Most people aren’t doing true CI/CD. Most teams wait far too long to get their code into prod after writing it. Most painful of all are the teams who have done all the hard parts — wired up continuous integration, achieved test coverage, etc — but still deploy by hand, thus depriving themselves of the payoff for their hard work.
Any time an engineer merges a diff back to main, this ought to trigger a full run of your CI/CD pipeline, culminating with an automatic deploy to production. This should happen once per mergeset, never batching multiple engineers’ diffs in a run, and it should be over and done with in 15 minutes or less with no human intervention.
Okay, but what if you don’t? How costly can it be, really?
Let’s do some back of the envelope math. First you’ll need to answer a couple questions about your org and deploy pipeline.
How many engineers do you have? ____________
How long typically elapses between when someone writes code and that code is live in production? _____________
Let (n) be the number of engineers it takes to efficiently build and run your product, assuming each set of changes will autodeploy individually in <15 min.
If changes typically ship on the order of hours, you need 2(n).
If changes ship on the order of days, you need 2(2(n)).
If changes ship on the order of weeks, you need 2(2(2(n)))
If changes ship on the order of months, you need 2(2(2(2(n))))
Your 6 person team with a consistent autodeploy loop would take 24 people to do the same amount of work, if it took days to deploy their changes. Your 10 person team that ships in weeks would need 80 people.
At cost to the company of approx 200k per engineer, that’s $3.6 million in the first example and $14 million in the second example. That’s how much your neglect of internal tools and kneejerk fear of autodeploy might be costing you.
It’s not just about engineers. The more delay you add into the process of building and shipping code, the more pathologies multiply, and you find yourselves needing to spend more and more time addressing those pathologies instead of making forward progress for the business. Longer diffs. Manual deploy processes. Bunching up multiple engineers’ diffs in a single deploy, then spending the rest of the day trying to figure out which one was at fault for the error.
Soon you need an SRE team to handle your reliability issues, build engineering specialists to build internal tools for all these engineers, managers to manage the teams, product folks to own the roadmap and project managers to coordinate all this blocking and waiting on each other…
You could have just fixed your build process. You could have just committed to continuous delivery. You would be moving more swiftly and confidently as a small, killer team than you ever could at your lumbering size.
✨✨15 minutes or bust✨✨
In 2021, how will *you* achieve the dream of CI/CD, and liberate your engineers from the shackles of pointless toil?
P.S. if you want to know my methodology for coming up with this equation, it’s called “pulled out of my ass because it sounded about right, then checked with about a dozen other technical folks to see if it aligned with their experience.”
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.
treat every alarm like a heart attack. _fix_ the motherfucker.
i do not care if this causes product development to screech to a halt. amortize it over a slightly longer period of time and it will more than pay for itself. https://t.co/JSck2u86ff
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.
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?
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? ✨Computers!✨ 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.
Dan Golant asked a great question today: “Any advice/reading on how to establish a team’s critical path?”
I repeated back: “establish a critical path?” and he clarified:
Yea, like, you talk about buttoning up your “critical path”, making sure it’s well-monitored etc. I think that the right first step to really improving Observability is establishing what business processes *must* happen, what our “critical paths” are. I’m trying to figure out whether there are particularly good questions to ask that can help us document what these paths are for my team/group in Eng.
“Critical path” is one of those phrases that I think I probably use a lot. Possibly because the very first real job I ever had was when I took a break from college and worked at criticalpath.net (“we handle the world’s email”) — and by “work” I mean, “lived in SF for a year when I was 18 and went to a lot of raves and did a lot of drugs with people way cooler than me”. Then I went back to college, the dotcom boom crashed, and the CP CFO and CEO actually went to jail for cooking the books, becoming the only tech execs I am aware of who actually went to jail.
Where was I.
Right, critical path. What I said to Dan is this: “What makes you money?”
Like, if you could only deploy three end-to-end checks that would perform entire operations on your site and ensure they work at all times, what would they be? what would they do? “Submit a payment” is a super common one; another is new user signups.
The idea here is to draw up a list of the things that are absolutely worth waking someone up to fix immediately, night or day, rain or shine. That list should be as compact and well-defined as possible. This allows you to be explicit about the fact that anything else can wait til morning, or some other less-demanding service level agreement.
And typically the right place to start on this list is by asking yourselves: “what makes us money?” as a proxy for the real questions, which are: “what actions allow us to survive as a business? What do our customers care the absolute most about? What makes us us?” That’s your critical path.
Someone will usually seize this opportunity to argue that absolutely any deterioration in service is worth paging someone immediately to fix it, day or night. They are wrong, but it’s good to flush these assumptions out and have this argument kindly out in the open.
(Also, this is really a question about service level objectives. So if you’re asking yourself about the critical path, you should probably consider buying Alex Hidalgo’s book on SLOs, and you may want to look into the Honeycomb SLO product, the only one in the industry that actually implements SLOs as the Google SRE book defines them (thanks Liz!) and lets you jump straight from “what are our customers experiencing?” to “WHY are they experiencing it”, without bouncing awkwardly from aggregate metrics to logs and back and just … hoping … the spikes line up according to your visual approximations.)
One of my stretch goals for 2019 was to start writing an advice column. I get a lot of questions about everything under the sun: observability, databases, career advice, management problems, what the best stack is for a startup, how to hire and interview, etc. And while I enjoy this, having a high opinion of my own opinions and all, it doesn’t scale as well as writing essays. I do have a (rather all-consuming) day job.
So I’d like to share some of the (edited and lightly anonymized) questions I get asked and some of the answers I have given. With permission, of course. And so, with great appreciation to my anonymous correspondent for letting me publish this, here is one.
I’ve been in tech for 25 years. I don’t have a degree, but I worked my way up from menial jobs to engineering, and since then I have worked on some of the biggest sites in the world. I have been offered a management role many times, but every time I refused. Until about two years ago, when I said “fuck it, I’m almost 40; why not try.”
I took the job with boundless enthusiasm and motivation, because the team was honestly a mess. We were building everything on-prem, and ops was constantly bullying developers over their supposed incompetence. I had gone to conferences, listened to podcasts, and read enough blog posts that my head was full of “DevOps/CloudNative/ServiceOriented//You-build-it-you-run-it/ServantLeaders” idealism. I knew I couldn’t make it any worse, and thought maybe, just maybe I could even make it better.
Soon after I took the job, though, there were company-wide layoffs. It was not done well, and morale was low and sour. People started leaving for happier pastures. But I stayed. It was an interesting challenge, and I threw my heart and soul into it.
For two years I have stayed and grinded it out: recruiting (oh that is so hard), hiring, and then starting a migration to a cloud provider, and with the help of more and more people on the new team, slowly shifted the mindset of the whole engineering group to embrace devops best practices. Now service teams own their code in production and are on-call for them, migrate themselves to the cloud with my team supporting them and building tools for them. It is almost unrecognizable compared to where we were when I began managing.
A beautiful story isn’t it? I hope you’re still reading. 🙂
Now I have to say that with my schedule full of 1:1s, budgeting, hiring, firing, publishing papers of mission statements and OKRs, shaping the teams, wielding influence, I realized that I enjoyed none of the above. I read your 17 reasons not to be a manager, and I check so many boxes. It is a pain in the ass to constantly listen to people’s egos, talk to them and keep everybody aligned (which obviously never happens). And of course I am being crushed between top-down on-the-spot business decisions and bottom-up frustration of poorly executed engineering work under deadlines. I am also destroyed by the mistrust and power games I am witnessing (or involved in, sometimes). while I long for collaboration and trust. And of course when things go well my team gets all the praise, and when things go wrong I take all the blame. I honestly don’t know how one can survive without the energy provided by praise and a sense of achievement.
All of the above makes me miss being an IC (Individual Contributor), where I could work for 8 hours straight without talking to anyone, build stuff, say what I wanted when I wanted, switch jobs if I wasn’t happy, and basically be a little shit like the ones you mention in your article.
But when I think about doing it, I get stuck. I don’t know if I would be able to do it again, or if I could still enjoy it. I’ve seen too many things, I’ve tasted what it’s like to be (sometimes) in control, and I did have a big impact on the company’s direction over time. I like that. If I went back to being an IC, I would feel small and meaningless, like just another cog in the machine. And of course, being 40-ish, I will compete with all those 20-something smartasses who were born with kubernetes.
Thank you for reading. Could you give me your thoughts on this? In any case, it was good to get it off my chest.
Holy shitballs! What an amazing story! That is an incredible achievement in just two years, let alone as a rookie manager. You deserve huge props for having the vision, the courage, and the tenacity to drive such a massive change through.
Of COURSE you’re feeling bored and restless. You didn’t set out on a glorious quest for a life of updating mission statements and OKRs, balancing budgets, tending to people’s egos and fluffing their feelings, tweaking job descriptions, endless 1x1s and meetings meetings meetings, and the rest of the corporate middle manager’s portfolio. You wanted something much bigger. You wanted to change the world. And you did!
But now you’ve done it. What’s next?
First of all, YOUR COMPANY SUCKS. You don’t once mention your leadership — where are they in all this? If you had a good manager, they would be encouraging you and eagerly lining up a new and bigger role to keep you challenged and engaged at work. They are not, so they don’t deserve you. Fuck em. Please leave.
Another thing I am hearing from you is, you harbor no secret desire to climb the managerial ranks at this time. You don’t love the daily rhythms of management (believe it or not, some do); you crave novelty and mastery and advancement. It sounds like you are willing to endure being a manager, so long as that is useful or required in order to tackle bigger and harder problems. Nothing wrong with that! But when the music stops, it’s time to move on. Nobody should be saddled with a manager whose heart isn’t in the work.
You’re at the two year mark. This is a pivotal moment, because it’s the beginning of the end of the time when you can easily slip back into technical work. It will get harder and harder over the next 2-3 years, and at some point you will no longer have the option.
Picking up another technical role is the most strategic option, the one that maximizes your future opportunities as a technical leader. But you do not seem excited by this option; instead you feel many complex and uncomfortable things. It feels like going backwards. It feels like losing ground. It feels like ceding status and power.
“Management isn’t a promotion, it’s a career change.”
But if management is not a promotion, then going back to an engineering role should not feel like a demotion! What the fuck?!
It’s one thing to say that. Whether it’s true or not is another question entirely, a question of policy and org dynamics. The fact is that in most places, most of the power does go to the managers, and management IS a promotion. Power flows naturally away from engineers and towards managers unless the org actively and vigorously pushes back on this tendency by explicitly allocating certain powers and responsibilities to other roles.
I’m betting your org doesn’t do this. So yeah, going back to being an IC WILL be a step down in terms of your power and influence and ability to set the agenda. That’s going to feel crappy, no question. We humans hate that.
You cannot go back to doing exactly what you did before, for the very simple reason that you are not the same person. You are going to be attuned to power dynamics and ways of influencing that you never were before — and remember, leadership is primarily exercised through influence, not explicit authority.Senior ICs who have been managers are supremely powerful beings, who tend to wield outsize influence. Smart managers will lean on them extensively for everything from shadow management and mentorship to advice, strategy, etc. (Dumb managers don’t. So find a smart manager who isn’t threatened by your experience.)
You’re a short-timer here, remember? Your company sucks. You’re just renewing your technical skills and pulling a paycheck while finding a company that will treat you better, that is more aligned with your values.
Lastly (and most importantly), I have a question. Why did you need to become a manager in order to drive sweeping technical change over the past two years? WHY couldn’t you have done it as a senior IC? Shouldn’t technical people be responsible for technical decisions, and people managers responsible for people decisions? Could this be your next challenge, or part of it? Could you go back to being an engineer, equipped with your shiny new powers of influence and mystical aura of recent management experience, and use it to organize the other senior ICs to assert their rightful ownership over technical decisions? Could you use your newfound clout with leadership and upper management to convince them that this will help them recruit and retain better talent, and is a better way to run a technical org — for everyone?
I believe this is a better way, but I have only ever seen these changes happen when agitated for and demanded by the senior ICs. If the senior ICs don’t assert their leadership, managers are unlikely to give it to them. If managers try, but senior ICs don’t inhabit their power, eventually the managers just shrug and go back to making all the decisions. That is why ultimately this is a change that must be driven and owned — at a minimum co-owned — by the senior individual contributors.
I hope you can push back against that fear of being small and meaningless as an individual contributor. The fact that it very often is this way, especially in strongly hierarchical organizations, does not mean that it has to be this way; and in healthy organizations it is not this way. Command-and-control systems are not conducive to creative flourishing. We have to fight the baggage of the authoritarian structures we inherited in order to make better ones.
Organizations are created afresh each and every day — not created for us, but by us. Help create the organization you want to work at, where senior people are respected equally and have domains of ownership whether they manage people or technology. If your current gig won’t value that labor, find one that will..
They exist. And they want to hire you.
Lots of companies are DYING to hire this kind of senior IC, someone who is still hands on yet feels responsibility for the team as a whole, who knows the business side, who knows how to mentor and craft a culture and can herd cats when nec
There are companies that know how to use ICs at the strategic level, even executive level. There are bosses who will see you not as a threat, but as a *huge asset* they can entrust with monumental work.
As a senior contributor who moves fluidly between roles, you are especially well-equipped to help shape a sociotechnical organization. Could you make it your mission to model the kind of relationship you want to see between management and ICs, whichever side you happen to be on? We need more people figuring out how to build organizations where management is not a promotion, just a change of career, and where going back and forth carries no baggage about promotions and demotions. Help us.
And when you figure it out, please don’t keep it to yourself. Expand your influence and share your findings by writing your experiences in blog posts, in articles, in talks. Tell stories. Show people people how much better it is this way. Be so magnificently effective and mysteriously influential as a senior IC that all the baby engineers you work with want to grow up to be just like you.
Hope this helps.
P.S. — Oh and stop fretting about “competing” with the 20-somethings kuberneteheads, you dork. You have been learning shit your whole career and you’ll learn this shit too. The tech is the easy part. The tech will always be the easy part. 🙂
I just read this piece, which is basically a very long subtweet about my Friday deploy threads. Go on and read it: I’ll wait.
Here’s the thing. After getting over some of the personal gibes (smug optimism? literally no one has ever accused me of being an optimist, kind sir), you may be expecting me to issue a vigorous rebuttal. But I shan’t. Because we are actually in violent agreement, almost entirely.
I have repeatedly stressed the following points:
I want to make engineers’ lives better, by giving them more uninterrupted weekends and nights of sleep. This is the goal that underpins everything I do.
Anyone who ships code should develop and exercise good engineering judgment about when to deploy, every day of the week
Every team has to make their own determination about which policies and norms are right given their circumstances and risk tolerance
A policy of “no Friday deploys” may be reasonable for now but should be seen as a smell, a sign that your deploys are risky. It is also likely to make things WORSE for you, not better, by causing you to adopt other risky practices (e.g. elongating the interval between merge and deploy, batching changes up in a single deploy)
This has been the most frustrating thing about this conversation: that a) I am not in fact the absolutist y’all are arguing against, and b) MY number one priority is engineers and their work/life balance. Which makes this particularly aggravating:
Lastly there is some strange argument that choosing not to deploy on Friday “Shouldn’t be a source of glee and pride”. That one I haven’t figured out yet, because I have always had a lot of glee and pride in being extremely (overly?) protective of the work/life balance of the engineers who either work for me, or with me. I don’t expect that to change.
Hold up. Did you catch that clever little logic switcheroo? You defined “not deploying on Friday” as being a priori synonymous with “protecting the work/life balance of engineers”. This is how I know you haven’t actually grasped my point, and are arguing against a straw man. My entire point is that the behaviors and practices associated with blocking Friday deploys are in fact hurting your engineers.
I, too, take a lot of glee and pride in being extremely, massively, yes even OVERLY protective of the work/life balance of the engineers who either work for me, or with me.
AND THAT IS WHY WE DEPLOY ON FRIDAYS.
Because it is BETTER for them. Because it is part of a deploy ecosystem which results in them being woken up less and having fewer weekends interrupted overall than if I had blocked deploys on Fridays.
It’s not about Fridays. It’s about having a healthy ecosystem and feedback loop where you trust your deploys, where deploys aren’t a big deal, and they never cause engineers to have to work outside working hours. And part of how you get there is by not artificially blocking off a big bunch of the week and not deploying during that time, because that breaks up your virtuous feedback loop and causes your deploys to be much more likely to fail in terrible ways.
The other thing that annoys me is when people say, primly, “you can’t guarantee any deploy is safe, but you can guarantee people have plans for the weekend.”
Know what else you can guarantee? That people would like to sleep through the fucking night, even on weeknights.
When I hear people say this all I hear is that they don’t care enough to invest the time to actually fix their shit so it won’t wake people up or interrupt their off time, seven days a week. Enough with the virtue signaling already.
You cannot have it both ways, where you block off a bunch of undeployable time AND you have robust, resilient, swift deploys. Somehow I keep not getting this core point across to a substantial number of very intelligent people. So let me try a different way.
Let’s try telling a story.
A tale of two startups
Here are two case studies.
Company X is a three-year-old startup. It is a large, fast-growing multi-tenant platform on a large distributed system with spiky traffic, lots of user-submitted data, and a very green database. Company X deploys the API about once per day, and does a global deploy of all services every Tuesday. Deploys often involve some firefighting and a rollback or two, and Tuesdays often involve deploying and reverting all day (sigh).
Pager volume at Company X isn’t the worst, but usually involves getting woken up a couple times a week, and there are deploy-related alerts after maybe a third of deploys, which then need to be triaged to figure out whose diff was the cause.
Company Z is a three-year-old startup. It is a large, fast-growing multi-tenant platform on a large distributed system with spiky traffic, lots of user-submitted data, and a very green house-built distributed storage engine. Company Z automatically triggers a deploy within 30 minutes of a merge to master, for all services impacted by that merge. Developers at company Z practice observability-driven deployment, where they instrument all changes, ask “how will I know if this change doesn’t work?” during code review, and have a muscle memory habit of checking to see if their changes are working as intended or not after they merge to master.
Deploys rarely result in the pager going off at Company Z; most problems are caught visually by the engineer and reverted or fixed before any paging alert can fire. Pager volume consists of roughly one alert per week outside of working hours, and no one is woken up more than a couple times per year.
Same damn problem, better damn solutions.
If it wasn’t extremely obvious, these companies are my last two jobs, Parse (company X, from 2012-2016) and Honeycomb (company Z, from 2016-present).
They have a LOT in common. Both are services for developers, both are platforms, both are running highly elastic microservices written in golang, both get lots of spiky traffic and store lots of user-defined data in a young, homebrewed columnar storage engine. They were even built by some of the same people (I built infra for both, and they share four more of the same developers).
At Parse, deploys were run by ops engineers because of how common it was for there to be some firefighting involved. We discouraged people from deploying on Fridays, we locked deploys around holidays and big launches. At Honeycomb, none of these things are true. In fact, we literally can’t remember a time when it was hard to debug a deploy-related change.
What’s the difference between Company X and Company Z?
So: what’s the difference? Why are the two companies so dramatically different in the riskiness of their deploys, and the amount of human toil it takes to keep them up?
I’ve thought about this a lot. It comes down to three main things.
Single merge per deploy
I think that I’ve been reluctant to hammer this home as much as I ought to, because I’m exquisitely sensitive about sounding like an obnoxious vendor trying to sell you things. 😛 (Which has absolutely been detrimental to my argument.)
When I say observability, I mean in the precise technical definition as I laid out in this piece: with high cardinality, arbitrarily wide structured events, etc. Metrics and other generic telemetry will not give you the ability to do the necessary things, e.g. break down by build id in combination with all your other dimensions to see the world through the lens of your instrumentation. Here, for example, are all the deploys for a particular service last Friday:
Each shaded area is the duration of an individual deploy: you can see the counters for each build id, as the new versions replace the old ones,
2. Observability-driven development.
This is cultural as well as technical. By this I mean instrumenting a couple steps ahead of yourself as you are developing and shipping code. I mean making a cultural practice of asking each other “how will you know if this is broken?” during code review. I mean always going and looking at your service through the lens of your instrumentation after every diff you ship. Like muscle memory.
3. Single merge per deploy.
The number one thing you can do to make your deploys intelligible, other than observability and instrumentation, is this: deploy one changeset at a time, as swiftly as possible after it is merged to master. NEVER glom multiple changesets into a single deploy — that’s how you get into a state where you aren’t sure which change is at fault, or who to escalate to, or if it’s an intersection of multiple changes, or if you should just start bisecting blindly to try and isolate the source of the problem. THIS is what turns deploys into long, painful marathons.
And NEVER wait hours or days to deploy after the change is merged. As a developer, you know full well how this goes. After you merge to master one of two things will happen. Either:
you promptly pull up a window to watch your changes roll out, checking on your instrumentation to see if it’s doing what you intended it to or if anything looks weird, OR
you close the project and open a new one.
When you switch to a new project, your brain starts rapidly evicting all the rich context about what you had intended to do and and overwriting it with all the new details about the new project.
Whereas if you shipped that changeset right after merging, then you can WATCH it roll out. And 80-90% of all problems can be, should be caught right here, before your users ever notice — before alerts can fire off and page you. If you have the ability to break down by build id, zoom in on any errors that happen to arise, see exactly which dimensions all the errors have in common and how they differ from the healthy requests, see exactly what the context is for any erroring requests.
Healthy feedback loops == healthy systems.
That tight, short feedback loop of build/ship/observe is the beating heart of a healthy, observable distributed system that can be run and maintained by human beings, without it sucking your life force or ruining your sleep schedule or will to live.
Most engineers have never worked on a system like this. Most engineers have no idea what a yawning chasm exists between a healthy, tractable system and where they are now. Most engineers have no idea what a difference observability can make. Most engineers are far more familiar with spending 40-50% of their week fumbling around in the dark, trying to figure out where in the system is the problem they are trying to fix, and what kind of context do they need to reproduce.
Most engineers are dealing with systems where they blindly shipped bugs with no observability, and reports about those bugs started to trickle in over the next hours, days, weeks, months, or years. Most engineers are dealing with systems that are obfuscated and obscure, systems which are tangled heaps of bugs and poorly understood behavior for years compounding upon years on end.
That’s why it doesn’t seem like such a big deal to you break up that tight, short feedback loop. That’s why it doesn’t fill you with horror to think of merging on Friday morning and deploying on Monday. That’s why it doesn’t appall you to clump together all the changes that happen to get merged between Friday and Monday and push them out in a single deploy.
It just doesn’t seem that much worse than what you normally deal with. You think this raging trash fire is, unfortunately … normal.
How realistic is this, though, really?
Maybe you’re rolling your eyes at me now. “Sure, Charity, that’s nice for you, on your brand new shiny system. Ours has years of technical debt, It’s unrealistic to hold us to the same standard.”
Yeah, I know. It is much harder to dig yourself out of a hole than it is to not create a hole in the first place. No doubt about that.
Harder, yes. But not impossible.
I have done it.
Parse in 2013 was a trash fire. It woke us up every night, we spent a lot of time stabbing around in the dark after every deploy. But after we got acquired by Facebook, after we started shipping some data sets into Scuba, after (in retrospect, I can say) we had event-level observability for our systems, we were able to start paying down that debt and fixing our deploy systems.
We started hooking up that virtuous feedback loop, step by step.
We reworked our CI/CD system so that it built a new artifact after every single merge.
We put developers at the steering wheel so they could push their own changes out.
We got better at instrumentation, and we made a habit of going to look at it during or after each deploy.
We hooked up the pager so it would alert the person who merged the last diff, if an alert was generated within an hour after that service was deployed.
We started finding bugs quicker, faster, and paying down the tech debt we had amassed from shipping code without observability/visibility for many years.
Developers got in the habit of shipping their own changes, and watching them as they rolled out, and finding/fixing their bugs immediately.
It took some time. But after a year of this, our formerly flaky, obscure, mysterious, massively multi-tenant service that was going down every day and wreaking havoc on our sleep schedules was tamed. Deploys were swift and drama-free. We stopped blocking deploys on Fridays, holidays, or any other days, because we realized our systems were more stable when we always shipped consistently and quickly.
Allow me to repeat. Our systems were more stable when we always shipped right after the changes were merged. Our systems were less stable when we carved out times to pause deployments. This was not common wisdom at the time, so it surprised me; yet I found it to be true over and over and over again.
This is literally why I started Honeycomb.
When I was leaving Facebook, I suddenly realized that this meant going back to the Dark Ages in terms of tooling. I had become so accustomed to having the Parse+scuba tooling and being able to iteratively explore and ask any question without having to predict it in advance. I couldn’t fathom giving it up.
The idea of going back to a world without observability, a world where one deployed and then stared anxiously at dashboards — it was unthinkable. It was like I was being asked to give up my five senses for production — like I was going to be blind, deaf, dumb, without taste or touch.
Look, I agree with nearly everything in the author’s piece. I could have written that piece myself five years ago.
But since then, I’ve learned that systems can be better. They MUST be better. Our systems are getting so rapidly more complex, they are outstripping our ability to understand and manage them using the past generation of tools. If we don’t change our ways, it will chew up another generation of engineering lives, sleep schedules, relationships.
Observability isn’t the whole story. But it’s certainly where it starts. If you can’t see where you’re going, you can’t go very far.
Get you some observability.
And then raise your standards for how systems should feel, and how much of your human life they should consume. Do better.
Because I couldn’t agree with that other post more: it really is all about people and their real lives.
Listen, if you can swing a four day work week, more power to you (most of us can’t). Any day you aren’t merging code to master, you have no need to deploy either. It’s not about Fridays; it’s about the swift, virtuous feedback loop.
And nobody should be shamed for what they need to do to survive, given the state of their systems today.
But things aren’t gonna get better unless you see clearly how you are contributing to your present pain. And congratulating ourselves for blocking Friday deploys is like congratulating ourselves for swatting ourselves in the face with the flyswatter. It’s a gross hack.
Maybe you had a good reason. Sure. But I’m telling you, if you truly do care about people and their work/life balance: we can do a lot better.
I made a vow this year to post one blog post a month, then I didn’t post anything at all from May to September. I have some catching up to do. 😑 I’ve also been meaning to transcribe some of the twitter rants that I end up linking back to into blog posts, so if there’s anything you especially want me to write about, tell me now while I’m in repentance mode.
This is one request I happened to make a note of because I can’t believe I haven’t already written it up! I’ve been saying the same thing over and over in talks and on twitter for years, but apparently never a blog post.
The question is: what is the proper role of alerting in the modern era of distributed systems? Has it changed? What are the updated best practices for alerting?
@mipsytipsy I've seen your thoughts on dashboards vs searching but haven't seen many thoughts from you on Alerting. Let me know if I've missed a blog somewhere on that! 🙂
It’s a great question. I want to wax philosophically about some stuff, but first let me briefly outline the way to modernize your alerting best practices:
implement SLOs and/or end-to-end checks that traverse key code paths and correlate to user-impacting events
create a secondary channel (tasks, ticketing system, whatever) for “things that on call should look at soon, but are not impacting users yet” which does not page anyone, but which on call is expected to look at (at least) first thing in the morning, last thing in the evening, and midday
move as many paging alerts as possible to the secondary channel, by engineering your services to auto-remediate or run in degraded mode until they can be patched up
wake people up only for SLOs and health checks that correlate to user-impacting events
Or, in an even shorter formulation: delete all your paging alerts, then page only on e2e alerts that mean users are in pain. Rely on debugging tools for debugging, and paging only when users are in pain.
To understand why I advocate deleting all your paging alerts, and when it’s safe to delete them, first we need to understand why have we accumulated so many crappy paging alerts over the years.
Monoliths, LAMP stacks, and death by pagebomb
Here, let’s crib a couple of slides from one of my talks on observability. Here are the characteristics of older monolithic LAMP-stack style systems, and best practices for running them:
The sad truth is, that when all you have is time series aggregates and traditional monitoring dashboards, you aren’t really debugging with science so much as you are relying on your gut and a handful of dashboards, using intuition and scraps of data to try and reconstruct an impossibly complex system state.
This works ok, as long as you have a relatively limited set of failure scenarios that happen over and over again. You can just pattern match from past failures to current data, and most of the time your intuition can bridge the gap correctly. Every time there’s an outage, you post mortem the incident, figure out what happened, build a dashboard “to help us find the problem immediately next time”, create a detailed runbook for how to respond to it, and (often) configure a paging alert to detect that scenario.
Over time you build up a rich library of these responses. So most of the time when you get paged you get a cluster of pages that actually serves to help you debug what’s happening. For example, at Parse, if the error graph had a particular shape I immediately knew it was a redis outage. Or, if I got paged about a high % of app servers all timing out in a short period of time, I could be almost certain the problem was due to mysql connections. And so forth.
Things fall apart; the pagebomb cannot stand
However, this model falls apart fast with distributed systems. There are just too many failures. Failure is constant, continuous, eternal. Failure stops being interesting. It has to stop being interesting, or you will die.
Instead of a limited set of recurring error conditions, you have an infinitely long list of things that almost never happen …. except that one time they do. If you invest your time into runbooks and monitoring checks, it’s wasted time if that edge case never happens again.
Frankly, any time you get paged about a distributed system, it should be a genuinely new failure that requires your full creative attention. You shouldn’t just be checking your phone, going “oh THAT again”, and flipping through a runbook. Every time you get paged it should be genuinely new and interesting.
Oh damn this talk looks baller. 😍 "Failure is important, but it is no longer interesting" — @this_hits_home… Netflix once again shining the light on where the rest of us need to get to over the next 3-5 years. 🙌🏅🎬 https://t.co/OY40Y0BTSa
And thus you should actually have drastically fewer paging alerts than you used to.
A better way: observability and SLOs.
Instead of paging alerts for every specific failure scenario, the technically correct answer is to define your SLOs (service level objectives) and page only on those, i.e. when you are going to run out of budget ahead of schedule. But most people aren’t yet operating at this level of sophistication. (SLOs sound easy, but are unbelievably challenging to do well; many great teams have tried and failed. This is why we have built an SLO feature into Honeycomb that does the heavy lifting for you. Currently alpha testing with users.)
If you haven’t yet caught the SLO religion, the alternate answer is that “you should only page on high level end-to-end alerts, the ones which traverse the code paths that make you money and correspond to user pain”. Alert on the three golden signals: request rate, latency, and errors, and make sure to traverse every shard and/or storage type in your critical path.
That’s it. Don’t alert on the state of individual storage instances, or replication, or anything that isn’t user-visible.
(To be clear: by “alert” I mean “paging humans at any time of day or night”. You might reasonably choose to page people during normal work hours, but during sleepy hours most errors should be routed to a non-paging address. Only wake people up for actual user-visible problems.)
Here’s the thing. The reason we had all those paging alerts was because we depended on them to understand our systems.
Once you make the shift to observability, once you have rich instrumentation and the ability to swiftly zoom in from high level “there might be a problem” to identifying specifically what the errors have in common, or the source of the problem — you no longer need to lean on that scattershot bunch of pagebombs to understand your systems. You should be able to confidently ask any question of your systems, understand any system state — even if you have never encountered it before.
With observability, you debug by systematically following the trail of crumbs back to their source, whatever that is. Those paging alerts were a crutch, and now you don’t need them anymore.
Everyone is on call && on call doesn’t suck.
I often talk about how modern systems require software ownership. The person who is writing the software, who has the original intent in their head, needs to shepherd that code out into production and watch real users use it. You can’t chop that up into multiple roles, dev and ops. You just can’t. Software engineers working on highly available systems need to be on call for their code.
But the flip side of this responsibility belongs to management. If you’re asking everyone to be on call, it is your sworn duty to make sure that on call does not suck. People shouldn’t have to plan their lives around being on call. People shouldn’t have to expect to be woken up on a regular basis. Every paging alert out of hours should be as serious as a heart attack, and this means allocating real engineering resources to keeping tech debt down and noise levels low.
And the way you get there is first invest in observability, then delete all your paging alerts and start over from scratch.
I hadn’t seen anyone say something like this in quite a while. I remember saying things like this myself as recently as, oh, 2016, but I thought the zeitgeist had moved on to continuous delivery.
Which is not to say that Friday freezes don’t happen anymore, or even that they shouldn’t; I just thought that this was no longer seen as a badge of responsibility and honor, rather a source of mild embarrassment. (Much like the fact that you still don’t automatedly restore your db backups and verify them every night. Do you.)
So I responded with an equally hyperbolic and indefensible claim:
If you're scared of pushing to production on Fridays, I recommend reassigning all your developer cycles off of feature development and onto your CI/CD process and observability tooling for as long as it takes to ✨fix that✨.
Now obviously, OBVIOUSLY, reassigning all your developer cycles is probably a terrible idea. You don’t get 100x parallel efficiency if you put 100 developers on a single problem. So I thought it was clear that this said somewhat tongue in cheek, serious-but-not-really. I was wrong there too.
So let me explain.
There’s nothing morally “wrong” with Friday freezes. But it is a costly and cumbersome bandage for a problem that you would be better served to address directly. And if your stated goal is to protect people’s off hours, this strategy is likely to sabotage that goal and cause them to waste far more time and get woken up much more often, and it stunts your engineers’ technical development on top of that.
Fear is the mind-killer.
Fear of deploys is the ultimate technical debt. How much time does your company waste, between engineers:
waiting until it is “safe” to deploy,
batching up changes into bigger changes that are decidedly unsafe to deploy,
debugging broken deploys that had many changes batched into them,
waiting nervously to get paged after a deploy goes out,
figuring out if now is a good time to deploy or not,
cleaning up terrible deploy-related catastrophuckes
Anxiety related to deploys is the single largest source of technical debt in many, many orgs. Technical debt, lest we forget, is not the same as “bad code”. Tech debt hurts your people.
Saying “don’t push to production” is a code smell. Hearing it once a month at unpredictable intervals is concerning. Hearing it EVERY WEEK for an ENTIRE DAY OF THE WEEK should be a heartstopper alarm. If you’ve been living under this policy you may be numb to its horror, but just because you’re used to hearing it doesn’t make it any less noxious.
If you’re used to hearing it and saying it on a weekly basis, you are afraid of your deploys and you should fix that.
It’s a smell. If you can’t deploy at 6pm on a Friday it means you don’t understand or don’t trust your systems or process. That might be ok if you openly acknowledge it, but if your not talking about it, that’s dangerous
If you are a software company, shipping code is your heartbeat. Shipping code should be as reliable and sturdy and fast and unremarkable as possible, because this is the drumbeat by which value gets delivered to your org.
Deploys are the heartbeat of your company.
Every time your production pipeline stops, it is a heart attack. It should not be ok to go around nonchalantly telling people to halt the lifeblood of their systems based on something as pedestrian as the day of the week.
Why are you afraid to push to prod? Usually it boils down to one or more factors:
your deploys frequently break, and require manual intervention just to get to a good state
your test coverage is not good, your monitoring checks are not good, so you rely on users to report problems back to you and this trickles in over days
recovering from deploys gone bad can regularly cause everything to grind to a halt for hours or days while you recover, so you don’t want to even embark on a deploy without 24 hours of work day ahead of you
your deploys are painfully slow, and take hours to run tests and go live.
These are pretty darn good reasons. If this is the state you are in, I totally get why you don’t want to deploy on Fridays. So what are you doing to actively fix those states? How long do you think these emergency controls will be in effect?
The answers of “nothing” and “forever” are unacceptable. These are eminently fixable problems, and the amount of drag they create on your engineering team and ability to execute are the equivalent of five-alarm fires.
Fix. That. Take some cycles off product and fix your fucking deploy pipeline.
It is difficult to combine "you shouldn't do this because it is a symptom of a systemic problem, you should instead address the systemic problem" with "yes actually you should do it for as long as the systemic problem exists, because it is adaptive".
If you’ve been paying attention to the DORA report or Accelerate, you know that the way you address the problem of flaky deploys is NOT by slowing down or adding roadblocks and friction, but by shipping more QUICKLY.
Science says: ship fast, ship often.
Deploy on every commit. Smaller, coherent changesets transform into debuggable, understandable deploys. If we’ve learned anything from recent research, it’s that velocity of deploys and lowered error rates are not in tension with each other, they actually reinforce each other. When one gets better, the other does too.
So by slowing down or batching up or pausing your deploys, you are materially contributing to the worsening of your own overall state.
If you block devs from merging on Fridays, then you are sacrificing a fifth of your velocity and overall output. That’s a lot of fucking output.
If you do not block merges on Fridays, and only block deploys, you are queueing up a bunch of changes to all get shipped days later, long after the engineers wrote the code and have forgotten half of the context. Any problems you encounter will be MUCH harder to debug on Monday in a muddled blob of changes than they would have been just shipping crisply, one at a time on Friday. Is it worth sacrificing your entire Monday? Monday-Tuesday? Monday-Tuesday-Wednesday?
The worst, most PTSD-inducing outages of my life have all happened after holiday code freezes. Every. Single. One.
Don't use rules. Practice good judgment, build tools to align incentives and deploy often; practice tolerating and recovering from pedestrian failures often too. https://t.co/GH7lef274z
I am not saying that you should make a habit of shipping a large feature at 4:55 pm on Friday and then sauntering out the door at 5. For fucks sake. Every engineer needs to learn and practice good technical judgment around deploy hygiene. LIke,
Don’t ship before you walk out the door on *any* day.
Don’t ship big, gnarly features right before the weekend, if you aren’t going to be around to watch them.
Instrument your code, and go and LOOK at the damn thing once it’s live.
Use feature flags and other tools that separate turning on code paths from deploys.
But you don’t need rules for this; in fact, rules actually inhibit the development of good judgment!
Policies (and enumerated exceptions to policies, and exceptions to exceptions) are a piss-poor substitute for judgment. Rules are blunt instruments that stunt your engineers' development and critical thinking skills.
Most deploy-related problems are readily obvious, if the person who has the context for the change in their heads goes and looks at it.
But if you aren’t looking for them, then sure — you probably won’t find out until user reports start to trickle in over the next few days.
So go and LOOK.
Stop shipping blind. Actually LOOK at what you ship.
I mean, if it takes 48 hours for a bug to show up, then maybe you better freeze deploys on Thursdays too, just to be safe! 🙄
I get why this seems obvious and tempting. The “safety” of nodeploy Friday is realized immediately, while the costs are felt later later. They’re felt when you lose Monday (and Tuesday) to debugging the big blob deplly. Or they get amortized out over time. Or you experience them as sluggish ship rates and a general culture of fear and avoidance, or learned helplessness, and the broad acceptance of fucked up situations as “normal”.
If pushing to production is a painful event, make it a *non-event* (same philosophy as chaos engineering)
But if recovering from deploys is long and painful and hard, then you should fix that. If you don’t tend to detect reliability events until long after the event, you should fix that. If people are regularly getting paged on Saturdays and Sundays, they are probably getting paged throughout the night, too. You should fix that.
On call paging events should be extremely rare. There’s no excuse for on call being something that significantly impacts a person’s life on the regular. None.
I’m not saying that every place is perfect, or that every company can run like a tech startup. I am saying that deploy tooling is systematically underinvested in, and we abuse people far too much by paging them incessantly and running them ragged, because we don’t actually believe it can be any better.
It can. If you work towards it.
Devote some real engineering hours to your deploy pipeline, and some real creativity to your processes, and someday you too can lift the Friday ban on deploys and relieve your oncall from burnout and increase your overall velocity and productivity.
On virtue signaling
Finally, I heard from a alarming number of people who admitted that Friday deploy bans were useless or counterproductive, but they supported them anyway as a purely symbolic gesture to show that they supported work/life balance.
This makes me really sad. I’m … glad they want to support work/life balance, but surely we can come up with some other gestures that don’t work directly counter to their goals of life/work balance.
That's it. Because if you make it a virtue signal, it will NEVER GET FIXED. Blocking Friday deploy is not a mark of moral virtue; it is a physical bash script patching over technical rot.
And technical rot is bad because it HURTS PEOPLE. It is in your interest to fix it.
Ways to begin recovering from a toxic deploy culture:
Have a deploy philosophy, make sure everybody knows what it is. Be consistent.
Build and deploy on every set of committed changes. Do not batch up multiple people’s commits into a deploy.
Train every engineer so they can run their own deploys, if they aren’t fully automated. Make every engineer responsible for their own deploys.
(Work towards fully automated deploys.)
Every deploy should be owned by the developer who made the changes that are rolling out. Page the person who committed the change that triggered the deploy, not whoever is oncall.
Set expectations around what “ownership” means. Provide observability tooling so they can break down by build id and compare the last known stable deploy with the one rolling out.
Never accept a diff if there’s no explanation for the question, “how will you know when this code breaks? how will you know if the deploy is not behaving as planned?” Instrument every commit so you can answer this question in production.
Shipping software and running tests should be fast. Super fast. Minutes, tops.
It should be muscle memory for every developer to check up on their deploy and see if it is behaving as expected, and if anything else looks “weird”.
Practice good deploy hygiene using feature flags. Decouple deploys from feature releases. Empower support and other teams to flip flags without involving engineers.
Each deploy should be owned by the developer who made the code changes. But your deploy pipeline needs to have a team that owns it too. I recommend putting your most experienced, senior developers on this problem to signal its high value.
Ultimately, I am not dogmatic about Friday deploys. Truly, I’m not. If that’s the only lever you have to protect your time, use it. But call it and treat it like the hack it is. It’s a gross workaround, not an ideal state.
Don’t let your people settle into the idea that it’s some kind of moral stance instead of a butt-ugly hack. Because if you do you will never, ever get rid of it.
There are plenty of good reasons to block deploys on Fridays, but it's not a good policy to cargo cult blindly. It imposes real costs and ultimately hinders you from achieving safe, boring deploys.
Remember: a team’s maturity and efficiency can be represented by how long it takes to get their shit into users’ hands after they write it. Ship it fast, while it’s still fresh in your developers’ heads. Ship one change set at a time, so you can swiftly debug and revert them. I promise your lives will be so much better. Every step helps. <3
You’ve convinced the security team and other stakeholders, you’ve gotten the integration running, you’re getting promising results from dev-test or staging environments… now it’s time to move from proof-of-concept to full implementation.Depending on your situation this might be a transition from staging to production, or it might mean increasing a feature flipper flag from 5% to 100%, or it might mean increasing coverage of an integration from one API endpoint to cover your entire developer footprint.
Taking into account Murphy’s Law, we expect that some things will go wrong during the rollout.Perhaps during coverage, a developer realizes that the schema designed to handle the app’s event mechanism can’t represent a scenario, requiring a redesign or a hacky solution.Or perhaps the metrics dashboard shows elevated error rates from the API frontend, and while there’s no smoking gun, the ops oncall decides to rollback the integration Just In Case it’s causing the incident.
This gives us another chance to practice empathy — while it’s easy, wearing the champion hat, to dismiss any issues found by looking for someone to blame, ultimately this poisons trust within your organization and will hamper success.It’s more effective, in the long run (and often even in the short run), to find common ground with your peers in other disciplines and teams, and work through to solutions that satisfy everybody.
Keeping the lights on
In all likelihood as integration succeeds, the team will rapidly develop experts and expertise, as well as idiomatic ways to use the product.Let the experts surprise you; folks you might not expect can step up when given a chance.Expertise flourishes when given guidance and goals; as the team becomes comfortable with the integration, explicitly recognize a leader or point person for each vendor relationship.Having one person explicitly responsible for a relationship lets them pay attention to those vendor emails, updates, and avoid the tragedy of the “but I thought *you* were” commons.This Integration Lead is also a center of knowledge transfer for your organization — they won’t know everything or help every user come up to speed, but they can help empower the local power users in each team to ramp up their teams on the integration.
As comfort grows you will start to consider ways to change your usage, for example growing into new kinds of data.This is a good time to revisit that security checklist — does the change increase PII exposure to your vendor?Would the new data lead to additional requirements such as per-field encryption?Don’t let these security concerns block you from gaining valuable insight using the new tool, but do take the chance to talk it over with your security experts as appropriate.
Throughout this organic growth, the Integration Lead remains core to managing your changing profile of usage of the vendor they shepherd; as new categories of data are added to the integration, the Lead has responsibility to ensure that the vendor relationship and risk profile are well matched to the needs that the new usage (and presumably, business value) is placing on the relationship.
Documenting the Intergation Lead role and responsibilities is critical. The team should know when to check in, and writing it down helps it happen.When new code has a security implication, or a new use case potentially amplifies the cost of an integration, bringing the domain expert in will avoid unhappy surprises.Knowing how to find out who to bring in, and when to bring them in, will keep your team getting the right eyes on their changes.
Security threats and other challenges change over time, too.Collaborating with your security team so that they know what systems are in use helps your team take note of new information that is relevant to your business. A simple example is noting when your vendors publish a breach announcement, but more complex examples happen too — your vendor transitions cloud providers from AWS to Azure and the security team gets an alert about unexpected data flows from your production cluster; with transparency and trust such events become part of a routine process rather than an emergency.
It’s all operational
Monitoring and alerting is a fact of operations life, and this has to include vendor integrations (even when the vendor integration is a monitoring product.)All of your operations best practices are needed here — keep your alerts clean and actionable so that you don’t develop pager fatigue, and monitor performance of the integration so that you don’t get blindsided by a creeping latency monster in your APIs.
Authentication and authorization are changing as the threat landscape evolves and industry moves from SMS verification codes to U2F/WebAuthn.Does your vendor support your SSO integration?If they can’t support the same SSO that you use everywhere else and can’t add it — or worse, look confused when you mention SSO — that’s probably a sign you should consider a different vendor.
A beautiful sunset
Have a plan beforehand for what needs to be done should you stop using the service.Got any mobile apps that depend on APIs that will go away or start returning permission errors?Be sure to test these scenarios ahead of time.
What happens at contract termination to data stored on the service?Do you need to explicitly delete data when ceasing use?
Do you need to remove integrations from your systems before ending the commercial relationship, or can the technical shutdown and business shutdown run in parallel?
In all likelihood these are contingency plans that will never be needed, and they don’t need to be fully fleshed out to start, but a little bit of forethought can avoid unpleasant surprises.
Year after year
Industry best practice and common sense dictate that you should revisit the security questionnaire annually (if not more frequently). Use this chance to take stock of the last year and check in — are you getting value from the service?What has changed in your business needs and the competitive landscape?
It’s entirely possible that a new year brings new challenges, which could make your current vendor even more valuable (time to negotiate a better contract rate!) or could mean you’d do better with a competing service.Has the vendor gone through any major changes?They might have new offerings that suit your needs well, or they may have pivoted away from the features you need.
Check in with your friends on the security team as well; standards evolve, and last year’s sufficient solution might not be good enough for new requirements.
Andy thinks out loud about security, society, and the problems with computers on Twitter.
❤️ Thanks so much reading, folks. Please feel free to drop any complaints, comments, or additional tips to us in the comments, or direct them to me on twitter.
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.
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.