How should deadlines be used in software engineering?

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Photo by #WOCinTech

How many conversations have you had about deadlines where at least one person scoffed at the concept? Pfft!

I have heard this a number of times — including from myself — and I want to fix this.

The world of software is very different from the world of print media, where our current concept of deadlines is derived. However, just because there can be no universal definition of deadlines across all software projects doesn’t mean we shouldn’t use them or that they aren’t valuable.

Deadlines are extremely important for planning and parallelizing work. Without expectations about when dependent work will be completed, all teams would have to work in serial. This would drastically slow down delivery times.

At the same time, deadlines can be frustrating and counter-productive if people disagree about what they actually mean.

Problems and solutions

In my experience, these are the most pertinent problems with deadlines in engineering organizations, and the most promising ideas for how to solve them.

1) They are interpreted differently from person to person.

Person A: “The deadline is next week so I’m pulling a ton of extra hours.”

Person B: “Why? It’s a fake deadline and doesn’t matter.”

Person A: “But I don’t want to get fired!”

This shows that a deadline means vastly different things to Person A and Person B. This can lead to confusion and frustration on the team working towards that deadline.

Instead, deadlines need to be a rallying point. Everyone needs to understand why this deadline is important. They need to know what impact missing the deadline has on their world (that can be other teams, customers, or the business as a whole).

More importantly, deadlines that are met need to be celebrated. Wildly. This is often overlooked. Building a culture around celebration for meeting deadlines is a much better practice than berating people for missing them.

2) They are used too early in a project life cycle.

Person A: “Hey we need to accomplish [insert_really_hard_unknown_thing]. When can we have that done by?”

Person B: [quickly wikipedia’ing what that thing even is] “uhhhhh, I don’t know.”

Person A: “I need a timeline!”

Person B: “Thre–FOUR! mmmmo-wee-months. Four. Months.”

Person A: “Great, see you in four months.”

Asking for a deadline when EVERY aspect of a project is unknown is a recipe for disaster. It’s stressful for everyone involved and sets the project up for failure. So let’s take a deep breath. Wait a few days for some exploration to be done. We will be spending time to buy information, but then we can come up with a meaningful estimation of the work. This information will help us set deadlines that have a better chance of being accurate.

3) They aren’t updated often enough.

Person A: “Hey, deadline is in 5 days. Are we still on track?”

Person B: “We’re a little behind but yeah, we can make it.”

Person A: “Great!”

[ 4 days, 23 hours later ]

Person A: “Just checking back on that project. We good to go?”

Person B: “Uhm, no we’re not gonna make it. Something came up. It looks like another week of work.”

Person A: “$%@!*”

In this case, the deadline wasn’t moved or re-evaluated when new issues became known. Instead of raising that flag immediately, Person B waited until the deadline itself to inform others. Now Person A is affected as well AND the team gets to feel the stress of coming up on yet another deadline in the future.

Deadlines shouldn’t be set to force humans to do inhuman amounts of work. They should be used to set expectations externally and enable a sense of predictability for planning. They need to reflect reality as accurately as possible or trust is lost and they can no longer deliver that predictability. Now, I’m not advocating for changing deadlines hourly or daily. But perhaps weekly, or at the very least within a standard planning cadence.

Updating a deadline isn’t limited to extending the date. Scope reduction is also an option. Choosing which action to take (or a combination) is a conversation the engineering and product teams need to have.

4) All the “knowns” aren’t taken into account… just the fun ones.

Person A: “How long to ship this feature?”

Person B: “Two weeks.”

[ two weeks later ]

Person A: “Why isn’t this done?”

Person B: “Well, it technically IS done. Now we’re working on testing it, building a new deployment mechanism for it, and we’re gonna roll out a beta first. Also, I was on vacation last week.”

This deadline was made without a complete understanding of the work to be done, and the time to dedicate to it. (not to mention Person B also threw problem #3 into the mix.)

We need to make sure we take all known challenges into consideration when determining a deadline. Will we be losing person-hours to a known cause? Vacation? Company offsite? Birthday party which will cause missed mornings due to hangovers?

Also, what un-sexy tasks are we potentially forgetting about? How many tests are we gonna write for this? How do we get this sucker into a production environment? Slow down and think thoughtfully about your process and the availability of resources. It’ll make your deadlines much easier to deliver against AND it will make deadlines easier to defend against scrutiny.

On estimation: uncomfortable but necessary

Deadlines that are set by engineering teams will largely be informed by estimating work. That means that everyone on the team is going to have to get comfortable with being wrong. A lot. Saying anything that you know to be wrong and have little confidence in can be a very difficult thing to do.

We need to have a collective understanding that it’s our best guess and that we’ll get better at it over time. Estimation is a skill that gets better with repeated use. In the early stages, it’s going to feel uncomfortable, but we need to do it.

Estimating tasks

Before we can define the delivery date of a large project, we should break the project down into tasks, where tasks are defined as things we believe we can accomplish in roughly 5 workdays or less.

Some helpful questions to ask when estimating a task:

  • Is the project green field or in a pre-existing area?
  • What is the quality of code in that area?
  • How well do I know the area of code?
  • How familiar am I with the programming languages involved?
  • What touchpoints or integration points with other pieces of code are there?
  • How good is existing test coverage?
  • Does this work touch any business-critical areas? (write path, billing, load balancers, signups)
  • Has anyone done this work before? What are their thoughts?
  • What are the tradeoffs I am making?
  • What is the objective of this task?
  • Does this task need to be done at all?

Estimating projects

Projects are typically defined as a larger body of work that multiple people can work on in parallel.

Some helpful questions to ask when estimating a project:

  • How much time will we actually be dedicating to working on it?
  • What is the objective of the project?
  • Do we have any known days off?
  • What are ALL the tasks required to be done?
  • Do we have any blocking dependencies on other teams?
  • Are any tasks blocking other tasks in the project?
  • Is any new infrastructure/hardware required for this project?
  • What are the Doneness Criteria for this project?

Doneness criteria

Even knowing when something is done is difficult. Different roles within the team can have different perspectives on “done” so we need to have specific criteria that can determine what that means for the project.

Some examples of typical Doneness Criteria:

  • Deployed in production
  • Tests fully automated
  • Communicated internally or externally
  • Spent a certain amount of time in an internal or external pilot
  • Documentation in production
  • Education of sales or marketing team complete
  • Landing page launched
  • Analytics and tracking
  • Operational runbook and observability


Deliverability is essential to any company as it grows and matures. Deadlines are a major tool in the toolbelt. When used properly, they are incredibly useful. But it takes time and practice to get better at using deadlines. So, I suggest that engineering organizations treat them as alive and breathing, continue to learn about them, and document shared experiences internally and with the engineering community.

If you have any tips or suggestions on using deadlines effectively, we’d love to hear them. You can drop me a line at or ping us on Slack

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SxSW Field Report, Day 1: Arrival / Destruction


There is simply no way on this earth I could’ve written this field report last night. Or, I mean, I could have done, but it probably would’ve been a 15,000 word treatise on the merits of Austin’s Deep Eddy grapefruit-infused vodka (which is pretty amazing, btw, but certainly feels a bit less so this morning), followed by the letter h 400 times. hhhhhhhhhhhhhhhhhhhhhhh

My point is, I made a judgment call, and I believe it was in your favor. OK, let’s go.


I think I made a joke in my first field report about how I was going to write an essay at some point about why birds exist. Well, let me answer that for you right now: Torment and destruction.

I am on the roof of our beautiful AirBnb right now, and I would just like to quietly and miserably plow through this field report, so that I can crawl back under the bathroom cabinets and hide there in peace, but there are these monstrous birds making just the absolute worst cacophony of peeps.

I mean, admittedly, I am not in the best state for any noises, so even normal, happy bird sounds feel like nails on a chalkboard right now (I keep protectively hunching down like the sounds might wound me), but I should also say that these are not normal, happy birds. These are GRACKLES.

Grackles (which is one of those perfect, hilarious-sounding names for something horrible — much like brambles), if you’ve never heard them, sound like a regular old bird maybe ate an 8-bit Nintendo, a faulty one, and now they just go around making these insane beepy explosion monster sounds.

Dustin Larimer and I spent the night in the RV, and we were absolutely cracking up at the massive ruckus these little monsters were creating, all rattling around in the bushes doing the music from the Chip & Dale Rescue Rangers NES game. (Here is that what sounds like, by the way, but you should under no circumstances go there if you are reading this as hungover as I am writing it.) Then we actually started watching a bunch of grackle YouTube videos (which are all terrible, by the way — maybe learn how to edit your damn grackle videos, people!)

Anyway, I just wrote an awful lot about grackles, so a) maybe I actually love them? and b) sorry I just did that? I maaaay be a little too stream-of-conscioius-y this morning. Let’s talk about something that’s not birds, shall we?


Not last night, the one before, I slept in the RV as well, because the hotel was a little crowded, and I am uncomfortable with human closeness.

It was pretty cold and stuff, which wasn’t great, but the shittier part happened when I woke up to go to the bathroom at 3 am and found I had no idea how to use the toilet.

Recreational vehicles have pretty much all the amenities of a home, but (naturally) there is a somewhat more involved process in using any of them. So, like, to use the toilet, you have to turn on some switches and pull and push a lever, and probably a few other things. It’s not complicated, exactly, but it’s also not the sort of thing you can intuit your way through all groggy and hungover at 4am while doing a pee-pee dance.

So, I had to go find the manual for the toilet, which sounds like a silly concept until you need it, and then you are thanking your lucky stars for whatever blessed, miserable copywriter had to write that thing up 17 years ago.

OK, I swear I am getting to Sx. I can feel it. We’re getting close.


I took 1 and a half sips and threw that garbage out.

I am not precisely sure what sorghum is, but I am positive I could taste it.

At least with a Shamrock Shake, you know you’re in for some trash. I was hoping for a nice little coffee beverage, not a caramel-flavored PlayDoh tube being squirted into my mouth. 1 star.


Yesterday I reported the dire need to give our glorious apartment on wheels a suitable moniker. I suggested Janet — to which Becky, like, immediately replied back, “ANYTHING BUT JANET.” So, say hello to our friend Not Janet. She is like a friendly whale, and I sleep in her belly.


Note that, despite the obvious temptation, I am not saying “‘Murica” here, because that is a lazy non-joke, and we are better than that.


Was pretty uneventful, to which I give full credit to the stable hands of our two amazing helmsmen, Tim Falls and Justin Johnson. I mostly lied in the little pirate bunk above the cockpit and tried to get a final bit of sleep in before The Reckoning. I used my shoe as a pillow, and only nearly rolled off once. Drool level: medium. 4 stars.


Phone people, phone people, phone people, phone people…


Yesterday I joked about our drunk-dialing AirBnb host, but that guy is rad, and he set us up. Beautiful place. Full bar of amazing, quasi-obscure, top-shelf stuff. A fridge full of drinks and treats. He even managed to track me down an iron, because I am a weirdo and iron my shirt literally every. single. day.

Listen, y’all, even if I’m puking next to a dumpster, I want to look fully-pressed and professional, OK? (I did not puke near a dumpster. That one was a joke.)


Listen, I love SF, and over the past 2 years, I have definitely come to think of it as home. But I don’t have the vehement level of enthusiasm that some people do for San Francisco.

Like, back when I used to use OK Cupid, I would say at least a full third of everyone’s profiles began with something about their intense love of SF or pride in their identity as a San Franciscan. Which, wonderful! Good on you for finding your place! But I’m not quite there yet with SF.

Austin, though. Hm.

I am not sure what it is, but we just click, Austin and I. It always feels hot and dark here even when it isn’t (that doesn’t make any sense, sorry), and it’s forward-thinking and inventive but still manages to hold on to some of the good, fun, gritty, twangy Texas parts. Also, the music scene is just astounding. My first time here as an adult, I was waiting for a friend to meet me, so I just poked into this random bar for a beer, and these amazing women called The Whiskey Sisters were doing a sound check and did this twanged-up version of “Like A Virgin” that was like the best thing I’ve ever heard in my life.

So, yeah, Austin.

It is on my bucket list to live here one day, so that then I can be the one complaining about all these tech money hacks taking over my city and stuff. (Sorry, by the way! We’ll be gone soon, and we’ll try not to make too many messes!)


Harmony isn’t one of my Top 5 StrengthsFinder strengths, but it’s pretty high up there. And I have definitely been sensing some animosity from the local Austinians (Austinites? Austrians? Argonauts?) about the tech invasion for Sx. So my question for the locals is this: What can we do to be less bothersome? As I said, I love it here, and I would like nothing more than to be a gracious guest. Anything we can do to endear ourselves to you? Besides, you know, FOAD?

I talked to this one bartender about this, and he said the main thing that annoys him is that, because our schedules aren’t exactly packed out here, he tends to see a lot of us standing around, doing poses and trying to look cool? Which, if that is the case, god, I’d hate us, too.

No posing, you guys. I feel like that one is a gimme. I know we nerds are finally having our heyday and stuff, but let’s keep a level head about it and not, like, artfully blow e-cigarette smoke in a slow arc as we regard the sunset. None of that please.


TF and JJ both just woke up, and told us that, after a full night of partying and meeting people, the only business card either of them had — actually, they both had it — was for the local weed club. Solid community outreach, fellows.


Yeah, sorry I am the guy who’s always ruining things, but listen: I met a friend for a drink last night at this new tiki bar here called Isla, and that place is both incredibly solid and, at the moment, disproportionately unpopulated. I was there around 6, and the place was mostly dead, whereas anything along Congress was just swarming with humans.

Anyway, the place is adorable, and the drinks are outstanding. It’s tiki stuff, but it’s not cloyingly sweet like island drinks can sometimes be. There is good balance there. Also, this is the most aesthetically perfect drink I’ve ever seen in my life:


Sorry I don’t take many photos, by the way. I’m a writer, not a photographer. I create pictures with worddddsssssssss.


It is an astounding skill. After Isla, my friend got us into two parties with live music and open bars and free food just by talking fast and acting confident and vaguely indicating she might know someone of importance at the company who was hosting them. It doesn’t sound that hard on paper, but, left to my own devices, I am pretty sure I would’ve just started nervous puking and weeping. Confidence, man. It is a super power.


We have capes! Which, OK, admittedly, I am a little too embarrassed to wear in public, but good for anyone who can!


(Side note to our designer, Micah Wolfe: Micah, do not look too closely at the colors used on the logo. They are all wrong, but it seems we went for glitter over brand cohesion, and I regret very little with regards to glitter.)

Apparently people kept asking us what our super powers are, which turns out is a pretty fun improv game. My answers, in order:

  • lead into gold
  • horses into gold
  • immortal life
  • giving ghosts restored bodies
  • frag trolls
  • trolls into gold
  • etc.


Which, not to brag (and I shouldn’t, because the Photoshop work is fairly atrocious), but I made them!


Backstory: I came stumbling into the Keen office a couple weeks ago, hazy and exhausted from the aftermath of our 2-day writeathon. Justin and Tim pulled me aside — “Hey, man, Josh had an idea for a t-shirt for Sx. Can you help us Photoshop it?” A blurry eyed-zombie, I grabbed a white board pen and said, “OK, talk me through it.”

“So, it’s a cat.” I draw a cat face.

“A cat professor.” I add a graduation cap, because I don’t really know what professors are.

“And he’s pointing at a bar chart made of bacon.” Yep. Got it.

“Next to a donut pie chart.” Done.

Now, at the time, I was running on like 2 hours of sleep, so I thought it might have been on me that this seemed like a totally fucking demented idea. A couple days later, though, when I consulted my notes and the photo I’d taken of my drawing, I was able to safely confirm that I was not the crazy one here. But, that certainly didn’t stop me from taking like 6 hours to make it.

Feedback has been pretty positive on them, though, it sounds like — except for Micah again, I imagine, who is probably drinking poison so as to not have to look at them any longer. Sorry about my skills, Micah! Sorry this is all I can do!

Hopefully we can have some of these shirts made for all y’all, too, so you can look as cool as we do. >_<


After the two parties we conned our way into (which I will talk about in a future post, because I certainly have Thoughts, but I imagine I am already trying your patience, word-count-wise), I caught back up with my fellow Keenies, who were still in East Austin and hadn’t made it past the second bar, which I found kind of hilarious.

I’m only just getting to know our Eric, Keen’s most recent Canadian acquisition, but apparently so far I have made a horrible impression by having been the only one so far to keep suggesting taking group shots together. This is a horrible, inaccurate framework.

I don’t even like shots, man. My body can’t really do ’em. Like, the whole point of shots, right, is to bypass the TSA in your mouth and get the alcohol straight to your belly. Except the way I do them, the shots hits the back of my throat, and my throat’s all like, “Um, NOPE. Exactly what in the hell are you trying to pull here, kid?” and then sends it back to my mouth for closer inspection. And upon inspection, yes, it does appear to be warm, low-grade tequila. Spit. Barf. Death.

Anyway, thankfully, Alexa has now taken the title from me, forcing tequila shots on us no less than 3 times in an hour. It is your fault I feel this way, Alexa. This is on you.


End of story.


Writing these, I mean. And not just finding the time and energy to do them, although that, too. I mean writing these quickly and not always clearheadedly, and (hopefully) making them fun and funny and authentic, but also making sure I don’t say something totally stupid or hurt people’s feelings because I didn’t think something all the way through. I mean walking that fine line been sassy and mean, and irreverent and inappropriate. Punching up at big chain restaurants for serving unhealthy food, and not punching down at the people who eat there. That sort of thing. And it is tricky.

This is not to make excuses. This is just to say that I know I am going to fail a little bit on each of these entries, and that is utterly terrifying. In all honesty, it’s a huge reason I’ve always been kind of reluctant to share my work with a wider audience — in the back of my head, I know that, pretty much no matter how careful I am about choosing my words or considering who’ll be reading my work, at some point, there are things I’m going to miss, and mistakes I’m going to make, and audiences I am going to marginalize or offend, and oh my god that is horrifying. That is the last thing I want to do. I mostly just want to make people laugh and enjoy themselves and maybe, MAYBE think about something new.

Because of this fear, though, I’ve mostly kept my work to myself, or to a group of close friends who know me, because it’s safe, and they are already familiar with my faults, and more or less forgive me them. But, doing that is also pretty cautious and limiting and yeah probably kind of cowardly.

So, I’m glad I’m taking this chance to write to a wider audience. Yeah, doing it is scary, and my inevitable failures will be shameful and disappointing, but, like, how the hell else am I going to get better? You can only learn so much in a vacuum — to start filling in my blind spots and growing as a writer, I have to present my work to the larger community and hear back from you, good and bad.

So, as I mentioned in my first post, please please get in touch if anything I say here bugs you — even if it’s just a passing flutter of annoyance. I would so much rather know than not, and hopefully over time, these mistakes will get fewer and fewer. Thank you for your patience, and for the opportunity.

OK, I am still on the roof, and I’ve had to keep moving to avoid the shifting gaze of the hateful, hateful sun, but I am pretty much out of room now, so let’s just call it. See you out there, I hope.