Academy / Master Outbound Sales / Chapter 1 - How to adopt a conversational approach ?

Chapter 1 – How to adopt a conversational approach ?

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Psychology of conversations on LinkedIn versus Email

Once a prospect replies, you’re no longer prospecting : you’re engaging.

And how you engage depends a lot on the channel.

  • On LinkedIn, conversations tend to be brief, casual, and reactive. People answer quickly, from their phone, sometimes between two meetings. The tone is often informal and a bit “chat-like.”
  • On email, however, the dynamic changes. Replies are more structured, often more formal, and may include longer sentences, signatures, and polite formulas. But here’s the catch: the prospect doesn’t change, just the format does.

 

Understanding this difference is essential. If you copy-paste your email tone into LinkedIn, you’ll sound robotic. If you’re too relaxed on email, you might lose credibility. Navigating this balance is key to building rapport and trust.

In both cases, your goal should be to sound like a real person who’s paying attention. Ask yourself: “If I received this, would I feel like someone is listening to me?” That’s the bar you want to hit.

When someone replies, the best mindset you can adopt is: “Let’s have a conversation, not a pitch.”

Advanced technics

The rule of three

When you get a reply, your job as a salesperson is simple but not easy: capture your lead’s attention, clearly and effectively, in three messages max.

That’s the Rule of Three.

You don’t have unlimited space to convince. In outbound, attention is currency, and you only get a few chances to earn it. Once someone replies, even vaguely, the countdown begins. You now have a short window to spark real interest. If you’re still explaining who you are or what you do after three messages, you’ve probably lost them.

This forces clarity. It pushes you to lead the conversation, not follow it.

The first message after a reply is often about context, showing you understood what they said and why it matters.

The second should already deliver value, a strong insight, a sharp angle, or a relevant case.

And the third? That’s the pivot. It’s where you test if you’ve earned attention or not. “Would it make sense to dig into this together?”

If they’re still passive or vague at that point, it’s a sign to reframe.

Think of it like a mini funnel inside your bigger sequence:

  • Message 1 — Spark
  • Message 2 — Substance
  • Message 3 — Action

 

Every touchpoint should move the needle forward. If it doesn’t, don’t insist, rethink. Either the message isn’t clear enough, the problem isn’t painful enough, or the timing just isn’t right. And that’s okay, your job isn’t to convert everyone, but to spot and activate the ones who are ready.

Mirroring your leads’ behavior

People trust people who seem like them. That’s not a theory, it’s neuroscience. Mirroring is a subtle but powerful way to build that trust.

It doesn’t mean copying someone’s message word-for-word, but rather matching their tone, style, and rhythm.

  • If a lead uses short, snappy answers with emojis? You don’t reply with a long, formal block of text. You keep it light, informal, and quick.
  • If they write long, detailed paragraphs? That’s your cue to slow down and respond more thoroughly.

 

This is true across channels, whether it’s LinkedIn, email, or even a voice message.

The art of mirroring is about empathy. You’re showing the prospect: “I get how you like to communicate, and I’ll meet you there.”

That alone lowers resistance. The message becomes easier to read, easier to reply to, and more likely to continue.

Strike while the iron is hot

The moment a lead replies is when their attention is highest. Maybe they’re between meetings. Maybe they’ve just checked your profile or clicked your link. Whatever it is, your timing matters.

Even if your answer isn’t complete, or even if you don’t have time to send all the info right away, acknowledge the message quickly. “Got it, thanks! I’ll get back to you in the afternoon with some details” is already enough to keep the momentum alive.

Because here’s the danger: if you wait too long, the emotional connection fades. The lead moves on. They forget who you are or why they replied. Every hour that passes makes your job harder.

Especially on LinkedIn, where people’s attention is fragmented, your response speed plays a huge role in the outcome.

If you’re managing many conversations at once, tag or label replies based on urgency. But don’t over-automate. You’re not managing tickets. You’re nurturing relationships.

How to reply depending on the situations

There’s no universal reply that works for every prospect. What you need is a way to recognize different types of replies and adjust accordingly.

Here are a few typical scenarios you’ll encounter:

  • Scenario A: The “Not Now” Lead

    They say: “Looks cool, but timing’s not right.” Your goal here is not to convince them to buy now. It’s to understand when the timing might be better, and to stay top-of-mind without being pushy. You can ask, “When would be a better time for me to follow up?” or offer a resource they can bookmark.

  • Scenario B: The “Tell Me More” Lead

    They reply with curiosity: “What exactly do you do?” or “How does this work?” These are hot leads. Be clear, concise, and compelling. Link to a short video, show quick social proof, and always include an easy next step. “Want me to show you in 2 mins over a call?”

  • Scenario C: The Skeptic

    You might get: “We’ve already tried tools like this before.” Don’t go into defense mode. Instead, ask questions. “Out of curiosity, what didn’t work last time?” The idea is to open the door instead of pushing it. Gathering data to turn them into opportunities.

 

Knowing how to read the intention behind a reply, even if it’s vague or cold, helps you keep the conversation alive. With a bit of practice, you’ll start responding not just with answers, but with opportunities.

Now that you have the basics, let’s move on to Chapter 2 : Analysing your performance!

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