Rapport Matters: People Still Buy From People

With all the talk about AI, sales automation, funnels, CRMs, and “efficient” sales processes, it’s easy to forget one of the oldest truths in selling:

People buy from people.

And before someone is willing to buy from you, they generally need to feel comfortable talking with you.

That’s why establishing rapport at the beginning of the sales process is still crucial.

Rapport isn’t about becoming best friends. It isn’t about spending 15 minutes talking about golf because you noticed a set of clubs in the prospect’s office. And it definitely isn’t about opening every Zoom call with, “So…how’s the weather today in Wichita?”

Rapport is about creating comfort, connection, and trust.

When prospects feel comfortable with you, they’re more likely to open up. When they open up, they give you better information. And when you have better information, you can have a much more productive sales conversation. You can discover what they’re doing, how it’s affecting them, what their issue is, and whether you can help them with it.

Without rapport, even great questions can feel like an interrogation.

With rapport, those same questions can feel like a conversation.

So, How Do You Establish Rapport?

1. Do your homework.
Before the conversation, invest a few minutes researching the person and, if they work for one, their company. Look at their LinkedIn profile, website, recent posts, company news, or mutual connections. You’re looking for legitimate conversation starters – not ammunition for cyberstalking.

Here’s a prompt you’re welcome to use:

I am a salesperson preparing for my first meeting with a prospect.

Prospect: [NAME]
Title: [TITLE]
Company: [COMPANY]
Company website: [WEBSITE]
LinkedIn profile: [LINK, if available]
What I sell: [BRIEF DESCRIPTION]
My ideal client: [BRIEF DESCRIPTION]

Act as my sales research assistant and meeting strategist. Research this prospect and company using current, publicly available information.

Give me a concise pre-meeting briefing covering:

• The Person
• • Career background and current responsibilities
  • How long they have been in their current role/company
  • Previous companies or roles that may be relevant
  • Recent LinkedIn activity, posts, interviews, podcasts, articles, or announcements
  • Professional interests, priorities, or initiatives
  • Any useful rapport-building information that is professionally appropriate
• The Company
  • What the company does and how it makes money
  • Approximate size, locations, markets, and customer types
  • Major products/services
  • Key competitors
  • Recent growth, acquisitions, leadership changes, product launches, funding, expansion, layoffs, or other significant developments
  • Current strategic priorities or challenges
• Why They Might Need What I Sell
  Based on what you discovered, identify 3-5 potential business issues, challenges, goals, or opportunities that could make my product/service relevant.

  Do not assume these are facts. Clearly label them as hypotheses I should explore during the conversation.

• What Might Matter to This Person
  Based on their role, identify the KPIs, outcomes, problems, and pressures they are most likely responsible for.
• Meeting Strategy
  Recommend:
  • A strong way to establish rapport
  • 3 intelligent observations I could mention that demonstrate I did my homework
  • 7 discovery questions tailored specifically to this prospect
  • 3 deeper follow-up questions based on likely answers
  • Potential objections or concerns I should be prepared for
  • Other people who may influence the buying decision
• Opportunity Assessment
  Give me your assessment of:
  • Why this could be a good opportunity
  • Why it might NOT be a good opportunity
  • What I need to learn during the first meeting before deciding whether to pursue it
• The 60-Second Brief
  Finish with a section called “Read This 5 Minutes Before the Meeting.”

  Give me the 5 most important things I should remember going into the conversation.

Important: Separate verified facts from assumptions. Include sources for important factual claims. Do not invent information when reliable information cannot be found. My objective is not to impress the prospect with how much I know. My objective is to use the research to ask better questions and have a better conversation.

2. Be genuinely curious.
People can tell when you’re going through the motions. Ask something you actually want to know and then listen to the answer. Genuine curiosity is one of the fastest ways to create connection.

3. Find common ground – but don’t force it.
Maybe you know someone in common. Perhaps you’ve worked in the same industry, attended the same event, lived in the same city, or share an interest. If there’s a natural connection, use it. If there isn’t, don’t manufacture one.

4. Match their energy.
Some prospects are warm and conversational. Others want to get right down to business. Pay attention. Rapport isn’t making them communicate your way – it’s making it comfortable for them to communicate their way.

5. Listen more than you talk.
Nothing builds rapport faster than making someone feel heard. Don’t listen while waiting for your opportunity to speak. Listen to understand. Ask follow-up questions. Be interested instead of interesting.

6. Don’t rush it – but don’t overdo it either.
Rapport doesn’t require 20 minutes of small talk. Sometimes you can establish it in two or three minutes. The goal isn’t to delay the sales conversation. The goal is to make the sales conversation better.

Most importantly, be yourself.

Prospects typically have finely tuned BS detectors. When you’re trying too hard to be charming, impressive, or “salesy,” they can usually tell.

Great selling isn’t about convincing people to like you.

It’s about creating an environment where they feel comfortable enough to have an open, honest conversation with you.

Rapport opens the door.
Trust keeps the conversation going.
And great questions help you discover whether there’s actually a reason to do business together.

Don’t skip the rapport because you’re anxious to get to the sale.

It may only take a few minutes—but those few minutes can make everything that follows much more effective.