Scope of this article

The 3 things almost every team does to meet deadlines that make things worse:
1. Hire more developers
2. Cut corners
3. Work long hours
Jason Gorman

I must admit, my deadline-missing expertise is fairly wide-ranging. But this piece is specifically about deadlines that arise when we undertake to develop software, and how you can do your level best to miss them.

Set deadlines

Don’t think too hard about whether they’re needed. When in doubt, set one.

Set deadlines unilaterally

Avoid taking input from the customer who depends on the outcome or the team trying to deliver it. Take your best guess and call it good.

Disagree on “deadline”

Some possible meanings of the word “deadline”:

  • If we miss, we go out of business
  • If we miss, our customer goes out of business
  • If we miss, my manager will blame me and/or I’ll be fired
  • If we miss, I’ll blame you and/or you’ll be fired
  • I don’t think you’ve been working hard enough lately

These meanings aren’t mutually exclusive. Several may be in play. To maximize the impact on nervousness and perceived pressure of these implied threats, your best move here is to keep things vague.

Disagree on “done”

”Done” is about completion. “Off my plate” is about avoidance.
Tim Ottinger

Some possible meanings of the word “done”:

  • Our customers have had it for weeks and haven’t noticed anything needing changing
  • Our customers just got it this second
  • Our customers could get it if they wanted
  • Our QA team is testing it
  • The code is feature-complete on a branch
  • It’s out of our hands
  • Nobody can blame us

Time wasted shuttling between various kinds of “done” is key. Avoid disambiguating. Use “done” to mean whatever’s convenient for it to mean right now.

Disagree on scope

Preconceive your own notions of what needs doing. Again, avoid taking input from your customer and your development team. Also, avoid letting them take input from each other. If they talk to each other regularly, you’ve got two problems:

  1. They might more directly understand each other’s needs
  2. They might find creative ways to meet their needs in less time

It’s mainly (2) you’re worried about here, for which (1) will put you at risk if you let it. Don’t let it. Get shallow agreement on a list of work items and don’t let anyone make you deviate from it.

Don’t have a customer (sort of)

If there’s definitively no customer, you’ve got big problems. Since nobody’ll be affected, there’s no harm in shipping whatever you’ve got right now.

Let me restate: With no customer, there’s nothing standing between you and deployment.

This constitutes an enormous impediment to your goal. What you need instead is a feeling of certainty that your customers exist, plus a lack of connection to any of them. Now you know there’s someone out there who’s supposed to be able to judge whether today’s product is better or worse for them than last week’s, and who can remind you every now and then why what you’re doing matters. Furthermore, your team knows that they can’t get direct answers to the most fundamental questions about their work, and that they can’t determine whether they’re doing anyone any good.

Well done! You’ve severed the most important feedback loop in their work.

Rate-limit deployments

If you’ve got customers and you talk to them — or, worse, the team is talking to them — all is not lost. You’ve got lots of options for making it difficult to get new code deployed:

  • Name an environment “production” without discussing uptime, reliability, or other aspects of service
  • Limit who has access to “production” systems (this also helps later, to complexicate debugging!)
  • Require several signoffs for each deployment
  • Provide as little information as possible to those responsible for signing off, so they waver, sometimes ask for more information, and occasionally exercise their veto powers
  • Make it just as difficult to roll back, which helps justify the elaborate signoff procedure

Now you’re considerably more likely to miss your deadline. If the team somehow manages to produce exactly what customers need, it’s going to take a while before they can get it. And otherwise, look how long it’ll take before customers can identify new needs, before the team can possibly hear about them, and before any work to address these needs can even begin!

Separate QA from Development

As part of your overall strategy, you need “QA” to be its own team and problem-identifying to be its own phase.

You want “Dev” working on their own, assuming QA will catch whatever they missed. You want QA working on their own, assuming Dev is following the most expedient path to claiming they’re done.

You want even the best-intentioned developer to say “done” as soon as possible and feel free of responsibility when it turns out not to be deployable. You want even the best-intentioned QA member to say “good enough” as soon as possible while finding a few unimportant bugs. You want Dev to be annoyed with QA when they find important problems, and you want QA to be annoyed with Dev when they repeatedly let important problems through.

This part of your strategy is very important. You slow down the work today by splitting it up, you slow down the work indefinitely by incentivizing placing blame over delivering value, and you make it very difficult to make predictable progress against the plan. At any given moment, it might look like you’re on target for a deadline when you’re really not. Perfect!

Separate Development from decision-making

If you’ve managed to keep your team from talking to the customer, good: they don’t know what you know about the business situation, so nobody but you is in a position to decide how the team should do its work.

You’ve heard Test-Driven Development takes longer because developers are also writing tests, and you’ve heard Pair Programming basically takes twice as long because two people are doing one person’s work, but you have the sneaking suspicion that pairing and TDD would save time by producing work output that’s frequently deployment-ready to begin with.

Can’t have that. What would happen to your standalone QA phase? What would happen if people’s attention were suddenly focused on your lengthy deployment signoff process?

Don’t let them pair or test-drive; above all, don’t let them make these choices themselves. Not on your watch. You’ve got deadlines to miss.

Keep code brittle

the only time we don’t change code is when there’s no existing code, a starting state that lasts about 10 minutes.
Michael D. “GeePaw” Hill

As a codebase grows, it tends to get harder to change. Because this stems from the number of components in interaction, the difficulty grows much faster than, say, lines of code. Great news! The odds are already stacked in your favor.

You still need to be careful. Besides Pair Programming and Test-Driven Development, you need to keep an eye out for the other Extreme Programming technical disciplines. Beware Refactoring, Continuous Integration, Collective Code Ownership, and the like. They tend to have the effect of greatly reducing the risk of changing code. That’s why the decisions to use these practices belong with you, so you can veto them. You need code-change risk as uncontrolled as possible.

Scope creep of this article

I said this article would only be about missing software deadlines. It seems like it could pretty easily be about a lot more. Also, if you’re a developer, I could give you lots more specific ideas for making deadlines whoosh by. But I’ve already missed my self-imposed Wednesday deadline for this week’s blog post. Like I said, I’m an expert on this topic.

This list is far from exhaustive, but I hope — from the bottom of my backlog — that I’ve helped you get started on more reliably missing your deadlines.

Posted Fri Nov 20 22:57:28 2015 Tags:

Similar, but different

Creating my podcast feels like debugging. After quite a bit of trial and error, not knowing how far I am from identifying and solving the problem, eventually and suddenly it’ll be working for me. It takes however long it takes, and then it’s a source-control commit message away from being done.

In the case of the podcast, there’s more to it than that. Besides recording — the fun part — there are a bunch of manual steps to post-process, encode, publish, and publicize. I’m annoyed by repetitive steps in general, and by these in particular, because they stand between me and a hard-earned adrenaline hit. That makes me slightly less happy to have finished another episode. Being able to push a figurative button (or run a literal program) would make me slightly more happy instead. I want that, and I’m getting closer.

I do recognize I’m optimizing away from the bottleneck, considering the script takes me hours to write. I’m not proud of that. If there were a faster, easier way to reach into my brain and pull out something of equal value, I’d do it in a second, or however many seconds it’d take. Meanwhile, I observe that, thus far, incremental value correlates roughly with incremental effort. As a lazy person I very much want to reduce effort, but as a perfectionist I very much don’t want to compromise value.



Or so it seemed, until I got to experiment with another way. Pillar has been making a series of short (3 minutes or less, usually) videos on various topics pertaining to our business, and our artist/producer Darrin Hoover came up to our Michigan office this week with his multimedia rig and a bagful of black crayons. I talked into the microphone on a couple technical topics I feel strongly about, Darrin drew some images directly or imaginatively related to what I said, we took some footage of me manipulating the drawings on or around my face, and that was that. What a change of pace! — the interactive collaboration with a creative partner who reflected and amplified my ideas, the video aspect, the being blessedly uninvolved in the production process.

Compared to my usual, this was similar, yet different. I came away reinvigorated about my usual. (I’ll share the two videos as soon as they’re up.)

Rate of flow

My podcast production has had no buffer (with one exception). Every week, if I’m to publish a new episode, that requires that I bring a new episode into existence. This needs to change, effective immediately, because the travel routine that has afforded my writing routine will come to an end in mid-December, to be followed by six weeks of deliberately routine-busting time off. So if I’m to continue shipping new episodes on schedule through the end of January, then for the next five weeks I need to be writing more than two new episodes per week.

That’s never felt possible before, but it feels possible now. For one thing, I’ve seized on a new sequence of topics that excites me (including this week’s Refactor). For another, if I’m smart, I’ll learn from Darrin’s fast, unfiltered creative process and tune my design for bringing you 3 valuable minutes.

Posted Thu Nov 12 20:55:42 2015 Tags:

What you’re looking at here is a razor-thin allegory about incremental improvement — why it can be hard to start, and why once started it can be easy to continue — in the guise of a story about improvements to this website.

I rang in 2015 by upgrading to a static site generator, hoping the switch would induce me to write more often. It has, but that’s its own story of incremental improvement.

Now that I’m making more and better use of my new, simplified setup, I’m motivated to seek further simplification. Unlike many other CMS-managed sites, this web page was neither brought into existence when you asked for it nor recalled from an application-level cache because someone else recently did so. This page already existed as a plain old file on disk before you asked, and it’ll continue to exist long after. It’s served slightly faster when it’s in the OS kernel’s filesystem cache, but it’s served plenty fast to begin with, because bringing it to you requires no application code to run — just webserver code. That’s why my next major improvement target is to stop needing Apache, a big featureful configurable complicated webserver. It’d be neat if the small, just-featureful-enough, and fairly simple bozohttpd bundled with NetBSD (my server OS of choice) sufficed to serve this site.

That’s a goal I couldn’t have seen from my previous traditional-CMS vantage point, and it’s still not a thing I can just go do. I feel pretty strongly about preserving URLs that have ever been published; if not for the featurefulness and configurability of Apache’s mod_rewrite, many of the URLs served under the old regime would have become broken under the new one. In order to convince myself I no longer need this handful of powerful URL-rewriting rules, I’ll need to convince myself the permanent HTTP redirects have had an impact by observing that old-regime links are hardly ever getting hit. And if that’s not the case, I’ll need to convince enough of the referrers with those old links to update them. Then, and only then, will switching webservers finally be within my incremental reach.

Another new-regime payoff I hoped for was that because making small improvements would be easier, I’d make more of them. That’s going well, too. Textpattern had generated imperfect URL slugs for some old posts, and that had always bothered me, but I’d never done anything about it. Last week I finally fixed them, committed the changes to source control, and added simple HTTP redirects (nothing bozohttpd can’t do) for the old URLs. While I was at it, since I discovered that “completionist” is more common usage than “completist”, I did the same for my recent post on reading Twitter like a madman. Ikiwiki lets me make changes across my entire site with familiar Unix tools — including git diff and git revert — rather than nerve-wracking, potentially-destructive-and-hard-to-restore-from database operations.

Since I feel safer about making changes, I act on a higher percentage of the little ideas that come to mind. On Monday, for instance, it occurred to me that since my posts have tags, and there are already autogenerated pages listing every post for each tag, I’d like to add a page with a cloud-like list of all the tags. With ikiwiki, it was really, really easy, so I did it. And once I’d done it and was inspecting the result, I noticed that some old posts needed more tags added. (Textpattern had no native tags, only categories, no more than two per post.) And since this is Unix, I could grep for files containing the keywords I wanted to tag, or find all the posts from 2014, pass them to my text editor for quick fixing, and git diff to double-check before publishing. So I followed the chain of affordances and did all these things. Exactly as I would not have bothered to in Textpattern.

Getting to where desirable improvements are available to be made in small increments can be difficult. It took me a couple weeks of disciplined effort to import my Textpattern site into ikiwiki in a way that I fully trusted. But once I got there, and improvements became easy to make and safe to try, it’s so rewarding to try them that I keep doing it.

One of these moons, before I know it and without making a concerted effort, flipping the switch to bozohttpd will be the next increment in front of me. And then, because I can just do it, I’ll just do it.

Posted Wed Nov 4 19:44:41 2015 Tags:

This week

Monday morning, in my regularly scheduled stupid-early cab to the airport, I reflected on where I’ve come from (besides being home, in bed, asleep, like a normal person) and where I’m going:

6 years ago today, I came back to software development. To relearn old tricks, uncover new ones, and enjoy. Headed to #agiledc to celebrate.

My celebration got off to a proper start when I didn’t miss James Grenning’s good-naturedly trenchant keynote, during which my still sleepy brain perked up at the mention of my colleague Erik Dietrich, in particular his How Developers Stop Learning: Rise of the Expert Beginner. For one thing, it induced a beperkifying spike of writerly ambition. Maybe, if I keep publishing something every week, I’ll eventually learn how to have written something worth being referred to by a respected keynoter. (Erik landed one of the guys who wrote the Agile Manifesto. Achievement unlocked.)

For another thing, hearing a familiar name put me in the right frame of mind to enjoy AgileDC in what is, for me, a whole new way of enjoying conferences. When I was an introverted outsider knocking on the door to this small, tight-knit community of human-loving, business-advancing Agilists, the primary way I felt I could extract value at conferences was to attend talks and workshops of interest. Now that I’m working in the field and getting to know some of the wonderfully generous and skilled folks in it, I spent most of my day in the “hallway track” I’d heard so much about. It was great. We conferred. I heard some terrific stories of personal growth interspersed with perfectly obnoxious jokes. And I saw some people I’d seen just last week.

Last week

Several of us June 2015 PSL participants schemed to hold a mini-reunion at the Toronto Agile Conference. Some were based in Toronto, and others got their talks accepted, so I accepted the need to get myself there from Detroit. I drove up Monday afternevening and joined a bunch of the already-fed speakers at a bar on a high floor overlooking downtown. (Toronto is for real. I want to visit again for real.) Almost everyone who was there I’d heard of, maybe Twinteracted with, but never met in person. I wasn’t a speaker; there was no need for them to have invited me along; and once again I found myself feeling, as I’ve been feeling so often lately, the generosity and inclusiveness of this community I’m getting to know.

Next year

Some of the folks I met in Toronto and D.C. have been invited to present at a new Agile Alliance Technical Conference being held in April 2016. What’s a little mind-boggling, considering what little I was doing a year ago, is that I’ve been invited too. And I’ll also be reviewing submissions for the Agile 2016 Leadership track.

Right now

There’s no way I can take in the pace of what’s happening for me and not see the pattern of generosity and inclusiveness. There’s no way I can not feel immense gratitude for all the people who’ve helped me find my new path and make my way along it.

I see it. I feel it. Thank you.

Posted Wed Oct 28 22:46:51 2015 Tags:

The power of associative memory

On Sundays, we’ve been taking the dog to one of the many forests of southern Indiana and going for a nice long walk. Conveniently, by the time we’re done, the sorry-ass Bears games I want to avoid watching have usually ended.

Haskell being done at Brown County State Park

Last weekend, as we drove home through a town named Trevlac, I remarked that that didn’t look like a word, but that backwards it’s Calvert, which does. My intuition about language and its constituent parts, developed over a lifetime of playful friendship, was validated by Wikipedia’s entry for Trevlac, Indiana. Bekki observed that when I perceive words and piles thereof, I’m also perceiving a “gestalt”, because the ways I comprehend, manipulate, and generate language are largely visual. For instance, when I hear words, I see them. When I’m fishing for a particular word, I often remember nothing about it besides how many letters I think it contains; while I’m almost always right, that rarely helps me find the word in any way I’m aware of. Maybe it narrows the search space in some way I’m not aware of.

I looked up Gestalt on Wikipedia to see whether the term made any more sense since I last tried to understand it.

If Haskell had anything to say about any of this, we couldn’t hear him with his head out the window. The last street he and I gazed upon before leaving Trevlac was named “Rogers.” I don’t know what he thought about that, but my associative memory was primed to bring me straight to Carl.


Carl Rogers was a psychologist, a student and teacher of human behavior. Bekki had somehow not encountered him in her studies of social learning behavior in animals (people not excluded). And my recollection of his approach was fuzzy. I pulled up Wikipedia’s Carl Rogers page and reviewed his 19 propositions, among other things. For the most part, what we heard lined up nicely with our own views.

Why had I heard of him?

I don’t know exactly, only approximately.

After spending much of my software development career indulging my introvert tendencies as a programmer, I became aware that the limiting factor in my effectiveness was not my ability to write code — and not because I’m such a gifted programmer. (This came up in conversation with Bryan Beecham and Ryan Ripley on Agile for Humans 019.) To grow as a person and become more effective in the workplace, I found that I needed to acquire skill at caring for people. In my consulting, coaching, podcasting, speaking, and writing, I’m always looking to acquire more skill at caring effectively.

It had been suggested to me, earlier in life, that I consider a career as a therapist. The suggestion had usually been intended as a compliment, and sometimes also as an idea to be considered seriously, but my immediate reaction to the prospect of making that kind of emotional effort all day every day was to cringe. How could I possibly have any love left to give when I got home? I tried to accept the compliment, but couldn’t see how to accept the suggestion. Yet here I am, years later, having found a context in which I could accept it. When I became a consultant and coach, I decided that someday, when I’m prepared to live up to the title, my business cards (if we’re still using those) will read “Corporate Therapist.”

In my exhaustive consumption of material from Twitter and elsewhere, I was pleased to discover that my self-imagining wasn’t original. Bob Marshall has billed himself as an Organizational Psychotherapist. So he’s long been one of the folks I try to read most exhaustively. When he expresses a sentiment, I try to make my own sense of it; when he points at a source, I look at it more closely. Another of the people I’ve learned most from following is Alex Harms. Maybe they, or others, are how I rediscovered Rogers.

But I’d heard of him before, too. Not sure how.

What more do I need to know?

Thanks to Bekki, I made my entrance into software development coaching with a highly useful frame of mind that averted my immediately doing terribly. (This came up in conversation with George Dinwiddie on Agile for Humans 002.) What luck for me! Career-wise, too, I mean.

Where I am now: having a somewhat better-developed intuition about how people operate themselves, based in part on extrapolation from how I operate myself, and in part on some basic mental models I’ve long since internalized. (I don’t really know which and from where. Rogers might say I’ve introjected them.)

Where I want to be: training to become a corporate therapist. Further developing my intuition about how people operate themselves, and about how organizations of people can adapt themselves to become more adaptive. Greatly expanding my map of the vast territory before me.

What I need to learn, then, is this: much, much more about human behavior.

Posted Thu Oct 22 19:37:20 2015 Tags: