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After Losing a $21,000 Deal, Here's What I Changed in My Email Follow-ups

Looking back, these are the things we could have done differently to win the deal.
After Losing a $21,000 Deal, Here's What I Changed in My Email Follow-ups
Image credit: Thomas Barwick | Getty Images
Guest Writer
Founder at Katallyze.io
6 min read
Opinions expressed by Entrepreneur contributors are their own.

Imagine you're a chef, and someone walks up to you. "I'm hungry, feed me now," he demands. Although you might be the greatest chef of all time, you might not be able to give the person food at that point. Making the food takes time, a process, your process.

Related: The 15 Characteristics of People Who Succeed at Sales

The same goes for B2B sales and prospecting. Rarely would you close the deal on the first email, call or event.

But, often, the challenge is what you do after the first meeting. What happens when you meet with a prospect for the first time, and she doesn't buy from you? Do you forget about her? Do you dump her into a marketing automation platform? Do you delete her from your pipeline?

How I lost the deal

A while back, I spoke with one potential customer who had an interest in working with us. We met a few more times after the first meeting to review the proposal. We narrowed down the project scope and showed how our team could execute. There was definite interest. If we signed the deal, it would be worth $21,000.

But, there was only one challenge: The time was not right. The prospect's team was re-structuring their business. That meant they would only move forward after that was complete. So, I put a note on my calendar to follow up with a call every month.

But, then a few months later when I called him, he said, "Kwesi, we just signed a contract with another vendor. You should have called me earlier."

"What?" I said. "I had spoken with you a month before."

"I know, but I did not remember," he said.

His words felt like a heavy knock that knocked me into one of those bottomless waterfalls in Jumanji.

Related: 7 Tips for Getting More Sales Meetings With Prospects

What I learned from the loss

That loss would become significant learning for our team.

When our team reviewed why we lost that potential customer, we realized one thing. The key was in prospect's response: "I did not remember." He didn't remember even when I had "followed up" a few weeks earlier.

We realized we did not have enough compelling top of mind awareness. Yes, we followed up, but we were not sticky enough. We did not dominate the prospect's mind share. I realized that if we were going to dominate, we had to nurture, not just follow up.

Related: 7 Key Selling Habits All Sales Professionals Must Develop

Three things we do differently now

Armed with this fact, we became obsessed with testing. We began testing different types of sale nurturing emails.

There were three things we found afterward. And looking back, these are the things we could have done differently to win the deal.

1. Make it (feel) personal.

If you plug your prospect's email into a fancy email marketing template, it rarely feels personal. Emails with fancy images and fonts don't connect on a personal note. Instead, write your emails in plain text. Would you write an email to a friend or colleague using fancy email templates with bright colors? You'd probably agree that a lot of people write daily emails in plain text. Fancy templates create psychological friction. This friction makes you less favorable and trustworthy. An email that feels personal is trustworthy.

Another smart way to do this is to start your email by referring to an "undeniable, confirmable truth." Communications strategist Ray Edwards describes why this is important in his book How to Write Copy That Sells"One of the hurdles we have to overcome is skepticism and the fact that our readers often don't believe us ... or aren't sure if they believe us."

When you're nurturing a prospect, you want to build trust. The more trustworthy you are, the more likely you are to getting the deal. Because people buy from the people they can trust. For example, we now start our nurture emails with: "Hi {{Prospect}} -- it's Kwesi here."

Related: 11 Ways to Boost Your Sales Performance

2. Tell a story of value.

This is one of the critical email follow-up techniques we developed after losing that deal. Most of our nurturing emails tell a story. We tell stories about new ideas the prospect can use. We tell stories about lessons we've learned from failing (like this article). We tell stories about our fears and hopes. The reason is that great stories have a great way to evoke emotions that build trust. Humans have been telling stories ever since the hunters and gatherers age, over 20,000 years ago.

Researcher Paul J. Zak found that stories with great characters cause the release of oxytocin. Oxytocin is the brain's shortcut to "it's safe to approach others." The more oxytocin your prospect's brain releases, the more willing they'll be to help.

Discussing his findings in the Harvard Business Review, Zak noted that "character-driven stories with emotional content result in a better understanding of the key points a speaker wishes to make and enable better recall of these points weeks later."

That's why storytelling is sticky. It makes you more memorable.

Related: AI Is Taking the Art Out of Sales

3. Be credible.

The key to being credible is to show social proof. Nurture the prospect by sharing specific recent results of a similar client.  I'm not talking about sending a lazy, generic email about a new client you signed. Craft a thoughtful story about a client's challenges and how your team helped them.

Your social proof story can include these:

  1. What was the specific challenge?
  2. What were the emotional effects of the client's challenge?
  3. How did your service or product help solve that challenge?
  4. What are the new emotions after the results you helped them get?

These three principles have become the foundation of our follow-up emails. We use them to build a nurturing sequence with prospects who are a fit but are not ready to buy yet. 

Now, our follow-ups generate engagement. Prospects come to us after reading the stories in the emails. They ask questions, which helps us to offer more value.

The point is: Have a system to continue adding value to prospects who say it's not a good time. You spend enough time to get prospects to meet with you. Put in a little more effort to engage with them with value until they are ready. Invest in your relationships for the long term.

That way when they are ready to buy, you'll be the first who comes to mind.

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