The Deal That Took 5 Months

There was a time when a prospect actually forgot what our first meeting was about.

I remember I was chasing this guy because I knew he needed what I was selling. He came on to the first meeting within a week. That right there was a clear sign that he was definitely interested in solving a problem. Whether my solution fit or not was a different discussion.

In the first meeting, he spoke for only about 10 minutes, and that was enough for me to understand that he had a real problem to solve.

After that, I kept following up. I texted him or reached out on LinkedIn every 3 days, sometimes once a week depending on how he responded.

He kept saying he was travelling. One day he was in Texas, another time in Washington. Then it was cold, snowing, and soon the holidays kicked in. There was no way he was going to respond in the last two weeks of December.

But I didn’t lose hope.

Because even after months of follow-ups, he never said that he didn’t want to talk to me. He knew there was a real person behind all the follow-ups. He knew that before reaching out, I had understood what he does and why I was contacting him.

He wasn’t annoyed. He wasn’t angry. In fact, every third follow-up or so, he made sure to reply. Emails were exchanged, and I even sent an NDA so he could move things forward.

After the holidays, I reached out again, and finally there was a breakthrough. He gave me a time to talk. I immediately sent the invite, and we spoke.

It took me 5 months to get that second meeting after the first one.

By then, he had already forgotten how the conversation even started. I quickly reminded him why I had reached out and what I was offering.

Within the next three weeks, the deal closed for $40,000.

No AI could have done what I did.

With every response he gave, I read between the lines to understand how to follow up in a way that respected his situation. I paid attention to signals. Whenever I saw him active on LinkedIn, I would sometimes reach out. I followed what he posted so I could learn more and be better prepared for the next conversation.

In those 5 months, I must have sent messages to hundreds of prospects. Some of them may have replied, but I chose to focus on a smaller set of people and see them through properly.

I would rather work 10 prospects in a month and get a clear yes or no than keep chasing someone for years without direction.

Because in the end, human connection is what breaks the ice.

And that is something AI cannot replace.