How To Relentlessly Follow Up With Prospects Without Annoying Them And Blowing The Sale

Posted on October 30, 2015

Ryan Stewman



You left the meeting and had a good feeling about this one. He said to follow up with him in the next few days and he’ll close the deal with you. You need the sale. You know the prospect is a busy man. You’ve already left a few messages and sent an email or two.

How much follow-up is too much?

There’s a fine, really fine line between follow up and annoyance. There’s also a weird part of the process where annoyances become follow up and the prospect respects your hustle. Oh, and that part about them getting mad and telling you to never to contact them again? That happens too.

The last thing any of us wants to do is piss off a prospect by bugging them too much. The first thing any of us wants to do is make a sale. Both are valid consequences of follow up. It’s your job as a salesman to know exactly how much follow up is the right amount. If you’re not sure, it’s cool, stick with me and I’ll teach you how I do it.

If You’re Gonna Close Sales, You’ve Got to Relentlessly Follow Up

Relentless follow up doesn’t have to be annoying. It doesn’t have to piss the prospect off. If you do it right, the prospect will love your follow up and close with you when the time is right. It’s all in the technique you use and the perception of that technique by the prospect.

I’ve sold cars, homes and everything in-between at some point in my life. I’ve had several sales “jobs” that required me to do daily follow up with prospects who weren’t exactly happy to be bothered so frequently. I don’t do well with “no,” so I had to concoct some creative ways to get myself back in front of the prospect every day to do my job and close the sale.

The car business probably required the most follow up of any job I’ve ever had. Selling cars is a “right now” business. If you don’t close them “right now,” your prospect most likely won’t be back. If a prospect leaves the dealership, you’ve got to be one BAMF on your follow up to get them back to the barn.

People don’t really care too much for salesmen, let alone car salesmen. That said, prospects don’t appreciate a car salesman calling, emailing and texting them every day. When I had to do so in order to feed my family, I had to figure out a way to follow up, get them back to the dealership and close them without pissing them off to where they’d go buy from my competitor.

If a Prospect Walked, I had a Surefire Way to Entice Them to Finish the Deal

I do everything in my life with intent. I’m not fearful of consequences, good or bad. Most people don’t have intentions. If you have intentions, you have consequences. Most people run from consequences and avoid doing anything intentionally. Because of this, a lot of the people you meet won’t expect you to have intent. They will almost always assume other people will think and act the same they do. When you’re different, you make the sale.

I believe it takes 12 touches to entice someone to buy. In my business, the average prospect reads my sh!t and watches me for eight months before they make a buying decision. It takes me getting in front of you a sh!t ton of times before you’ll actually buy from me. I’m okay with that. If you think about it, you reading this right now is me following up with you. Doesn’t really seem like it, though does it?


Here’s how to creatively follow up with prospects in a way that makes them buy from you:

Day 1:

You just met the prospect. You had a good sales conversation and you need to follow up. As soon as you get off the phone or get back to your car, if it was an in-person meeting, send them an email. Not just any email, an email with something you mentioned in the meeting that you thought they would like.

During the initial meeting (phone or in-person) I mention a third-party service or review that will help them, not me. This shows them I care about them and that I have expert information for them. I make them want this during the meeting, so they’ll look forward to getting the email from me with the information.

Day 2:

I call them up and double check to make sure they got my email yesterday. I also tell them I enjoyed meeting them yesterday. I never thank them for their time. My time is just as valuable as theirs in my mind. If I thank them, that means they did me a favor. By telling them I enjoyed meeting them it puts me on their level subconsciously.

I also give them the heads up I have some more cool stuff they will like, so I warn them to be on the lookout for my emails. I want them hanging and expecting my contacts so that when they happen it’s anticipated. It’s almost like setting another meeting with them.

Day 3:

I send another email with more cool information to either reinforce or add to the info I sent them on day one. “Oh, hey, by the way, I found this video that’s perfect for you.” I’m following up, but with more stuff they want. I haven’t asked for the sale again yet. I’m simply doing what I call “stacking the good.” This means I’m giving them a ton of value and demonstrating my use and expertise at the same time.

The law of reciprocity is a real thing. If I do enough cool stuff for a prospect that brings value to their life, they will want to restore order and give value to my life. Most times this is in the form of a sale. They buy from me because they feel like they owe it to me.

Day 4:

On this day, I’ll send a video I’ve personally made for them. Really, I’ve made it for everyone, but it seems as if it’s just for them. On this video, I’ll give value and show social proof of the results the prospect wants. In other words, I might show them testimonials or examples of current and past clients who have gotten the results the prospect wants.

At the end of this video, I ask for their business through a clear, strong and precise call to action. At this point, they have a really good idea if I’m their guy or not. The decision has to be made. My call to action gives them a time period in which to reply to me. They have to reach out with an answer of either “Yes” or “No.”

Day 5:

I follow up and make sure they got the video from yesterday. If I have to leave a voicemail, I do so as well and send the same message via text. I want them to feel like the video is super important, that they have a sense of urgency to watch it. It’s as if the video is expiring or going away soon.

I’m not asking for business on this call. If I do get them on the phone instead of going to voicemail, I hit them with a call to action just like the video. Not begging for the sale, but insisting they need to make a decision of “Yes” or “No.”

Day 6:

They get another email from me. This email explains I’ve been trying to catch them so we can close our business and get started moving forward. I highlight what was in the previous emails, how it benefits them and how what I sell can solve their problems. I also point out that a week has already passed. And in doing so, make them feel six days behind.

This email is full of scarcity, sales pitches and benefits just waiting for them, which will be theirs as soon as they take action. This is also the first time I’ve aggressively asked for the business. This email needs to lay it all out to them. Be firm, but empathetic.

Days 7 – 10:

I make them miss me. They’ve gotten value, follow up and an aggressive sales pitch via email from me, so I’ll give them a break. Take the scarcity to a new level. Act as if I don’t need them. They’ll think I’ve moved on, but again, I’m operating with intent. They have no clue.

Day 11:

I call them and make sure they are all good. Most times it’s a voicemail and text they get. Anytime I call the phone and leave a VM, I send the same message via text. This is why it’s important to always get the mobile number, not the office number. I let them know I’m here for them and ready to make it happen when they are. Keep it short and simple.

This call is simply a check-up. I let them know I’ll be sending another important video tomorrow via email. The purpose of this text and VM is 100 percent to set the hook for tomorrow’s follow up video.

Day 12:

This will be the last “real” follow up they get from me. I’ll send them the video I mentioned in yesterday’s text and voicemail. This video simply states that it’s been two weeks since we first got into contact. When I show them the results of other clients after two weeks with me, I make them feel the pain of what they are missing out on, using social proof all the way.

I also let them know I’m gonna let them off the hook. I’ll get off their a$$ for now. I reassure the excuses they are thinking, such as being busy, not ready, etc. I’m empathetic but at the same time, I show them what it’s costing not to get this done.

After the 12 days, I start following up via email once a week and phone call/text every two weeks. Anytime I have something of value for them, I send it at those times and follow up. I keep them in long-term, weekly follow up mode until they decide to reach back out to me. I don’t put much more time or focus on them.

You can easily implement this same intentional process into your follow up. More times than not, the prospect will buy from you at the fourth or eighth follow up. Rarely do I have to go the distance for 12 days. It’s all a matter of expert positioning on your end. Prospects buy from experts at 3X the rate they buy from salespeople.

If you’re ready to invest in your personal success and you’d like to find out about the programs we have developed especially for you, simply head over to and we’ll have a sales conversation about your future.


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