5 Ways For Salespeople To Reconnect With A Old Prospect

It’s far easier to sell to people who have already bought from you in the past.

You already know this. So why aren’t you spending more time reconnecting with old prospects?



I’ve always found the biggest barrier to reconnecting with old prospects is just the shear awkwardness of it.

“Hi, I’m that guy you didn’t buy from, a little while ago… but yeah, things have changed…”

Even worse when their reply is, “er have we met?”.

There is nothing more embarrassing than someone you have worked hard to impress, shooting you down like this.

It reminds me of when I chatted up girls when I was 12…

Before attempting to reconnect with an old prospect there are 3 things questions you need to ask yourself –


A) Is the prospect really qualified?

First thing to do is assess why you didn’t manage to close a deal with this prospect the first time around.

Were there budget issues, was the timing just wrong?

Then you might be in with a shot.

However if you couldn’t solve a problem they were facing or they simply didn’t have a need for your product then there is no point in wasting your time twice over with the same prospect.


B) Can you get over their cognitive dissonance?

Humans are dumb.

We rely on a set of rules to reduce the amount of possessing our brains have to do each day.

One of the rules we follow is called cognitive dissonance which is the process that “causes people to dig in their heels and hold on to their beliefs even when faced with overwhelming evidence to the contrary.”

Smoking when there is overwhelming evidence that it kills people is an example.

The belief of a prospect that your product sucks is another (even if there is a crap tonne of evidence to say the opposite).

This means that if a buyer thought that your product was stupid the first time around, they’re going to believe it even more strongly the second time.

It’s far easier for a prospect to hold onto these beliefs than it is for them to change them and so your work is truly cut out for you.

However if your product has been updated, you’re a better salesperson than before or there are other variables at play you have a chance.


C) Will you be able to re-break out of obscurity?

The first issue to overcome is breaking back out of obscurity.

Busy business folks meet a lot of salespeople throughout the year. It’s likely they don’t remember you, have no idea what your product is and they only kinda remember the name of the company you represent.

Feeling confident still?

Here are the top 6 ways for you to reconnect with an old prospect and smash your way through the barrier of obscurity into the arms of the close –


1) Social media

Millenials reading this will likely want to start with the easiest option, social media.

It’s easy because you can hide behind it and the rejection is less obvious and direct if someone doesn’t tweet you back.

You can connect and message your prospect on Twitter, Linkedin, Facebook, it doesn’t matter. The only thing of importance is that the prospect sees your face, company and message as this might remind them of your previous conversations.

Once you’ve done a little social selling it’s time to step up your game and…


2) Email

Get direct with the prospect. No more games.

Reply to a previous chain of emails so they have context on your previous conversations and see if you can set up a phone call.

Email is not for selling over, it’s for setting up real time conversations.

If the prospect ignores you or tries to brush you off it’s time to get a…


3) Referral

If the prospect is either ignoring you or is still under the impression that your product sucks then you need to break the ‘pattern’ that they’re in.

They’re no longer consciously thinking about whether they’re going to speak with your or if your product has the opportunity of making their lives better, they’re just on auto-response.

They’re brains are spitting out the same message, don’t engage, don’t engage, ignore.

Your job is to knock them out of this state and a simple of way of doing this is via a referral.

Log into LinkedIn and see if there is anyone you’re working with now that perhaps has had prior contact with the prospect.

Get your sales director or CEO to contact the prospect on your behalf.

Do what ever it takes to have someone else change up the narrative of ‘salesman chases prospect’ and break the pattern they’re running.


4) Lumpy mail

Send them something lumpy in the post.

I’m 100% confident that no salesperson since the 1970’s is doing this on a regular basis.

Send them a cool shirt with your companies logo on the front of it.

It doesn’t have to be anything expensive. You’re not trying to bribe the prospect to do business with you.

Just give them a real good reason to get back in touch to say thank you.

If lumpy mail doesn’t get a reaction then send them a message by a vehicle they can’t ignore.

Get a carrier pigeon to fly in through their office door and land in their lap.

Send them a singing telegram.

Something to break through their barriers which are clearly now raised.


5) Horses head in their bed

If you’ve sent them a message by a transportation method they couldn’t ignore and you had no response, it’s time to step things up a notch.

It’s time to “send them a message they can’t ignore”.

Now I don’t mean a literal horses head in a bed, Mafia style. I’m just suggesting you do something totally unorthodox and extreme to grab their attention, by the throat, kicking and screaming and drag it back into your life.

This is likely your last shot. 

If after a few attempts to reconnect you’re not getting through it’s likely the prospect is creating and cementing the habit if ignoring you into their brains.

You need to shock them out of this and get some response. ANY response.


No good?

If you’ve tried all the options and the prospect just doesn’t want to know, then perhaps it’s time to move on.

I don’t say that lightly. You should be pushing 8-10+ times before you throw in the towel.

After a certain point though you might be doing more harm than good. In this interconnected world your reputation as a sales professional can be dashed by a few comments across the internet.

Please stop the chasing before they start sending you cease and desist letters.

At this point your time is going to be better spent with people who at least showed a slight bit of excitement the first time you connected with them.

Time is the only real resource you have.

Make sure you’re using it responsibly.


Will Barron is the founder of Salesman.Red and host of the Salesman Podcast where he entertains hundreds of thousands of millennial salespeople every month. If he isn't recording or editing shows he's racing his RX8 or riding bicycles down mountains.

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