Jesse Hertzberg Jesse Hertzberg

How We Work with AI at Lineage

We didn't hire you to absorb the system. We hired you because your experience and instincts are going to change it. Most companies are adding AI to their workflows. We built the company around it. The default at Lineage is that Claude runs the workflow. We don't start with a job and ask where AI can help. We start with what Claude can do alone, then add humans where judgment actually matters.

We didn't hire you to absorb the system. We hired you because your experience and instincts are going to change it.

Most companies are adding AI to their workflows. We built the company around it. The default at Lineage is that Claude runs the workflow. We don't start with a job and ask where AI can help. We start with what Claude can do alone, then add humans where judgment actually matters.

We're a financial services company. Nothing ships without a human in the loop. The only question is how much Claude does and what the human is on the hook for.

Three modes.

  • AI-forward. Claude does the work. A human verifies specific claims before it ships.

  • Bridge. Claude does the heavy lifting. A human applies judgment.

  • Human-led. A person does the work. Claude prepares the inputs.

The speed comes from Claude working faster, not from cutting the human out. A human-led task at Lineage still moves faster than the same task at a company where the human is also doing the prep.

Taste is the hire.

The people who thrive here aren't the best prompters. They're the ones who think clearly, write precisely, and know when to trust the machine and when to override it. That's taste. We don't automate it. We hire for it.

If your instinct when Claude gives you a confident answer is to ship it, this isn't the place for you. If your instinct is to ask what it got wrong, keep reading.

Last month Claude drafted a borrower communication that was technically accurate and completely wrong in tone. Confident, polished, and going to land badly with the customer it was written for. The underwriter caught it, rewrote the opening, and we updated the skill so the next draft starts from a better place. That's the loop. The skill got sharper because someone with taste pushed back on it.

Onboarding works the same way.

Before you start, Claude drafts your first-week plan and loads the skills for your role. On day one, you're not reading a manual. You're doing the work with a chief of staff that knows how Lineage operates. Your manager owns the relationship and the read on whether you're set up to succeed.

Then the part that matters. Within your first weeks, the skills evolve because of what you push back on, what you do differently, what you think we've got wrong. The system gets smarter because you're in it, not in spite of you.

We challenge every process. If something exists because "that's how we've always done it," it's on the table. Writing stays on the human side more than most things, because writing is how you think. You can't outsource the part where ideas get distilled. The draft is the thinking. We use Claude to pressure test and sharpen, not to replace the act.

This isn't a tools initiative. It's how the company operates. We build on skills. Modular, composable units of instruction and context that load based on what the agent is doing. Our skills encode how Lineage works, and they evolve every time someone pushes back on them. That's the compounding asset we're building alongside the business.

That's our OS.

AI: 25% | Human: 75% — Jesse directed the framing, wrote the content, and edited every draft. Claude structured the essay, ran prompted research agents, and drafted iterations.

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Jesse Hertzberg Jesse Hertzberg

How I use Claude to think

I don't use AI to write for me. I use it to think with me. That's not a semantic difference. If you hand Claude a prompt and publish what comes back, you've outsourced your judgment. You'll produce a lot of mediocre work very fast. If you use it to pressure test your thinking from angles you'd miss alone, you've gained something you can't get any other way.

I don't use AI to write for me. I use it to think with me. That's not a semantic difference. If you hand Claude a prompt and publish what comes back, you've outsourced your judgment. You'll produce a lot of mediocre work very fast. If you use it to pressure test your thinking from angles you'd miss alone, you've gained something you can't get any other way.

I start with a position. I never open a session with "what should I think about X." I come in with a thesis, a half-formed plan, an argument I'm not sure holds up. Claude is a thinking partner, not a thinking replacement. If you don't have a point of view going in, you'll accept whatever comes back.

I build the thing, then I break it. First session, I work with Claude on the research. Then I start a new session and begin kaizen. I launch a bunch of agents to stress test it, each with a different point of view. How many depends on the problem. If I'm testing website copy for conversion, it's twenty personas across different buyer segments. If I'm evaluating vendors, perhaps it's three. If it's something internal, it's the actual team members who'll be affected. Claude is good at sizing the right set of perspectives when you give it the context.

I synthesize and loop. I take those reactions, decide what's signal and what's noise, and synthesize a revised version. New session. New agents, different lenses. Synthesize again. Sometimes that's one loop. Sometimes it's three. Sometimes I walk away for a few days, find something new on the web, and come back with the original doc and the new input and say "run a kaizen loop against this with these personas." The loop reopens whenever the thinking needs it.

One of my most frequent prompts is "convince me why I'm totally wrong." If Claude can't make a strong case against my position, I have more confidence in it. If it can, I just learned something.

Then I write for the team. Once the plan is solid, new session. I write the execution version. Then I run agents as the actual people who'll be reading the work. Does this make sense to Oliver? Is Liz going to push back on the timeline? Will the customer convert? That round isn't about the idea anymore. It's about how the people receiving it will receive it and whether they can act on it.

Fresh sessions are the discipline. Long conversations rot. Claude starts agreeing with you, echoing your framing, losing its edge. Every phase gets a clean session. Planning, stress testing, drafting, etc. It feels slower but it's faster and the output is incomparably better.

You have to think. This is the part that doesn't fit in a process doc. You can run kaizen loops all day, but if you're not a critical reader of what comes back, you're just generating noise. The tool multiplies whatever you bring to it. Bring sharp, critical thinking and you get sharper thinking back. Bring nothing and you get polished nothing, and you will be exposed.

AI: 20% | Human: 80% — Jesse described his full workflow, directed the framing, wrote the content, and edited every draft. Claude structured the essay, ran research agents to validate the approach against published best practices, and drafted iterations.

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Jesse Hertzberg Jesse Hertzberg

Goodbye, BigSoccer

People sometimes refer to the USA/Mexico match in Columbus on Feb 28, 2001 as "The Woodstock of American Soccer". Unlike today, it was a spontaneous assemblage of fans from all over the US who sold out the stadium as individuals, one ticket at a time. The one common thread running through the unexpected crowds filling Columbus bars and the 18 hour pregame parking lot was your BigSoccer alias. It was like nobody had an actual name. People just introduced themselves as "(screen name)" and guys would smile and say "great to finally meet you".

Twenty years ago this month I started posting MetroStars (one of the original MLS clubs) news and tidbits to my personal website. From this modest beginning grew BigSoccer, which thru the late 90s and much of the 00s was the largest community of American soccer fans on the web. The time has finally came for me to say goodbye and move on to new endeavours.

Our little BigSoccer community has played a small but meaningful part in the success of soccer in the United States. On our site supporters organized for teams not yet franchised and stadiums not yet built. Players, coaches, and league officials connected directly (publicly and secretly) with their fans. People even got married.

The 2002 World Cup in Japan/Korea stands out as watershed moment for many American soccer fans, including myself. BigSoccer has received a lot of touching tributes this week, but none moved me as much as this story about that 2002 World Cup run and our coach, Bruce Arena:

People sometimes refer to the USA/Mexico match in Columbus on Feb 28, 2001 as "The Woodstock of American Soccer". Unlike today, with SuperCapos flying in from Seattle to lead [the American Outlaw's] version of the Hitlerjugend via a loudspeaker system while millions watch on TV, it was a spontaneous assemblage of fans from all over the US who sold out the stadium as individuals, one ticket at a time.

The one common thread running through the unexpected crowds filling Columbus bars and the 18 hour pregame parking lot was your BigSoccer alias. It was like nobody had an actual name. People just introduced themselves as "(screen name)" and guys would smile and say "great to finally meet you".

Sadly the post game threads disappeared long ago in one of the many crashes over the following 18 months as BS was repeatedly overwhelmed by a crush of users no one could have anticipated, but there were literally hundreds and hundreds of posts where people listed dozens and dozens of screen names they had met in CBus.

In a very real sense it was the dawn of a feeling of community in American soccer, the idea that the days when being a soccer fan made you the weirdo at the party were coming to a close. To borrow a phrase, it was the end of the beginning.

Strangely – or maybe not – it was Bruce Arena who provided the punctuation.

When the US team arrived at their hotel in South Korea for the World Cup a year later, there was some snafu with the reservations or something so while the USSF travel gerbils huddled with the management and SK/J officials, il Bruce sat down at one of those pre-laptop-and-wifi era lobby computers and got on the Internet.

Several observers walked by and noted that the place he logged into, after 14 hours in airports, airplanes and buses, was BigSoccer.

Thanks Jesse.

I love soccer. My grandpa and I argued about Chinaglia as Cosmos season ticket holders. My brother and I cheer for Flamengo even when they're breaking our hearts. The MetroStars/Red Bulls alienated me into the arms of NYCFC. The World Cup takes over my life every four years with blessings (and egg sandwiches) from the missus. And for some unknown reason I support Watford. 

Most importantly, my kids and their kids will get to enjoy top flight domestic competition from here on out. 

It's been a great 20 years to be a soccer fan in America.

PS: That quote above is courtesy of Bill Archer and you must read his regular teardowns of FIFA, which he has been publishing for nearly as many years as this corruption investigation was secretly going down.

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Eric Fixler Eric Fixler

Eric Fixler Responds to 'Pull a Fixler'

Pulling A Fixler hasn’t [yet] entered the mainstream vocabulary in the way that pulling pork has, but it’s clearly resonating among the lot of us who find too much of our time, creative energy, and productive output neutralized by ill-conceived and poorly run meetings. I get that.

Taking control of your time is a powerful act, particularly in tandem with an expression of integrity and competence, both of which are wrapped in the core of Pulling A Fixler. It’s also a loosening of the grips of both FOMO and careerism, and declaring that you know that you’re not actually missing anything, career consequences be damned.

Many of us find ourselves voiceless inside organizations that are needlessly and illogically off the rails. Etsy in 2011 had gone through 3 CEOs in 3 years, and you’d be hard pressed to find anyone who thought it was in a healthy organizational state, or anyone who believed that the level of success that the company has seen under Chad Dickerson was inevitable or assured.

This guest post by Eric Fixler is in response to my blog post, which has managed to go pretty viral over the past six weeks. -Jesse

Pulling A Fixler is a well-intentioned and maybe even effective antidote to a suboptimal situation, but it’s not the best way.

Pulling A Fixler hasn’t [yet] entered the mainstream vocabulary in the way that pulling pork has, but the concept is clearly resonating among the lot of us who find too much of our time, creative energy, and productive output neutralized by ill-conceived and poorly run meetings. I get that.

Taking control of your time is a powerful act, particularly in tandem with an expression of integrity and competence, both of which are wrapped in the core of Pulling A Fixler. It’s also a loosening of the grips of both FOMO and careerism, and declaring that you know that you’re not actually missing anything, career consequences be damned.

Many of us find ourselves voiceless inside organizations that are needlessly and illogically off the rails. Etsy in 2011 had gone through 3 CEOs in 3 years, and you’d be hard pressed to find anyone who thought it was in a healthy organizational state, or anyone who believed that the level of success that the company has seen under Chad Dickerson was inevitable or assured.

Saying no at work is a million times more complicated than ducking out of a meeting, because it cuts to issues of hierarchy, integrity, intent, communications, and tribal competition.

In that context, Pulling A Fixler becomes what one insightful colleague of mine calls a Larry David Moment. I didn't at first believe that the apparently well-adjusted types with whom Pulling A Fixler struck a chord could have an internal Larry David struggling to show itself. The umpteen reposts, high-fivey emails, slides devoted to Pulling A Fixler in management-practice decks, and the Pulling A Fixler cutout cards that have come my way over the past few weeks have proven me wrong in this regard.

I’m here to tell you that Pulling A Fixler is a well-intentioned and maybe even effective antidote to a suboptimal situation, but it is not the best way. It’s also something I haven’t done in years, in part because I’ve evolved as an individual, and in part because my role in the professional universe is different now than it was then.

Walking out of a meeting in-progress should be an approach of last resort. At best it’s awkward, at worst it’s rude. The truth is, you may need to walk out of a meeting sometimes, and it may be the right thing to do, but if you’re already there, your victory in leaving will be at best partial, and at worst pyrrhic.

As a manager, you should be enhancing workplace rhythm, not disrupting it.

In reality, the outcomes of “The Fixler” are mixed. You might feel empowered, but that’s mostly ego. You might get a little bit more done, but you already interrupted your flow to get to the $#*%^ meeting. You might send a message, but its effectiveness will be diminished by the friction generated by the act itself. You haven't created any dialogue. The witnesses to your act may empathize with you, but they won’t all be as perceptive and reflective as Jesse Hertzberg.

As an invitee, the right thing to do — and at its root this whole topic is really about doing what’s right — is to bow out of the meeting ahead of time, and make sure that you really know the meeting context and that the meeting organizer understands that you won’t be there and why.

If the right time to decline is ahead of time, and the invitee can accept some responsibility for communicating, we’re really not talking about meetings at all anymore. We’re talking about saying ‘no’. And saying no at work is a million times more complicated than ducking out of a meeting, because it cuts to issues of hierarchy, integrity, intent, communications, and tribal competition that 'The Fixler' doesn’t even begin to touch.

Saying ‘no' — in particular when saying no is authentically believed to be the right thing to do for the collective effort — deserves its own conversation. For now, let me just assert what I think most of us know intuitively: A ‘No’ that means, “No, I don’t want to do that because it’ll detract from a more important effort,” is really a very high form of ‘yes’; and a ‘Yes’ that really means, “I’ll go along to get along,” is actually a very low form of ‘no’. It’s complicated.

Pulling A Fixler makes some sense because it takes place inside a particular circumstance where the intent and the integrity behind the ‘no’ are hard to misinterpret. It is a rare case of late binding in the space of office work. It feels powerful, and disrupts the lack of agency we feel when we get unwanted meeting invites from people above us on the organizational totem pole.

Not long after the events depicted in Jesse’s post, I switched to a different position on the organizational totem pole. I wouldn’t necessarily describe the move in vertical terms — our totem poles at Etsy were sort of 3-dimensional — but I was a manager (again). More to the point, I was now a scheduler, not just an invitee.

There’s a time and a place for meetings. Work is made of people, and getting together is necessary sometimes. It can also be collaborative and challenging and interesting and productive and zesty.

As a scheduler I’ve tried to incorporate self-awareness about what made me walk out of those meetings into scheduling (dare I say organizing) my own meetings, including:

Make sure that the intent and goals of the meeting are clear ahead of time. You’d be amazed at how little I often knew ahead of time about the meetings I ‘Fixlered’.

Keep the invitee lists smallish, and make people optional. Too small is always better than too big.

The onus is on the organizer to justify people's presence. Make everyone optional if you can, or at least let people know that you are generally OK with them using their own judgment about whether they need to attend.

Keep a rhythm. If you’re frequently creating meetings at random times, with little or no lead time and inviting a lot of the same participants, you’re doing it wrong. For engineers, designers, writers, and others, getting into a zone is critical to happiness and performance. Having a regular-ish schedule, and knowing your schedule when you get to work in the morning are both components of a kick-ass day. As a manager, you should be enhancing workplace rhythm, not disrupting it, so use regular time slots as much as possible. Don't schedule less than a day in advance, unless it's truly urgent.

Get off the screens. Computers and phones help perpetuate lousy meetings by letting people be there when they're really not.

Keep setting an example by saying no, ahead of time, to meetings that aren't the best use of your time, and aren't in the best interest of your company. My best self is honest and respectful about the best use of time and about communicating that to others in the way that I would want it communicated to me. I do say no to meetings. It does raise people's hackles, but it also provides an opportunity to set an example and express real values about work and collaboration.

I’m not going to say that Pulling A Fixler isn’t sometimes justified or even necessary. I’m also not going to say that skipping meetings definitely isn’t going to hurt your career. It is reasonably obvious that Pulling A Fixler is not the best way to elevate yourself and those around you. It reflects, in part, being stuck in a shitty game. But if you know that, and it bothers you, there’s probably a different approach that you can come up with to set a better example and to raise the discourse of everyone around you.

If you’re organizing meetings thoughtfully you can almost certainly prevent the preconditions for an attendee Pulling A Fixler from ever transpiring. It is actually your responsibility to do precisely that, even if no one ever tells you as much.

You can’t make every meeting perfect, and you probably can’t fully erase FOMO and the career anxieties that come with it, but you can put them on the table and be honest about them. And being as honest as you can be is what’s going to enhance the collaboration and camaraderie that meetings are really meant to advance.

I'm sorry, but I have to go now.

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Jesse Hertzberg Jesse Hertzberg

Happy

Happy wife, happy life.

Happy employees, happy customers.

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