The Salesperson's Guide to Having Better Conversations

Good Morning. Last night the Knicks pulled off the biggest comeback in NBA Finals history, coming back from a 29 point deficit to beat the Spurs 107-106 with 1.2 seconds left on the clock. New York now leads the series 3-1 and is one win away from a championship. This is the equivalent of being at 10% of quota with 1 week left in the month and somehow closing at 100%. It happens. Not often, but it happens. Now, let's get into today's Follow Up. (:

Sponsor The Follow Up | Subscribe

Think about the best conversation you've had with a prospect. 

It feels like you’re in a flow state. It has a certain rhythm to it.

You can ask almost anything, they open up about their real problems, and you log off the call in a great mood knowing the deal is moving forward.

Now think about how much more you'd close if every conversation felt like that.

Better conversations = more sales. They change how much you sell, how fast deals move, and how strong your relationships are with customers, teammates, and even people outside of work. 

The good news is that being great at conversations is a skill, and there's a simple framework that makes it easy to practice.

Pulitzer Prize-winning journalist Charles Duhigg breaks down the framework in his book Supercommunicators. 

Every conversation you have falls into one of three categories. And the key to being better at all of them is figuring out which one the other person is in.

Practical conversations are about solving a problem or making a decision. In sales, this is the default. Features, pricing, timelines, implementation. Most reps live here because it feels the most productive. You're exchanging information and moving the deal forward.

Emotional conversations are about how someone feels. When a prospect says "we've been burned by vendors before" or "I'm honestly frustrated with how things work right now," they're telling you how they feel. They want to feel heard before they're ready to hear your solution.

Social conversations are about identity, status, and how someone fits into the people around them. These usually show up when a prospect is thinking about how a decision will affect their standing internally. Will their boss see them as someone who made a smart call or a risky one? Will their team support the change or push back? Will they be the person who championed a new vendor that ended up failing? Most prospects never say any of this out loud, but they’re always thinking about it.

All three of these conversations can take place on sales calls. Sometimes in the same call. 

Communication feels broken when two people are in different conversations at the same time. 

One person could be emotional, while the other responds with something practical. I’m definitely guilty of this. 

If a prospect tells you they're frustrated with their current setup, it’s emotional. So if you immediately jump into "well, our platform does X and here's how I can help," you've switched to practical. 

You need to make them feel understood first, before trying to offer a solution.

If they're emotional, be emotional first. Acknowledge what they said. Ask a follow-up about their experience. Show that you actually heard them. Once they feel understood, they'll move into practical mode on their own and be way more open when they get there.

Same thing with social conversations. If a prospect is worried about internal buy-in, responding with more product features doesn't help. What helps is asking how their team usually evaluates new tools, who else would need to be involved, and what a successful rollout would look like from their perspective.

The difference between a mediocre discovery call and a great one is all about the questions you ask.

Surface questions will get you facts. "What's your budget?" "Who's the decision maker?" "What's your timeline?" You need to ask these, but they don't build a connection.

Better questions ask about values, experiences, and motivations.

When someone shares something real with you, they start treating you like someone who understands their situation. And that's where sales magic happens. 

Today’s newsletter was written by Nic Conley