[HN Gopher] Stuff I Learned at Carta
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Stuff I Learned at Carta
Author : blueridge
Score : 66 points
Date : 2025-05-24 01:24 UTC (21 hours ago)
(HTM) web link (lethain.com)
(TXT) w3m dump (lethain.com)
| nssnsjsjsjs wrote:
| 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).
| baobun wrote:
| 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 wrote:
| Well, the answers to your questions don't sell books, right?
| drewbug01 wrote:
| > 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.
| tuyguntn wrote:
| > 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 wrote:
| 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 wrote:
| 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.
| adamesque wrote:
| > 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 wrote:
| 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?"
| calderwoodra wrote:
| Communication doesn't scale and there are many examples of
| that. It's not possible to convey complex topics to a large
| audience, well, at all times. The audience has to do some
| work too.
| braza wrote:
| > 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 wrote:
| > 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).
| about3fitty wrote:
| This is super difficult for me to parse. Could you please dumb
| it down for me?
| gregorvand wrote:
| 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 wrote:
| Seems like Will hasn't stayed anywhere for more than 2-3 years?
| returningfory2 wrote:
| 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.
| sleazebreeze wrote:
| I've read his writing for years, and he knows how to express
| things that feel real and true to me. However the skill of
| writing for a broad audience doesn't mean you are more
| effective in your specific job or company.
|
| It can be true that Lethain is an excellent writer and also a
| job hopper who doesn't bear the consequences of his
| decisions.
| mrdoodleturd wrote:
| This guy blows
| vladf wrote:
| why
| pavel_lishin wrote:
| > _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.
| thinkxl wrote:
| 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 wrote:
| 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.
| thinkxl wrote:
| I agree. You describe how it happens; however, I still
| don't find a justification for these:
|
| - rely on competent people directly under the executive to
| guess what that means
|
| - after-meetings in which everyone tries to interpret the
| executive's feedback
|
| - the executives are busy and hard to get access to
|
| Imagine having a riddle as feedback in which people from
| different backgrounds and cultures gather to decipher a
| meaningful direction.
| bensonperry wrote:
| 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!
| hn_throwaway_99 wrote:
| Your framing here, while I admit is quite clever, is so overly
| cynical that I think it misses the point entirely.
|
| I think a more generous interpretation of his point is:
|
| 1. Everyone (execs and others) needs to translate their true
| goals and motivations into language, and some people do this
| better than others. Even great communicators have some delta
| between what they say and what they truly mean.
|
| 2. Thus, it pays to keep this in mind, and think from the
| perspective of "OK, what is the top-priority, primary thing
| that this exec is really trying to get across", which can
| sometimes mean you need to separate the wheat from the chaff of
| what they're saying.
|
| Frankly, I think this is good advice for anyone on the
| receiving end of a message. I think this HN guideline deserves
| a reminder: "Please respond to the strongest plausible
| interpretation of what someone says, not a weaker one that's
| easier to criticize. Assume good faith." Thus, you can either
| interpret his statement in a positive manner about how you can
| be more effective when on the receiving end of a message, or
| you can complain about needing to be a Kremlinologist.
| basket_horse wrote:
| 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.
| harryquach wrote:
| Thanks for the laugh friend. I was thinking the same thing.
| Zanfa wrote:
| 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 wrote:
| 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
| Zanfa wrote:
| Terrible people can be good at things, so their advice may
| be useful, but it still doesn't mean taking leadership
| advice from a terrible leader is a good idea. Maybe if he
| was blogging about how to fail upwards. It's more about
| separating the con from artist.
| lobotomizer wrote:
| 1) pee pee
|
| 2) poo poo
| swyx wrote:
| 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
| hn_throwaway_99 wrote:
| While I perhaps wouldn't have put it the same way, I agree.
|
| This may go against "SV standards", but I've found that the
| execs that I most admire at any particular company put in _at
| minimum_ 4 years - that 's the time it takes not just to get a
| project or two off the ground, but to really instill structural
| and cultural objectives at any company, and as you put it , to
| really deal with the consequences of their decisions and refine
| as necessary. While everyone have some "misfires" in their
| career, I'm extremely wary of advice from someone that has
| literally never hit the 4 year mark despite nearly 2 decades of
| experience.
| slt2021 wrote:
| 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 wrote:
| 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"
| financetechbro wrote:
| "Bit too painful" sounds like they're just being lazy
| beardedwizard wrote:
| A master class on how to say exactly nothing.
| RainyDayTmrw wrote:
| > 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. None of
| these are the sort of inspiring topics that excite folks, but
| they are all essential to the long term stability of your
| organization.
|
| There it goes. The mask comes off. The sad reality of it is that
| your average exec views their work, indeed their life, as
| strictly zero sum. We should not praise this. We should not
| celebrate this. If anything, we should call this out.
| hn_throwaway_99 wrote:
| I'm not quite sure how you interpreted a section about CTOs
| managing their organization's costs - which, given that money
| doesn't grow on trees is obviously a core part of their job -
| with some pretty rational and reasonable advice as "The sad
| reality of it is that your average exec views their work,
| indeed their life, as strictly zero sum."
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