> The arguments articulated are entirely false

I’d would disagree - I had the exact experience that the autor described. But you are right on this point

> it’s entirely possible to build that intoxicating environment anywhere. It’s more about having a dynamic leader who assembles teams into collections of individuals who know precisely why they are there

I still think it’s related to size and bad incentives. I heard stories of people at FAANG that said that department X is like a startup but Y is soul sucking boredom

Yes, thats correct. However the existence of X department at all refutes the authors premise and conclusion - and if X exists, it’s entirely possibly for Y to become better.

Specifically this is entirely false due to the existence of X:

> Is this preventable? I think not.

I> f you look closely, all these problems fundamentally come from:

> Decreased skin in the game, which reduces team alignment

> N^2 communication, which creates need for managers and specialization, which reduces individual agency and breadth of learning

> Reduced risk tolerance, which slows everything down

> #1 and #2 are inevitable results of having more employees. #3 is an inevitable result of having more users, partially due to government regulation.

I think a large company enables Y departments to exist without the company imploding immediately. Survivorship bias ensures most startups that last longer than a short amount of time to appear like X, when I know there are plenty of dysfunctional startups (a friend tells me Ghost is a great example). But due to the economics of a startup they evaporate quickly. In a large company Y departments can limp along for a long time or indefinitely because Y’s function needs to exist and the company can afford for it to suck ass to work there without it going out of business. However invariably X departments in large corporations are where the magic happens, where people want to work, and what moves the large enterprise forward.

I’d also note that not everyone wants to work in a startup environment or are able to. Many engineers got into it for a good paycheck and don’t have much interest in anything particularly dynamic or engaging. They’re perfectly happy committing once a month and sitting in meetings. That’s not me, but I can also see when you build an army, you can’t build it out of special forces only.

So, instead of saying X can’t exist, when it clearly does, I think it’s more useful to say you should be careful where you work in a large company and seek out actively the X departments by learning what Y departments look like and how to spot an X department.

Would you describe your work at large companies as "intoxicating"?

Absolutely. The most exciting work I’ve done that has literally changed our world was done at systemically important multinational megacorps, where we created environments of unfettered innovation and an assembled teams of amazing individuals working as a coherent team. I had some really great leaders early in my career that showed it’s not only possible it’s the only way to enjoy any role at any company no matter the size. While you can’t clone their method to work in any environment, you can adapt their method to any environment with enough energy applied. The essential secrets are the ones I outlined. As an IC though it’s all about finding those leaders among the functionaries.

Likewise, most of the startups I worked at were exciting by not intoxicating. They were relatively banal in their goals (change the world through prestige makeup e-commerce or something), their technology modern but not innovative, and the teams tight but not always coherent like a well oiled machine.

big companies have resources that give you reach (channels, marketing, human talent, legal, international presence, longer term investments) that you can never get with a smaller company.

being able to apply them effectively can really be really frustrating though. and there is always the danger that your two year development arc will be demolished by 'shifts in overall strategy' or 'belt tightening' or a reorg.

Yeh. But startups can and do fail, pivot, get restructured by their VC.

> I had some really great leaders early in my career that showed it’s not only possible it’s the only way to enjoy any role at any company no matter the size.

I'm not persuaded anyone is in a position to know that there's only one way for people to enjoy work, and to know what that one way is.

That’s the secret. Most management is about the one way people work. The right way is to realize everyone is an individual and everyone has a different way of working, and what they enjoy about work. This forms a complex optimization problem for the manager, whose job, IMO, is to figure out the puzzle of how to maximize everyone’s individual value in the team. The way you do that is match their style of work and strengths with the teams needs and find other team mates to backfill their weaknesses. Then giving people the space to do things the way they prefer it while keeping a strong common collaboration medium within the team.

Return to office is a current example. My strategy here is that people know how they work best and that’s up to them. We have ways of getting together and collaborating, asynchronously and synchronously, and don’t enforce a mandatory hybrid approach. I encourage the team to intentionally meet up in person regularly, and the team self organizes synchronous in person time on a regular basis. I set up a drop in zoom room that’s always signed in on a conference room and people drop in for adhoc stuff all the time. Some people stay signed in all day on the conference room. I make sure ticketing systems, chats, and other mediums are well used. I regularly talk to people about their well being to be sure folks remote are OK, as sometimes fully remote can mean fully depressed.

Compare this to a “standard” managers approach. “We will be in the office three days a week, with a mandatory day on Wednesday. This is necessary because people work best in person but we want to give people flexibility because we know employees value that. Failure to comply will result in performance review impact. Our company’s culture is built on in person interactions. We do this for the children.”

Typical management is about treating people as butts in seat filling a role with a define set of measurable performance metrics - aka conforming cogs in a machine. that is the method that assumes there is one way for people to enjoy work, and knowing what that one way is.

My way is acknowledging I don’t know any one way that’s best, and specifically, there is no one way for people to enjoy work. It’s my job as a manger to figure out what each and every person on my teams way is, and to do my damnedest to create that environment for each individual. I work hard to hire managers that will also do this, and I meet randomly with people at all levels of my org to be sure they’re being treated like this by the people on my direct team.

The down side for me is I stick out like a sore thumb in the great cog machine of other managers. They don’t understand what I’m doing, it bothers them, and they feel like I’m getting some sort of preferential treatment. And maybe I am, because my organizations are almost always considerably more effective and successful than the rest of the org, so we get enormous latitude. But shielding my people from the game of thrones is exhausting - more exhausting than the rest of my job.

All this said, I’m not the only one who does this. I have encountered a lot of leaders that do this. They’re the ones people want to work for. That’s why I paid attention to what my early leaders were doing and emulated it - the one way is there is no one way ;-)

> All this said, I’m not the only one who does this. I have encountered a lot of [managers] that do this. They’re the ones people want to work for

How about people who don't want to work for a "manager"? Where should we go?

That was a pleasant read, thank you for the comment. I've felt something similar about management, but not quite clear enough to put in to words.

Maybe I'm late in my comment but, I have two questions if you do not mind.

If you have a manager that is not quite like that, but probably somewhere in their mind would agree to that stance, how could one push that person to that direction? I have my manager (and a friend) in mind, gives good autonomy and let everyone work in the way they feel is optimal. But it also most often lead to aimless or fuzzy goal setting, a lot of ambiguity. My guess is that the thing lacking is the inquisitive nature; like you mentioned you do, he does not check in on people how they feel, what's blocking them, what's suboptimal for them. He simply check in for an update on progress and set meeting to update what he's up to.

Is there any good material or pointer that could make someone manage more like that?

I also informally manage one person due language barrier and the question also applies to me.

> I’d also note that not everyone wants to work in a startup environment or are able to. Many engineers got into it for a good paycheck and don’t have much interest in anything particularly dynamic or engaging.

This is an excellent point. In my experience a majority of people value stability and predictability in their lives. They would rather have someone tell them what to do within well-structured bounds than contend with the ambiguity inherent in an early stage startup, or with solving massive product/business/technical problems with too many stakeholders to fit in a room.

I think the challenge is the people with the intrinsic motivation and stomach for the ambiguity can struggle to grow in large corporate environments that are full of good soldiers who stay in their lane. It's not uncommon for entry level ICs to come in with 3 or 4 layers of management between them and VP level, and then become pawns in middle management games, or stuck reporting to Peter-principle cases who teach them all the wrong lessons.

This is why I was really glad to have worked in startups when I was young, to really get exposed to all the moving parts and fundamentals of an operating business. It's just much easier to learn when the big picture is more legible, you have the latitude to iterate faster, make more mistakes, and see first-hand how things scale (or don't!) from the ground up. These days I see too many ivy league grad ex-FAANG who have all kinds of ideas of best practices with no understanding of why things are done that way at the tech giants, and extremely limited ability to reason from first principles about what makes sense in a different context.

I am the most senior engineering IC by position and years of experience at my current company in a 100+ person engineering group. The only problems I deal with are non technical and organisational in nature, despite on paper being expected to code 30 percent of the time.

I’m sorry - I’d advise either making your role better or finding a better team. They exist.

Sound advice - currently going down the path of try to make the role better. It will however be a long journey, so need to work out whether I am sufficiently committed to the path. Also need to work out what the ejection criteria are, regardless of my commitment or not.

> The arguments are entirely false: ex N^2 communication. No team depends on every [other] team in the org.

From the article:

"You can’t just work on whatever you want; coordinating would be an O(N^2) communication mess."

Evidently, you're agreeing with the article. So which part is false then?

That coordinating is a quadratic mess, because no task requires bidirectional communicating with everyone else.

I also disagree with all the other points they make about large companies. Not that there exists teams in large companies that suffer these issues, but that there exists no teams in large companies that don’t have these issues. I further extended it to say startups also aren’t without issue, and many are totally screwed up. They just don’t last very long.

Let's set aside value judgements. After all, I don't know that small startups are optimal any more than you know that they aren't. Hopefully, what we can agree on is that small startups are different from large companies, even those with teams. Given that, someone who LIKES their small startup for whatever reason may feel it's lost its lustre when it evolves into a large company. For those people, this article offers an explanation for why that might be.

Or, it gives a guide for the problems to avoid and figure out strategies to solve for to avoid that path. But, yes, if the article were written that way, I would have agreed with it more. But it wasn’t :-)

Hopefully you'll forgive me if I think it WAS written that way.

> The arguments articulated are entirely false: ex. N^2 communications. This is reductionist and absurd

I think you’re being unnecessarily harsh and reductionist of the article’s arguments. I’ve experienced exactly this failure mode in startups.

The counter-example you described is an example of properly managing the N^2 complexity, not an example of it not existing.

But it doesn’t exist. For any task the number of contact points is almost always fairly small. Just because the possible N might be large most are occluded by lack of relevance to any specific task.

I would note that the author categorically says it’s not possible for a startup like environment to exist in a large company. That’s what I disagree with.

How have you developed a sense for organizational friction? What observations of culture can I use to make an educated guess about how easy it is to do my work?

I agree with your point that a large org does not guarantee what the author claims. The author claims that the organizational friction can be measured by productivity, but you recognize culture as the better diagnostic criterion. The big O metaphor does not extend well to the argument, as you point out.

I'm looking for hard hitting interview questions so I don't waste my time on "soul sucking" positions.

That’s the trick isn’t it? As “the boss” I’ve been able to self create my culture around me so it’s been easier. I have landed in management teams that were so oppressive I couldn’t even then. I’ve watched my peer leaders for signs. It’s very hard in an interview to know where you’re landing.

A few things I’ve noticed that might help:

* ask people in the team what they do and how they work, and how the team helps them work best. If they answer “oh I’m a programmer 2” and have wishy washy answers on the rest, that’s a bad sign. They’re being managed by a “by the book” manager. If they describe some complex role that isn’t out of the HR leveling guide, and a unique way of working that’s accommodated by the team, that’s a good sign. If you hear everyone in the team describing a role that’s unique and tailored to them, then that’s a great sign.

* this is controversial but I think any org that slavishly follows modern day agile / scrum can not be dynamic. Nothing more to say other than back in the 90’s Bay Area hanging with thought works and those folks, agile was something very different than today.

* the manager themselves should be very open to questions with thoughtful answers that aren’t rote. They should likewise spend more time understanding you than usual. They should be assessing your fit in their team - do you fill a gap? Do your weaknesses complement others strengths? Are you looking to turn the crank or are you looking to innovate?

Also, be aware of yourself. Not everyone does well in a dynamic environment. It’s more chaotic and less structured. If you like clearly defined and regimented work, go for the clearly defined and regimented team.

Organizations are structured as trees as a strategy to combat N^2 complexity. You talk up, or down. The tradeoff is of course N^2 relationships still exist in reality , so you duplicate effort, and sometimes collide, but it's a good tradeoff.

I think it’s more like an adhoc graph that’s more dependent on the task than the organization. Tree based management is only useful for reporting and dictates. The actual work is more like “I need to get X done, I need to work with I,j,k to do it.” Often the real issue is NOT that it’s N^2 interactions, but the space for identifying who I,j,k actually are is quadratic and there’s no index. This is often the immense value of “lore masters” in a team - they have an unnatural ability to know who to talk to about what. If you don’t have one in your team, get one.

I agree here. The opening statement of the article is simplistic and inaccurate. Sure, most big corp jobs might be rather dull, but you can lit that spark in the right circumstances.