This is definitely a rare exception, but at my first job, my boss's boss's boss (basically the #2 in the engineering organization, although probably only like 2/3 of it was under his purview) somehow seemed to have an unfathomable ability for knowing not only everyone under him the org tree, but details about what they were working on. I think it must have been at least 150, maybe even 200 people, and as far as I could tell he could recall every single person's name, project, and the general status of their work without needing anyone to remind him before talking with them. Maybe he did just really studiously review notes or something before any meeting or even chance of an ad hoc conversation in the halls, but I never really saw him typing at meetings or writing stuff down to keep track of later, so at the very least he'd need to have been able to retain a lot of information long enough to accurately record it later. Witnessing this firsthand for a few years was easily one of the most impressive mental feats I've ever observed.

Rather than trusting the same principles used for scaling the doing side of the business. Things like empowering people to make decisions [1] or being clear about what/how/why you make certain types of decisions [2]. Working on staying aligned with your closest team, which then spent energy on staying aligned with their teams, etc. Sample randomly from the whole org, but mostly at your pace.

The biggest mistake I've made was that I've pulled myself (for legitimate reasons, it seemed) from having a true conversation with every single hire before they've gotten an offer, when we were around 70. 30 minutes is typically enough, but I feel you need a singular person as a gatekeeper for the final values-fit check. Partially thinking that 70 is already good enough, but later I've come across people talking about, like, 500 people before pulling out [3] :)

[1]: https://www.bobek.cz/decisions/ [2]: https://www.bobek.cz/work-principles/ [3]: https://mastersofscale.com/reed-hastings-culture-shock/

This seems like a concrete example of why this logic is flawed.

To me I believe it more useful to start with the premise of: I'm already communicating and leading trillions, how do I actually do that?

A common issue is that we hold thoughts, logic and language as a type of universal gold standard, while ignoring that most of our communication isn't even verbal to begin with. It's context, observation, pattern recognition, a self-serving goal which aligns with the collective, because we're all wanting the same things. What feels good, what's expansive, what's beautiful etc. These are the reward functions for healthy communication in the human body, the more that we align and work with these, the better the results.

Though I agree with the larger point, there is a critical way to overcome that. The second line of leadership must own the culture at their team's level. This only works if you have direct access to the larger group. An open-door policy where anyone can schedule time with you is essential.

You might not understand their struggle, but you can hear and route it to the right people. Sometimes the best way to show empathy is simply to listen.

I've read somewhere that company politics is necessary. Whether that's true, I'll probably never know.

You are still 100 people short to know 200 people, but I got the idea.

The 100 people limit is already know by most of teachers. Having more than 3 classes, it is mostly impossible (very hard) to have a "deep" follow up of each student. Having more than 6 classes and it is strictly impossible to follow them even in the best conditions.

Good luck with that.

In most cronytocracies (typical, at the top levels of most companies), you get who you get. They may be really good engineers and "first line" managers, but suck at anything else.

A big problem is that companies don't have career tracks that match people's skills. The Peter Principle[0] applies.

Bad managers hire and promote other bad managers. Highly skilled engineers can often be terrible managers, but want to be managers, because that is the position they equate with "success," at an organization.

A Principal Engineer should be just as valued and well-treated as a CTO. Most companies fail to do this, so everyone wants to be the CTO. Establish a career track, where technical people aspire to technical positions.

And hire good managers; not ones that don't make the CEO uncomfortable.

[0] https://en.wikipedia.org/wiki/Peter_principle

I like the Jason Fried-ism of: If something really matters, you’ll hear it again. If you have to write it down to remember it, it’s probably not important.

Theoretically, yes, but in practice those 10 don’t really know 10 people. And if you don’t hire well and don’t have everything you need to keep them motivated, some of your 10 won’t even care about their 10 people or may actively be sabotaging you, peers, and/or their subordinates.

I'd say it scales pretty darn good!

Going and seeking out the feedback you want does not stop scaling.

I would not say it this way; it is too simplistic. In fact, I generally caution against the dominant metaphor here of comparing feedback to scaling. It falls apart quickly.

Here’s a counter point. In many scenarios and settings, relationships provide transitive benefits. For example, if a leader builds trusted relationships with other leaders, a significant amount of trust can flow through that relationship.

To build a better understanding, I suggest building diverse models. Try to answer the question: What kind of qualities do relationships confer and why?

There’s also a generational aspect here. I started my career in the 2000 tech boom and bust. I’ve seen a lot of up-and-down cycles in the industry. I’ve seen lots of management styles and organizational cultures. People that had formative years during peak social media and/or COVID often have a different kind of socialization and this affects their default expectations. I won’t attach normative judgments without research, but there are significant differences.

When I think of the most impressive collaborations I’ve participated in with amazing results, relatively few of them involve tech organizations.

Building a scalable culture over various company sizes feels hard in the sense that generalizing prescriptive advice is tricky. A two person start up is cake because you only have to manage one internal relationship (a pair). People know great culture when they see it, but that is nothing like growing it.

I agree this is a necessary cost of being at the top of a large organization.

But I am very suspicious of the kind of people that seem to have no trouble at all being misunderstood and disliked by many. Yes, decent people can be in those positions. But it's often a honeypot for sociopaths.

It is really important to recognize that it is the perception of an attack that triggers certain responses. For a counter example, watch how puppies play. It can very rough at some level but at another the intent is clearly benign.

There are ways to shape and modify perceptions! Culture. Norms. Timing. Technology. Inclusion and exclusion criteria. Information architecture.

Never assume that the technology or protocols you use have been designed for your core values. Often you have to redesign it for your purposes. Please do.

Feedback *can* scale if one carefully defines protocols to suit particular goals. We are not helpless even if it seems we are hapless. Leaders and designers (often social scientists) must step up and show better ways.

Computer scientists and software engineers must show curiosity and intellectual humility here. Better to draw broadly from other fields: social work, negotiation, psychology, anthropology, public policy, and more.