How Conversational Should I Be On A Sales Call?

One of my least favorite pieces of sales advice is to chat a prospect up to build rapport. Specifically to open up a prospecting call or a first demo.

Why? As a sales rep I never saw success doing it. Not because I was bad at it, because it didn’t warm anyone up, period. Now I get calls as a prospect, and it truly annoys me when a sales rep I don’t know wants to chit-chat about trivial things.

Yet if you do a little digging around you’ll find tons of advice like these nuggets:

“Find a personal connection to break the ice!”

“Asking a question like, ‘How was your weekend?’ opens up the conversation!”

“See what’s the big topic where the prospect lives – sports team, new restaurant – and find out their opinion!”

All of this is great advice… if you already have some kind of relationship and you know it’s a smart topic to bring up with this particular person.

Early on? Not so much. You can get lucky using this approach every once in a while if a chatty prospect picks up the phone. Most of the time it’s going to be a huge turnoff.

The dilemma is that you do need to build rapport to have any shot at the next step and eventually closing the deal.

What kind of rapport do I need to build?

There’s the old saying, “If the prospect likes you and trusts you, he’s more likely to buy from you.” Which is true. It’s in the wrong order, though.

Developing trust is more important than being liked any day of the week in sales.

Many of the best sales reps I’ve known in my career are miles away from being the lovable schmoozers people tend to associate with sales. Having this innate charisma works great to a point. Buying decisions are being made with more people involved than ever. More involvement means one person’s affinity for a particular sales rep becomes a moot point when everyone gets together to discuss who they’re doing to buy from.

When a decision is made it’s often the vendor who everyone believes will actually deliver on their promises once the contract is signed.

It’s better to be great at steadily building trust across an organization than it is to butter prospects up. Personally I’d rather be trusted and liked well enough. It’s better than being loved yet somewhat unreliable.

Even though trust matters the most, being liked is still important.

One thing to keep in mind is that the opposite of likable isn’t unlikable. In fact if people think you’re unlikable you can gain an advantage in specific instances. Someone who seems unlikable is controversial, and being controversial means you’re going to have loyal supporters backing you up against your sworn enemies.

The opposite of likable isn’t unlikable, it’s being boring.

Boring kills sales calls.

At the heart of every decision is emotion. Yes, including rational decisions. What we’re doing is weighing the consequences of saying “yes” and “no” by projecting how we’ll feel after we’ve made a choice.

It’s so easy to say no to boring, which is why it’s the polar opposite to likable. One is a strong emotion and the other is devoid of emotion.

This is why being unlikable to some, or even many, is far more desirable than being boring. You’re basically invisible if you’re boring.

Being likable is more about acting similarly than it is about sharing common interests.

Because let’s face it, are you really going to narrow your target audience down to people who share the same interests as you? Would you stop talking to a prospect who’s into fly fishing or quilting because you don’t have a common connection around a hobby?


So don’t get hung up on someone’s LinkedIn profile. Pay less attention to their alma mater and where they volunteer. Pay more attention to their tone of voice, their body language, their mannerisms, and the words they use.

Building rapport is more about developing a sense that the two of you are similar people than it is about small talk.

If you can find a way to slip in their alma mater or make a quilting reference then you should do it, assuming it fits the conversation. It’s good reinforcement. Making that reference won’t change anything if you struggle to establish a baseline common thread between the two of you as human beings.

Personal details are far more important the longer you have a relationship with someone. Having that casual chat is a sign that you’re comfortable with one another.

Wait, if having a casual chat is a sign we’re comfortable with one another, shouldn’t I have a casual chat with the prospect?

Think about it for a moment. Think about a time someone walked up to you and acted like you two knew each other. How did you feel in that moment? Confused, a little out of touch, struggling to come up with who this other person is.

Then the ball dropped: you realized you didn’t know this person and it was all a ruse.

Now turn that from an in-person conversation into a cold phone call and what do you get? The prospect hanging up at the other end of the line.

We have casual conversations with people we’ve become comfortable with.

I’m sure you can think of someone who you’d be happy to shoot the breeze with yet you wonder how much of what comes out of his mouth is hot air. If he tries to sell you something you’re not going to listen. Casual conversation is entertainment, not a sign of a strong relationship.

A strong relationship is built on trust first, then some form of likability. That’s what you need to be in the running for the deal.

How have you built rapport with prospects in a meaningful way?

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