How to Build Rapport When Selling Remotely

I wasted years thinking small talk about weather made me good at sales. My process was embarrassingly simple: Pull up their LinkedIn, scan their last email, then wing it with some chitchat about their location or the weather. I assumed "natural rapport" meant improvising my way through calls. And I was wrong. Truth is, I was resisting structure. I believed scripting meant being robotic and proper preparation would kill authentic conversation. So I kept it casual, kept it flowing, and… kept missing opportunities. Then I started working with a sales coach. Every Wednesday at 10am, I'd get on a call to hear exactly why my approach was wrong. It was expensive, uncomfortable, and exactly what I needed. One day, he caught me using my favorite line (among others) while I talked through a sales call: "Any thoughts on that?" His feedback was brutal: "You're swinging between closed-ended questions that shut people down and questions that leave them hanging. What if, instead, you guided the conversation?" Ouch. Mind blown. He was right. In trying to keep things casual and unstructured, I'd been failing to guide meaningful conversations. My resistance to "scripted" questions wasn't just making my calls superficial—it was leaving both me and my prospects without direction. So we changed… direction: Create and rehearse a flow and replace every closed question with an open one. Instead of "Should I walk you through our services?"   → "What’s the goal?" then… “What’s behind that?” Instead of "Any thoughts?"   → "How would this fit into your current process?" Instead of "Does that pricing work for you?"   → "How does this compare to what you were thinking?" The difference was immediate. Prospects started sharing their actual concerns. Their real budgets. Their true decision-making process. All the things they used to hold back when I gave them an easy "no thoughts" escape hatch. Last quarter alone, we added a record in new MRR—twice our typical close rate. Sales cycles that used to drag on for 8 months now wrap up in 4. But the biggest change is that I finally see sales calls for what they *should* be: guided conversations with clear direction and open ended questions, *not* let-me-wing-this-trust-me-I-got-this improv sessions. The beauty of this approach is that it's not in any way manipulative or calculating. When you introduce structure and direction, you're also helping prospects quickly decide if what you have to offer is what they actually need. Everyone wins. P.S.   Try this today: Take your most common closed question and flip it into an open one, directing one. You'll be amazed at what people tell you when you stop giving them permission to say nothing.

Your first 60 seconds on a sales call can make or break the close. Most reps open calls like this: “How’s your day going?” “Crazy weather lately, huh?” Harmless? Sure. But it wastes valuable time and sets the wrong tone. Your prospect didn’t book a call to talk about the weather. They booked because they’re curious if you can solve their problem. The best reps know this and they build trust from the get go. Here are 3 call openers I’ve used to instantly establish authority & connection on sales calls 👇 1. “Just so I understand where you’re coming from—what made you take the call today?” This one flips the dynamic. You’re not chasing. You’re curious. It invites the prospect to open up and gives you gold: context, motivation, and urgency all in one question. No small talk. Straight to the signal. 2. “Out of curiosity—why now?” Timing is everything in sales. If someone booked a call, something triggered it. Your job is to find out what. This question helps surface pain points fast, without sounding pushy or scripted. You’ll learn what’s happening in their world right now—and that’s where the real sale lives. 3. “Before we dive in—mind giving me the 60-second recap of where you’re at?” This one does 2 things at once: ✅ Puts the prospect in the driver’s seat ✅ Shows them you value their time and context It feels casual, but it gives you everything you need to tailor the rest of the conversation. These 3 openers have shortened my sales cycles, reduced objections, and made calls feel more like collaborations than interrogations. In remote sales, trust isn’t built at the end of the call. It’s built in the first few minutes. Set the tone. Lead with intention. Ask better questions.

2 great discovery calls yesterday where buyers gave me next steps. Buyer-led next steps are the true measure of great discovery. Here are the 2 most important techniques that cause the buyer to lead the process? 1. Don't rush rapport I used to think I took too long to build rapport. You know when you feel like you are spending too long on rapport? When you aren't building rapport and just doing boring chit chat. Both calls had 10 of 30 mins of rapport building, and it paid off. I created credibility and legitimacy in the first 10 mins with: - commonality - finding common interests creates relatability - TMI - sharing too much personal info shows I'm transparent - humor - laughing and making people laugh creates connection - stories - telling stories sets the stage for being interesting Rapport is the seed of friendship. Friends help each other. Both my new "friends" helped me by telling me what I need to do next to help them make a confident buying decision. 2. Clarification I have a habit that drives some people nuts at times. I ask people to repeat what they just said. It's not bc I have hearing issues or bc I'm not listening. It's bc most people's first explanation/question isn't really what they want to communicate. When I ask them to restate what they just said to make sure I understand, I get about 3x the amount of info from them, and I get what they truly want to communicate. Sometimes, people will even throw out a questions or statement bc I gave them a couple seconds to think it through. Never forget that we all have our own definitions for words. Making sure you know your buyer's meaning for the words they use (and how it differs from yours) is maybe the most critical thing you can do to increase the amount and speed of understanding. When you do these 2 things well, buyers tell you what they will do next and what you need to do next. Once you make sure those are the right things to do, you are moving forward WITH them, as opposed to moving forward DESPITE them. P.S. Ask Corporate Bro about how funny I am. He knows. Rapport built. (Damn...I'm so nervous Corp is gonna blow me up for this bc I'm not that funny and he actually thought I was a jerk.)

Here's a challenge for your next meeting. Ban yourself from asking: -How are you? -How is the weather? -How have you been? Renowned Questionologist, Warren Berger, calls these "rote" questions. They aren't bad. They just don't accomplish anything. They don't build trust or create conversational flow. Try this instead: Spend 5 minutes before your meeting finding something the prospect or client is passionate about. For prospects --> do some research online to learn something about them. Here's an example from a meeting I was in last week. I was with someone I had never met before. Prior to the conversation, I went to his professional bio. It said he moved from Israel to the US when he was an adult. So, instead of kicking things off by asking "Man can you believe this weather??" I asked: "I can't help but ask...what made you decide to leave Israel when you did??" For clients -->research your past conversations. Ask about the vacation they went on over the summer. Ask about how it was dropping off their kids at college. If all else fails, find something in their past that you want to know more about. My favorite default question was: "You've been running this business since before we met, but I've never thought to ask you...how did you even come up with the idea for this business in the first place??" Ask better questions. Get better answers. Create life-long clients. (And, yes, I intentionally use two question marks "??" after my questions to signal a genuine interest and curiosity! Try it in your text conversations...people love it.)