How I AI - How this former NYT columnist uses ChatGPT to brainstorm ideas, do research, and find the perfect metaphor | Farhad Manjoo

Episode Date: April 28, 2025

Farhad Manjoo, a former New York Times and Wall Street Journal columnist, reveals his AI-enhanced writing workflow, from research to finding the perfect metaphor, and how these tools have transformed his creative process without replacing his unique voice.What you’ll learn:• How AI evolved from a simple tool to an essential writing companion• Using ChatGPT as a research assistant with web search capabilities• The “super-thesaurus” technique for finding the perfect words and idioms• How AI helps brainstorm ideas and refine arguments• The benefits of having an “always-on” writing partner in a remote work world• Using AI as a first reader to evaluate drafts in progress• Why AI enhances rather than replaces a writer’s unique voice• Practical tips for getting unstuck when AI doesn’t deliver• How AI speeds up the writing process while improving quality• The future improvements that would make AI even more valuable for writers—Brought to you by:• Enterpret—Customer SuperIntelligence Platform for Product and CX teams• Vanta—Automate compliance and simplify security with Vanta—Where to find Farhad Manjoo:• LinkedIn: https://www.linkedin.com/in/farhad-manjoo-161229/• X: https://x.com/fmanjoo—Where to find Claire Vo:• ChatPRD: https://www.chatprd.ai/• Website: https://clairevo.com/• LinkedIn: https://www.linkedin.com/in/clairevo/• X: https://x.com/clairevo—In this episode, we cover:(00:00) Intro(02:40) Farhad’s journey from skepticism to adoption of AI tools(04:20) Brainstorming with ChatGPT(06:54) Assessing the quality of AI-sourced information(08:34) How ChatGPT helps identify new angles and perspectives(10:52) Using ChatGPT to find alternatives to clichéd expressions(16:44) The “super-thesaurus” technique for finding perfect words and idioms(20:12) Using AI as a first reader for draft evaluation(22:15) Lightning round—Tools referenced:• ChatGPT: https://openai.com/chatgpt/overview/• Cursor: https://www.cursor.com—Other references:• New York Times: https://www.nytimes.com/• The Wall Street Journal: https://www.wsj.com/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail].

How do you walk through the process of brainstorming an idea instead of using Google? Right off the bat, it tells me, you know, about the main people in the administration who are talking about this. It gives me links to articles that I can read. This is the stuff that when I was writing a column every week. It would take me probably half a day or so to just find all the stuff and kind of figure out what I was going to write about. I'm presuming in the past you would have done this with colleagues in a newsroom and you could have these conversation live. You know you're not talking to a colleague. You know you're not talking to a human.

But in many ways, it sort of has that same function because the interface is similar. Probably it's not as smart as that person, but it's maybe 80%. And it's great and instant and available all the time. I think there's a lot of fear that chat GPT or AI generator writing is slop and it's all generic. I love seeing this idea of you making the writing more specific and more impactful. Quickly, I just discovered that it was so useful that now when I write, I have like two windows open on my screen. One is chat GPT and one is. is the document I'm working on.

Hey everyone, welcome to How I AI. I'm Claire, product leader and AI obsessive on a mission to help you build better with this new technology. Today we're talking about how AI is transforming the writing experience with none other than Farhad Manjou, former columnist for the New York Times and one of the most interesting voices in tech writing out there. Farhad's going to give us practical tips and tricks

on how to make our own writing better using AI, and you're definitely not going to miss his special word-finding technique to discover that perfect idiom or metaphor. Let's get to it. This episode is brought to you by Enterpret. Enterpret is a customer intelligence platform used by leading CX and product orgs like Canva, Notion, Strava, Hinge, and Linear, to leverage the voice of the customer and build best-in-class products. Enterpret unifies all customer conversations in real time, from Gong recordings to Zendes tickets to Twitter threads, and makes it available for your team for analysis. What makes Interpret unique is its ability to build and update a customer-specific knowledge graph

that provides the most granular and accurate categorization of all customer feedback and connects that feedback to critical metrics like revenue and CSAT. If modernizing your voice of the customer program to a generational upgrade is a 2025 priority, like customer-centric industry leaders Canva, Notion, and Linear, reach out to the team at interpret.com slash how IAA. That's E-N-T-E-R-P-R-E-T dot com slash how-I-A-I. Hi, Farhad. It's amazing to have you here.

I'm super excited to see some of the workflows you use in your writing. But before we get in it, I have to ask, as someone who writes for a living, what made you curious about these tools versus skeptical? I was a columnist at the New York Times for a while. And I was a columnist when ChatteePT came out in New York. in 2023, I think it was. And, you know, I just looked at it because everyone was looking at it. And then the first versions were not good enough to kind of help with writing.

It was very poor writing. But it quickly got better. And there was a lot of, just from creative people generally, there's this sense that, like, AI is a replacement. But I've always been sort of like an earliest adopter of things. And I really noticed, even when it was in a... its, you know, infancy and, like, not great. It could be helpful for, like, circumstances that in the past would take me a long time to do in Google. Like, for example, like, the most basic is just, like, finding another word. Like, this is better, the best thesaurus I've ever used,

because you can, like, talk to it about, you know, what things that have meaning. It soon sort of started to become like a little bit of like a companion. No, it was sort of like, first I would just like consult with it, I don't know, maybe once or twice when I was writing an article. But quickly I just discovered that it was so useful that now when I write, I have like two windows open on my screen. One is chatypt and one is the document I'm working on. So let's just get into the writing. And I'd love to go through sort of your step-by-step flow about how you use this companion through the whole process. So let's start with brainstorming. How do you walk through the process of brainstorming an idea instead of using Google using some of these AI tools?

It's become sort of like crucial in the brainstorming stage, especially after they added web search to it. So sort of it now knows like what's on the web. So a very sort of easy thing that I start with is like, say I'm writing, Sarah was writing an article about Trump's tariffs. And I wanted to know just sort of generally, let's say I was arguing that the tariffs were great. And so I wanted to know, like, what's the kind of general consensus in the news about, like, about the tariffs and, like, are there, is there anyone saying they're great? Because everything I've read is that they're, you know, going to cause lots of trouble. So that's, like, kind of a difficult question that in the past I would have just Googled,

like spent a lot of time Googling, getting together, you know, articles and kind of synthesizing after reading a bunch of things. And now, I mean, maybe we could just ask it right now. I just made that example. But can you, could you share your screen? Okay. So I've been using the latest version, which is 4.5, which is just really great at writing. Like, it's sort of like the biggest writing improvement I've seen. But it is slow. Like the earlier ones were just sort of much faster. So I'm going to just switch to Ford. If we have any, if it, if it's, doesn't work very well. Then we could just go to the old one.

We'll switch back. The new one. But so then, like, if you, if you turn on web search down here and you ask it something like, tell me about, like, all the commentary on Trump's tariffs and especially any that say the tariffs are good. Okay. So, like, right off the bat, it tells me, you know, about the kind of mean people in the administration who are talking about this. It gives me links to articles that I can read.

This is the stuff that when I was writing a column every week. It would take me, you know, probably half a day or so to just find all the stuff and kind of figure out what I was going to write about. But then now, here, I could just kind of interrogated and ask it for, like, is there anyone in the automotive industry who has commented on the tariffs? And I have a question while this is returning the results, which is, do you find the sources are of equal quality of what you would find if you were doing a Google search, good, bad? How are you assessing the quality of the sources here? Since they added web search, they put a little link next to all the things that they, next to the source of whatever statement they're making. So, for example, like I just asked it, is there anyone who is in the automotive industry who has commented? So it showed me a business insider article, a Detroit Free Press article, Reuters. I generally, if you ask it about news stuff, it generally will show you sources that are, you know, kind of well-named, well-known news sources.

But it also just shows you everything, like all at the bottom here, you can kind of click and it shows you all the things it consulted. And, you know, they're like if there's something that seems off, like you can just check the sources. So, you know, initially, when it wasn't sort of giving you links, it was telling you how it got this information, it was kind of really dodgy to use it for that kind of thing for brainstorming because you didn't know. And it was also like there was this real problem with like hallucinating where it would just make up stuff and then you wouldn't know where it found that.

But now you can really like ask it for sources and then click and find those. And it makes it much faster. and not only faster, like you can get kind of deeper into the subjects because you're asking, you're asking kind of real questions and you're not spending your time kind of just like reading the articles and trying to figure out what's happening. Yeah, that was my question, which is it seems like a really effective research tool, but it also seems like it could take you on a path where you could actually identify new interesting things to explore or write about.

So are you getting that effect by doing this sort of open-ended, research? The better that it's gotten, the more, like, deeply, it becomes kind of integrated in my workflow. So before chat, GPT, the hardest part about writing an article was kind of figuring out where it's start. And now I can just ask it sort of like, what is the most kind of compelling argument or sort of the main points or things that I should kind of highlight? I mean, I would have ideas of what to do that. But then I can ask it and it can suggest some things that I may not have thought of, and then we could talk about those things. And, you know, it's not, it's not as good as, or it's not as good a writer as, like, an editor, a professional

editor that I would work for. But it's, like, as good as, like, a research assistant who understands, you know, who understands, like, the material. And so you can, you can get kind of deeper into it and, like, it can suggest new ways or new, just new things. you might not have thought of. And the other thing is it's like doesn't have, it doesn't have like, you don't have to worry about hurting its feelings. You could say,

that's dumb, like that's a dumb idea or whatever. And like, you could just have like this very, kind of free and honest conversation. It doesn't care about like you misspelling stuff. So like I type very quickly and like there's lots of misspellings, but like it gets the gist of what I want.

And so it feels very, very much like, you know, like chatting with someone, like texting someone rather than kind of talking to like a computer. So it's like very close to like how I used to talk to like my research assistant at the New York Times. Like probably it's not as smart as that person, but like it's maybe 80 percent. And it's like, you know, great and instant and available all the time. So there's those advantages. I like to say always on eager to please. Like that's one of its competitive advantages.

Yep. Yeah. Well, let's actually get into the writing piece. I think this is the most fascinating part, which is how you use these tools to find the right words and the right phrases for when you're working on an article. So can you walk us through a couple examples of that process? Okay, so this is based on something real that I was writing. And it involved, let me paste it in here. So it involves this phrase, you know, pay the piper, which is like, you know, it's an idiom that has a definite meaning, but I didn't want to use that.

It's, you know, kind of cliche and people say that all the time. And so I would just take that and paste it in here. And this is something that, like, Google couldn't give me before. Like, you know, you could get a thesaurus, but that's not going to have, give you sort of like, this, like, it's not going to help you search idioms. So, you know, like, these are kind of easy, foot the bill, pick up the tab, settle the bill. But it could get, like, a lot deeper than that. Like, I often have these extended conversations with it about, like, just, like, weird things in English that we think we know the origin of, but we don't really are sort of what it means exactly in how those differ in, like, nuances.

So, like, I had this sentence or something like it, which is involving pay the, piper again, which is, so for months, the mayor ignored public outrage. Let me paste it in here, too. Over the polluted lake, eventually he realized he had to pay the piper. And that's just basically like not the correct usage of pay the piper, but it was like the closest I could think of, you know, like any of those others foot the bill or something. But I wanted something like, I want to say this in a catchier way, but also, with some kind of metaphor that describes like paying for something or that like your previous actions are coming home to roost or something.

It's just like a very vague idea of the word you want. And so then it suggests they gave you the chickens came home to roost. They gave me the chicken one, yeah. Like the devil came to collect. I, that's not bad. I might use that, and it's not like something I've heard a lot before. So this one, the storm he'd been whistling past finally broke. I would be like, that doesn't make any sense because you don't really whistle past a storm.

And then we could just have like a conversation about it. This episode is brought to you by Vanta. Building a business? Achieving ISO-4201 compliance shows your customers that you're taking the necessary steps to ensure responsible usage and development of AI. But the process can be time-consuming, tedious, and very expensive. With Vanta, achieving compliance can be done in a fraction of the time and at a fraction of the cost. 95% of the required document templates are pre-built for you, accelerating the process,

helping you demonstrate trustworthy AI practices and scale your business. Start with Vanta's free ISO-4201 checklist, which gives you a breakdown of the compliance process and the road ahead. Download it at Vanta.com slash how I... A-A-I-I-I-I-I for the free compliance for AI checklist. One thing that makes me reflect on that I'm curious your point of view is, you know, you and I are dialing into this from our respective homes. And I'm presuming in the past you would have done this with colleagues in a newsroom and you could have these conversation live.

And I'm imagining it's very beneficial to just have this partner for you to bounce ideas off and get this cycle on. Is that something that kind of in this post-remote world has also been a benefit for you? If I was working with colleagues, basically I would talk to them through Slack. So it's essentially like a very similar interface. You know you're not talking to a colleague. You know you're not talking to a human. But in many ways it sort of has that same function because the interface is similar.

Like instead of a Slack chat, this is a chat, GBT chat. But otherwise, like we could sort of still have that conversation. So then I asked it, you know, like, can we fix that storm imagery to make it the, make it more coherent? And it says, you know, it suggests some others. Like the storm he'd been pretending wasn't coming finally broke. Those are like much better. And like I had this thought, like I think a fear that people have, you hear it from like professors and you hear it from like professional writers and just creative people generally is that like AI is going to like replace you. and that could easily happen.

But like, I find that it speeds up a lot of the things that you used to spend a lot of time thinking about. I used to be perfectionistic or prosnickety about, like, the specific words I use in a paragraph before I could start writing the next one. And this allows me to just sort of like get to a point where I'm comfortable enough with it. And then I can really spend a lot of time, like, working on edits to, like, fix this particular word or sentence. It feels much more like you create a rough draft and because of this tool, you form it into like something that you like more often. And it's really like my work. Like even if it suggests some of these things, like it's suggesting ideas and then I'm like thinking about them and integrating them. And I don't feel like it's writing for me, which is something that I'm worried about.

Like, you know, this is like, is this really my work? if I tossed it off to like an AI. But it really feels like it's integrated into my writing rather than kind of replacing it. Yeah. And what I love about what you're showing us here is I think there's a lot of fear that chat GBT or AI generated writing is slop and it's all generic. And I love seeing this idea of you making the writing more specific and more impactful by using these tools instead of less.

Could we, I love this, you know, idiom metaphor seeking. and you mentioned a thesaurus. Do you do this at the word level, too? Oh, yeah, I do it at the word level all the time. And basically that's how I started. So, like, what are alternatives to outrage? So it gives me a whole bunch. And then, you know, and this I could have found in a thesaurus,

but probably not all of these because they're not, like, exactly, you know, linked. Like, it would be hard to find all of these in a thesaurus. so outrage like fewer condemnation like furor is a good word and I feel like I would have found that in a

the thesaurus but it's just so much faster and easier to ask this than like go on Google, type in the word, finds the kind of correct link to like the good thesaurus or whatever and then if it wasn't quite right like you couldn't get any you couldn't ask it about like other words

kind of like it so it's it's basically like you know what super thesaurus, just at the word level. And you can also ask it if your word is like, if you're using a word and you're not quite sure that that word is correct, you can ask it if it's correct. And like ask it sort of the shades of meaning about it and then, you know,

find an alternative if it's not. So in that way it functions as like, I've never, not even a human editor, you talk about like the specific, words you're writing for like you would talk you know for like a specific part of the article or when you're editing but like as you're writing like getting the right word is like something that was used to all happen in my head and now you get a chance to like talk it out and then you know get a real result at the end which is like a tiny thing like you you changed outrage to fewer but like it used to take me like three minutes or something to figure out like some other word and now I could do it in

you know, 10 seconds. What I like about this super thesaurus that I see here is it actually categorizes the words depending on the intent you want to drive for it. So I'm seeing here there's kind of a straight up, you know, synonyms for these words. And then there's what's more dramatic, what's more colloquial, what's more ironic. And that's a really interesting, I'm guessing, surface area to explore against. What if I chose like grief from this list, which is totally does not work? And I could just ask it, does this work?

For months, the mayor ignored public grief over the polluted lake. It should tell me that that's like not quite right. I think if 40 doesn't tell you it's not quite right, 4.5 will definitely tell you. I found it's a slightly more critical reader. Yeah. So it says that's close. Public grief has a mournful sorrowful tone. More about sorrow than anger.

So it gives me a way to like keep grief in there. while changing the sentence slightly. But then it also gives me examples that don't involve grief that, like, it tells me essentially that that's not quite the right word. So you're able to, you know, go over the surface area, find the right words or phrases, use those, integrate them to your own writing. And then you're working with an editor, but you also have used these tools as a first reader. So how does what does that process look like?

Or what are the things that you want out of AI as a first reader that you find really helpful as a writer? So the way that I've been using it recently is like I will start writing an article and I'll write maybe like, I don't know, like six or seven paragraphs, like just like the start of it or so. And I want to know if I'm like heading in the right direction. And that, you know, I wouldn't have called an editor to ask about that in the past because I'm not done with the article. So I can pass it off, like, just those six paragraphs or whatever and say, you know, does this get my point across quickly enough? Is there a way you can, like, suggest a way to, like, get to this argument, like, much quicker? Am I sort of, like, doing too much, like, unnecessary commentary here? You know, it's just basically, like, questions about, like, writing structure.

It's not going to find, like, logical inconsistencies or something in your argument. I don't think it's that sophisticated, but it will find, like, you know, better ways to say something if you pass it like a first version. And basically, so that's what I do. Like, I write several paragraphs. I pass it to it. I sort of like get its input, kind of change the article, then I'll write more. Then I'll, you know, I'll basically, like, read the article, read the words by myself and then sort of pass it off to that to chat GPT. and just like work on like polishing after that.

So in that sense it's like a first reader, but it's also like reading while I'm writing it. So it's like even more kind of integrated than like the first person that you would like present the kind of roughest draft to. Well, I appreciate you. Now I'm trying to think of the right, right metaphor idiom here, you know, raising the curtain or showing us how you do this behind the scenes because I think something like writing.

writing is really mysterious, high quality writing is really mysterious folks. And I think you've shown us how technology can have a role in that that still allows someone like you with an amazing, independent voice, write great stuff that has impact on the public. And I think that's pretty cool. So I'm going to wrap up with a couple lightning round questions. I have to ask the first one because I've been observing you copying and pasting a bunch. What is one thing if you had a magic wand and you could have a tool that would make this process easier for you. You'd love to see. Is there something that you want?

One of them is it doesn't have like very good persistent memory. So like if I talked to it about something yesterday and then we get back to it and I'm maybe in a different chat, I sort of have to go back and look at that chat and kind of figure things out. And I can't say like, tell me all the things we talked about last week and about this article. Another one is like I would love if they had like the, ability to share the screen so that I could just, instead of copying and pasting, I could just ask it about like the sentence over here in a different app. And it does for some apps, but I don't think it does for like all. So you can, so cursor is this programming app that you can connect to it. But like

it doesn't for most apps. And so kind of improving that feature would be great because then I wouldn't need to copy and paste. It would sort of know what's on my screen at any time. You were the first person that I've seen as a true writer of non-technical documents show a little snippet into using cursor for writing. So I think that's a really exciting little timbit you showed us there. Okay, my last lightning round question, everyone has a different answer. When AI does not do what you want, it's getting the wrong answer or it's just not responding. What is your strategy? Do you control? Do you bully? Do you yell? Do you compliment? How do you get AI to get over its own hurdle and do what you want it to. Yeah, I find myself being like very kind of brusk with it.

Like I have, if there's this like freedom of saying like you're totally like I would tell a person like you're on the wrong track like let's think about something else but I can just tell it like this is the very stupid thing. Please like let's talk about something else. Like and so you could be much more direct with it and I feel like that really works like being direct. But sometimes if it's like there are lots of things where it just can't help you. And I feel like. I feel like I have to figure out a place at some point where like we're talking in circles and it's not really like helping me and then I kind of have to do it without the AI. Well, this has been super interesting to watch.

Thank you so much for giving us an honest look into how AI is changing and improving the craft of writing. Cool. Thank you so much. This is fun to talk about. Thanks so much for watching. If you enjoyed this show, please like and subscribe here on YouTube or even better, leave us a comment with your thoughts.

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