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

I mean, it's sort of outside the point of this article (which i understand and agree with), but as a person who once set his job description as "C++, Lawyering, C++ Lawyering" i'm going to offer the answer to this question may be simply that

1. Programming lawyers often are trained at being self-reflective

2. Big-company CTO's have bigger issues to worry about than programming languages, and have to delegate very effectively. So the answer the big company CTO should give you should probably be "I probably should not have thoughts about them, but this highly qualified person x who I ask to help me understand this area when i need to is who you should talk to"

If the article said "small company CTO's", I think it would make more sense.



Extremely fair. #2 is a tricky one. On one hand, I know a few executives who genuinely have some demonstrable area of expertise that isn't related to technology. On the other hand, an executive whose area of expertise always seems to be "It's in things that are impossible for you to understand" is unfalsifiable from my viewpoint. I err on the side of caution until they do something that simply can't be explained away... like scheduling a four hour meeting to say nothing as the outcome of a six month process.


Sure, I think that is a fair view. I almost added to the comment the following, which i suspect you would agree with: "obviously they should have some area of significant technical competence that is within an area the company cares about or works on. I just wouldn't necessarily expect it to be programming languages, and they should definitively not try to overstep their competency".

You are giving the case where either they have no area of technical competence, or one that, uh, charitably, is so far outside anything the company does/cares about that they can't explain it to you.

That one is a clear fail of this particular test :)

also obviously, this is a necessary but not sufficient condition to be a good CTO. Another good condition would be "generally assumes the time of people 'on the ground' is the most valuable time the company has, as this is what directly leads to features/revenue/customers/etc".[1]

As such, the number of situations where such a meeting would be net positive for the company amount to something like:

1. you are about to save everyone 4.001 hours worth of work, increase per-employee revenue by 4.001 hours worth, etc, by talking at them for 4 hours.

2. The company is going under and therefore you are saving everyone 100% of their time :)

#1 is actually within the bounds of possibility, but I would certainly agree that it is much more likely that anyone who believes they are about to accomplish that is probably suffering from hubris of the highest order.

[1] I tend to believe that most management is not net positive value (whether they are necessary or not for various reasons is somewhat orthogonal), and managers/leaders who generate net positive value are rarer than they should be.

To the point of your article, I tend to believe you have to start as viewing yourself as net negative, and then trying to understand how to either lower your overhead, or generate enough value to overcome the overhead, or both.

Instead, i think you see managers/leaders who start by believing they exist as a net positive and think occasionally they screw it up and are only a little net positive.

On day 1 i would give them a 1 question test that says "do you believe you are already adding net positive value to your team by being here" and send anyone who answers 'yes' to the reprogramming station.


Just wanted to say that this was one of the most thought-provoking and sensible exchanges on the post.

>To the point of your article, I tend to believe you have to start as viewing yourself as net negative, and then trying to understand how to either lower your overhead, or generate enough value to overcome the overhead, or both.

An unexpected side effect of starting my own business is that I can't help but view myself and my team this way. We're bootstrapped and have day jobs, but there is absolutely no avoiding the gap between how much revenue we generate and how much we'd need to work on the business full time.

>[1] I tend to believe that most management is not net positive value (whether they are necessary or not for various reasons is somewhat orthogonal), and managers/leaders who generate net positive value are rarer than they should be.

I read a lot of Taleb in my early 20s, and he'd call this iatrogenics in a non-medical context, and I'd agree. One of the ex-Pivotal guys I spoke to mentioned that most of the highest-performing teams emerged from "benign neglect" from management - i.e, they got busy and left the team alone. Could be a recipe for disaster, certainly, but there's also compelling anecdata out there that it could be the grounds for great things with the right people.

>On day 1 i would give them a 1 question test that says "do you believe you are already adding net positive value to your team by being here" and send anyone who answers 'yes' to the reprogramming station.

I really wonder how many people would say "yes" to this. It seems like an insane thing to say, but I'm honestly not 100% sure how many people would pick up on that.


"I read a lot of Taleb in my early 20s, and he'd call this iatrogenics in a non-medical context, and I'd agree. One of the ex-Pivotal guys I spoke to mentioned that most of the highest-performing teams emerged from "benign neglect" from management - i.e, they got busy and left the team alone. Could be a recipe for disaster, certainly, but there's also compelling anecdata out there that it could be the grounds for great things with the right people."

Alan Eustace, who was Google's SVP of engineering forever, used say he would deliberately put enough on director's plates that they couldn't pay attention to everything, in the hopes that exactly this would happen.


> you are about to save everyone 4.001 hours worth of work, increase per-employee revenue by 4.001 hours worth, etc, by talking at them for 4 hours.

It’s much more than that, because of opportunity cost. If all company was doing is how to get 0.025% improvements, it would never get off the ground.


Yes, that's fair. I meant it as sort of "the barest possible minimum to even start to argue it's worth it".

Most of the time, the issue is not the error bars in thinking about the quantity. They aren't thinking it needs to be worth 4.001 and it needs to be worth 6, instead, they aren't thinking about it at all.




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