6 ms·

Stuff I Learned at Carta

79 points by blueridge 1y ago

nssnsjsjsjs 1y ago
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 1y ago
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 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 1y ago
  Well, the answers to your questions don't sell books, right?
drewbug01 1y ago
> 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 1y ago
  > 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 1y ago
    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 1y ago
      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.
    - tuyguntn 1y ago
braza 1y ago
> 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 1y ago
  > 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 1y ago
  This is super difficult for me to parse. Could you please dumb it down for me?
  - deleted 1y ago
    [deleted]
gregorvand 1y ago
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 1y ago
  Seems like Will hasn't stayed anywhere for more than 2-3 years?
  - returningfory2 1y ago
    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 1y ago
    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.
- hn_throwaway_99 1y ago
  Not making any assumption one way or the other as this is obviously one side of the story, but the previous CTO split in an incredibly acrimonious situation: https://medium.com/@jerrytalton/when-your-company-tries-to-cancel-you-a93a9a8e5d86 https://medium.com/@jerrytalton/when-your-company-tries-to-c...
mrdoodleturd 1y ago
[flagged]
- vladf 1y ago
  why
pavel_lishin 1y ago
> 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 1y ago
  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 1y ago
    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 1y ago
      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.
basket_horse 1y ago
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 1y ago
  Thanks for the laugh friend. I was thinking the same thing.
- Zanfa 1y ago
  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.
  - OmarIsmail 1y ago
    [flagged]
  - swyx 1y ago
    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 1y ago
      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 1y ago
      [flagged]
- swyx 1y ago
  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
slt2021 1y ago
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 1y ago
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 1y ago
  “Bit too painful” sounds like they’re just being lazy
beardedwizard 1y ago
A master class on how to say exactly nothing.
RainyDayTmrw 1y ago
> 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 1y ago
  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."

79 points by blueridge 1y ago

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 1y ago

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 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 1y ago
Well, the answers to your questions don't sell books, right?

drewbug01 1y ago

> 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 1y ago
> 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 1y ago
  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 1y ago
    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.
  - tuyguntn 1y ago

braza 1y ago

> 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 1y ago
> 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 1y ago
This is super difficult for me to parse. Could you please dumb it down for me?
- deleted 1y ago
  [deleted]

gregorvand 1y ago

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 1y ago
Seems like Will hasn't stayed anywhere for more than 2-3 years?
- returningfory2 1y ago
  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 1y ago
  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.
hn_throwaway_99 1y ago
Not making any assumption one way or the other as this is obviously one side of the story, but the previous CTO split in an incredibly acrimonious situation: https://medium.com/@jerrytalton/when-your-company-tries-to-cancel-you-a93a9a8e5d86 https://medium.com/@jerrytalton/when-your-company-tries-to-c...

mrdoodleturd 1y ago

[flagged]

vladf 1y ago
why

pavel_lishin 1y ago

> 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 1y ago
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 1y ago
  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 1y ago
    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.

basket_horse 1y ago

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 1y ago
Thanks for the laugh friend. I was thinking the same thing.
Zanfa 1y ago
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.
- OmarIsmail 1y ago
  [flagged]
- swyx 1y ago
  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 1y ago
    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 1y ago
    [flagged]
swyx 1y ago
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

slt2021 1y ago

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 1y ago

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 1y ago
“Bit too painful” sounds like they’re just being lazy

beardedwizard 1y ago

A master class on how to say exactly nothing.

RainyDayTmrw 1y ago

> 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 1y ago
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."