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Here’s a real life example how I got in front of a hard to reach prospect for a tough sell.

How long does it take you to get ahold of a prospect for a really tough sell? 4 calls? 6 emails? Months?

Did you know that it takes on average 8 to 12 attempts to reach a prospect by phone, however most salespeople give up after 2 attempts?

How many calls would you make to reach an unreachable lead? Would you persevere for 2 years?

Ask most salespeople and they will say the hardest part of sales is prospecting. You have to have a well thought out game plan, a ton of patience, and the ability to get over rejection pretty quickly.

Not to mention a lot of time. Studies show that salespeople spend about 17% of their business day prospecting and researching leads.

Perhaps you are one of the chosen few who has it all together — a very targeted buyer profile, a marketing department feeding you qualified leads and time set aside to focus on prospecting. But you still are struggling to connect. Maybe you just know your list of prospects is ideal… if only you could get ahold of them…

Let me tell you a story about a friend who was on the receiving end of this prospecting relationship. He was the unreachable prospect that finally answered the phone after 2 years!

The Initial Contact

About 24 months ago, a friend of mine, who works in Business Systems, received a call from a B2B salesperson looking to sell him a software solution for his org. The stars must have aligned that day for him to even answer the phone.

But he did and accepted her request for a quick demo to learn more about the product she was selling.

For him, he wasn’t really interested in doing the demo, but was feeling nice that day. The product she was pitching was solid. She knew it was a great solution for his company.

His response was that it just wasn’t the right time. And so began the tough sell.

When a salesperson initially connects with a prospect, they have to be able to gage very quickly where they stand on the “timing, fit and budget” spectrum. If you’re receiving qualified leads, then theoretically your product and/or service should align with their fit and budget.

A stellar prospecting process begins with building out a buyer profile, and then only targeting leads that fit into that persona. With all the market research and data out there, you can pre-assess a lead based on their overall company revenue (can they fit you into their budget) and pain points (are you a good fit for their needs). So, the only piece that is left out is timing.

A requirement for a tough sell is perseverance and this is where it comes in.

The Chase

This sales rep knew all the signs to look for if a lead was a hot lead. She was steadfast that my friend was a great prospect, and time was the only thing that stood in her way.

After that initial connection and short demo, she was told to “try back in 6 months or so”. A tough sell indeed.

Like any good salesperson, she then immediately put a note in her calendar to call him back 6 months to the date. In those next 6 months, she continued to track the progress of his company, virtually scoping out any new pain points they may have, and keeping an eye on any big changes. In today’s world, all you need is Google and LinkedIn to keep you up to date on all of this.

6 months later, right on queue, she was in his inbox with a follow-up message referring to the demo, her product’s benefits, and how she still believes it’s an ideal fit for his company. My guess is that she was using a Proactive CRM that helped her stay on top of who to call, and when, so no deals slipped through the cracks.

She asked in her email if the timing had changed for him. Was he ready to re-evaluate?

Dead silence.

Another email.

No response.

A few phone calls.


For the next 18 months, she continued to reach out every 6-8 weeks, but received no feedback.

She was being ghosted.

Now, I’m sure if you’re in sales, you’ve definitely been ghosted, even if you didn’t know there was a term for it. Getting ghosted by a prospect is when you get a sign that things are going well, you’re feeling good, and then they disappear without a trace.

There are few things that typically run through a salesperson’s mind at this point… Like, “I bet they just forgot they voicemail password and can’t retrieve the messages I’ve left. Perhaps I should just call once more?”

But in reality, you are most likely getting ignored because it’s a timing, fit, or budget issue. In my personal opinion, I’d rather get a definite “No” from a prospect than silence. Silence leaves a door open. This sales rep saw that door and wasn’t going to let it shut unless it was slammed in her face.

She tried everything during this ghosting period to reach my buddy, including:

  • The “lost email” ploy, where you say “hey, my email must have got lost in your inbox…”
  • A guilt-inducing voicemail that mentions your manager breathing down your neck.
  • Using a “negative close” tone to push the onus back on them to get in touch.

This sales rep was determined! She was going to push past the silence and get a yes or a no from my friend.

And that’s when she came up with a brilliant idea to reach the unreachable prospect.

The Catch That Worked

Two years after that initial contact, my Business Systems friend received a package on his desk. It was a hard copy sports book, with a handwritten note inside from this persistent sales rep saying that she thought he may enjoy this.

Now, what did this book about the life of Muhammad Ali have to do with the SaaS she was hoping to sell to this company? Absolutely nothing. But it was just one more creative way to get noticed.

He put the book aside on his already cluttered desk and went off to his next meeting.

The following morning he receives an email from the rep. She had the shipment of the book tracked, so was alerted when it was delivered. This way, she was able to follow up with a note referencing the book’s confirmed arrival and hoping that he likes it.

Oh, and also, can we get that meeting on the calendar? Wondering if timing is now good for you guys…

This time, he responded. Yes, he’d take the meeting, and even pulled in two other key players that would possibly benefit from her product.

He figured, hey, if she was going to believe strongly enough that her product was right for them, and he was worth the effort, then maybe she knew more than him… Maybe the timing, fit and budget finally were right.

So, did she close the deal?

It’s to be determined. The meeting was set, all attended, and it looks like there is a very promising opportunity in her pipeline for about $150,000 next quarter.

Going to show that no prospect is unreachable, and persistence does pay off.

Had a tough sell? How about a sales opportunity that was seemingly impossible to get a hold of? We’d love to hear about it in the comments!