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Convincing your boss to embrace testing isn’t easy, but Jay Schwedelson has a smart way to flip the conversation. Instead of begging to try new subject lines or tactics, he shows how to reframe experiments as an insurance policy against being left behind. Plus, he shares a hilarious story about a supermarket parking lot that’ll make you think twice about where you stand with your shopping cart.

Best Moments:

(01:00) Josh asks how to convince a CEO to try proven email tactics instead of sticking to personal preference

(02:28) Why creating a 10 percent “laboratory environment” changes the way testing is perceived internally

(03:31) Framing experiments as an “insurance program” to prevent competitors from pulling ahead

(05:26) Using AI prompts to quickly benchmark your marketing against competitors and show executives the gaps

(08:00) Jay debates whether to shop after being dive-bombed by a bird in the parking lot

(09:26) A cart-return showdown in the supermarket lot sparks Jay’s reflection on being a “cart putter backer”

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Transcript

Jay Schwedelson: we are back for Ask us anything from the Do This, not that Podcast presented by Marigold. These were all week long. We get in work questions, we get in ridiculous questions. We try to tackle one of each. And if you wanna submit a question, it's real easy. Just go to jay schon.com. There's a button that says podcast, another one that says, ask us anything.

Jay Schwedelson: We love getting your questions. And now we're getting a little fancy. People have been submitting. Audio questions. So this week for the first time ever, and we'll see how it all goes. We're gonna play some of the audio questions that we've gotten in and we're gonna try to answer them. Ooh, very fancy.

Jay Schwedelson: Alright, so let's hear the first

Jay Schwedelson: question.

Josh: Hi Jay, this is Josh. I have a question for you. I attended a session. You gave a lot of really great tips on how to boost my emails and my open rates, and a lot of these tips I have pitched to my CEO and she is against all of them. And you said something really specific that it's not about what we like or what I like.

Josh: It's about what works. And so how do I convince my CEO that these are the tricks? That we should be testing and this is what works, and we have to move away from what she likes and what she thinks is right. Thanks.

Jay Schwedelson: Josh, that is a great question. How do you win over your boss? How do you win over your team when they are totally against trying the new things, the things that you keep hearing that are working, and that can be super, super frustrating. There's two very specific things that you can do, but before we get into the specific things that you can do.

Jay Schwedelson: You need to have a culture of testing. Whatever it is, doesn't even matter if it's uh, uh, email related, social media, marketing related, whatever it is. If there's not a culture of testing and trying to innovate in the business that you're in, that's an overall problem. Okay? Now, that's not gonna win the day.

Jay Schwedelson: If you tell your boss or whoever that they have an overall problem, they're gonna like, uh, later, dude. So that's not it. So what are the two things that you could actually do to get people to jump on board with this idea of testing? So the first one is this idea of creating a laboratory. Environment and you wanna win the day, not just on a singular test.

Jay Schwedelson: You don't want to go and say, Hey, can we test, uh, you know, putting an emoji in the subject line or something ridiculous like that? No, that is very transactional. That's a one-off thing. You wanna try to establish a laboratory environment and what you wanna really do is say, we need a 10% laboratory. That's the number, a 10% laboratory where you can, uh, take 10% of your database.

Jay Schwedelson: Okay? Or maybe it's 10% of the social media posts or 10% of your email sense, whatever it is. And say with this 10%. This is where we're, we're gonna test stuff. Always an ongoing, right? And you really don't wanna pitch it internally as this is just for testing. What it really is, it's really an insurance policy.

Jay Schwedelson: Okay? Because a lot of times, you know, bosses or whatever, they don't like testing. 'cause it sounds like it's a risk. But when you call your 10% insurance program, and basically what you're saying is, listen, we're gonna dedicate 90% to what we know works. No doubt about it, but this 10% ongoing is our insurance against being left behind.

Jay Schwedelson: Our competitors are evolving every single week. We need this 10% insurance environment. And then you really always wanna frame it in terms of money. Okay. If we're not testing this, this, and this, then we may have profit leakage. And that's what bosses care about. They cost, they care about money. Okay. Now the other big thing is that you always wanna make sure that they realize.

Jay Schwedelson: It's kind of risk free. You're not going to your whole audience, okay? It's only going to 10%. And then if you can show traction that 10%, then you could win. And the showing traction is what's really important. You need to go into this with a dashboard that you've created to show how you're gonna show whether the test was successful or not.

Jay Schwedelson: And you want to be able to show in your dashboard, you know, what was the hypothesis about why you were doing the test? What was the result? You know, what was the lift, what was the fail? And the reason you wanna create this laboratory environment is there's a really good chance that your test doesn't work.

Jay Schwedelson: And if you do it transactional and we just wanna try this one thing and it doesn't go well, then that's it. You're never gonna be able to do another test again. You need to create this environment. This testing laboratory environment, and when you do do the test, make sure it is big enough. That is absolutely critical.

Jay Schwedelson: It's a giant mistake to be like, okay, let's test the subject line that says, you know, webinar this Thursday V versus this Thursday's webinar. You are gonna see a nominal difference. You've gotta go bigger to make sure there's a test that has result, good or bad in the test, right? So instead of doing that, you would say something like, let's test free webinar.

Jay Schwedelson: And you capitalize the word free versus three sec, three secrets to boost ROI two completely, radically different things. And that way you can actually see if the results happen. Now what is the second thing that I would do to win over my boss? What is every company in fear of they're in fear of their competition.

Jay Schwedelson: So what you wanna do is to be able to show what your competition is doing and saying, listen, we're being left behind. They're doing this. And AI is a great thing to be able to tap into what your competition is doing. So you can go in the free version of Chate or Clot or whatever, and you use a prompt like this, okay?

Jay Schwedelson: You go and you put this prompt in something like this. And you say this act as a competitive marketing strategist, compare, and then you put your company name and the URL of your company. Compare Acme company@acmecompany.com, and then you put in your competitor or competitor's names. You can put five of them and their URLs or whatever.

Jay Schwedelson: Across key digital marketing channels and email marketing and create a side-by-side table that shows email marketing frequencies, subject lines, styles, social media posting, frequency, engagement levels, content types, data collection, use of popups, gated content, surveys, newsletters, website optimizations, CTAs above the fold, all this stuff.

Jay Schwedelson: Okay? And then at the end you say, highlight where our brand is falling behind, where the competitor is aggressive. The easy wins we could implement immediately. Keep it simple, visual and tactical, so a non marketer executive could grasp the gaps in under two minutes. It doesn't have to be this exact prompt, but something like that where you're asking AI to go out there, give it to URLs, give it your competition.

Jay Schwedelson: Okay. And, and if it's not even your competition, it's who you aspire to be. Have it give you all this stuff. And then you go back and say, listen, we need a laboratory environment. 'cause this is what our competition is doing. I just need 10% ongoing that I can market to, and this is how you win the day. So, all right, let's get into now.

Jay Schwedelson: The ridiculous question. We always get in ridiculous questions. Again, we're getting fancy because we have an audio question coming in, so let's hear the audio question.

Dana: Hi Jay. This is Dana from Long Island. My question is, what is the most unhinged thing you've seen gone down in a parking lot? Bye.

Jay Schwedelson: Dana, what is up? I appreciate the question. I too, and from Long Island, go, Jericho moved down to Florida when I was 15. I always say I'm from Florida, but people are like, no, you're not. I'm like, yes I am. I don't have that whole New York, whatever vibe. But Dana, let's get into your question. Unhinged things that have happened in parking lots.

Jay Schwedelson: So first off. This happened to me just the other day, which was difficult for me to process. I got outta my car and a bird took a deuce on me. Yeah, a bird, um, dropped. Um. I got crap down by a bird. I dunno how to say. It hit my shoulder as I got in my car. I looked at my shoulder, I'm like, what? What? What just happened?

Jay Schwedelson: And I looked around, of course, nobody was near me. Nobody cared. And then I was like, do I go into the supermarket and still buy my stuff with. Knowing I just got, you know, a bird just went to the bathroom on me. And so I debated this for 30 seconds. I dug in my car while this stuff was like, kind of dripping on my arm.

Jay Schwedelson: It was so disgusting. And, um, I found a, an old weird napkin and I wiped it off and I said, you know what? I'm going in. And I went to the supermarket. I got what I needed to get. And the whole time I was thinking about I have bird duty on my arm. What do I do about this? And then I got home. It was disgusting.

Jay Schwedelson: Everything about was disgusting. But in terms of unhinged things. I did see a few weeks ago and I made me nervous. I saw a woman yelling at this dude because he didn't put his cart back. You know, like in the supermarket, like after you go food shopping and then you're in the parking area and you have your cart, and then they have those like areas where you bring your cart to like line them up in that little kind of.

Jay Schwedelson: Cart area, whatever. So the dude unpacked his car and then he just put the cart next to his car and he was getting into his car and this woman went crazy, like, you gotta bring your cart back. That's not right. You know, all just screaming. And the guy's like, what, what is, what is your deal? Now I, I can relate to both sides.

Jay Schwedelson: No, I would never scream at somebody for bringing their cart back, but I then debated in my mind, so I. I, I had a new solution like two years ago. This is so random. What just popped in my head that I was gonna be a person that always brought my cart back when I was in the parking lot, that I was always gonna bring my cart back.

Jay Schwedelson: I was never not gonna do it. And for like, I don't know, six months. I did it. Anytime I went shopping at Target or supermarket, whatever, I would take my cart. I would find the little area you're supposed to put your cart in. I did it, but then over time I started to become a non-car putter backer, if that's an official term.

Jay Schwedelson: And so, but after I saw this woman screaming at the guy go, whoa, I gotta get back on the train of putting the card back because you gotta pay it forward. Or I don't know what I'm supposed to do, but she scared me. So I am now back on the card. Puter backer. Team. I don't know. Is that like, I wonder what percentage of people are on that team?

Jay Schwedelson: I'm gonna go with just by the sheer volume of carts. I see. Not in that area. I'm gonna go with 50% E. Everyone that listen, you gotta tell me, do you put your cart back? I don't know. Does everybody, am I just a horrible person? Meanwhile? Um, yeah. So that's what goes on me. What did we just talk about? I don't know.

Jay Schwedelson: Listen, I appreciate you. I'm being real. We are running out of our free virtual spots at Guru Conference. It's our large email marketing event. It is free. It is virtual. It is two days. We have Nicole Kidman, we have Ann Hanley. We have Amy Porterfield, we have Donald Miller. Uh, it is going to be Wild. Okay.

Jay Schwedelson: Guru conference.com. Grab a free virtual seat before it runs out. You are awesome. And watch out for them. Birds in the parking lot later.