I recently wrote an article on Effectiveness.  It could have easily been called Winning.  The opposite of winning is failure.  As I’ve said, the first step to effectiveness (winning) is awareness.  To that end,  I am going to enumerate many of the causes of failure that I have seen in action lately.  This is a perhaps exhausting, though not exhaustive, list.  There are many paths to failure–it is no surprise so much of it happens in the world.


  • Let’s jump straight to the root cause of a lot of failure: assholes.  These sociopaths destroy the trust and psychological safety necessary to foster a culture that enables extreme effectiveness. Unfortunately, they tend to rise to the top because they are good at looking good and making other people look bad. It’s all an illusion: they are a huge net loss in any organization.  Kill them with fire (figuratively, of course, as in fire them or get them fired if you can).  If your boss is an asshole, and you can’t get rid of him, look for another job.

bad culture

  • Beyond the assholes who create bad culture, the bad culture itself is the #1 cause of organizational failure.  You simply cannot organize effectively and run an effective process if the culture established by the leadership of your organization does not support it.

cognitive biases

  • Even if you are aware, your brain is messed up.  It has lots of blind spots.  You are predictably irrational.  One such blind spot is the fundamental attribution error.  Are these assholes intrinsically that way?  Or does the culture bring out the worst in them?  Well, I say if you are the CEO that creates the culture, and you are still an asshole, then you are intrinsically an asshole.  You need to be replaced.

morale failure, unhappiness, turnover

  • Abysmal leadership establishes a toxic culture that generates widespread unhappiness.  The unhappy workers (death-marched, micromanaged, underpaid, etc.) just try to mark time and get paid (all the while plotting their escape) rather than trying to win because they realize (after many futile attempts to fix it from below) that their context is irredeemably incompatible with winning.  Rome: Total War, Stronghold, and Civilization V/VI do justice to the power of this mechanic.

freeloaders, yes-men, sycophants, and other leeches

  • What’s worse than personally driving all the best people out of your company?  Not getting rid of all the freeloaders first.  You’ve just created a corporate welfare state.  But those guys never strive for improvement (raise troublesome, “negative” issues) or question your bad decisions (or do anything else of value for that matter), so it’s okay.

lack of empathy

  • Empathy is the key to listening which is a key to awareness which is a key to effectiveness.
  • Assholes do not have empathy.  They may feign it when their back is to the wall.
  • How much empathy should I have for assholes though?  Killing them with fire sounds extreme.  This is a difficult thing to consider.  It becomes the Baldur’s Gate Battle not with monsters lest ye become a monster” problem to some degree.

black and white thinking

  • Blanket statements like “assholes have no empathy” will probably not lead you to the nuanced distinctions in thinking necessary to solve difficult problems.
  • If you are practicing awareness, you should notice that many causes of failure (underbatching/overbatching, underplanning/overplanning, etc.) are just extreme versions of good concepts (batching, planning, etc.).  Often there is an optimal sweet spot in the middle that changes given context for any such vector of effectiveness.

making assumptions, thinking you are always right

  • You are not always right.  Other people do not think the same way you do.  Deal with it.
  • Even with a healthy dose of empathy, you are not a perfect mind reader nor are the people around you.  A lot of your assumptions are therefor wrong as are other people’s perceptions of you.  This means that often no one is actually aware: you are acting on faulty information and allowing others to act on faulty information.  Improve communication.

taking things personally

  • It’s becoming clear that failing is easy–the default state.  You, and a lot of people around you are failing constantly.  This causes many problems for you.  Generally, others aren’t even aware of the problems they are causing (lack of awareness being a huge part of the reason they are failing in the first place).  Taking it all personally, as if everyone is out to ruin you, is a mistake.  Take a page from the Taylor Swift playbook and shake it off.  You need a degree of kindness (linking this may have been unkind) and forgiveness for others as well as for yourself to even allow actual teamwork to happen.
  • However, this doesn’t imply being a timid doormat.  When you confirm conscious, repeated maliciousness (real asshole behavior), burn it down with fire.  If you can’t destroy the problem, use another page from the Taylor Swift playbook and just leave.  Then go back to being the nice, reasonable, patient person you are.

wielding golden hammers, shooting silver bullets

  • To a hammer, everything looks like a nail.  Unfortunately, everything is most certainly not a nail.  Use the right tool rightly for the right job.
  • There are no silver bullets.  Unfortunately, there is this thing called context, and it is always changing.  Try opening your eyes and actually aiming at the target.

multitasking, not limiting WIP

  • Just stop.  It does not work.  People who do this and organize their companies this way think they look good because they are so “busy, busy, busy”–the reality is, they are naïve, frantic, headless chickens who get nothing of value done.  They are “stupid, stupid, stupid.”  Being busy != being effective.
  • Any employee in an effective company should have exactly three tasks
    • Being a good corporate citizen.
    • One project that creates value for customers.
    • Improvements to the process used in the value creation project.

reinventing the wheel (badly)

  • A four-sided wheel will be simpler to maintain because it has less moving parts.  Also, round wheels are looking tired in fashion circles.
  • Rewriting your code base from scratch without extremely compelling reasons.

adding more people to a broken system

  • Adding more people to a late project generally just makes it later.
  • Having a child to save a broken marriage probably won’t work.

premature optimization

  • Optimizing without profiling.  Optimizing non-bottlenecks.

premature disambiguation

  • Trying to plan things in excessive detail up front. You have no idea what weather you will face or what roadblocks will actually occur.  Scrum is all about using JIT planning to avoid this path to failure.
  • Buying something you are ABSOLUTELY SURE you will use only to have it become another dust collector (like 90% of your possessions).  Marie Kondo is not happy with you!

failure to capture valuable information

  • This is an aspect of awareness.  GTD is all about “ubiquitous capture” to sidestep this path to failure.
  • If you have a great song idea and don’t record it right then, it will be lost forever.

doing things manually

  • Not having automated builds for your software project.

not having enough choices

  • A micromanaging boss taking away all your autonomy. This will destroy your motivation.

having too many choices

  • Which of the five billion varieties of cereal will you buy at the store? Or should you avoid carbs and not buy the cereal at all?  Should it be gluten free?  If you do buy it, should you use almond milk or regular milk? If regular milk, what fat % content?
  • Which of my 600+ Steam games should I play today, if any?

obsession with things that create no value
(yak shaving, bike shedding, productive procrastination)

  • You notice all the blades of grass on your lawn aren’t equal in length and you take out a pair of scissors and a laser caliper to remedy the situation.
  • Which of my 600+ Steam games should I play today, if any?  (Okay, yes, I do think there can be significant value in playing video games, but it can be taken to excess.)

inability to deliver value

  • You have 90% of 7 different projects done, but you can’t deliver anything to anybody.  You have produced no actual value.  You have completely failed.

inability to let go, clinginess

  • Sunk costs are irrelevant.
  • Dwelling on the past excessively is dangerous.

not having the basics down

inability to execute

  • My brother was recently injured. Although he had the awareness, motivation, and decisiveness to be effective, he lacked the ability to execute anything (let alone efficiently).  Recovering from such injuries, staying healthy, and avoiding future injuries are therefor a priority in remaining effective.

excessive pickiness, ridiculously high standards

  • A group of friends wants to go out to lunch. But you are only willing to eat free range Vermont broccoli (?) picked on Aug 2nd with a digitally signed certificate of authenticity.

low standards, low quality

  • You accept whatever garbage comes your way or whatever sloppy work you do without any standard of quality.  You are not early Simon Cowell.

defect rework costs, phase escapes

  • A bug you catch today might take you an hour to fix; three weeks later (when it has escaped into the production phase, and you can’t remember what you did way back then), it will take you, say,  24 hours to fix.
  • Letting a network hardware issue escape all the way into production can easily cause 1000x rework costs and kill a project completely.  This is why you should absolutely not in a million years let an intern lead your engineering department.

overprotection, coddling

  • Doing all of your child’s laundry until he/she goes off to college.

overprocessing, gold plating

  • The new accounting system passes user acceptance, but you spend another week making the gray GUI skinnable because you think that it “would be cool”.  The accountants like gray.  Don’t underestimate how much engineers tend to do this.


  • You do all your requirements gathering and analysis in excruciating detail for a multi-year project all up front.  As Jeff Sutherland says, “The map is not the trip.”

underbatching, excessive transaction costs

  • For each item on your grocery list, you make a separate trip to the grocery store.

excessive coordination costs

  • You try to go to lunch with 7 people.  It takes you the whole lunch hour to figure out where to go.  At least you’ll lose some weight today.

unavailability of tool, input, person, etc.

  • Time to go to the store.  Where did you put your car keys?
  • You need (?) a decision from your boss to move forward (because he set his blamethrower on maximum last time you took any initiative), but it takes him two weeks to get back to you.  Executive bottleneck is a form of organizational indecision, and is thus not effective.  This means authoritarian, command and control, fear and blame organizations are inherently suboptimal.  Unsurprisingly, assholes tend to run their companies this way because it optimizes for their own ego-driven sense of power and superiority rather than for value creation (organizational effectiveness).

things obtusely getting in the way

  • You are going down the aisle at Walmart, and yet another person has conveniently decided to orient their cart such that it blocks the entire aisle.  Their lack of awareness and greedy optimization has contributed to your failure.

interruptions, distractions, context switching, chain yanking

  • You work on one of the five projects assigned to you for a few days only to have your boss make you abandon it to deal with the emergency du jour.
  • Micromanaging assholes like to yank chains because it makes them feel powerful.

interface violation, no rule of law

  • You are the CEO.  You repeatedly take expensive things out of inventory without following the process you endorsed.  When confronted, you get angry and say “How dare you question me?  This is my company, and I’ll do whatever the hell I want.”  Guess what?  You are a giant bag of failure.  Give up.  You can’t lead water downhill.

disorganization, not knowing what you know, not having what you have

  • You go to find your notes on failure only to realize you do not know where they are!  They’re in Dropbox . . . somewhere.  And the CEO still has those expensive inventory items . . . somewhere.

moving in the wrong direction, ladder against the wrong wall

  • Before the days of Google Maps, my dad once drove an hour in the wrong direction while trying to drive to Florida.  My mom was asleep.  When she woke up and found out an extra two hours had been added to our trip, she FREAKED out (she has back issues, so the long trip was already pushing her limits).

faulty goals, unclear requirements

  • Your “goals” and “requirements” are just vague wishful thinking–more delusional visions.  They are not specific, measurable, actionable, realistic, or time-boxed (SMART).  They are not independent, negotiable, value-producing, estimable, small, and testable (INVEST).  The only course they chart is to the land of failure.


  • Assuming you deserve something just because you are something (beautiful, rich, a genius, the CEO, etc.), rather than because you do anything of value.
  • Being appointed to an organizational position that you are not qualified to be in just because you know someone in power.

ignorance, lack of awareness

  • If you don’t know the causes of failure, chances are you won’t avoid them.
  • Assholes who are not self-aware enough to know they are assholes.

lack of motivation

  • How did you read this far into my article?
  • Would you show up to work unless you were getting paid?


  • Indecision is the skeleton of someone who starved to death staring into a full refrigerator.

foolish aversion to risk, assuming outcomes imply past correctness of action

  • You shy away from +EV actions that even usually result in “failure” because your ego can’t handle the mere short-term appearance/pain of failure/loss.
  • You assume that because a course of action failed, it was a bad decision at the time you made the decision.  This is not necessarily true.  I call this the “hindsight is 50/50” fallacy.

foolish affinity to risk

  • While pushing your entire life savings all in with AA is +EV, it’s still dumb because your risk of falling below the financial death line is extremely high for that single transaction.

lack of discipline, entropy

  • Your natural inclination is to fail (unless your life goal really is to watch Netflix with a bag of chips all day).  This guy makes eating a single potato chip as epic as it can be though.


  • Showing up to your job one day out of the week is not enough.

unrealistic thinking

  • Hypernegativity (catastrophization).  Chicken Little.
  • Hyperpositivity (delusion).  Most CEOs.  They’ve gotta wear shades.

not prioritizing for value creation

  • Trying to not look lame instead of actually doing right by your customers.

lack of balance

  • Who’s up for another death march?

oversteering, overreaction

  • There is nothing so small that it cannot be blown out of all proportion, but that’s just the tip of the ice cube!
  • Often this is due to executive feedback bottlenecks inherent in command and control cultures (which are usually also fear and blame cultures).

goal inversion

  • A leader becomes more concerned with increasing his own power rather than performing the work he was given the power to do.
  • This is why we have presidential term limits in the USA.


  • I built a bird house once. A skyscraper is really just a giant bird house. I can build a skyscraper.
  • I wrote a Python script once in an hour. It was easy. I therefor estimate my team can build a scaleable SaaS enterprise app that seamlessly integrates with a dozen legacy systems for 10,000 concurrent users in two weeks max.  After all, they are experts.

virtual meta hyper-excessive over-complificationation analysis methodology

greedy optimization

  • If I commit this piece of shit code I wrote that I haven’t even tested once, I can call it done and go home for the day.  My coworker who depends on it to get his work done will have to clean up my mess, so I win, especially since I’m going on vacation next week.

lack of accountability, invisible costs

  • Allowing people to get away with their greedy optimizations.  This will lead to massive accumulation of technical debt.


2 thoughts on “Failure

  1. Pingback: Effectiveness | Software Development with Jeff

  2. Pingback: Scrum: The Role of the Development Team | Software Development with Jeff

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