In short
Part 2 of “How AI Is Changing Email,” focused on how Gmail/Outlook/Apple Mail AI summaries select content from promotional and sales emails, and how marketers can optimize for those summaries.
Guests
Daniel Murray (Marketing Millennials; co-host) and Jay Schwedelson (Do This Not That podcast; subjectline.com).
Key claims
AI summaries average about 29 words; the first 150–200 characters of written text matter most. Using “Action + product + deadline” in the first 200 characters increases business/consumer email click-through rates by ~19%. Bullets are highly likely to be pulled into summaries (Gmail 77%, Apple Mail 84%, Microsoft Copilot 92%). Headlines should be more descriptive than “spammy/catchy” claims.
Notable examples
“Shop 40% off Nike running shoes through Sunday night/midnight”; “Start a 30-day Peloton free trial by September 30th”; “Register for the 2027 HR compliance briefing by Friday.”
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOHaircut Dilemma
0:45 to 2:49
The hosts discuss the anxiety of switching barbers and the challenges of scheduling haircuts.
“how to but I really think that you like your hair is getting a little too long right now and I think you need a haircut and I know you like thinking about it but you haven't done it yet.”
AI in Email Marketing - Part 2
2:49 to 3:38
The hosts introduce the topic of AI summaries in email marketing, building on last week's discussion.
“So we did an episode last week about live text and how it's impacting email marketing and basically what's showing up in the AI summaries.”
Optimizing Email Summaries
3:38 to 5:44
Explore strategies to optimize email content for AI summaries, including character limits and urgency.
“Now, we talked last week about certain things that you can do.”
The Power of Bulleted Content
5:44 to 7:35
The significance of using bullets in emails to enhance AI summarization and reader engagement.
“And if you're, if you have something urgent happening and you're not, that urgency is not showing up in the overview, you got a problem because that's where like as a consumer, they're going to respond to this.”
Consumer Comfort with AI Summaries
7:35 to 10:15
Discussion on consumer comfort levels with AI summarizing emails for deals and recommendations.
“So the game now is not what's the most beautiful email, but what do you have to be doing?”
Personal Preferences at the Salon
10:15 to 12:19
The hosts share their quirky preferences and experiences during haircuts, particularly regarding shampooing.
“So literally every single time I go in there and I say to the person, all I want you to do is the fastest shampoo ever.”
Transcript
Automatic transcript. May contain errors.0:07Jay:Welcome to a new special series called The Bathroom Break. That extra 10 minutes you either have to listen to marketing tips or use the bathroom or both. But I don't recommend both, but that's your choice. This collab is going to be super fun. We have Daniel Murray from the Marketing Millennials and me, Jay Schwetelson, from the Do This Not That podcast and subjectline.com. each episode in the series we are going to go over quick tips about different marketing topics and if you want to be in the bathroom fine just don't tell us about it thanks for checking it out we are back with another bathroom break I am here with Jay Schwedelson I wanted to bring this up to you but I don't know how to but I really think that you like your hair is getting a little too long right now and I think you need a haircut and I know you like thinking about it but you haven't done it yet.
0:58Jay:But what is the dilemma that's going on in your head about getting a haircut? Like why haven't you done it? Cause you do have the best hair in marketing. Thank you for that. No. So I have a dilemma, but this is a real problem. I want to know your take on this. So I absolutely need a haircut. I look like a disaster, but here's my problem. I get a haircut from the same dude all the time and he's in the salon that has a bunch of other people working there and he's fully booked up. I cannot get a time with this dude. and the problem is I want to go to some other dude in the salon and like cheat on him but the amount of anxiety that that gives me if I book with somebody else and then I walk in I see him I go oh I'm going over to that chair I feel like he's going to give me like the the death stare and then he won't want to work with me again and like so I don't know if I can cheat on my haircut dude what do you think about cheating on your haircut dude I have two thoughts probably if If someone, because I ran into this problem with like having a trainer and like they were booked the whole time.
2:02Jay:And I was like, I've been texting them and I want to like go to a time where they're booked all the time. And then I'm like, screw it. I just need to, I need to do this. But I do think you just should go to another salon so they don't know. Oh, that's a good idea. That's a good idea. Yeah, like probably go to another salon they don't know. But the other one, I would go and be like, I tried. I called your salon. I texted you. I really need a haircut for next week. You're fully booked. Sorry, I just need to do that. But if you don't want to make it awkward, I just go to another salon. Yeah, I have to go maybe to another state or something.
2:39Jay:Like, Jay, why is your hair so short? It's not growing as long anymore. Was your haircut like three months ago with me? I'd have actual anxiety over this topic. But what we're going to talk about today is actually a part two. So we did an episode last week about live text and how it's impacting email marketing and basically what's showing up in the AI summaries. And there's a lot more to cover. People seem interested in it. Daniel, is that what we're talking about? Yeah, people responded to the podcast and I wrote a little bit about it in my newsletter about it. And people were asking a lot of questions about it.
3:16Jay:but also they were just like wondering like, okay, we gave some tips about it, but what are like some other things that they could do to make sure they show up in AI overviews for email? So like, what is something you're saying? Yeah, let me rip through some things that people aren't aware of. So we're really talking about again, and this applies to business, consumer, nonprofit, doesn't matter who you market to, that, and this is gonna become a bigger and bigger topic that when you send out your emails, promotional emails, doesn't matter, sales emails, whatever you're sending out, graphic heavy emails, the different Gmail, Outlook, Apple Mail, they're all using AI summaries to grab the most relevant parts of your email and either put that in the preheader, that second subject line, or they're putting that into a summarization above the email in the inbox.
4:04Now, we talked last week about certain things that you can do. I want to talk about a few other things that people don't realize. So first of all, the average number of words that the summary pulls is actually 29 words. That's the average number of words that the AI summaries are pulling into their summarizations. Now, here's what we found to be the most important thing that you could do. The first 150 to 200 characters of actual written live text characters are what matters most because that's what it's scanning. But if you do this combination specifically, And I'll give you examples. Action plus product plus deadline.
4:48That's the formula. Action, product, deadline. And you write that in your first 200 characters. We're seeing that increased click-through rates of business and consumer emails by about 19%. So what does that look like in practical sense? What does action, product, deadline look like or sound like? So if you're a consumer marketer, it would say shop 40 % off all Nike running shoes through Sunday night, through Sunday at midnight. Or start your 30-day Peloton free trial by September 30th and get full access to all the classes. Or on the business side, register for the 2027 HR compliance briefing by Friday to learn about these five changes in HR.
5:32It's this idea of the action plus your product plus the deadline. You need to be getting that out in those first 200 characters to really have an impact.
5:43Jay:And it also sounds that I think that the overviews to me are two different things. It's like one people want to know something that's urgent like urgency like I need to like hop on this now or like there's a deadline like like something that's happening now because they're like they're trying to pop up. And if you're, if you have something urgent happening and you're not, that urgency is not showing up in the overview, you got a problem because that's where like as a consumer, they're going to respond to this. Or it's something that is like very personalized to them and feels like this is something I need to do right now.
6:18Jay:Or I, I need to read this because this is very interesting to me. So I think those are like the two things that would trigger someone to like want to dive in deeper from their overview. But what are like, what are some other things that they could do? So I would say the most annoying thing that's working really well, but it's the number one thing is actually having bullets in your emails. So here's the data, which is pretty wild. In Gmail, 77 % of Gmail promotional emails that go out that have bulleted content, 77 % of bullets are being pulled into the summaries. In Apple Mail, it's 84%. And in Microsoft co-pilot summaries, it's 92%.
7:03So if you include bulleted items in your emails, the AI summaries are going and they are grabbing that stuff. Why do I say that that's terrible and annoying? Because, you know, we try to design these beautiful emails, these e-commerce emails, whatever. And you're like, I'm going to stick bullets in that. And in some ways, we're back to 1995, you know, where emails are going to look a little bit not like the greatest thing of all time. Because if you can't get that stuff in the summaries, no one's going to look at your emails, open your emails, read your emails. So the game now is not what's the most beautiful email, but what do you have to be doing?
7:41doing light bullets, like the first 29 words. What do you have to be doing to actually be showing up?
7:47Jay:And you know what I actually think it's going to stop? What you probably need to do more of is there's going to be less of the like spammy headlines that people did where it was like, this is crazy. Or like this, like things that are like a little too catchy and more, and you have to be a little bit more, you could be, have the urgency and stuff, but you had to be a little bit more descriptive than at the same time. Because I think if you just say this is crazy and there's nothing pertaining that, people are like, what is crazy? What is in my email that's crazy that you're trying to do? So I think being with your headlines and your email, you should be a little bit more descriptive of what they're getting out of this email that they're trying to do.
8:35Yeah, and along those lines, I want to know your take on this. There was an article that came out last week from Media Post. They did a survey and they asked people specifically about AI summaries and email. And they asked, how comfortable are you with an AI tool reading all your emails to surface deals and recommendations? And would you, I couldn't believe this, over 70 % of people said they were either very comfortable or somewhat comfortable with the email tools summarizing their emails so they can get the deals and recommendations like assorted for them. I was shocked about how high that percentage was.
9:14Are you shocked by that?
9:17Jay:I think that there's so many people who have such cluttered inboxes that they just want to find what is useful for them quickly. I do love that they, I know this is like a little old, but they added that like, what is Gmail? It has like a purchase tab. So you can go to all your, like which like before you had to like go into like promotions or updates and find it and now they have it so i think like there's never been really that good at sorting and ai is really good at sorting so like um and gmail is going to doing it anyway like the part of gmail they're going to scan your emails anyway i think the only people who probably aren't okay with this is probably businesses like they don't want you to scan my emails to figure out like strategy that is in my email so i think consumers more on the b2c side are probably more entailed to not care but it's still scary like you're some people get their taxes sent to the email and they're scanning those emails which is crazy oh i know totally i know people um they get all sketched out so i have one other random question for you related back to the haircut situation here's something i hate and i'm very weird so when you go to get a haircut they take you back there to like, you know, put shampoo in your hair and then, you know, massage your head and all this stuff.
10:39So literally every single time I go in there and I say to the person, all I want you to do is the fastest shampoo ever. And I have absolutely no interest in the rest of all the stuff that you do. And they always look at me like, and I still give them a tip. I'm not like not giving them a tip, But I say, I just want rapid shampoo. That's it. These people go back there and they want this full-blown massage and I'm not into it. What do you think about that?
11:08Jay:To be honest, I might need to step into why you have good hair because it's like a barber shop. And they go quickly and then they're not touching me. So I don't really get that fancy haircut where it's like I'm getting a massage. I'm bougie. I didn't know I was bougie. Yeah, you're a bougie hair. But his hair is great. So I might need to go to like one of these salons. But I don't think like I don't think a lot of these people's specialty is like giving massages. And when I want to massage, I want to like like deep tissue and like like. I hate massages. I know you do. You hate people touching you.
11:44It's just disgusting. It's like enough. I don't need you just I don't need you doing that. It's unnecessary.
11:51Jay:At a haircut place, I don't know how much I want someone to do that. You know those little things where they have like, I don't know what it's called, but like you can go on your hair and they can like massage your head, but they don't touch you. You know? Oh yeah, yeah. With the five like metal things. Yeah, that thing feels good. I would want that. That's fine because you do it to yourself. That's fine. Yeah, I want that. But I don't want someone touching like my head like that. Sorry. Okay. Well, we've covered a lot. Once again, another great episode. Listen, everybody leave Daniel and I some comments.
12:21Let us know other topics you want us to cover because clearly nothing is off limits. And we'll see the next one. Daniel, come on, man. I got to get back to work. Get out of there. All right. While he's still in there, this is Jay. Check out my podcast, Do This, Not That, for marketers. Each week, we share really quick tips on stuff that can improve your marketing. And I hope you give it a try. Oh, here's Daniel. He's finally out.
12:48Jay:Back from my bathroom break. This is Daniel. Go follow the Mark and Malay podcast, but also tune into this series. It's once a week, the bathroom break. We talk about marketing tips that we just spew out. And it could be anything from email, subject line, to any marketing tips in the world. We'll talk about it. Just give us a shout on LinkedIn and tell us what you want to hear. Peace out. Later.
From the publisher
AI summaries pull an average of just 29 words from your email, so every word in that window counts. Jay's formula for the first 150 to 200 characters is action plus product plus deadline, things like "Shop 40% off all Nike running shoes through Sunday at midnight" or "Register for the 2027 HR compliance briefing by Friday," and testing it is driving a 19% increase in click through rates. Bullet points matter even more: bulleted content gets pulled into AI summaries 77% of the time in Gmail, 84% in Apple Mail, and 92% in Microsoft Copilot.
Daniel argues Marketing headlines need to evolve too, since vague hooks like "this is crazy" lose their punch once AI strips away the context. He and Jay also unpack a MediaPost survey showing over 70% of people are comfortable with AI scanning their inbox for deals and recommendations, though Daniel notes businesses are far warier about AI reading emails with internal strategy. The bigger idea: email Marketing is being rebuilt around what AI can actually read, and the prettiest template loses if it's not structured to get pulled into a summary. If you want the exact formulas and formatting Marketers are using to win in AI summaries right now, this is the episode for you.
Follow Jay:
LinkedIn: https://www.linkedin.com/in/schwedelson/
Podcast: Do This, Not That
Follow Daniel:
YouTube: https://www.youtube.com/@themarketingmillennials/featured
Twitter: https://www.twitter.com/Dmurr68
LinkedIn: https://www.linkedin.com/in/daniel-murray-marketing
Sign up for The Marketing Millennials newsletter:https://themarketingmillennials.com/
Daniel is a Workweek friend, working to produce amazing podcasts. To find out more, visit:https://workweek.com/




