Month: March 2023

Questionable Advice: “People Used To Take Me Seriously. Then I Became A Software Vendor”

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I recently got a plaintive text message from my magnificent friend Abby Bangser, asking about a conversation we had several years ago:

“Hey, I’ve got a question for you. A long time ago I remember you talking about what an adjustment it was becoming a vendor, how all of a sudden people would just discard your opinion and your expertise without even listening. And that it was SUPER ANNOYING.

I’m now experiencing something similar. Did you ever find any good reading/listening/watching to help you adjust to being on the vendor side without being either a terrible human or constantly disregarded?”

Oh my.. This brings back memories. ☺️🙈

Like Abby, I’ve spent most of my career as an engineer in the trenches. I have also spent a lot of time cheerfully talking smack about software. I’ve never really had anyone question my experience[1] or my authority as an expert, hardened as I was in the flames of a thousand tire fires.

Then I started a software company. And all of a sudden this bullshit starts popping up. Someone brushing me off because I was “selling something”, or dismissing my work like I was fatally compromised. I shrugged it off, but if I stopped to think, it really bothered me. Sometimes I felt like yelling “HEY FUCKERS, I am one of your kind! I’m trying to HELP YOU. Stop making this so hard!” 😡 (And sometimes I actually did yell, lol.)

That’s what I remember complaining to Abby about, five or six years ago. It was all very fresh and raw at the time.

We’ll get to that. First let’s dial the clock back a few more years, so you can fully appreciate the rich irony of my situation. (Or skip the story and jump straight to “Five easy ways to make yourself a vendor worth listening to“.)

The first time I encountered “software for sale”

My earliest interaction with software vendors was at Linden Lab. Like most infrastructure teams, most of the software we used was open source. But somewhere around 2009? 2010? Linden’s data engineering team began auditioning vendors like Splunk, Greenplum, Vertica[2], etc for our data warehouse solution, and I tagged along as the sysinfra/ops delegate.

For two full days we sat around this enormous table as vendor after vendor came by to demo and plump their wares, then opened the floor for questions.

One of the very first sales guys did something that pissed me off me. I don’t remember exactly what happened — maybe he was ignoring my questions or talking down to me. (I’m certain I didn’t come across like a seasoned engineering professional; in my mid twenties, face buried in my laptop, probably wearing pajamas and/or pigtails.) But I do remember becoming very irritated, then settling in to a stance of, shall we say, oppositional defiance.

I peppered every sales team aggressively with questions about the operational burden of running their software, their architectural decisions, and how canned or cherry-picked their demos were. Any time they let slip a sign of weakness or betrayed uncertainty, I bore down harder and twisted the knife. I was a ✨royal asshole✨. My coworkers on the data team found this extremely entertaining, which only egged me on.

What the fuck?? 🫢😧🫠 I’m not usually an asshole to strangers.. where did that come from?

What open source culture taught me about sales

I came from open source, where contempt for software vendors was apparently de rigueur. (is it still this way?? seems like it might have gotten better? 😦) It is fascinating now to look back and realize how much attitude I soaked up before coming face to face with my first software vendor. According to my worldview at the time,

  1. Vendors are liars
  2. They will say anything to get you to buy
  3. Open source software is always the safest and best code
  4. Software written for profit is inherently inferior, and will ultimately be replaced by the inevitable rise of better, faster, more democratic open source solutions
  5. Sales exists to create needs that ought never to have existed, then take you to the cleaners
  6. Engineers who go work for software vendors have either sold out, or they aren’t good enough to hack it writing real (consumer facing) software.

I’m remembering Richard Stallman trailing around behind me, up and down the rows of vendor booths at USENIX in his St IGNUcious robes, silver disk platter halo atop his head, offering (begging?) to lay his hands on my laptop and bless it, to “free it from the demons of proprietary software.” Huh. (Remember THIS song? 🎶 😱)

Given all that, it’s not hugely surprising that my first encounter with software vendors devolved into hostile questioning.

(It’s fun to speculate on the origin of some of these beliefs. Like, I bet 3) and 4) came from working on databases, particularly Oracle and MySQL/Postgres. As for 5) that sounds an awful lot like the beauty industry and other products sold to women. 🤭)

Behind every software vendor lies a recovering open source zealot(???)

I’ve had many, many experiences since then that slowly helped me dismantle this worldview, brick by brick. Working at Facebook made me realize that open source successes like Apache, Haproxy, Nginx etc are exceptions, not the norm; that this model is only viable for certain types of general-purpose infrastructure software; that governance and roadmaps are a huge issue for open source projects too; and that if steady progress is being made, at the end of the day, somewhere somebody is probably paying those developers.

I learned that the overwhelming majority of production-caliber code is written by somebody who was paid to write it — not by volunteers. I learned about coordination costs and overhead, how expensive it is to organize an army of volunteers, and the pains of decentralized quality control. I learned that you really really want the person who wrote the code to stick around and own it for a long time, and not just on alternate weekends when they don’t have the kids (and/or they happen to feel like it).

I learned about game theory, and I learned that sales is about relationships. Yes, there are unscrupulous sellers out there, just like there are shady developers, but good sales people don’t want you to walk away feeling tricked or disappointed any more than you want to be tricked or disappointed. They want to exceed your expectations and deliver more value than expected, so you’ll keep coming back. In game theory terms, it’s a “repeated game”.

I learned SO MUCH from interviewing sales candidates at Honeycomb.[3] Early on, when nobody knew who we were, I began to notice how much our sales candidates were obsessed with value. They were constantly trying to puzzle out out how much value Honeycomb actually brought to the companies we were selling to. I was not used to talking or thinking about software in terms of “value”, and initially I found this incredibly offputting (can you believe it?? 😳).

Sell unto others as you would have them sell unto you

Ultimately, this was the biggest (if dumbest) lesson of all: I learned that good software has tremendous value. It unlocks value and creates value, it pays enormous ongoing dividends in dollars and productivity, and the people who build it, support it, and bring it to market fully deserve to recoup a slice of the value they created for others.

There was a time when I would have bristled indignantly and said, “we didn’t start honeycomb to make money!” I would have said that the reason we built honeycomb because we knew as engineers what a radical shift it had wrought in how we built and understood software, and we didn’t want to live without it, ever again.

But that’s not quite true. Right from the start, Christine and I were intent on building not just great software, but a great software business. It wasn’t personal wealth we were chasing, it was independence and autonomy — the freedom to build and run a company the way we thought it should be run, building software to radically empower other engineers like ourselves.

Guess what you have to do if you care about freedom and autonomy?

Make money. 🙄☺️

I also realized, belatedly, that most people who start software companies do so for the same damn reasons Christine and I did… to solve hard problems, share solutions, and help other engineers like ourselves. If all you want to do is get rich, this is actually a pretty stupid way to do that. Over 90% of startups fail, and even the so-called “success stories” aren’t as predictably lucrative as RSUs. And then there’s the wear and tear on relationships, the loss of social life, the vicissitudes of the financial system, the ever-looming spectre of failure … 👻☠️🪦 Startups are brutal, my friend.

Karma is a bitch

None of these are particularly novel insights, but there was a time when they were definitely news to me. ☺️ It was a pretty big shock to my system when I first became a software vendor and found myself sitting on the other side of the table, the freshly minted target of hostile questioning.

These days I am far less likely to be cited as an objective expert than I used to be. I see people on Hacker News dismissing me with the same scornful wave of the hand as I used to dismiss other vendors. Karma’s a bitch, as they say. What goes around comes around. 🥰

I used to get very bent out of shape by this. “You act like I only care because I’m trying to sell you something,” I would hotly protest, “but it’s exactly the opposite. I built something because I cared.” That may be true, but it doesn’t change the fact that vested interests can create blind spots, ones I might not even be aware of.

And that’s ok! My arguments/my solutions should be sturdy enough to withstand any disclosure of personal interest. ☺️

Some people are jerks; I can’t control that. But there are a few things I can do to acknowledge my biases up front, play fair, and just generally be the kind of vendor that I personally would be happy to work with.

Five easy ways to make yourself a vendor worth listening to

So I gave Abby a short list of a few things I do to try and signal that I am a trustworthy voice, a vendor worth listening to. (What do you think, did I miss anything?)

🌸 Lead with your bias.🌸
I always try to disclose my own vested interest up front, and sometimes I exaggerate for effect: “As a vendor, I’m contractually obligated to say this”, or “Take it for what you will, obviously I have religious convictions here”. Everyone has biases; I prefer to talk to people who are aware of theirs.

🌸 Avoid cheap shots.🌸
Try to engage with the most powerful arguments for your competitors’ solutions. Don’t waste your time against straw men or slam dunks; go up against whatever ideal scenarios or “steel man” arguments they would muster in their own favor. Comparing your strengths vs  their strengths results in a way more interesting, relevant and USEFUL discussion for all involved.

🌸 Be your own biggest critic.🌸
Be forthcoming about the flaws of your own solution. People love it when you are unafraid to list your own product’s shortcomings or where the competition shines, or describe the scenarios where other tools are genuinely superior or more cost-effective. It makes you look strong and confident, not weak.

What would you say about your own product as an engineer, or a customer? Say that.

🌸 You can still talk shit about software, just not your competitors‘ software. 🌸
I try not to gratuitously snipe at our competitors. It’s fine to speak at length about technical problems, differentiation and tradeoffs, and to address how specifically your product compares with theirs. But confine your shit talking to categories of software where you don’t have a personal conflict of interest.

Like, I’m not going to get on twitter and take a swipe at a monitoring vendor (anymore 😇), but I might say rude things about a language, a framework, or a database I have no stake in, if I’m feeling punchy. ☺️ (This particular gem of advice comes by way of Adam Jacob.)

🌸 Be generous with your expertise.🌸
If you have spent years going deep on one gnarly problem, you might very well know that problem and its solution space more thoroughly than almost anyone else in the world. Do you know how many people you can help with that kind of mastery?! A few minutes from you could potentially spare someone days or weeks of floundering. This is a gift few can give.

It feels good, and it’s a nice break from battering your head against unsolvable problems. Don’t restrict your help to paying customers, and, obviously, don’t give self-serving advice. Maybe they can’t buy/don’t need your solution today, but maybe someday they will.

In conclusion

There’s a time and place for being oppositional. Sometimes a vendor gets all high on their own supply, or starts making claims that aren’t just an “optimistic” spin on the facts but are provably untrue. If any vendor is operating in poor faith they deserve to to be corrected.

But it’s a shitty, self-limiting stance to take as a default. We are all here to build things, not tear things down. No one builds software alone. The code you write that defines your business is just the wee tippy top of a colossal iceberg of code written by other people — device drivers, libraries, databases, graphics cards, routers, emacs. All of this value was created by other people, yet we collectively benefit.

Think of how many gazillion lines of code are required for you to run just one AWS Lambda function! Think of how much cooperation and trust that represents. And think of all the deals that brokered that trust and established that value, compensating the makers and allowing them to keep building and improving the software we all rely on.

We build software together. Vendors exist to help you. We do what we do best, so you can spend your engineering cycles doing what you do best, working on your core product. Good sales deals don’t leave anyone feeling robbed or cheated, they leave both sides feeling happy and excited to collaborate.[4]

🐝💜Charity.

[1] Yes, I know this experience is far from universal; LOTS of people in tech have not felt like their voices are heard or their expertise acknowledged. This happens disproportionately to women and other under-represented groups, but it also happens to plenty of members of the dominant groups. It’s just a really common thing! However that has not really been my experience — or if it has, I haven’t noticed — nor Abby’s, as far as I’m aware.

[2] My first brush with columnar storage systems! Which is what makes Honeycomb possible today.

[3] I have learned SO MUCH from watching the world class sales professionals we have at Honeycomb. Sales is a tough gig, and doing it well involves many disciplines — empathy, creativity, business acumen, technical expertise, and so much more. Selling to software engineers in particular means you are often dealing with cocky little shits who think they could do your job with a few lines of code. On behalf of my fellow little shits engineers, I am sorry. 🙈

[4] Like our sales team says: “Never do a deal unless you’d do both sides of the deal.” I fucking love that.

Questionable Advice: “People Used To Take Me Seriously. Then I Became A Software Vendor”

Architects, Anti-Patterns, and Organizational Fuckery

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I recently wrote a twitter thread on the proper role of architects, or as I put it, tongue-in-cheek-ily, whether or not architect is a “bullshit role”.

It got a LOT of reactions (2.5 weeks later, the thread is still going!!), which I would sort into roughly three camps:

  1. “OMG this resonates; this matches my experiences working with architects SO MUCH”,
  2. “I’m an architect, and you’re not wrong”, and
  3. “I’m an architect and I hate you.”

Some of your responses (in all three categories!) were truly excellent and thought-provoking. THANK YOU — I learned a ton. I figured I should write up a longer, more readable, somewhat less bombastic version of my original thread, featuring some of my favorite responses.

Where I’m Coming From

Just to be clear, I don’t hate architects! Many of the most brilliant engineers I have ever met are architects.

Nor do I categorically believe that architects should not exist, especially after reading all of your replies. I received some interesting and compelling arguments for the architect role at larger enterprises, and I have no reason to believe they are not true.

Also, please note that I personally have never worked at a company with “architect” as a role. I have also never worked anywhere but Silicon Valley, or at any company larger than Facebook. My experiences are far from universal. I know this.

Let me get suuuuuper specific here about what I’m reacting to:

  • When I meet a new “architect”, they tend toward the extremes: either world class and amazing or useless and out of touch, with precious little middle ground.
  • When I am interviewing someone whose last job title was “architect”, they often come from long tenured positions, and their engineering skills are usually very, very rusty. They often have a lot of detailed expertise about how their last company worked, but not a lot of relevant, up-to-date experience.
  • Because of 👆, when I see “architect” on a job ladder, I tend to feel dubious about that org in a way I do not when I see “staff engineer” or “principal engineer” on the ladder.

What I have observed is that the architect role tends to be the locus of a whole mess of antipatterns and organizational fuckery. The role itself can also be one that does not set up the people who hold it for a successful career in the long run, if they are not careful. It can be a one-way street to being obsolete.

I think that a lot of companies are using some of their best, most brilliant senior engineers as glorified project manager/politicians to paper over a huge amount of organizational dysfunction, while bribing them with money and prestige, and that honestly makes me pretty angry. 😡

But title is not destiny. And if you are feeling mad because none of what I’ve written applies to you, then I’m not writing about you! Live long and prosper. 🖖

Architect Anti-patterns and fuckery

There is no one right way to structure your org and configure your titles, any more than there is any one right way to architect your systems and deploy your services. And there is an eternal tension between centralization and specialization, in roles as well as in systems.

Most of the pathologies associated with architects seem to flow from one of two originating causes:

  1. unbundling decision-making authority from responsibility for results, and
  2. design becoming too untethered from execution (the “Frank Gehry” syndrome)

But it’s only when being an architect brings more money and prestige than engineering that these problems really tend to solidify and become entrenched.

Skin In The Game

When that happens, you often run into the same fucking problem with architects and devs as we have traditionally seen with devs and ops. Only instead of “No, I can’t be on call or get woken up, my time is far too valuable, too busy writing important software”, the refrain is, “No, I can’t write software or review code, my time is far too valuable, I’m much too busy telling other people how to do their jobs.”

This is also why I think calling the role “architect” instead of “staff engineer” or “principal engineer” may itself be kind of an anti-pattern. A completely different title implies that it’s a completely different job, when what you really want, at least most of the time, is an engineer performing a slightly different (but substantially overlapping) set of functions as a senior engineer.

My core principle here is simple: only the people responsible for building software systems get to make decisions about how those systems get built. I can opine all I want on your architecture or ours, but if I’m not carrying a pager for you, you should probably just smile politely and move along.

Technical decisions should be ultimately be made by the people who have to live with the consequences. But good architects will listen to those people, and help co-create architectural decisions that take into account local, domain, and enterprise perspectives (a Katy Allred quote).

Architecture is a core engineering skill

When you make architecture “someone else’s problem” and scrap the expectation that it is a core skill, you get weaker engineers and worse systems.

Learning to see the forest as well as the trees, and factor in security, maintainability, data integrity and scale, performance, etc is a *critical* part of growing up as an engineer into senior roles.

The story of QA is relevant here. Once upon a time, every technical company had a QA department to test their code and ensure quality. Software engineers weren’t expected to write tests for their code — that was QA’s job. Eventually we realized that we wrote better software when engineers were held responsible for writing their own tests and testing their own code.

Developers howled and complained: they didn’t have time! they would never get anything built! But it gradually became clear that while it may take more time up front to write and test code, it saved immensely more time and pain in the longer run because the code got so much better and problems got found so much earlier.

It’s not like we got rid of QA  — QA departments still exist, especially in some industries, but they are more like consulting experts. They write test suites and test software, but more importantly they are a resource to make sure that everybody is writing good tests and shipping quality software.

This was long enough ago that most people writing code today probably don’t remember this. (It was mostly before my own time as well.) But you hear echoes of the same arguments today when engineers are complaining about having to be on call for their code, or write instrumentation and operate their code in production.

The point is not that every engineer has to do everything. It’s that there are elements of testing, operations, and architecture that every software engineer needs to know in order to write quality code — in order to not make mistakes that will cost you dearly down the line.

Specialists are not here to do the job for you, they’re to help you do the job better.

“Architect” Done Right

If you must have architects at all, I suggest:

  1. Grow your architects from within. The best high-level thinkers are the ones with a thorough grounding in the context and the particulars.
  2. Be clear about who gets to have opinions vs who gets to make decisions. Having architects who consult, educate, and support is terrific. Having “pigeon architects” who “swoop and poop” — er, make technical decisions for engineers to implement — is a recipe for resentment and weak architectures.
  3. Pay them the same as your staff or principal engineers, not dramatically more. Create an org structure that encourages pendulum swings between (eng, mgr, arch) roles, not one with major barriers in form of pay or level disparities.
  4. Consider adopting one of the following patterns, which do a decent job of evading the two main traps we described above.

If your architects don’t have the technical skills, street cred, or time to spend growing baby engineers into great engineers, or mentoring senior engineers in architecture, they are probably also crappy architects. (another Katy Allred quote)

The “Embedded Architect” (aka Staff+ Engineer)

The most reliable way I know to align architecture and engineering goals is for them to be done by the same team. When one team is responsible for designing, developing, maintaining, and operating a service, you tend to have short, tight, feedback loops that let you ship products and iterate swiftly.

Here is one useful measure of your system’s complexity and the overhead involved in making changes:

“How long does it take you to ship a one-character fix?”

There are many other measures, of course, but this is one of the most important. It gets to the heart of why so many engineers get fed up with working at big companies, where the overhead for change is SO high, and the threshold for having an impact is SO long and laborious.

The more teams have to be involved in designing, reviewing, and making changes, the slower you will grind. People seem to accept this as an inevitability of working in large and complex systems far more than I think they should.

Embedding architecture and operations expertise in every engineering team is a good way to show that these are skills and responsibilities we expect every engineer to develop.

This is the model that Facebook had. It is often paired with,

The “Architecture Group” of Practicing Engineers

Every company eventually needs a certain amount of standardization and coordination work. Sometimes this means building out a “Golden Path” of supported software for the organization. Sometimes this looks like a platform engineering team. Sometimes it looks like capacity planning years worth of hardware requirements across hundreds of teams.

I’ve seen this function fulfilled by super-senior engineers who come together informally to discuss upcoming projects at a very high level. I’ve seen it fulfilled by teams that are spun up by leadership to address a specific problem, then spun down again. I’ve seen it fulfilled by guilds and other formal meetings.

These conversations need to happen, absolutely no question about it. The question is whether it’s some people’s full time job, or one of many part-time roles played by your most senior engineers.

I’m more accustomed to the latter. Pro: it keeps the conversations grounded in reality. Con: engineers don’t have a lot of time to spend interfacing with other groups and doing “project management” or “stakeholder management”, which may be a sizable amount of work at some companies.

The “architect-engineer” pendulum

The architect-to-engineer pendulum seems like the only strategy short of embedded architects / shared ownership that seems likely to yield consistently good results, in my opinion.

The reasoning behind this is similar to the reasons for saying that engineering managers should probably spend some time doing hands-on work every few years. You need to be a pretty good engineer before you can be a good engineering manager or a good architect, and 5+ years after doing any hands-on work, you probably aren’t one anymore.

If you’re the type of architect that is part of an engineering team, partly responsible for a product, shipping code for that product, or on call for that product, this may not apply to you. But if you’re the type of architect that spends little if any time debugging/understanding or building the systems you architect, you should probably make a point of swinging back and forth every few years.

The “Time-Share Architect”

This one has aspects of both the “Architecture Working Group” and the “Architect-Engineer Pendulum”. It treats architecture is a job to be done, not a role to be occupied. Thinking of it like a “really extended pager rotation” is an interesting idea.

Somewhat relatedly — at Honeycomb, “lead engineer” is a title attached to a particular project, and refers to a set of actions and responsibilities for that project. It isn’t a title that’s attached to a particular person. Every engineer gets the opportunity to lead projects (if they want to), and everybody gets a break from doing the project management stuff from time to time. The beautiful thing about this is that everybody develops key leadership skills, instead of embodying them in a single person.

The important thing is that someone is performing the coordination activities, but the people building the system have final say on architecture decisions.

The “Advisor Architect”

I honestly have no problem with architects who are not seen as senior to, and do not have opinions overriding those of, the senior engineers who are building and maintaining the system.

Engineers who are making architectural decisions should consult lots of sources and get lots of opinions. If architects provide educated opinions and a high level view of the systems, and the engineers make use of their expertise, well  that’s fan fucking tastic.

If architects are handing them assignments, or overriding their technical decisions and walking off, leaving a mess behind … fuck that shit. That’s the opposite of empowerment and ownership.

The “skin in the game” rule of thumb still holds, though. The less an architect is exposed to the maintenance and operational consequences of decisions, the less sway their opinion should hold with the group. It doesn’t mean it doesn’t bring value. But the limitations of opinions at a distance should be made clear.

The Threat to Architects’ Careers

It’s super flattering to be told you are just too important, your time is too valuable for you to fritter it away on the mundane acts of debugging and reviewing PRs. (I know! It feels great!!!) But I don’t think it serves you well. Not you, or your team, your company, customers, or the tech itself.

And not *every* architect role falls into this trap. But there’s a definite correlation between orgs that stop calling you “engineers” and orgs that encourage (or outright expect) you to stop engineering at that level. In my experience.

But your credibility, your expertise, your moral authority to impose costs on the team are all grounded in your fluency and expertise with this codebase and this production system — and your willingness to shoulder those costs alongside them. (All the baby engineers want to grow up to be a principal engineer like this.)

But if you aren’t grounded in the tech, if you don’t share the burden, your direction is going to be received with some (or a LOT of) cynicism and resentment. Your technical work will also be lower quality.

Furthermore, you’re only hurting yourself in the long run. Some of the most useless people I’ve ever met were engineers who were “promoted” to architect many, many years ago, and have barely touched an editor or production shell since. They can’t get a job anywhere else, certainly not with comparable status or pay, and they know it. 🤒

They may know EVERYTHING about the company where they work, but those aren’t transferable skills. They have become a super highly paid project manager.

And as a result … they often become the single biggest obstacle to progress. They are just plain terrified of being automated out of a job. It is frustrating to work with, and heartbreaking to watch. 💔

Don’t become that sad architect. Be an engineer. Own your own code in production. This is the way.

Coda: On “Solutions Architects”

You might note that I didn’t include solutions architects in this thread. There is absolutely a real and vibrant use for architects who advise. The distinction in my mind is: who has the last word, the engineers or the architect? Good engineering teams will seek advice from all kinds of expert sources, be they managers or architects or vendors.

My complaint is only with “architects” who are perceived to be superior to, and are capable of overruling the judgments of, the engineering team.

Exceptions abound; the title is not the person. My observations do not obviate your existence as a skilled technologist.  You obviously know your own role better than I do. 🙃

charity

Architects, Anti-Patterns, and Organizational Fuckery

Deploys Are The ✨WRONG✨ Way To Change User Experience

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This piece was first published on the honeycomb.io blog on 2023-03-08.

….

I’m no stranger to ranting about deploys. But there’s one thing I haven’t sufficiently ranted about yet, which is this: Deploying software is a terrible, horrible, no good, very bad way to go about the process of changing user-facing code.

It sucks even if you have excellent, fast, fully automated deploys (which most of you do not). Relying on deploys to change user experience is a problem because it fundamentally confuses and scrambles up two very different actions: Deploys and releases.

Deploy

“Deploying” refers to the process of building, testing, and rolling out changes to your production software. Deploying should happen very often, ideally several times a day. Perhaps even triggered every time an engineer lands a change.

Everything we know about building and changing software safely points to the fact that speed is safety and smaller changes make for safer deploys. Every deploy should apply a small diff to your software, and deploys should generally be invisible to users (other than minor bug fixes).

Release

“Releasing” refers to the process of changing user experience in a meaningful way. This might mean anything from adding functionality to adding entire product lines. Most orgs have some concept of above or below the fold where this matters. For example, bug fixes and small requests can ship continuously, but larger changes call for a more involved process that could mean anything from release notes to coordinating a major press release.

A tale of cascading failures

Have you ever experienced anything like this?

Your company has been working on a major new piece of functionality for six months now. You have tested it extensively in staging and dev environments, even running load tests to simulate production. You have a marketing site ready to go live, and embargoed articles on TechCrunch and The New Stack that will be published at 10:00 a.m. PST. All you need to do now is time your deploy so the new product goes live at the same time.

It takes about three hours to do a full build, test, and deploy of your entire system. You’ve deployed as much as possible in advance, and you’ve already built and tested the artifacts, so all you have to do is a streamlined subset of the deploy process in the morning. You’ve gotten it down to just about an hour. You are paranoid, so you decide to start an hour early. So you kick off the deploy script at 8:00 a.m. PST… and sit there biting your nails, waiting for it to finish.

SHIT! 20 minutes through the deploy, there’s a random flaky SSH timeout that causes the whole thing to cancel and roll back. You realize that by running a non-standard subset of the deploy process, some of your error handling got bypassed. You frantically fix it and restart the whole process.

Your software finishes deploying at 9:30 a.m., 30 minutes before the embargoed articles go live. Visitors to your website might be confused in the meantime, but better to finish early than to finish late, right? 😬

Except… as 10:00 a.m. rolls around, and new users excitedly begin hitting your new service, you suddenly find that a path got mistyped, and many requests are returning 500. You hurriedly merge a fix and begin the whole 3-hour long build/test/deploy process from scratch. How embarrassing! 🙈

Deploys are a terrible way to change user experience

The build/release/deploy process generally has a lot of safeguards and checks baked in to make sure it completes correctly. But as a result…

  • It’s slow
  • It’s often flaky
  • It’s unreliable
  • It’s staggered
  • The process itself is untestable
  • It can be nearly impossible to time it right
  • It’s very all or nothing—the norm is to roll back completely upon any error
  • Fixing a single character mistake takes the same amount of time as doubling the feature set!

Changing user-visible behaviors and feature sets using the deploy process is a great way to get egg on your face. Because the process is built for distributing large code distributions or artifacts; user experience gets changed only as a side effect.

So how should you change user experience?

By using feature flags.

Feature flags: the solution to many of life’s software’s problems

You should deploy your code continuously throughout the day or week. But you should wrap any large, user-visible behavior changes behind a feature flag, so you can release that code by flipping a flag.

This enables you to develop safely without worrying about what your users see. It also means that turning a feature on and off no longer requires a diff, a code review, or a deploy. Changing user experience is no longer an engineering task at all.

Deploys are an engineering task, but releases can be done by product managers—even marketing teams. Instead of trying to calculate when to begin deploying by working backwards from 10:00 a.m., you simply flip the switch at 10:00 a.m.

Testing in production, progressive delivery

The benefits of decoupling deploys and releases extend far beyond timely launches. Feature flags are a critical tool for apostles of testing in production (spoiler alert: everybody tests in production, whether they admit it or not; good teams are aware of this and build tools to do it safely). You can use feature flags to do things like:

  • Enable the code for internal users only
  • Show it to a defined subset of alpha testers, or a randomized few
  • Slowly ramp up the percentage of users who see the new code gradually. This is super helpful when you aren’t sure how much load it will place on a backend component
  • Build a new feature, but only turning it on for a couple “early access” customers who are willing to deal with bugs
  • Make a perf improvement that should be bulletproof logically (and invisible to the end user), but safely. Roll it out flagged off, and do progressive delivery starting with users/customers/segments that are low risk if something’s fucked up
  • Doing something timezone-related in a batch process, and testing it out on New Zealand (small audience, timezone far away from your engineers in PST) first

Allowing beta testing, early adoption, etc. is a terrific way to prove out concepts, involve development partners, and have some customers feel special and extra engaged. And feature flags are a veritable Swiss Army Knife for practicing progressive delivery.

It becomes a downright superpower when combined with an observability tool (a real one that supports high cardinality, etc.), because you can:

  • Break down and group by flag name plus build id, user id, app id, etc.
  • Compare performance, behavior, or return code between identical requests with different flags enabled
  • For example, “requests to /export with flag “USE_CACHING” enabled are 3x slower than requests to /export without that flag, and 10% of them now return ‘402’”

It’s hard to emphasize enough just how powerful it is when you have the ability to break down by build ID and feature flag value and see exactly what the difference is between requests where a given flag is enabled vs. requests where it is not.

It’s very challenging to test in production safely without feature flags; the possibilities for doing so with them are endless. Feature flags are a scalpel, where deploys are a chainsaw. Both complement each other, and both have their place.

“But what about long-lived feature branches?”

Long-lived branches are the traditional way that teams develop features, and do so without deploying or releasing code to users. This is a familiar workflow to most developers.

But there is much to be said for continuously deploying code to production, even if you aren’t exposing new surface area to the world. There are lots of subterranean dependencies and interactions that you can test and validate all along.

There’s also something very psychologically different between working with branches. As one of our engineering directors, Jess Mink, says:

There’s something very different, stress and motivation-wise. It’s either, ‘my code is in a branch, or staging env. We’re releasing, I really hope it works, I’ll be up and watching the graphs and ready to respond,’ or ‘oh look! A development customer started using my code. This is so cool! Now we know what to fix, and oh look at the observability. I’ll fix that latency issue now and by the time we scale it up to everyone it’s a super quiet deploy.’

Which brings me to another related point. I know I just said that you should use feature flags for shipping user-facing stuff, but being able to fix things quickly makes you much more willing to ship smaller user-facing fixes. As our designer, Sarah Voegeli, said:

With frequent deploys, we feel a lot better about shipping user-facing changes via deploy (without necessarily needing a feature flag), because we know we can fix small issues and bugs easily in the next one. We’re much more willing to push something out with a deploy if we know we can fix it an hour or two later if there’s an issue.

Everything gets faster, which instills more confidence, which means everything gets faster. It’s an accelerating feedback loop at the heart of your sociotechnical system.

“Great idea, but this sounds like a huge project. Maybe next year.”

I think some people have the idea that this has to be a huge, heavyweight project that involves signing up for a SaaS, forking over a small fortune, and changing everything about the way they build software. While you can do that—and we’re big fans/users of LaunchDarkly in particular—you don’t have to, and you certainly don’t have to start there.

As Mike Terhar from our customer success team says, “When I build them in my own apps, it’s usually just something in a ‘configuration’ database table. You can make a config that can enable/disable, or set a scope by team, user, region, etc.”

You don’t have to get super fancy to decouple deploys from releases. You can start small. Eliminate some pain today.

In conclusion

Decoupling your deploys and releases frees your engineering teams to ship small changes continuously, instead of sitting on branches for a dangerous length of time. It empowers other teams to own their own roadmaps and move at their own pace. It is better, faster, safer, and more reliable than trying to use deploys to manage user-facing changes.

If you don’t have feature flags, you should embrace them. Do it today! 🌈

Deploys Are The ✨WRONG✨ Way To Change User Experience