Stuff I Learned at Carta
29 comments
·May 24, 2025pavel_lishin
thinkxl
Additionally, the explanation might work for the exec asking the question, but not for others.
I don't like that executives don't have to put in the effort to communicate their concerns and put pressure on the people who already have the pressure of researching, validating, and presenting the solution.
I'm probably going deeper than I should. Still, if the executive asking the question isn't technical, he could direct the question to the executive who's supposed to have a technical background that earned their position in the company. You know, people making decisions should have an understanding of what they are building/selling.
noworriesnate
One common leadership trend is to give minimal feedback like “this is not cool” and rely on competent people directly under the executive to guess what that means.
Competent people can often lead themselves in the right direction, especially with the use of copious after-meetings in which everyone tries to interpret the executive’s feedback.
After all, the executives are busy and hard to get access to.
bensonperry
Completely agree. And I think a lot of roles frame this as "part of the job", something always unavoidable. But if I was an exec and my team was spending half their time trying to read between the lines of my poor communication, fixing that would be priority #1; what an enormous waste of time for people who I (ostensibly) hired for their other skills!
basket_horse
Ah, the classic two-year exec tour - just enough time to write a book, roll out a pet program, and peace out before any long-term consequences set in.
Zanfa
I never take any leadership-adjacent blog post seriously since I found out that by far the most toxic manager I’ve ever worked with in my career has apparently risen to a CTO position at a respectable startup and has since published numerous blog posts and a book on management. His resume looks amazing though.
swyx
1) bad people can give useful advice. generally life is richer when you can separate art from artist.
2) 1 person bad does not make all people bad
OmarIsmail
Is this CTO in the room with us right now?
swyx
i understand the criticism but i also wonder at how to improve the status quo. Lethain is regarded as an authority because he has such a wide experience and writes so much and so thoughtfully. The truth is we just barely and rarely get such insight from people at his level so we just take whatever we can get.
the people who are in-deep for decades 1) have no time or motivation to write/build a brand^, 2) have political reasons you can't write anything insightful esp while your own house is messy (and it never isn't).
so how to change this?
my approach is to run a conference where practitioners do short ted-talk-like-but-technical talks about their work and learnings while still on the job. but ofc they all have their own motivations to speak.
^ though i will be the first to say that you CAN be primarily self-motivated to write-to-think-out-loud and this is a thing, do not let jaded HN people tell you different
harryquach
Thanks for the laugh friend. I was thinking the same thing.
braza
> The three biggest levers are (1) “N-1 backfills”, (2) requiring a business rationale for promotions into senior-most levels, and (3) shifting hiring into cost efficient hiring regions.
I had the experience to work in a scale up like Carta couple years ago where the company stoped to hire in NYC/Berlin and as far as I know they shifted their hiring to Philippines.
Fair play, the end of the day the company had their incentive structures to support this decision.
However, after that and other events I just started to do career movements towards companies that I know that I would bring unique features in my position (eg language skills, legal settings, specific regulatory knowledge, local compliance) to be more not entrenched but in a non-constant second thoughts professional relationships in a good sense or be in epistemically different worlds where international competition is irrelevant (eg clearance filters based in nationality, government and military, market that has exotic languages, etc).
I say that because I really do not like of this “Employee as a Service” where line an AWS console you just change the region and spin up labor like some EC2 machine; where in this scenario, you are seen as some expensive spot instance in us-east-1.
Maybe I am being highly defensive, but I do not see hereafter anything I that regard getting better since we have remote work and talent everywhere.
melvinmelih
> or be in epistemically different worlds where international competition is irrelevant (eg clearance filters based in nationality, government and military, market that has exotic languages, etc).
I like this hedging strategy, can probably also apply this to the risk of AI taking over our jobs (licensed professions won’t be going away any time soon).
drewbug01
> Extract the kernel
If you follow the link within the article, he goes on to say:
> The most frequent issue I see is when a literal communicator insists on engaging in the details with a less literal executive. I call the remedy, “extracting the kernel.”
Most engineers I’ve worked with have been “literal communicators.” Of course, both parties can always improve. But part of being a good leader is having excellent communication skills, and that includes anticipating how your audience will receive your message. The bulk of the responsibility is, and should be, on the leader to avoid misunderstandings in the first place.
adamesque
> The bulk of the responsibility is, and should be, on the leader to avoid misunderstandings in the first place.
This can be both true and unhelpful at the same time. “Extracting the kernel” is about putting agency back into your own hands when someone else is less-than-perfect. How do you read beyond the utterance to understand the intent? Will that lead to better outcomes?
Since you sadly cannot force leaders to improve, and sadly cannot usually also pick for yourself perfect leadership, what power do you have to make things better?
drewbug01
So I think you are scratching at something interesting here - as a (senior) engineer who values communication intensely, I also try to “read between the lines” and extract what someone meant and not just what they said.
And so in that sense, I agree with you - from the perspective of the engineer in this example, yes: try to figure out what they meant and don’t get lost in the details. It’s a good example of not trying to control things that are fundamentally out of your hands.
But the other side is: this blog post (and the linked one explaining the “kernel” idea more deeply) is written from the perspective of the CTO! And it’s framed as a strategy - “encourage your engineers to learn how to intuit what you mean, and not what you say” (paraphrasing, of course).
I think that’s where it rubs me the wrong way. It subtly puts the responsibility for effective communication the receiving end. If we are considering it from a pragmatic standpoint, it’s just far more efficient for the CTO to say what he means from the get-go.
I mean, honestly even with the example: how much harder would it have been for the CTO to say “is it possible to go faster with something off-the-shelf rather than build our own?”
tuyguntn
> The bulk of the responsibility is, and should be, on the leader to avoid misunderstandings in the first place.
How do you avoid misunderstandings as an executive when you sometimes literally should hide the information?
I heard many many executives (probably, that's why I am not an executive), a lot of them try to hide information for different reasons. Even the technical one's are trying to keep doors open for interpretation, so that anytime they can change their mind and blame team for the failure, then label them for layoffs
Loughla
Good leaders don't do that? There is a difference between legitimately confidential information, and keeping your cards close to your chest to protect yourself. If you have confidential information, you can explain the reason it's confidential and everyone can move past.
I've worked with two teams where layoffs had to happen. The people weren't happy, but they were at least satisfied that the results were fair and honest. They appreciated my transparency, and worked to train up other members of the group to prepare for their own departure.
If you spend your time building trust and relationships when times are good, and weed out the toxic personalities during those times, then it's better (not easy or good at all) when times are tough. Allowing even the slightest amount of toxicity is completely unacceptable.
If your boss hides information or is intentionally vague to provide an out for themselves, they shouldn't be in a leadership role. They shouldn't be employed at the company.
Being a boss means that 99.999% of your actual job is communicating clearly and openly.
dafelst
I agree with everything that you say here, but I think it is important to differentiate "good leaders" (which you have described) with "successful leaders" whose motives are often far more self-serving.
There are "good, successful leaders" but in my experience they are few and far between, and often the "successful" aspect is forced to plateau by the "good" part.
slt2021
a lot of text with very little value. Typical executive talk.
the hard truth is that most of the time executives are really absolutely clueless and have only shallow understanding of whats going on inside the tech.
and their usual levers are mostly just distributing resources: more resources to this org, fewer resources to that org. and another level is high level program management: checking the milestones, schedules, and timelines. thats it
bix6
Carta has insane turnover and is making a big revenue push right now. Concerning to see the CTO leave during that.
I’m most interested in the part he doesn’t share: “I’ve also learned quite a bit about venture capital, fund administration, cap tables, non-social network products, operating a multi-business line company, and various operating models. Figuring out how to sanitize those learnings to share the interesting tidbits without leaking internal details is a bit too painful, so I’m omitting them for now“
gregorvand
I know at least two people leaving Carta within one year of joining (recently) and CTO within 2 years suggests something amiss (looking more at the company here than anything) The article is frustrating since it tries to be transparent and 'what i've learned' but doesn't really give anything away to the relatively short tenure.
blueridge
Seems like Will hasn't stayed anywhere for more than 2-3 years?
returningfory2
Yeah, I find it very strange that he's a well known thought leader even though he hasn't had a long tenure anywhere. To me, software is easy in the short term and hard in long term.
baobun
Any lessons learned from the 2024 incident? Was/is it possible to put in place internal controls to prevent future compromise?
https://news.ycombinator.com/item?id=38897363
And I guess related to the section and post on heavily and quickly adopting LLMs: Do you have any thoughts on how to ensure that sensitive customer/shareholder data is not inadvertently mixed in to some new workflow involving third-parties while keeping it accessible for production apps and services?
Keeping confidential/sensitive data from leaking into marketing workflows seems to have been a historical and relatively recent challenge for Carta so would love to hear how you were able to transition from that to securely managing the mentioned level of LLM deployment integrating across the org.
thinkxl
Well, the answers to your questions don't sell books, right?
beardedwizard
A master class on how to say exactly nothing.
nssnsjsjsjs
Extracting the kernel sounds like a good idea, but it sort of depends on having a reasonable executive who'll take the time. Some executives won't tell you the kernel, may not know it themselves and the power gradient can make it hard to ask (you don't want to look foolish).
> Extract the kernel – everywhere I’ve ever worked, teams have struggled understanding executives. In every case, the executives could be clearer, but it’s not particularly interesting to frame these problems as something the executives need to fix. Sure, that’s true they could communicate better, but that framing makes you powerless, when you have a great deal of power to understand confusing communication. After all, even good communicators communicate poorly sometimes.
I gotta say, nothing fills me with as much excitement for a job as much as having to have a second job as a Kremlinologist, attempting to scry the motivations of the opaque execs, whose whims come down from On High, either engraved on stone tablets dropped directly into our teams, or brought down to us through three translation layers of middle-management.