

Preparing for compromise

You’ve considered your options carefully, you’ve learned how to harness negative thinking to your advantage, and you’re ready to talk to your colleagues in security – but sometimes, even with all of these tools at your disposal, you may not walk away with all of the things you are hoping for.

Being willing to compromise and anticipating some of those compromises before you approach the security team will help you negotiate more successfully.

While your Land Astronaut helmets are still within reach, consider using your negative thinking mindset game to identify areas where you may be asked to compromise. If you’re asking for production access to this new service for observability and debugging purposes, think about what kinds of objections may be raised about this and how you might counter them or accommodate them. Consider continuing the activity with half of the team remaining in the Land Astronaut role while the other half advocates from a positive thinking standpoint. This dynamic will get you having conversations about compromise early on, so that when the security team inevitably raises eyebrows, you are ready with answers.

Be prepared to consider compromises you had not anticipated, and enter into discussions with the security team with as open a mind as possible. Remember the team is balancing priorities of not only your team, but other business and development teams as well. If you and your security colleagues are doing the hard work to meet each other halfway then you are more likely to arrive at a solution that satisfies both parties.

Working together for the long term

While the previous strategies we’ve covered focus on short-term outcomes, in this continuous-deployment, shift-left world we now live in, the best way to convince your security team of the benefits of a third-party service – or any other decision – is to have them along from day one, as part of the team.

Roles and teams are increasingly fluid and boundary-crossing, yet security remains one of the roles least likely to be considered for inclusion on a software development team. Even in 2019, the task of ensuring that your product and stack are secure and well-defended is often left until the end of the development cycle. This contributes a great deal to the combative atmosphere that is common.

Bringing security people into the development process much earlier builds rapport and prevents these adversarial, territorial dynamics. Consider working together to build Disaster Recovery plans and coordinating for shared production ownership.

If your organisation isn’t ready for that kind of structural shift, there are other ways to work together more closely with your security colleagues.

Try having members of your team spend a week or two embedded with the security team. You may even consider a rolling exchange – a developer for a security team member – so that developers build the security mindset, and the security team is able to understand the problems your team is facing (and why you are looking at introducing this new service).

At the very least, you should make regular time to meet with the security team, get to know them as people, and avoid springing things on them late in the project when change is hardest.

Riding off together into the sunset…?

If you’ve taken the time to get to know your security team and how they think, you’ll hopefully be able to get what you want from them – or perhaps you’ll understand why their objections were valid, and come up with a better solution that works well for both of you.

Investing in a strong relationship between your development and security teams will rarely lead to the apocalypse. Instead, you’ll end up with a better product, probably some new work friends, and maybe an exciting idea for a boundary-crossing new career in tech.

But this story isn’t over! Once you get the green light from security, you’ll need to think about how to roll your new service out safely, maintain it, and consider its full lifespan within your company. Which leads us to part three of this series, on rolling it out and maintaining it … both your integration and your relationship with the security team.

Lilly Ryan is a pen tester, Python wrangler, and recovering historian from Melbourne. She writes and speaks internationally about ethical software, social identities after death, teamwork, and the telegraph. More recently she has researched the domestic use of arsenic in Victorian England, attempted urban camouflage, reverse engineered APIs, wielded the Oxford comma, and baked a really good lemon shortbread.

Engineering Management: The Pendulum Or The Ladder

January 4, 2019October 18, 2022 mipsytipsyculture, engineering leadership, engineering management, engineers, influence, management, software engineering, tech culture62 Comments

Last night I was out with a dear friend who has been an engineering manager for a year now, and by two drinks in I was rattling off a long list things I always say to newer engineering managers.

Then I remembered: I should write a post! It’s one of my goals this year to write more long form instead of just twittering off into the abyss.

There’s a piece I wrote two years ago, The Engineer/Manager Pendulum, which is probably my all time favorite. It was a love letter to a friend who I desperately wanted to see go back to engineering, for his own happiness and mental health. Well, this piece is a sequel to that one.

It’s primarily aimed at new managers, who aren’t sure what their career options look like or how to evaluate the opportunities that come their way, or how it may expand or shrink their future opportunities.

The first fork in the manager’s path

Every manager reaches a point where they need to choose: do they want to manage engineers (a “line manager”), or do they want to try to climb the org chart? — manage managers, managers of other managers, even other divisions; while being “promoted” from manager to senior manager, director to senior director, all the way up to VP and so forth. Almost everyone’s instinct is to say “climb the org chart”, but we’ll talk about why you should be critical of this instinct.

They also face a closely related question: how technical do they wish to stay, and how badly do they care?

Are you an “engineering MANAGER” or an “ENGINEERING manager”?

These are not unlike the decisions every engineer ends up making about whether to go deep or go broad, whether to specialize or be a generalist. The problem is that both engineers and managers often make these career choices with very little information — or even awareness that they are doing it.

And managers in particular then have a tendency to look up ten years later and realize that those choices, witting or unwitting, have made them a) less employable and b) deeply unhappy.

Lots of people have the mindset that once they become an engineering manager, they should just go from gig to gig as an engineering manager who manages other engineers: that’s who they are now. But this is actually a very fragile place to sit long-term, as we’ll discuss further on in this piece.

But let’s start at to the beginning, so I can speak to those of you who are considering management for the very first time.

“So you want to try engineering management.”

COOL! I think lots of senior engineers should try management, maybe even most senior engineers. It’s so good for you, it makes you better at your job. (If you aren’t a senior engineer, and by that I mean at least 7+ years of engineering experience, be very wary; know this isn’t usually in your best interest.)

Hopefully you have already gathered that management is a career change, not a promotion, and you’re aware that nobody is very good at it when they first start.

That’s okay! It takes a solid year or two to find new rhythms and reward mechanisms before you can even begin to find your own voice or trust your judgment. Management problems look easy, deceptively so. Reasons this is hard include:

Most tech companies are absolutely abysmal at providing any sort of training or structure to help you learn the ropes and find your feet.
Even if they do, you still have to own your own career development. If learning to be a good engineer was sort of like getting your bachelor’s, learning to be a good manager is like getting your PhD — much more custom to who you are.
It will exhaust you mentally and emotionally in the weirdest ways for much longer than you think it should. You’ll be tired a lot, and you’ll miss feeling like you’re good at something (anything).

This is because you need to change your habits and practices, which in turn will actually change who you are. This takes time. Which is why …

The minimum tour of duty as a new manager is two years.

If you really want to try being a manager, and the opportunity presents itself, do it! But only if you are prepared to fully commit to a two year long experiment.

Commit to it like a proper career change. Seek out new peers, find new heroes. Bring fresh eyes and a beginner’s mindset. Ask lots of questions. Re-examine every one of your patterns and habits and priorities: do they still serve you? your team?

Don’t even bother thinking about in terms of whether you “enjoy managing” for a while, or trying to figure out if you are are any good at it. Of course you aren’t any good at it yet. And even if you are, you don’t know how to recognize when you’ve succeeded at something, and you haven’t yet connected your brain’s reward systems to your successes. A long stretch of time without satisfying brain drugs is just the price of admission if you want to earn these experiences, sadly.

It takes more than one year to learn management skills and wire up your brain to like it. If you are waffling over the two year commitment, maybe now is not the time. Switching managers too frequently is disruptive to the team, and it’s not fair to make them report to someone who would rather be doing something else or isn’t trying their ass off.

It takes about 3-5 years for your skills to deteriorate.

So you’ve been managing a team for a couple years, and it’s starting to feel … comfortable? Hey, you’re pretty good at this! Yay!

With a couple of years under your belt as a line manager, you now have TWO powerful skill sets. You can build things, AND you can organize people into teams to build even bigger things. Right now, both sets are sharp. You could return to engineering pretty easily, or keep on as a manager — your choice.

But this state of grace doesn’t last very long. Your technical skills stop advancing when you become a manager, and instead begin eroding. Two years in, you aren’t the effective tech lead you once were; your information is out of date and full of gaps, the hard parts are led by other people these days.

More critically, your patterns of mind and habits shift over time, and become those of a manager, not an engineer. Consider how excited an engineer becomes at the prospect of a justifiable greenfield project; now compare to her manager’s glum reaction as she instinctively winces at having to plan for something so reprehensibly unpredictable and difficult to estimate. It takes time to rewire yourself back.

If you like engineering management, your tendency is to go “cool, now I’m a manager”, and move from job to job as an engineering manager, managing team after team of engineers. But this is a trap. It is not a sound long term plan. It leads too many people off to a place they never wanted to end up: technically sidelined.

Why can’t I just make a career out of being a combo tech lead+line manager?

One of the most common paths to management is this: you’re a tech lead, you’re directing ever larger chunks of technical work, doing 1x1s and picking up some of the people stuff, when your boss asks if you’d like to manage the team. “Sure!”, you say, and voila — you are an engineering manager with deep domain expertise.

But if you are doing your job, you begin the process of divesting yourself of technical leadership responsibilities starting immediately. Your own technical development should screech to a halt once you become a manager, because you have a whole new career to focus on learning.

Your job is to leverage that technical expertise to grow your engineers into great senior engineers and tech leads themselves. Your job is not to hog the glory and squat on the hard problems yourself, it’s to empower and challenge and guide your team. Don’t suck up all the oxygen: you’ll stunt the growth of your team.

But your technical knowledge gets dated, and your skills atrophy.. The longer it’s been since you worked as an engineer, the harder it will be to switch back. It gets real hard around three years, and five years seems like a tipping point.[1]

And because so much of your credibility and effectiveness as an engineering leader comes from your expertise in the technology that your team uses every day, ultimately you will be no longer capable of technical leadership, only people management.

On being an “engineering manager” who only does people management

I mean, there’s a reason we don’t lure good people managers away from Starbucks to run engineering teams. It’s the intersection and juxtaposition of skill sets that gives engineering managers such outsize impact.

The great ones can make a large team thrum with energy. The great ones can break down a massive project into projects that challenge (but do not overwhelm) a dozen or more engineers, from new grads to grizzled veterans, pushing everyone to grow. The great ones can look ahead and guess which rocks you are going to die on if you don’t work to avoid them right now.

The great ones are a treasure: and they are rare. And in order to stay great, they regularly need to go back to the well to refresh their own hands-on technical abilities.

There is an enormous demand for technical engineering leaders — far more demand than supply. The most common hackaround is to pair a people manager (who can speak the language and knows the concepts, but stopped engineering ages ago) with a tech lead, and make them collaborate to co-lead the team. This unwieldy setup often works pretty well.

But most of those people managers didn’t want or expect to end up sidelined in this way when they were told to stop engineering.

If you want to be a pure people manager and not do engineering work, and don’t want to climb the ladder or can’t find a ladder to climb, more power to you. I don’t know that I’ve met many of these people in my life. I have met a lot of people in this situation by accident, and they are always kinda angsty and unhappy about it. Don’t let yourself become this person by accident. Please.

Which brings me to my next point.

You will be advised to stop writing code or engineering.

✨

Fuck

That.

✨

Everybody’s favorite hobby is hassling new managers about whether or not they’ve stopped writing code yet, and not letting up until they say that they have. This is a terrible, horrible, no-good VERY bad idea that seems like it must originally have been a botched repeating of the correct advice, which is:

Stop writing code and engineering

in the critical path

Can you spot the difference? It’s very subtle. Let’s run a quick test:

Authoring a feature? ⛔️
Covering on-call when someone needs a break? ✅
Diving on the biggest project after a post mortem? ⛔️
Code reviews? ✅
Picking up a p2 bug that’s annoying but never seems to become top priority? ✅
Insisting that all commits be gated on their approval? ⛔️
Cleaning up the monitoring checks and writing a library to generate coverage? ✅

The more you can keep your hands warm, the more effective you will be as a coach and a leader. You’ll have a richer instinct for what people need and want from you and each other, which will help you keep a light touch. You will write better reviews and resolve technical disputes with more authority. You will also slow the erosion and geriatric creep of your own technical chops.

I firmly believe every line manager should either be in the on call rotation or pinch hit liberally and regularly, but that’s a different post.

Technical Leadership track

If you love technology and want to remain a subject-matter expert in designing, building and shipping cutting-edge technical products and systems, you cannot afford to let yourself drift too far or too long away from hands-on engineering work. You need to consciously cultivate your path , probably by practicing some form of the engineer/manager pendulum.

If you love managing engineers — if being a technical leader is a part of your identity that you take great pride in, then you must keep up your technical skills and periodically invest in your practice and renew your education. Again: this is simply the price of admission. You need to renew your technical abilities, your habits of mind, and your visceral senses around creating and maintaining systems. There is no way to do this besides doing it. If management isn’t a promotion, then returning to hands-on work isn’t a demotion, either. Right?

One warning: Your company may be great, but it doesn’t exist for your benefit. You and only you can decide what your needs are and advocate for them. Remember that next time your boss tries to guilt you into staying on as manager because you’re so badly needed, when you can feel your skills getting rusty and your effectiveness dwindling. You owe it to yourself to figure out what makes you happy and build a portfolio of experiences that liberate you to do what you love. Don’t sacrifice your happiness at the altar of any company. There are always other companies.

Honestly, I would try not to think of yourself as a manager at all: you are an “engineering leader” performing a tour of duty in management. You’re pursuing a long term strategy towards being a well-respected technologist, someone who can sling code, give informed technical guidance and explain in detail customized for to anyone at any level of sophistication.

Organizational Leadership Track

Most managers assume they want to climb the ladder. Leveling up feels like an achievement, and that can feel impossible to resist.

Resist it. Or at least, resist doing it unthinkingly. Don’t do it because the ladder is there and must be climbed. Know as much as you can about what you’re in for before you decide it’s what you want.

Here are a few reasons to think critically about climbing the ladder to director and executive roles.

Your choices shrink. There are fewer jobs, with more competition, mostly at bigger companies. (Do you even like big companies?)
You basically need to do real time at a big company where they teach effective management skills, or you’ll start from a disadvantage.
Bureaucracies are highly idiosyncratic, skills and relationships may or may not transfer with you between companies. As an engineer you could skip every year or two for greener pastures if you landed a crap gig. An engineer has … about 2-3x more leeway in this regard than an exec does. A string of short director/exec gigs is a career ender or a coach seat straight to consultant life.
You are going to become less employable overall. The ever-higher continuous climb almost never happens, usually for reasons you have no control over. This can be a very bitter pill.
Your employability becomes more about your “likability” and other problematic things. Your company’s success determines the shape of your career much more than your own performance. (Actually, this probably begins the day you start managing people.)
Your time is not your own. Your flaws are no longer cute. You will see your worst failings ripple outward and be magnified and reflected. (Ditto, applies to all leaders but intensifies as you rise.)
You may never feel the dopamine hit of “i learned something, i fixed something, i did something” that comes so freely as an I.C. Some people learn to feel satisfaction from managery things, others never do. Most describe it as a very subdued version of the thrill you get from building things.
You will go home tired every night, unable to articulate what you did that day. You cannot compartmentalize or push it aside. If the project failed for reasons outside your control, you will be identified with the failure anyway.
Nobody really thinks of you as a person anymore, you turn into a totem for them to project shit on. (Things will only get worse if you hit back.) Can you handle that? Are you sure?
It’s pretty much a one-way trip.

Sure, there are compensating rewards. Money, power, impact. But I’m pointing out the negatives because most people don’t stop to consider them when they start saying they want to try managing managers. Every manager says that.

The mere existence of a ladder compels us all to climb.

I know people who have climbed, gotten stuck, and wished they hadn’t. I know people who never realized how hard it would be for them to go back to something they loved doing after 5+ years climbing the ladder farther and farther away from tech. I know some who are struggling their way back, others who have no idea how or where to start. For those who try, it is hard.

You can’t go back and forth from engineering to executive, or even director to manager, in the way you can traverse freely between management and engineering as a technologist.

I just want more of you entering management with eyes wide open. That’s all I’m saying.

If you don’t know what you want, act to maximize your options.

Engineering is a creative act. Managing engineers will require your full attentive and authentic self. You will be more successful if you figure out what that self is, and honor its needs. Try to resist the default narratives about promotions and titles and roles, they have nothing to do with what satisfies your soul. If you have influence, use it to lean hard against things like paying managers more than ICs of the same level.[2]

It’s totally normal not to know who you want to be, or have some passionate end goal. It’s great to live your life and work your work and keep an eye out for interesting opportunities, and see what resonates. It’s awesome when you get asked to step up and opportunistically build on your successes.

If you want a sustainable career in tech, you are going to need to keep learning your whole life. The world is changing much faster than humans evolved to naturally adapt, so you need to stay a little bit restless and unnaturally hungry to succeed in this industry.

The best way to do that is to make sure you a) know yourself and what makes you happy, b) spend your time mostly in alignment with that. Doing things that make you happy give you energy. Doing things that drain you are antithetical to your success. Find out what those things are, and don’t do them.

Don’t be a martyr, don’t let your spending habits shackle you, and don’t build things that trouble your conscience.

And have fun.

Yours in inverting $(allthehierarchies),
charity.

[1] Important point: I am not saying you can’t pick up the skills and patience to practice engineering again. You probably can! But employers are extremely reluctant to pay you a salary as an engineer if you haven’t been paid to ship code recently. The tipping point for hireability comes long before the tipping point for learning ability, in my experience.

[2] It is in no one’s best interest for money to factor into the decision of whether to be a manager or not. Slack pays their managers LESS than engineers of the same level, and I think this is incredibly smart: sends a strong signal of servant leadership.

Software Sprawl, The Golden Path, and Scaling Teams With Agency

December 2, 2018March 7, 2023 mipsytipsyculture, developers, engineering, engineers, management, operations, scaling, software engineering, sre, tech culture27 Comments

Stop me if you’ve heard this one before.

The company is growing like crazy, your engineering team keeps rising to the challenge, and you are ferociously proud of them. But some cracks are beginning to show, and frankly you’re a little worried. You have always advocated for engineers to have broad latitude in technical decisions, including choosing languages and tools. This autonomy and culture of ownership is part of how you have successfully hired and retained top talent despite the siren song of the Faceboogles.

But recently you saw something terrifying that you cannot unsee: your company is using all the languages, all the environments, all the databases, all the build tools. Shit!!! Your ops team is in full revolt and you can’t really blame them. It’s grown into an unsupportable nightmare and something MUST be done, but you don’t know what or how — let alone how to solve it while retaining the autonomy and personal agency that you all value so highly.

I hear a version of this everywhere I’ve gone for the past year or two. It’s crazy how often. I’ve been meaning to write my answer up for ages, and here it (finally) is.

First of all: you aren’t alone. This is extremely common among high-performing teams, so congratulations. Really!

There actually seems to be a direct link between teams that give engineers lots of leeway to own their technical decisions and that team’s ability to hire and retain top-tier talent, particularly senior talent. Everything is a tradeoff, obviously, but accepting somewhat more chaos in exchange for a stronger sense of individual ownership is usually the right one, and leads to higher-performing teams in the long run.

Second, there is actually already a well-trod path out of this hole to a better place, and it doesn’t involve sacrificing developer agency. It’s fairly simple! Just five short steps, which I will describe to you now.

How to build a golden path and reverse software sprawl

Assemble a small council of trusted senior engineers.
Task them with creating a recommended list of default components for developers to use when building out new services. This will be your Golden Path, the path of convergence (and the path of least resistance).
Tell all your engineers that going forward, the Golden Path will be fully supported by the org. Upgrades, patches, security fixes; backups, monitoring, build pipeline; deploy tooling, artifact versioning, development environment, even tier 1 on call support. Pave the path with gold. Nobody HAS to use these components … but if they don’t, they’re on their own. They will have to support it themselves.
Work with team leads to draw up an umbrella plan for adopting the Golden Path for their current projects as well as older production services, as much as is reasonable or possible or desirable. Come up with a timeline for the whole eng org to deprecate as many other tools as possible. Allocate real engineering time to the effort. Hell, make a party out of it!
After the cutoff date (and once things have stabilized), establish a regular process for reviewing and incorporating feedback about the blessed Path and considering any proposed changes, additions or removals.

There you go. That’s it. Easy, right??

(It’s not easy. I never said it was easy, I said it was simple. 👼🏼)

Your engineers are currently used to picking the best tool for the job by optimizing locally. What data store has a data model that is easiest for them to fit to their needs? Which language is fastest for I/O throughput? What are they already proficient in? What you need to do is start building your muscles for optimizing globally. Not in isolation of other considerations, but in conjunction with them. It will always be a balancing act between optimizing locally for the problem at hand and optimizing globally for operability and general sanity.

(Oh, incidentally, requiring an engineer to write up a proposal any time they want to use a non-standard component, and then defend their case while the council grills them in person — this will be nothing but good for them, guaran-fucking-teed.)

Let’s go into a bit more detail on each of the five points. But quick disclaimer: this is not a prescription. I don’t know your system, your team, your cultural land mines or technical interdependencies or anything else about your situation. I am just telling stories here.

1. Assemble your council

Three is a good number for a council. More than that gets unwieldy, and may have trouble reaching consensus. Less than three and you run into SPOFs. You never want to have a single person making unilateral decisions because a) the decision-making process will be weaker, b) it sets that person up for too much interpersonal friction, and c) it denies your other engineers the opportunity to practice making these kinds of decisions.

Your council members need technical breadth more than depth, and should be widely respected by engineers.
At least one member should have a long history with the company so they know lots of stupid little details about what’s been tried before and why it failed.
At least one member should be deeply versed in practical data and operability concerns.
They should all have enough patience and political skill to drive consensus for their decisions. Absolutely no bombthrowers.

If you’re super lucky, you just tap the three senior technologists who immediately come to mind … your mind and everyone else’s. If you don’t have this kind of automatic consensus, you may want to let teams or orgs nominate their own representative so they feel they have some say.

2. Task the council with defining a Golden Path

Your council cannot vanish for a week and then descend from the mountain lugging lists engraved on stone tablets. The process of discovery and consensus is what validates the result.

The process must include talking to and gathering feedback from your engineers, talking to experts outside the company, talking to teams at other companies who are farther along using that technology, coming up with detailed pro/con lists and reasons for their choices. Maybe sometimes it includes prototyping something or investigating the technical depths … but yeah no mostly it’s just the talking.

You need your council members to have enough political skill to handle these conversations deftly, building support and driving consensus through the process. Everybody doesn’t have to love the outcome, but it shouldn’t be a *surprise* to anyone by the end.

3. Know where you’re going

Your council should create a detailed written plan describing which technologies are going to be supported … and a stab at what “supported” means. (Ask the experts in each component what the best practices are for backups, versioning, dependency management, etc.)

You might start with something like this:

* Backend lang: Go 1.11           ## we will no longer be supporting
backend scripting languages
* Frontend lang: ReactJS v 16.5
* Primary db: Aurora v 2.0        ## Yes, we know postgres is "better", 
but we have many mysql experts and 0 pg experts except the one guy 
who is going to complain about this.  You know who you are.
* Deploy pipeline: github -> jenkins + docker -> S3 -> custom k8s 
deploy tooling
* Message broker: kafka v 2.10, confluent build
* Mail: SES
* .... etc

Circulate the draft regularly for feedback, especially with eng managers. Some team reorganization will probably be necessary to bear the new weight of your support specifications, and managers will need some lead time to wrangle this.

This is also a great time to reconceive of the way on call works at your company. But I am not going to go into all that here.

4. Set a date, draft a plan: go!

Get approval from leadership to devote a certain amount of time to consolidating your stack and paying down a lump sum of tech debt. It depends on your stage of decay, but a reasonable amount of time might be “25% of engineering time for three months“. Whatever you agree to, make sure it’s enough to make the world demonstrably better for the humans who run it; you don’t want to leave them with a tire fire or you’ll blow your credibility.

The council and team leads should come up with a rough outer estimate for how long it would take to rewrite everything and move the whole stack on to the Golden Stack. (It’s probably impossible and/or would take years, but that’s okay.) Next, look for the quick wins or swollen, inflamed pain points.

If you are running two pieces of functionally similar software, like postgres and mysql, can you eliminate one?
If you are managing something yourself that AWS could manage for you (e.g. postfix instead of SES, or kafka instead of kinesis), can you migrate that?
If you are managing anything yourself that is not core to your business value, in fact, you should try to not manage it.
If you are running any services by hand on an AWS instance somewhere, could you try using a service?
If you are running your own monitoring software, etc … can you not?
If you have multiple versions of a piece of software, can you upgrade or consolidate on one version?

The hardest parts are always going to be the ones around migrating data or rewriting components. Not everything is worth doing or can afford to be done in the time span of your project time, and that’s okay.

Next, brainstorm up some carrots. Can you write templates so that anybody who writes a service using your approved library, magically gets monitoring checks without having to configure anything? Can you write a wrapper so they get a bunch of end-to-end tests for free? Anything you can do to delight people or save them time and effort by using your preferred components is worth considering.

(By the way, if you don’t have any engineers devoted to internal tooling, you’re probably way overdue at this point.)

Pay down as much debt as you can, but be pragmatic: it’s better to get rid of five small things than one large thing, from a support perspective. Your main goal is to shrink the number of types of software your team has to support, particularly databases.

Do look for ways to make it fun, like … running a competition to see who can move the most tools to AWS in a week, or throwing a hack week party, or giving dorky prizes like trophies that entitle you to put your manager on call instead of you for a day, etc.

5. Make the process sustainable

After your target date has come and gone, you probably want to hold a post mortem retrospective and do lots of listening. (Well — first might I recommend a bubble bath and a bottle of champagne? But then a post mortem.)

Nothing is ever fixed forever. The company’s needs are going to expand and contract, and people will come and go, because change is the only constant. So you need to bake some flex into your system. How are you going to handle the need for changes to the Golden Path? Monthly discussions? An email list? Quarterly meetings with a formal agenda? I’ve seen people do all of these and more, it doesn’t really matter afaict.

Nobody likes a cabal, though, so the original council should gradually rotate out. I recommend replacing one person at a time, one per quarter, and rotating in another senior engineer in their place. This provides continuity while giving others a chance to learn these technical and political skills.

In the end, engineers are still free to use any tool or component at any time, just like before, only now they are solely responsible for it, which puts pressure on them not to do it unless REALLY necessary. So if someone wants to propose adding a new tool to the default golden path, they can always add it themselves and gain some experience in it before bringing it to the council to discuss a formal place for it.

That’s all folks

See, wasn’t that simple?

(It’s never simple.)

I dearly wish more people would write up their experiences with this sort of thing in detail. I think engineering teams are too reluctant to show their warts and struggles to the world — or maybe it’s their executives who are afraid? Dunno.

Regardless, I think it’s actually a highly effective recruiting tool when teams aren’t afraid to share their struggles. The companies that brag about how awesome they are are the ones who come off looking weak and fragile. Whereas you can always trust the ones who are willing to laugh about all the ways they screwed up. Right?

In conclusion, don’t feel like an asshole for insisting on some process here. There should be friction around adding new components to your stack. (Add in haste, repent at leisure, as they say.) Anybody who argues with you probably needs to be exposed to way, way more of the support load for that software. That’s my professional opinion.

Anyway. You win or you die. Good luck with your sprawl.

charity

On Engineers and Influence

August 17, 2018March 7, 2023 mipsytipsyculture, developers, engineers, influence, management, operations, software engineering, tech culture5 Comments

(Based on yesterday’s tweetstorm and the ensuing conversation, https://twitter.com/mipsytipsy/status/1029608573217587201)

Let’s talk about influence. As an engineer, how do you get influence? What does influence look like, what is it rooted in, how do you wield it or lose it? How is it different from the power and influence you might have as a manager?[0]

This often comes up in the context of ICs who desperately want to become managers in order to have more access to information and influence over decisions. This is a bad signal, though it’s sadly very common.

When that happens, you need to do some soul-searching. Does your org make space for senior ICs to lead and own decisions? Do you have an IC track that runs parallel to the manager track at least as high as director level? Are they compensated equally? Do you have a career ladder? Are your decision-making processes mysterious to anyone who isn’t a manager? Don’t assume what’s obvious to you is obvious to others; you have to ask around.

If so, it’s probably their own personal baggage speaking. Maybe they don’t believe you. Maybe they’ve only worked in orgs where managers had all the power. Maybe they’ve even worked in lots of places that said the exact same things as you are saying about how ICs can have great impact, but it was all a lie and now they’re burned. Maybe they aren’t used to feeling powerful for all kinds of reasons.

Regardless, people who want to be managers in order to perpetuate a bad power structure are the last people you want to be managers.[1]

But what does engineering influence look like? How do your powers manifest?

I am going to avoid discussing the overlapping and interconnected issues of gender, race and class, let’s just acknowledge that it’s much more structurally difficult for some to wield power than for others, ok?

The power to create

Doing is the engineering superpower. We create things with just a laptop and our brain! It’s incredible! We don’t have to constantly convince and cajole and coerce others into building on our behalf, we can just build.

This may seem basic, but it matters. Creation is the ur-power from which all our forms of power flow. Nothing gets built unless we agree to build it (which makes this an ethical issue, too).

Facebook had a poster that said “CODE WINS ARGUMENTS”. Problematic in many ways, absolutely. But how many times have you seen a technical dispute resolved by who was willing to do the work? Or “resolved” one way.. then reversed by doing? Doing ends debates. Doing proves theories. Doing is powerful. (And “doing” doesn’t only mean “write code”.)

Furthermore, building software is a creative activity, and doing it at scale is an intensely communal one. As a creative act, we are better builders when we are motivated and inspired and passionate about our work (as compared to say, chopping wood). And as a collaborative act, we do better work when we have high trust and social cohesion.

Engineering ability and judgment, autonomy and sense of purpose, social trust and cooperative behaviors: this is the raw stuff of great engineering. Everybody has a mode or two that they feel most comfortable and authoritative operating from: we can group these roughly into archetypes.

(Examples drawn from some of the stupendously awesome senior engineers I’ve gotten to work with over the years, as well as the ways I loved to fling my weight around as an engineer.)

Archetypes of influence

“Doing the work that is desperately hard and desperately needed — and often desperately dull.” SOC2 compliance, backups and restores, terrifying refactors, any auth integration ever: if it’s moving the business forward, they don’t give a shit how dull the work is. If you are this engineer, you have a deep well of respect and gratitude.
“Debugger of last resort.” Often the engineer who has been there the longest or originally built the system. If you are helpful and cheerful with your history and context, this is a huge asset. (People tend to wildly overestimate this person’s indispensability, actually; please don’t encourage this.)
The “expert” archetype is closely related. If you are the deep subject matter expert in some technology component, you have a shit ton of influence over anything that uses or touches that component. (You should stay up on impending changes to retain your edge.)
There are people who deliver a bafflingly powerful firehose of sustained output, sometimes making headway on multiple fronts at once. Some work long hours, others just have an unerring instinct for how to maximize impact (this sometimes maps to junior/senior manifestations). Nobody wants to piss off those people. Their consent is critical for … everything. Their participation will often turbo charge a project or pull a foundering effort over the finish line.

Not all influence is rooted in raw technical strength or output. Just a few of the wide variety of creative/collaborative/interpersonal strengths:

Some engineers are infinitely curious, and have a way of consistently sniffing a few steps ahead of the pack. They might seem to be playing around with something pointless, and you want to scold them; then they save your ass from total catastrophe. You learn to value their playing around.
Some engineers solve problems socially, by making friends and trading tips and fixes and favors in the industry. Don’t underestimate social debugging, it’s often the quickest path to the right answer.
Some are dazzlingly lazy and blow your mind with their elegant shortcuts and corners correctly cut.
Some are recruiting magnets, and it’s worth paying their salary just for all the people who want to work with them again.
Some are skilled at driving consensus among stakeholders.
Some are killer explainers and educators and storytellers.
Some are the senior engineer everyone silently wants to grow up to be.
Some can tell such an inspiring story of tomorrow that everyone will run off to make it so.
Some teach by turning code reviews into a pedagogical art form.
Some make everyone around them somehow more productive and effective. Some create relentless forward momentum. Some are good at saying no.

And there are a few special wells of power that bear calling out as such.

Engineers who have been managers are worth their weight in gold. They can translate business goals for junior engineers in their native language with impeccable credibility (something managers never really have, esp in junior engineers’ eyes.). They make strong tech leads, they can carve up projects into components that challenge but do not overwhelm each contributor while hitting deadlines.
Some engineers are a royal pain in the ass because they question and challenge every system and hierarchy. But these are sharp, powerful rocks that can polish great teams. Though they do require a strong manager, to channel their energy towards productive dialogue and improvement and keep them from pissing off the whole team.
And let’s not forget engineers who are on call. If you have a healthy on call culture,your ownership over production creates a deep, deep well of power and moral authority — to make demands, drive change, to prioritize. On call should not be a shit salad served up to those who can’t refuse, it should be a badge of honor and seriousness shouldered by every engineer who ships code. (And it should not be miserable or regularly life-impacting.)

… I could go on all day. Engineering is such a powerful role and skill set. It’s definitely worth unpacking where your own influence comes from, and understanding how others perceive your strengths.

Most forms of power boil down to “influence, wielded”.

But just banging out code is not enough. You may have credibility, but having it is not the same as using it. To transform influence into power you have to use it. And the way you use it is by communicating.

What’s locked up in your head has no impact on the rest of us. You have to get it out.

You can do this in lots of ways: by writing, in 1x1s, conversations with small groups, openly recruiting allies, convincing someone with explicit authority, broadcasting inpublic, etc.

Because engineering is a creative activity, authoritarian power is actually quite brittle and damaging. The only sustainable forms of power are so-called “soft powers” like influencing and inspiring, which is why good managers use their soft power freely and hard power sparingly/with great reluctance. If your leadership invokes authority on the regular, that’s an antipattern.[2]

If you don’t speak up, you don’t have the right to sit and fume over your lack of influence. And speaking up does mean being vulnerable — and sometimes wrong — in front of other people.

This is not a zero-sum game.

Most of you have far more latent power than you realize or are used to wielding, because you don’t feel powerful or don’t recognize what you do in those terms.

Managers may have hard power and authority, but the real meaty decisions about technical delivery and excellence are more properly made by the engineers closest to them. These belong properly to the doers, in large part because they are the ones who have to support the consequences of these decisions.

Power tends to flow towards managers because they are privy to more information. That makes it important to hire managers who are aware of this and lean against it to push power back to others.

In the same way that submissives have ultimate power in healthy BDSM relationships, engineers actually have the ultimate power in healthy teams. You have the ultimate veto: you can refuse to create. Demand is high for your skills. You can usually afford to look for better conditions. Many of you probably should.

And when technical and managerial priorities collide, who wins? Ideally you work together to find the best solution for the business and the people. The teams that feel 🔥on fire🔥 always have tight alignment between the two.

Pick your battles.

One final thought. You can have a lot of say in what gets built and how it gets built, if you cultivate your influence and spend it wisely. But you can’t have a say in everything. It doesn’t work that way.

Think of it like @mcfunley’s famous “innovation tokens”, but for attention and fucks given.

The more you use your influence for good outcomes, the more you build up over time, yes … but it’s a precision tool, not background noise. Imagine someone trying to give you a massage by laying down on your whole back instead of pushing their elbow or hand into knots and trigger points. A too-broad target will diffuse your force and limit your potential impact.

Spend your attention tokens wisely.

And once you have influence, don’t forget to use it on behalf of others. Pay attention to those who aren’t being heard, and amplify their voices. Give your time, lend your patronage and credibility, and most of all teach the skills that have made you powerful to others who need them.

charity

P.S. I owe a huge debt to all the awesome senior engineers i’ve gotten to work with. Mad love to you all. <3

[0] I successfully answered one (1) of these questions before running out of steam. Later.
[1] Sheepish confession: this is why I became a manager.
[2] It’s also a bad sign if they won’t grant any explicit authority to the people they hold responsible for outcomes. I’m talking about relatively healthy orgs here, not pathological ones where people (often women) are told they don’t need promotions or explicit authority, they should just use their “soft power” — esp when the hard forms of power aligned against with them. That’s setting you up for failure.
[3] Some people seem caught off guard by my use of “power” to signal anything other than explicit granted powers by the org. This doesn’t make any sense to me. I find it too depressing and disempowering to think of power as merely granted authority. It doesn’t map to how I experience the world, either. Individual clout is a thing that waxes and wanes and only exists in relation to others’. I’ve seen plenty of weak managers pushed around by strong personalities (which is terrible too).