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Here's the dangerous way I put it that I only tell senior people: understand why rules were made and make sure the people who made them would be happy.

As a supervisor I didn’t resonate with this until I remembered in some jobs I have communicated the company attendance policy but didn’t enforce it unless someone was a poor performer. I trust adults to manage their own time until they give me a reason to believe otherwise.

For my part, I’d rather trust people’s judgment and intrinsic motivation than enforce the rules. Enforcement is annoying, tedious, and distracting to my mission. However once I decide their judgement can’t be trusted I use rules to extrinsically motivate them.

So I'm fascinated with military culture and how systems work on this scale (ie millions of employees). And one interesting aspect is the E4 Mafia [1].

For those that don't know, you're generally either a commissioned officer (with ranks from 0-1 and up) or enlisted (E-1 to E-9). Some branches have warrant officers too but let's ignore that.

So if you join as an enlisted you start off as a private in the Army (it's called something else in different branches). By the time you finish bootcamp you're an E-2 private, possibly an E-3 (Private First Class). If you're not an E-3 it's automatic promotion after ~6 months assumpting you don't have any red flags AFAIK.

By the time you make it to E-4 (Corporal in the Army) you kinda know how things work BUT you're also in the last rank before you're in a leadership position. The next position (E-5, Sergeant in the Army) is a noncomissioned officer ("NCO"). Some people want to avoid that so they kinda hang around E-4 far longer than they should and they build up a body of knowledge on how to get things done. Or they may have been a higher rank and get busted down from an Article 15 (or NJP or whatever the specific branch calls it).

Requisitions can be a huge issue in the military, evne for simple things like office supplies. So you may find that E-4s can "acquire" needed supplies from other units. NCOs, Staff NCOs and command tend to be aware of it but will ignore it because it kinda needs to happen. And those E-4s are called the "E4 Mafia".

This, I believe, is the kind of "rule breaker" this post is referring to.

[1]: https://www.youtube.com/watch?v=SEgh-w4FIFc

In any large organization, there are basically two classes of rules: 1) stupid red tape rules that slow everyone down and 2) really important rules that you can never break ever. Effective people learn which rules fall into which group so they can break the red tape rules and get more stuff done.

Fundamentally, rules almost always come with compromises — for the sake of making rules understandable by humans, they have to be relatively simple. Simple rules for complex situations will always forbid some amount of good behaviour, and allow some bad behaviour. Many of society's parasites live in the space of "allowable bad behaviour", but there is a lot of value to knowing how to exploit the "forbidden good behaviour" space.

A more palatable phrasing, "supervisors prefer people that engage with the rules with purpose." That is, choosing to break a rule because you are making a cost call based on what you were able to achieve is not, necessarily, a bad thing.

The "point" where this fails, of course, is where the "cost" call above is such that the supervisor can't agree.

Anecdotally I’ve heard from professional athletes that steroid use is actually liked by coaches because it gives them better control over the locker room. If someone becomes an issue in the locker room, guess who is getting randomly selected for testing without a heads up warning.

> “Rule breaking appears to signal a team member’s commitment—a willingness to do whatever it takes to get the job done,” wrote Wakeman, Yang, and Moore, all of whom are hockey fans.

Beyond "taking one for the team", in business, I didn't see the article make some key distinctions:

* What is the origin of the rules? (Originated in the interests of the organization, or came from outside, such as regulatory requirements.)

* How much does the organization care about the rules? (Some rules they just need to make a paper trail show of effort, and worst impact is a transactional cost-of-business fine, or an unflattering news cycle. Other rule violations could dethrone a CEO, or even send them to prison.)

* Would the organization actually love to get away with violating that rule, when the right individual comes along to execute it without getting caught? (Say, some very lucrative financial scheme that's disallowed by regulations.)

* How aligned is the manager with the organization wrt the rules in question? (Say, the company actually really doesn't want people to violate this one rule, but a manager gets bonuses and promotions when their reports have the advantage of breaking the rule.)

Depending on those answers, a manager's claim of "Doing what it takes to get the job done!" can sound very different.

> While incompetence is merely a barrier to further promotion, "super-incompetence" is grounds for dismissal, as is "super-competence". In both cases, "they tend to disrupt the hierarchy." One specific example of a super-competent employee is a teacher of children with special needs: they were so effective at educating the children that, after a year, they exceeded all expectations at reading and arithmetic, but the teacher was still fired because they had neglected to devote enough time to bead-stringing and finger-painting.

https://en.wikipedia.org/wiki/Peter_principle#Summary_2

As one of my friends used to joke: "rules are for other people".

I live in a place that loves rules (Germany) and I come from one (Netherlands) that has people like I just quoted taking a more relaxed attitude to rules. Being pragmatic about rules and not placing blind trust in them is key to being able to adapt to changing circumstances.

Germany is having a hard time adjusting to modern times. It's something that's being complained about a lot in the country. The topic of "Digitization" (capitalized, because that's a German grammar rule) has been a topic in elections for the last 20 years or so. They can't do it. There are rules that say that only paper signatures are valid. Never mind that this rule has been challenged, relaxed, etc. They stubbornly revert to doing everything on paper. It's infuriatingly stupid. You get this whole ritual of people printing paper, handing out copies, and insisting it's all done in person. I get plenty of docusign documents to sign as well these days. So I know that this perfectly acceptable. For official documents for the tax office even (via my accountant). It's fine. This rule no longer applies. But try explaining that to Germans.

Breaking rules when they stop making sense and don't apply to changed circumstances is a sign of intelligence. Supervisors can't foresee all circumstances and they like people that can think for themselves that can adjust and follow the spirit of the rule rather than the letter of the rule.

Hard to see the negatives. Rule breakers allow you to reap the rewards while removing liability.

"If you ain't cheatin', you ain't tryin'"

Reminds me of an incident early in my career. I was developing embedded software and needed an expensive, specialized signal analyzer. Management refused to purchase or assign one to me. I was stuck sharing with my lead, which was highly inconvenient for both of us.

Well, turns out one of those analyzers was assigned to a guy (Dave) about to retire. I wandered over to Dave's cube the day after he left and sure enough, there is my much-needed analyzer. It is poorly locked to a table leg by a rather long cable. So I tilted up the table, slid the cable off the bottom of the leg, lugged the analyzer to my office and enjoyed an relaxing afternoon of debug.

I got a nice talking-to from management once they realized what happened. And most importantly, became the new assignee of Dave's analyzer.

This study is about the NHL, hardly applicable to other contexts.

Preprint: https://www.celiamoore.com/uploads/9/3/2/1/9321973/wakeman_y...

A useful concept here is the 'incompleteness of contracts' (https://en.wikipedia.org/wiki/Incomplete_contracts): essentially, even for the simplest contract, it is impossible to write down an unambiguous set of rules or contract terms covering every possible outcome or disagreement. Contracts can only be starting points. This is similar to the failure of GOFAI to turn the world into symbolic rules: it may be possible in theory, but not in practice. Anytime a principle hires an agent, they have to leave a lot up to the agent, which is why we have principle-agent problems. So what does that imply for any 'rule'? Well, that it has to be wrong and destructive some of the time. (See also: "work-to-rule strike" or sabotage.) This will be especially true for rules imposed from the outside: if it's impossible for individuals or organizations given a free hand to make perfect rules that should always be followed, how on earth is some third party, like the dead hand of a regulation from a century ago, going to do so? So you want your agents to break the rules... but only, of course, when it's a good thing to break the rules. How do you know that? Well, if it was easy to do so cheaply, you probably wouldn't have the rule in the first place! So in practice, a lot of what happens is just this: if your agent breaks the rules periodically and nothing bad happens, then they probably were doing the right thing; and if your organization encourages the right amount of rulebreaking, it will slightly tend to do better than the ones which don't.

Of course, sometimes your agents weren't doing the right wrong things, just the wrong wrong things, and you just normalized their deviance which is going to explode in someone's face eventually. That is of course true. But if you cherrypick just a few sensational cases and treat them as if that was what supervisors were trying to encourage, you implicitly are denying that the lubricant of the world is often well-chosen rule-breaking.

"We found that when people broke the rules, teams were less likely to win games."

This seems like a prima facie bad conclusion to their hockey study, considering that the Panthers won the cup while being effectively tied for the lead in penalty minutes, with #3 not being particularly close. Yes there's a weak correlation between penalties and losing, but considering that the absolute best teams usually have a high rat index, there's a big lost opportunity to go into the rat factor in hockey and how it translates to the corporate world!

If I have to make a rule, it's to prevent the worst people from doing the worst things. If I have an opportunity to use my judgement and you are neither doing the worst thing or someone I consider the worst person, there's bound to be wiggle room.

Every job I have worked, there's the rules, and the actual rules. The rules are what is written down, the actual rules is what is enforced.

If the company wants you out or considers you low value/high maintenance, they use the rules. If the company likes you, they use the actual rules. If you are on the promotion track, they use the actual rules.

Also, it turns out the actual rules actually have serious revisions as you go up the corporate ladder - things that would get you fired might not get your boss fired, and definitely wont get the CFO fired.

I can't work under more than three layers of management, largely because I've found that to be the practical maximum of managers who will care more about my results than whether I'm following the inefficient set of rules laid down when the target results were different.

I don't think this is a problem, exactly. It just means I'm the kind of person who works much better in startups than mega corps. I can't not notice all the ways poorly made rules get in the way of getting things done, but once we hit the fourth layer of management, at least one of them WILL be the kind of manager who has gotten ahead in their career by writing and enforcing rules.

All that means is that the company has grown to the point that it's time for me to move on to the next project.

(And before anybody asks, of course there are some rules that are incredibly important. Many of them are codified as laws. Most of the rest would bring down the company. If I'm not willing to work within those rules, the company is the wrong fit for me from the start, regardless of size.)

As the old saying goes, "it's easier to ask for forgiveness than permission."

The important thing is to know fundamentally "why" a rule exists and what goal / organizational objective it's existence and constraints provides. Then breaking it can be productive if it meets the same ends. This usually puts the rule breaker at conflict with people in the organization who put adherence to process higher in priority than the actual organizational goals.

The key is understanding the purpose of the rules, its pros and cons, and recognizing the impact of your behavior, both its benefits and harm, considering the feelings of others at the same time. That's essential and most challenging part - the part that requires wisdom.

Breaking rules by subordinates frees supervisors from properly delegating power (implies taking responsibility for the delegation) or changing the rules (again taking responsibility). It is a quite convenient stance - something works you win - it fails not your fault.

They prefer rule breakers because rigidly following the rules means things won't get done on time in almost all cases.

Rules are like abstraction of a software library, or OKR of a team. It is for people to follow with good enough result. But the abstraction need to be constantly reviewed, by library author, team leader, and legislative body to be useful and relevant. That's when rules become outdated, library got rotten, and OKRs complained

Supervisors might let it slide if the organization's rules (that they didn't make or don't necessarily agree with) are broken.

Supervisors will care if their own unofficial rules are broken.

If you have a supervisor, pay attention to their own personal set of rules more than the org rules.

You cant break rules yourself. But you sure can "scold" a rule breaker and then claim credit when they never break rules again.

90% of my best bosses just tanked the bad news when things went wrong but otherwise loved it when you do your best to work around the system.

David Snowden does/did a lot of talks about these, how hard rules break catastrophically and you need systems of constraints with flexible rules which have rules baked in about when and how you can break the rules.

Worth looking up the talks they have on youtube. Just be prepared to hear the same few anecdotes 50 times.

What has really come with experience and what has made me a great software engineer is knowing when rules matter, when to bend where to make things move more quickly.

I prefer forgiveness over permission ...

Most people will gloss over the fact you broke a few rules to get there when the end result is good.

Especially in large organizations, all rules exist for plausible deniability.

Of course they do, if someone below them break the rules and make more money, they profit. And if that same person then breaks the rules again but makes a mistake or loses money, they will use the rule breaking as an excuse to shed both inter-political and legal liability from themselves onto the lower employee with the excuse that they broke the rules.

With sports, I'd just assume they were told to break the rules. They aren't breaking the rules their employer set, but the rules of the sports league.

I mean… I’m a supervisor and in that position primarily because I have a good sense of when to bend or break rules. And, yes, the employees that can strategically do the same are noticed.

Yes and no. A more extreme example of this is the US Army's Mission Command Philosophy.

The yes part:

Leaders like velocity and don't want rules to slow people down. Rules exist for a reason, because somebody in the past has fucked it up for the rest of us. Leadership still wants goal accomplishment in the shortest time frame and at the cheapest cost, though. The US Army baked this into the cornerstone of their leadership approach more than 20 years. The central concept is for a leader to tell their people at set of goals and then release their people into the wild and figure it out on their own. This provides flexibility with minimal constraints, which is especially important in a rapidly changing environment of fluid changes where the senior leader has outdated information.

Its also why corporate leadership doesn't discourage working on personal code projects if that value comes back to the organization.

The no part:

Leaders, at least the non-toxic ones, don't want to cannibalize their people. Even if rules are not important ethics certainly are. Good leaders don't want narcissistic assholes rotting the organization from the inside even if it does mean higher velocity. If your organization reaches a market milestone first but everybody has left the organization then its purely a Pyrrhic victory and the organization will still lose. This is why up to 25% of flag officers in the US military are continually under investigation at any time.

In the corporate world this is crystal clear when you look at your leadership and your peers. Are they primarily interested in releasing a product or reaching an organizational goal or are they primarily interested in their place within the organization or the appearance of relationships.

In the short term rule breaking generally leads to better productivity.

In the long term rule breakers can just job hop .

I hate when I rely on others following the rules and they screw me over by breaking them. We had "focus hours" at work. They would have been amazing if not for some special individuals that decide it's OK to waste my 15 minutes to save their 10. Now we don't have focus hours. Or we should document everything on wiki. But why do it when better "documentation" is "ask A". And A is on vacation. That's why I despise rule breakers, they almost always make someone's life worse. And that someone else follows the rules. Rules should be for everybody or nobody.

This reminds me of the stories that Gary's economics shared with his time at Citigroup which corroborates some of the stories my dad had as an accountant in investment firms.

That is, a lot of dicey stuff happens and management tends to only care about the results and intentionally places the responsibility on the traders by operating a very loose leash. This is combined with a % based commission which encourages rule breaking, given how high the rewards can be. The loose leash means when something bad is discovered (and this was the sort of thing my dad would uncover as an accountant) supervisors had this plausible deniability they could fall back on. This meant they could reap the rewards of positive returns while mitigating the blowback on them in the worst case outcomes.

Gary specifically shared a story when he tried to quit in that he was threatened with an investigation to dredge up all the bad stuff he'd done in order to be one of the more successful traders, which ultimately ended up as a big nothing burger as he didn't break any rules to get his returns. What was telling, was the assumption that they _would_ find something to use a cudgel to keep him there, as if it was almost expected.

The relevant aphorism is 'everything is negotiable'

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What's with the random musky quote shoved in there...

Dont add Elon Musk quotes to any serious thing please

productivity (making money) is better than following rules

unless your break rules that negatively impact productivity

This is why businesses will break laws when fines are less than profits.

Being mission focused can help in this regard. Knowing what you are trying to do and why you are trying to do it can guide you when to break the rules. This requires you to understand the business/organization and how the organization works. If a rule was set up to protect the company from breaking the law, you do not break those rules (unless you work in finance). If a rule was set up because someone with bad judgment did something dumb in the past which caused a snafu, make sure you aren’t being dumb.

If you aren’t sure if you are being dumb or not, you are probably dumb. If you are sure you are not dumb, you are probably dumb. If you think you may not be dumb, you may in fact not be dumb.

> “We found that when people broke the rules, teams were less likely to win games. Rule breaking hurts teams, despite the fact that people in positions of power, or coaches, might look at the rule breakers as people who are facilitating a better team,” Wakeman said. “The big caveat is that this is correlational, not causational.”

This is a really surprising piece of commentary considering the finding in the immediately prior paragraph:

> Different situations had different effects on coaches’ assessments of penalized players. Their generally favorable views [were] absent during winning streaks.

So the thought process here is, first we observe that coaches like fouls when the team is losing, and don't like them when the team is winning. And then we say that the coaches must be misguided (unless there's some kind of bias in the sample, but come on, look at the data) because teams committing a lot of fouls are doing worse than teams that aren't.

at a former startup the vp of eng liked to say "there are rules then there's enforcement of the rules"