March 3, 2026
Good retargeting ads don’t feel like pressure. They feel like reassurance, and that’s why they work. Retargeting is one of the most misunderstood parts of ads. It isn’t about chasing people. It’s about answering the questions they didn’t get answered the first time.
Most people don’t flat out say no to your offer. They say “not yet,” because they’re busy, uncertain, or comparing. Retargeting exists for that exact moment. In this episode of Bringing Simplicity Unfiltered, Greta (founder) and Judy (CEO) explain what good retargeting looks like and why it’s not talked about enough.
Judy feels retargeting isn’t talked about enough. People focus on “let’s get new leads, let’s get new leads,” but in Greta’s strategy there’s always a retargeting piece.
If you or your ad agency are running a retargeting campaign and it’s not converting, it probably feels like begging to your audience. Begging means retargeting with the same message, the same headline, the same ad. Nothing looks new.
Bad retargeting is the same pitch, louder and more often. That repels potential clients. Every time you do it, you train them to ignore you, and they keep ignoring you. It becomes pressure to buy instead of an invitation back in. Retargeting is really a friendly reminder.
Good retargeting isn’t louder. For us, it does three things:
In practice, that means killing objections, showing proof (and more proof), and establishing authority in your space. That’s it. People sometimes try to do too much. You’re not pitching more.
Instead of “book a call, my spots are filling up,” go back to:
Greta doesn’t want people to gloss over this. Download the transcripts from your sales calls, especially the ones where you didn’t make the sale. Include the ones where you did, too, because you may have overcome objections without realizing it.
Put them in ChatGPT and ask: what were the objections I overcame, or missed the mark on overcoming? It will analyze your language and give you a list. If people keep saying “I don’t have the money,” ChatGPT will walk you through what you needed to say so they didn’t say that back to you.
Judy adds: people often ask what to put into ChatGPT. Ask ChatGPT how to do it. “I have transcripts from my sales calls. How do I get objection breakdowns from you?” It will tell you.
If you have hundreds of sales transcripts and no time, have your VA do it. And if you don’t have a VA, Judy’s take is that in 2026 you should not only have one, but if you’re a true entrepreneur and business owner, you should have a couple. That might be some inner work to overcome, but these aren’t things you need to be doing.
Here’s where Judy thinks people miss the mark. They explain their method step by step: “First we do this, second we do this.” That’s boring. Greta does a great job with clients of telling the story while explaining the method, so people visualize themselves in it.
On a recent call with a solar panel company, it was clear they weren’t telling the story of how you feel after you’re relieved of a $500 or $1,000 electricity bill, or what that means for a big family. There was no story beyond “I’m going to come install these solar panels.” You need to tell that story. Each touch, each line, each word should be sequenced to fill in the missing pieces.
For us, retargeting is about showcasing new messages to the same audience, as personalized as possible. If we’re retargeting people who downloaded a low-ticket item and haven’t bought the upsell, we say that in the ad. It shouldn’t feel like another pitch. It should build on what you’ve already given them.
The goal is that people feel understood, because when they feel understood, they move forward confidently.
Greta says it one more time so you can’t say they didn’t say it: retargeting isn’t about persuasion. It’s about creating trust and confirmation that you’re the right person for them to move forward with. Once this layer is in place, results become predictable. Retargeting works when it respects the buyer’s process.
Most likely they feel like begging: the same message and headline, shown louder and more often. That trains people to ignore you. Show something new instead.
Objection breakdowns, testimonials that mirror the viewer’s situation, client stories and case studies, and behind-the-scenes explanations of why your method works.
Download your sales call transcripts, especially calls that didn’t close, and ask ChatGPT which objections you overcame or missed. A VA can do this for you.
Yes. If someone bought a low-ticket item but not the upsell, say that in the ad so it builds on what they already have.
If you want retargeting ads that reassure instead of pressure, see our services or reach out to us.
Want more? Watch every episode of Bringing Simplicity Unfiltered on our YouTube channel.
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