Evidence receipt / prediction
Published · transcript-backedDan Shipper: prediction
24 May 2026 Lenny's Podcast The AI paradox: More automation, more humans, more work | Dan Shipper
“One last thing that I think is really interesting is I think that we will be reading way more AI generated writing in documents and emails and we will like it.”
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Everything needed to verify it.
- Speaker
- Dan Shipper
- Attribution
- Verified speaker
- Claim type
- prediction
- Recorded
- 24 May 2026
- Publisher
- Lenny's Podcast
Transcript context
…Yeah. Sales is where my mind went. The top of funnel AI is helping a lot with sourcing and qualifying things like that. It feels like the work of a salesperson is not fundamentally different and Customer support's fundamentally changed. So that's interesting. Sales so far so good for those folks. Okay. So maybe just summarizing some of the predictions in this bucket of just the shape of the work, how it's going to change. What I'm hearing so far is just going to be a lot more reviewing of other people's output as a part of the work. And then two, there's going to be a lot of like almost babysitting of AI agents to make them do the thing you want them to do for deploying and then just gardening them along the way, make sure they continue to do their work. Anything else before we get into our third bucket? I would sort of split it into less babysitting agents and more your forward deployed team is trying to build a whole system that makes it so that people who have less knowledge can use that system without doing something dumb. And that's like a really interesting engineering challenge. I think babysitting kind of makes it feel like it's, yeah, you're just kind of waiting for it to fuck up and then fixing it or whatever. And that can be the case, but I think a lot of it is this extremely interesting engineering challenge of building a system to enable everybody else in your organization to do what used to be a technical job. And then if you're not one of those people, like you're the data scientist or whatever, you can go a lot deeper with AI into really important questions that eventually probably filter into the work that the forward deployed engineering team is doing, but is like more generative and more new and you're dealing with harder questions. One last thing that I think is really interesting is I think that we will be reading way more AI generated writing in documents and emails and we will like it. And I think we are already doing this in coding where we read plan documents. I don't want an engineer to hand write a plan document. That would be very silly. It would be obviously silly. And I think the same is true when we did our quarterly planning for every at the end of 2025, we did it all with Notion Agents and we just had a bunch of Notion agents and we had really one Notion agent and then we had a top level company strategy and then we had everybody in the company just talked to an agent and it asked them about what happened last year, how did it go, what were your goals? What do you want to do this year? What are your metrics? It pushed back and then it was like, how does this relate to the overall company idea? All that kind of stuff. And then I got these incredibly good AI generated strategy reports or quarterly plans for each part of each team. And then I could go in and be like, "Okay, who needs to talk to each other? Which teams need to talk to each other that don't know they need to talk to each other? And which one of these is actually low quality or which one of these is high quality?" All that kind of stuff, it makes it a lot easier to process. And I see that all the time now. I consistently get AI generated stuff and there's a difference between an AI generated document that's slop and not. And the slap one is it took them less time to make it than it takes me to read it and they don't stand behind every line. So my expectation is if you send me an AI generated document, I think that's great. And if we talk about it and it's clear you have no idea what's in it, big no-no, not allowed to do that. every line. So my expectation is if you send me an AI generated document, I think that's great. And if we talk about it and it's clear you have no idea what's in it, big no-no, not allowed to do that. And I think we have this aversion to AI-generated stuff that will go away because the kind of strategy document that GBT 5.5 can write when it's directed well by someone on my team is way better than them just like dinking and dunking their fingers on the keyboard.…
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