September 20, 2025 | Read online​

In this newsletter I’m going to break down a tactical way for you to stay top of mind with your prospects and clients without being annoying while building your business acumen and personal brand along the way.

Here’s the scenario.

You call a client or a prospect, have a decent conversation and they say something to the effect of:

“Sounds good but I just have too much on my plate right now. Why don’t you call me back in 6 months.”

Obviously you want to try and deal with the objection right there and ask questions like:

• What’s going to change in 6 months?
• What are some of the other priorities projects you’re working on right now?
• Is there someone else in your organization I can talk to in order to gain some insights so when we do talk we can have a more meaningful conversation?

However, regardless of what you ask or what objection handling technique you try and use, inevitably the answer is still going to be to call back in 6 months.

So what do most sales reps do? They touch base and check in with them in about 2-3 months to “see how everything is going” and then they send an email in 6 months reminding them the client they told them to reach back out in 6 months.

This is about as meaningless as it gets and does nothing to keep them engaged. In fact it might annoy them to the point where they’re even less likely to engage with you if/when they need a solution like yours.

So how do we stay top of mind without being annoying?

Ask that exact question to them.

Here’s how I do it.

At the end of the initial call when they tell you to call them back in 6 months, say this:

“I’m happy to call you back in 6 months. How do I stay top of mind without being annoying?”

Don’t just end there though. You have to give them a good reason why you're asking and some examples.

I give them my reason before they can answer. It sounds something like this:

“How do I stay top of mind between now and then without being annoying? The reason I ask is because I tend to stay on top of a lot of the trends and topics out there related to (insert title/industry here) and I wanted to see if there was any type of information that you were interested in and would get value from. For instance, some of the tools, tech, trends, methodologies (in the case of sales training).”

Hopefully, they’ll engage with you and give you a few examples of information they would get value from which does not include information about your company by the way.

From there, you want to track what they’re interested in and then find a way to consume that type of content.

I personally have a section I created in my CRM (Salesforce) under ‘Contacts’ called ‘Interests’ where I include a bunch of topics with check boxes next to them. When I get off the phone with a prospect or client and learn about what they’re interested in, I go into their contact field and check off all the relevant boxes.

Then, I set up folders in Feedly (not a sponsor) for those specific topics and add all the relevant blogs I can find.

Feedly is now effectively my “morning paper” that I read as part of my morning routine.

Every morning I open up the folder, skim through the headlines and see if any of them catch my eye or seem interesting.

When I come across an article I find interesting, I read it. If I learning something (improving my business acumen) I share it on social with some of my thoughts/insights (building my personal brand), and then I run a report on Salesforce for any of my Tier1 clients/prospects who said they were interested in that specific topic and send them each a personalized message that sounds something like this:

“Hi Sarah, I remember you said a few months ago that you were interested in X. I came across this article on the topic recently and thought you might find it interesting because….(context)”

I don’t even add a CTA or ask them to meet about it or talk about it.

This is how I touch base and check in without touching base or checking in.

As an added bonus, another way of staying top of mind without being annoying, I set up my top 25 Tier1 prospects on tracking tools like Owler (not a sponsor) to get alerts on very specific trigger events like M&A, new product launches, hiring, etc.

I also track trigger events like Awards and Funding.

When I get an alert that a Tier1 target account got an award, I forward it to them and say something like:

“Congrats on the award. It looks like you guys are crushing it right now.”

Again, with no CTA.

When I get an alert that one of them received funding, I don’t do what everyone else does and hit them with an email that effectively says:

“Congrats on the funding. Let me show you how I can help you spend that money.”

Instead, I simply say:

“Congrats on the funding. I hope that means something good for you personally and professionally.”

This is my way of “touching base” and “checking in” without being generic and it works:

The reason it works for me is because it shows I’m paying attention and always trying to add value in every interaction. There’s also a bit of reverse psychology involved with it when you don’t add a CTA.

Try it out and let me know what you think.
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SPOTLIGHT: Otter One of the best ways to stay top of mind without being annoying is by actually bringing value into every conversation. That starts with how you prep, run, and follow up on your meetings. That’s why I worked with Otter to create The Sales Conversation Playbook — a tactical guide to help you: Prep smarter with shared agendas Ask better impact questions that uncover urgency Send summary emails that actually move deals forward This isn’t theory — it’s the exact system I use in my own sales process, with Otter helping me capture, organize, and act on every conversation. 👉 Grab your copy of the playbook here.

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How did I do with this edition? Amazing - can't wait till next week It was okay Needs work