In recent columns, we have talked about the evolution of media sales. The seller’s role has shifted from order taker to trusted adviser, and thought leadership is becoming one of the most powerful ways to build credibility with advertisers.
But even when sellers do everything right, like having strong discovery conversations, presenting thoughtful strategies and delivering solid proposals, many deals still stall.
A proposal goes out. A meeting ends with “This looks great, let me think about it.” Then the follow-up begins. I call this “maybeville.”
For years, you’ve heard me say the same thing in sales training sessions: the days of “just checking in” are over. Yet it still happens all the time. “Just checking in to see if you had a chance to review the proposal.” “Bumping this to the top of your inbox.” (That one really kills me when I receive it).
Business owners are busy. Messages like this don’t add value; in fact, they can really erode your rapport and trust. And they rarely move deals forward.
In previous columns, I’ve referred to one of my frameworks, which I call the Circle of Romance. The premise is simple: most deals require five to 12 meaningful touchpoints before a prospect is ready to say yes. But every touchpoint must deliver something useful, relevant or insightful. If every interaction adds value, the relationship deepens. If the messages feel repetitive or self-serving, the conversation fades.
I received a question this week from a reader who asked, “How do I possibly find the time to hit 5-12 touchpoints with every prospect plus do the rest of my job?” I totally empathize here; we are all so busy. So, I wanted to address this question and share some real-world examples you can use. Today, AI gives sellers a powerful way to make follow-ups more thoughtful, helpful and much easier to create.
Why ‘checking in’ doesn’t work
When a prospect receives a message that says, “Checking in,” it’s really about the seller’s needs, not the client’s.
It signals:
But buyers respond much better to something different: new ideas and insights that empower and inform.
When sellers share useful information like trends, observations or marketing tips, the follow-up becomes part of an advisory relationship instead of just a reminder about a pending decision. This is where AI becomes incredibly useful.
Insights your prospect will care about
AI can quickly surface trends, challenges and opportunities that affect a specific client or industry.
For example, if your prospect owns a local restaurant, you might ask AI: “What are the biggest marketing challenges facing independent restaurants right now?”
If the prospect runs a home services business: “What digital marketing trends are affecting HVAC companies in local markets?”
Within seconds, AI can surface insights like:
These insights form the basis for meaningful follow-up messages.
Instead of “checking in,” a seller might send a note like this: “I saw an interesting trend about how customers are searching for restaurants on mobile and thought of our conversation. More people are using Google Maps searches than traditional search results when choosing where to eat. That’s one reason local search and display campaigns are working so well together right now.” Now the message is helpful instead of just transactional.
Turn insights into thoughtful follow-ups
The goal of follow-up messages is not to resell the proposal every time. The goal is to remain relevant and valuable.
A helpful structure for these messages is:
Each touchpoint reminds the prospect that you are not just selling advertising; you are bringing ideas.
A simple three-email follow-up sequence
Here is a simple follow-up sequence media sellers can use after sending a proposal. AI can help generate the insights that fuel each message.
Email 1: Industry insight
Subject: Thought you might find this interesting
Hi [Name],
I came across a trend affecting businesses in the [industry] space that reminded me of our conversation.
More customers are starting their buying journey through search and local listings rather than social media. Businesses that show up consistently across search, display and local listings are seeing stronger lead flow.
It’s one of the reasons we recommended the multi-channel approach in the proposal.
Happy to share a few examples if helpful.
Best,
[Name]
Email 2: Helpful tip
Subject: One quick marketing idea
Hi [Name],
One thing we’re seeing across several local businesses right now is that many are missing opportunities in their Google Business profile.
Simple updates, such as adding seasonal photos, promotions and updated service information, can significantly improve local visibility.
It’s a small change, but it can make a big difference in search results.
Let me know if you'd ever like a quick review of yours.
Best,
[Name]
Email 3: Client insight
Subject: Something we’re seeing with other local businesses
Hi [Name],
We recently worked with a client in a similar category who combined search and display campaigns to capture both active shoppers and people earlier in the buying process.
What surprised them was how much traffic came from people who had seen the display ads first and then searched for them later.
That kind of behavior is becoming more common, which is why integrated campaigns tend to perform better.
If you'd like, we can walk through a few examples together.
Best,
[Name]
The real power of the ‘Circle of Romance’
The Circle of Romance works because relationships grow through consistent, thoughtful interactions. Every helpful message reinforces three things in the prospect’s mind:
Over time, the conversation shifts from selling advertising to solving marketing challenges. That is when deals start to move forward.
AI doesn’t replace the salesperson in this process. Instead, it removes one of the biggest barriers: the time it takes to keep coming up with fresh insights. Instead of wondering what to say next, sellers can use AI to quickly generate ideas that keep the conversation going.
When every follow-up adds value, prospects don’t feel like they’re being chased. They feel like they’re being helped. That’s the real power of the Circle of Romance. With the help of AI, it’s easier than ever to put it into practice.
Dream Local Digital Founder and Client Success Officer Shannon Kinney brings more than 30 years of experience in leadership roles, developing scalable digital marketing strategies and supporting and training media companies with scalable digital revenue growth. She played a vital role in the development of prominent internet giants, including Cars.com, CareerBuilder.com, Knight Ridder Digital, LinkedIn, Google, eBay and Microsoft. She worked with media companies worldwide until pivoting to found Dream Local Digital. Since Dream Local Digital's creation in 2009, Shannon has served on the Local Media Association board, been awarded the LMA Digital Innovation Award, appeared on hundreds of stages as a keynote speaker and helped media companies transform their business model. She currently also serves as a project lead on the Local Media Association Branded Content Project Cohorts, helping media companies transform through new revenue streams. Shannon can be reached at shannon@dreamlocal.com.
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