Leadership Is A Hell Of A Drug

Last week, I received the following invitation to a compulsory on-site meeting, following management's repeated engagements with some sort of Agile shaman.

You have been invited to:

Compulsory On-Site: Continuous Improvement Playback & Strategy

Notes: This will be an all-morning meeting so arrive energized as we hit the ground running on Monday morning

The Leadership Team

Oh man, where do I even start to make fun of this? There's so much here.

Firstly, why did you clowns make it a compulsory on-site event? Do you really think that it was worth dragging everyone into the office against their will because we needed to listen to you talk for four hours in a row? That level of self-regard is narcissistic to such a degree that I have screeched so far past horror that I've looped around to arrive at a grudging respect. I can only imagine this is the equivalent of a meditator achieving perfect concentration on the breath, but instead it is the all-consuming feeling that people like listening to you say the word strategy for four hours.

Secondly, do we really need to "be energised" and "hit the ground running" for a goddamn four hour meeting on a Monday.? Are you trying to help me sell cryptocurrency or get involved in a pyramid scheme? Half of us just write SQL for enterprise dashboards that no one reads, you absolute sickos. You don't work at SpaceX - the largest project we're working on right now is a big spreadsheet that is nonetheless six months behind schedule. Sleeping is higher energy than that.

Thirdly, did you have a stroke and forget how to talk like a human? Continuous Improvement Playback and Strategy? How about "Our plans to improve working conditions for 2024", you fucking weirdos? Does the part of your brain that produces normal speech ossify naturally as part of becoming an enterprise manager, or is that a prerequisite for the job?

Fourthly, given that half of you love turning up on stages and talking about your decades of leadership experience, why did you need someone from outside the organization who doesn't know a damn thing about our work to come in and tell you how you're screwing up? I'll tell you for free! That is a breathtaking level of disconnection.

Finally, and most importantly, what kind of maniac signs off on something as "The Leadership Team"? That's what we're talking about today - leadership.


I've spoken to plenty of people that I'd actually call good leaders in the past year but I strongly hold that theory is no substitute for lived experience. And I've never formally held a position of leadership in an organization. Nonetheless, at some point we must concede you don't have to be a chef to notice that not only is this cake unbaked, it is a slurry of yolk, whites, eggshells, and flour that someone has flung into a bucket and declared finished.

Of course, leadership is not like baking a cake. There are no yolks, eggshells, or flour. However it occurred to me after writing the above that all of my would-be leaders since getting to Australia have been white despite all the engineers being Asian, so maybe I'm onto something.

David Whyte's Consolations is a beautiful book on the quiet re-association of words with all the little connotations they have that fall to the wayside amidst the modern coarsening of them. The blending of leadership with management is one such coarsening that I think needs to be addressed before we continue. They describe radically different things that are merely occasionally carried out by the same person.

Management is mundane and unsexy, and that's fine. Not everything requires a manic Silicon Valley energy. You can roster employees for the next shift at McDonald's with basically none of what we'd call leadership. Just be halfway competent, have a basic understanding of what you're doing, and ensure the thing gets done by the people that are paid to do the thing. The supermarket remains open because of the relatively efficient repetition of this task every day. Calling yourself "The Management Team" is not offensive to my eyes, and while I am certain that the word "management" is deployed in retail stores by petty tyrants across the globe with all the subtlety of a tactical nuclear device, the warning bells do not sound loudly to my ears.

But leadership, oh baby, that's what everyone wants to do. Managing is mundane and leadership is exciting. A manager handles trivialities, like hiring and firing. A leader has the privilege of serving as a shining moral beacon, soothing the trouble, reading the psychodynamic eddies (read: vibes) in the organization. At its best, it is a genuinely noble endeavor, not carried out by whoever happens to be at the top of an organizational chart, but whoever has the capacity to encourage other people to be their best selves at a given moment. The most inspiring person in my life yesterday was not anyone that gives talks about how amazing their own skills are, but the seven year old in the house next door who was drilling table tennis so determinedly that I guiltily got some piano practice in.

Unfortunately, I have never experienced anything I'd call leadership from anyone that has called themselves a member of "the leadership team". From my friends, yes. From some serious thinkers, yeah. From "leadership", not even close. Instead, society presents us with an endless parade of people parroting nonsense ranging from the insanely over-excited ("Get shit done! Woo!") to the utterly soulless ("Continuous Improvement Playback & Strategy"). Shut the fuck up! All we do is land the output of APIs in a warehouse, guys. You sound insane.

King: "That's not a luxury, though, coffee and socks are not a luxury."
Pudi: "All right - give me a luxury - what luxury should I have?"
King: "Private plane."
Pudi: "... Larry, I'm on Ducktales."

These people are running some horrific version of leadership that consists entirely of them turning up and repeating the same tired cliches on a loop. Reduce silos. Be more Agile. We must go forward, not backwards. Can you imagine how fucked in the head you'd have to be to imagine you can hold a four hour unrehearsed session and that you expect it to be so good that you demand everyone be there for it?

There is something genuinely scary about the idea of people so caught up in their own self-image that they think leadership is turning up on stage to dispense divine corporate manna unto the huddles masses, then expectantly waiting for the choir to raise their voices in sickly-sweet supplication: "That's a great idea, boss."

II. Thoughtfulness

The most scathing condemnation I have of the majority of people that would call themselves leaders is the fact that... well, most of them don't read, or proudly proclaim that they do most of their study on LinkedIn. I have heard multiple people say the latter without a hint of shame. And with this, I cannot help but question whether they're bad at technology, or bad at everything.

The majority of people that unironically call themselves leaders seem to be fighting a constantly losing rearguard action around what their area of competence actually is. Leadership in the absence of a skill is just aspiring to run a cult of personality. I am assured that while they can't program, they know a lot about running I.T projects. Then all our projects run late, but I am assured they actually know a lot about finance. Then we are unprofitable, but I am assured they know a lot about retaining staff. Then the staff leave, and I have most recently been assured that they are working hard on increasing salaries - that must be the reason everyone is leaving because it couldn't be that they've lost faith in leadership.

Why is it so easy for the readers here to assure me that they have actual competence in some domain, but it is impossible for all these dorks? All they would have to do is say one sentence that indicated some level of original thought - I'm not even hard to trick! There are so many domains that I don't know much about that they could basically string together any insightful-sounding series of syllables and I'd conclude they're smart.

Consider this: the lawyer I mentioned in this post had opinions on whether statically typed languages are superior to dynamically typed languages, and had engaged in some complex meta-cognition. See, they reflected on how every time they felt that something in Go was ugly, it later turned out that Go was well-designed and they simply didn't understand the issues being designed around. This turned into a rough rule that seeing a problem with Go typically reflected a flaw in their own understanding, thus flaw with Go is actually best processed as flaw in own brain until proven otherwise.

I don't know much about Go, but that's not important. What is important is that I'm on my knees, arms outstretched, gazing up at the sky, tears streaming down my face, and begging to have one question answered:

Why does a practicing lawyer have more thoughts on programming than every CTO I've had a 1:1 with at a big company?

III. Ego

If someone doesn't have the ability to award someone else status or money, they're told they're a good manager. This is usually a person whose job it is to hover in the air, screaming, while the organization channels all their dysfunction like bolts of Atlassian-branded lightning into their twitching, smoking mortal coil. This hopefully gives the people beneath them time to actually do their jobs uninterrupted for up to ten seconds. When that person burns out, you discard their charcoal corpse, slap in a new one, and set the machine going once again. That job is horrible and we all thank you for your service, you glorious bastards.

However, if a person can provide someone status or money, they will be told that they're a great leader, and by the way, I heard that there might a role opening up on that new prestigious project and I'd like to throw my hat in the ring. Being called a leader shoots an LD50 dose of status-infused dopamine directly into the average person's system, and this is absolutely exploited to the hilt by every grifter under the sun.

I can only imagine that this is extremely corrosive for your development as a person, but it is also dreadfully obvious when it happens. A few years ago, I had dinner with a guy in his early twenties who had a very successful non-profit take off. He was very seriously despairing at how many events he was being invited to where people would fawn over him despite the fact he was twenty-one. I believe his exact words were a very sarcastic "Society isn't broken at all!" with a very distressed look on his face. If a twenty-one year old could figure out that adulation is unhealthy, what's everyone else's excuse?

It is tragic to see how easy it is to push the ego button on some people. Someone once wrote in and referred to LinkedIn as the "clout factory", and it is hard not to think about almost all non-athletic awards in this way. These processes become so easily corrupted that I think the most impressive thing a person can do is reject all awards on the principle that they're bad for you spiritually. I'll leave it to the reader to decide how prescient this is, but Taleb wrote the following in 2007, which I think those Americans among you will appreciate:

Nor did the committee come to us practitioners to ask us our opinions; instead it relied on an academic vetting process that, in some disciplines, can be corrupt all the way to the marrow. After that award I made a prediction: "In a world in which these two get the Nobel, anything can happen. Anyone can become president."

Of course, the Agile consultant I mentioned above has done something to flatter the leadership team, though the specifics are invisible to the rest of us. It might have been as simple as calling them leadership a lot, and the consultant might genuinely be unaware that this is the secret to their success. After flattering leadership for a while, they arranged some group sessions with the teams and immediately blundered away all their reputation, with such brilliant questions as:

"Rate how well you think you understand our strategy going into 2024? We know leadership hasn't put out a strategy yet." Well, this question doesn't make any fucking sense then, does it?

"Rate how well-trained you are at Agile, on a scale of 1 - 5?" Firstly, what the hell does this even mean? Do you mean Scrum? Secondly, someone said 2 and the Agile folks rounded his answer up to 3 for no discernible reason.

I can only conclude that, behind the scenes, they had spent the past few weeks just telling management whatever they wanted to hear, and didn't think the peasants were smart enough to feel patronized by all this.

IV. Doing Better

Management, Again

The best manager I've ever worked for was Healthscope's Dave Coulter, who has been mentioned previously here. The only reason I say manager instead of leader is that we worked in an organization that was fundamentally disempowering, so we spent most of our time trying the conventional corporate wisdom of "educating our stakeholders", which did not work, I've never seen work, and I've never met someone that has seen it cause true organizational transformation. But he did the hard work, knew the tools, read, and took care of the team. It was really simple, and I learned that there's no real trick to this. Use your brain and your empathy.

Also he is in an organizationally-sanctioned leadership role now, but has never called himself a "leader" because that would indicate fucking madness.

Leadership, Again

The best leader I've ever worked for was, to everyone's surprise including my own, Stephen Deutsch in the state government (the surprise is because the government is genuinely pretty bad at most things). I was burned out on tech work by the time I got to him, and I remember still enjoying working with him. We were in the fire service, which occupies a place of huge civic importance in the Australian psyche, and he would turn up and be absolutely honest every single day. Right as the latent burnout from my previous role reached a crescendo, I told him I intended to leave for a place that was offering me three days of work a week so I could do some recovering.

Over the course of a call, he commiserated, shared his own struggles with me, and then completely unilaterally disarmed. He got me an offer to work there for three days a week, explained that it would never be as stable as taking a permanent role doing the same elsewhere, further explained that I currently had a lot of power due to the way their budget and projects were set up, and otherwise completely collapsed his own negotiating position so that I would have the tools to take care of myself. It made his life substantially harder in exchange for making mine much easier.

I ended up leaving, and he made the decision to leave easier, yes. But we stayed in touch because you don't run into people like that every day. He's a co-director with me now, I play board games with his friends every week, and that disarmament was so radical that I still think "J'ds hasfak 'ds'" every time it comes up, which I dare everyone to recognize without looking up.

Getting Involved Myself

I've considered getting into a leadership role myself to see what it's really like, but this is complicated by a few things.

The first one is that I don't think leadership roles should really exist in many domains, as I've indicated earlier. Leadership should naturally flow between team members based on the task being performed, competence of each member, and psychodynamic energy (read again: vibes) on any given day. Taking a role as a team lead somewhere sounds almost paradoxical - the whole goal would be to not behave as a team lead, which is clearly not how the organization functions or they wouldn't have a role called team lead. I can certainly imagine a version of a team lead that encourages a healthy culture, but this would run counter to the true values of most companies.

The second issue is that I think I'd be good at it, which strikes me as a huge CAUTION! sign. Everyone knows what I mean, and everyone must also concede that this is also a sign of how dire the situation is out in the real world. When I tell my teammates that I think I can design a simple application, their first thought is (hopefully) not "Wow, he must be about to fucking bomb this!". When I tell myself that I think I could do a decent job managing two juniors, my first thought is "I might be a sociopath". The people that consistently rate as the most insane authority figures I've seen over the past few years have been the ones that said "I'm a natural leader" during the interview process.

However, it is also incredibly common for people to remark that those most suited for "leadership" roles are those that don't want leadership roles. I think that protects from the worst excesses of getting a narcissist in charge, but doesn't actually consistently produce great leadership. I asked Stephen about this, and he happily said that he loves leadership roles (and I can confirm that I never felt like a subordinate working with him). Simultaneously, one of the most senior people in my current reporting chain is a great person that was forced to take up leadership despite promises that they wouldn't have to. Haven't seen them in months. Great person, lots of respect for them, sadly absolutely useless to me. I don't think they'd even disagree with that assessment, they'd just feel guilty. So I guess that whole line of thought belongs in the dumpster if you want to pursue human flourishing rather than limp sustainably onward.

This is still something I'm mulling over, but I reckon it's best not to force it by explicitly looking for a role in the space. It'll happen organically or it won't, and there's no point doing it at mediocre organizations. Instead, I thought it would be nice to share some reading and my thoughts on doing it right before wrapping up.

Some Reading

I've mentioned High Output Management before, and I think this is really the quintessential book on management devoid of leadership (and that's not a bad thing). It's full of nothing other than guidance on how to manage operations smoothly and not screw up your meetings. Can't go wrong with it, even though everyone has qualms with some part or another.

I've been enjoying Managing Humans but something that really bothers me is... well, the environments described in it are accurate, but they also suck. There's a huge amount of stuff in it about managing rumors, organizational politics, and so on. All the ugliness is baked right in. It's probably the perfect book for someone that wants to do a good job at a huge company that has no real chance for reaching the Nirvana of everyone being high-performing and psychologically comfortable - and that's fine, some of us have to work at those places, but I know the readers here don't want to, so there's limited long-term utility to developing those skills.

Pivotal Software

What I've really been into these days has been covering some of the original Extreme Programming material and, more uniquely, talking with some of the people that used to work down in Pivotal Software. There's a lot to write about this, but I had a three-hour long conversation with Jesse Alford a few weeks ago, and was immediately intrigued by what the experience of working there sounded like. Jesse himself was brilliant, but there's also a lot of material on their functioning that I had never heard of before.

Their alumni community is some sort of cult where they're all chasing the high of working at an organization that good again. There's a podcast dedicated to spreading some of their operating model out there, hosted by alumni with plenty of other alumni coming on as guests. Every single episode slaps and has leadership wisdom that makes most other sources seem tragically oversimplified. Here's a big essay on what made working there so special.

Hell, I read a book called Turn The Ship Around! which I really enjoyed on leadership - I dare say it was the best book on the topic I've ever read, or at least as good as a leadership book can possibly get. I wrote up a whole post on it, really thought about it, then realized that I wasn't comfortable publishing it because I didn't have enough experience and the author does management consulting now, which I thoroughly distrust. Lo and behold, here is the author on their podcast, with admittedly terrible microphone quality, making statements that are socially expensive enough about the median employer for me to be willing to endorse his book. I can't recommend the book and the episode highly enough, in that order.

I'm hoping to spend the next few weeks getting deep into the Pivotal lore/cult and figuring out what worked so well for them.


I stare at the invitation for a long moment.

It is from someone in the C-suite.

I ensure that my response is going to be sent to the organizer.

I click decline.

No one remarks on my absence, and I receive only these messages from the attending engineers:

I'm bored of hearing the word strategy.

Someone just turned around and asked me "Wtf are they saying?"

They are suggesting dumb shit.

The world has gone mad.

Absolutely hilarious.

Leadership is a hell of a drug.