Building Rapport With Customers During Sales Calls

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.

You’re either talking AT your prospects or WITH them And trust me the difference is everything Heres a quick reality check One of the SDRs I worked with this week was using an opener like this on their cold calls “On a scale of 1-5 hows your experience with XYZ?” Its well intentioned but thats a dead end question that usually leads to a quick number and then silence right? Now you’re stuck trying to dig deeper without much context Instead we refined it like this “Saw you’re using XYZ for customer support. I was talking with Sara and Mike last week who said it’s about a 3.5 on a good day. Just curious hows the experience been for you?” This approach 👉 gives the prospect something real to work off of 👉 shows credibility by referencing peers in their space 👉 and opens the door for a genuine conversation If they say “It’s a 5! We love it!”- perfect! Now ask whats really moving the needle for them If they say “Yeah it’s about a 3 for us too” Awesome! Thats your chance to dig deeper “What’s holding it back from being a 4 or 5?” Now you’re not just grilling them with basic questions you’re guiding a conversation driven by real curiosity and insights As sales reps remember we get the chance to talk to a ton of folks in our ICP every week Use those conversations to refine your approach and bring real value into the next call It’s all about talking WITH them—not AT them But hey if you’d rather keep talking at your prospects… Well maybe cold calling is dying and you’ll end up like these guys ☠️📞

Are your direct questions killing your deals with indirect buyers? Most sales reps approach every conversation the same way. Direct questions. Pushy tone. Bad timing. I learned this lesson the hard way selling to “softer” personas like HR, generally speaking. I'd ask "What's driving this to be a priority?" and watch them instantly close up. What changed my results was what I call the Triple T approach: 1️⃣ TACT: Frame questions through a third party lens ("I typically find that leaders like yourself...") 2️⃣ TONE: Slow down, soften your voice, appear thoughtful and curious rather than interrogating 3️⃣ TIMING: Build rapport first, then ease into business questions gradually Here's a practical example: BEFORE: "What's your pain point? Why now? What's your budget?" AFTER: "What's interesting is... usually when I talk to HR leaders like yourself who are considering a change... I find there's something happening in the business driving this to be key priority for them. What's that look like in your situation?" Same core question. Completely different response. This approach creates psychological safety for indirect buyers to open up about their real challenges. Since implementing this method, I've uncovered 10X more pain points and closed deals other reps couldn't touch. The best part? This works in ANY high stakes conversation (personal or professional). - Want to run better discovery than last time? You’d be foolish not to check this out: https://lnkd.in/gexS_66B

“My customer doesn’t want to talk about their goals.” I hear this from CSMs all the time. But when you listen to those calls, here’s what’s actually happening: 𝗧𝗵𝗲 𝗖𝗦𝗠 𝘀𝗮𝘆𝘀 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝗹𝗶𝗸𝗲, “𝘋𝘶𝘳𝘪𝘯𝘨 𝘰𝘶𝘳 𝘤𝘢𝘭𝘭 𝘵𝘰𝘥𝘢𝘺 𝘐 𝘸𝘰𝘶𝘭𝘥 𝘭𝘰𝘷𝘦 𝘵𝘰 𝘵𝘢𝘭𝘬 𝘢𝘣𝘰𝘶𝘵 𝘴𝘰𝘮𝘦 𝘰𝘧 𝘺𝘰𝘶𝘳 𝘨𝘰𝘢𝘭𝘴... 𝘈𝘭𝘴𝘰 𝘐 𝘩𝘢𝘷𝘦 𝘢𝘯 𝘶𝘱𝘥𝘢𝘵𝘦 𝘰𝘯 𝘵𝘩𝘦 𝘶𝘱𝘤𝘰𝘮𝘪𝘯𝘨 𝘳𝘰𝘢𝘥𝘮𝘢𝘱 𝘧𝘦𝘢𝘵𝘶𝘳𝘦𝘴.” Guess which topic the customer jumps to? Of course they choose the shiny new roadmap updates. Not because they don’t care about their goals… But because we gave them an easy out from a harder, more vulnerable conversation. The truth is: Your customer 𝘥𝘰𝘦𝘴 want to talk about strategy. They just need two things from you first:  1. A reason to trust you with their goals.  2. A clear and confident setup for the conversation. 𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝘁𝗼 𝘀𝗮𝘆 𝗶𝗻𝘀𝘁𝗲𝗮𝗱: “𝘓𝘦𝘵’𝘴 𝘵𝘢𝘬𝘦 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 10 𝘮𝘪𝘯𝘶𝘵𝘦𝘴 𝘵𝘰 𝘢𝘭𝘪𝘨𝘯 𝘰𝘯 𝘺𝘰𝘶𝘳 𝘬𝘦𝘺 𝘨𝘰𝘢𝘭𝘴 𝘵𝘩𝘪𝘴 𝘲𝘶𝘢𝘳𝘵𝘦𝘳.  𝘐𝘧 𝘐 𝘶𝘯𝘥𝘦𝘳𝘴𝘵𝘢𝘯𝘥 𝘸𝘩𝘢𝘵 𝘺𝘰𝘶’𝘳𝘦 𝘸𝘰𝘳𝘬𝘪𝘯𝘨 𝘵𝘰𝘸𝘢𝘳𝘥, 𝘐 𝘤𝘢𝘯 𝘣𝘳𝘪𝘯𝘨 𝘪𝘥𝘦𝘢𝘴 𝘢𝘯𝘥 𝘴𝘰𝘭𝘶𝘵𝘪𝘰𝘯𝘴 𝘧𝘳𝘰𝘮 𝘰𝘵𝘩𝘦𝘳 𝘤𝘶𝘴𝘵𝘰𝘮𝘦𝘳𝘴 𝘸𝘩𝘰’𝘷𝘦 𝘴𝘶𝘤𝘤𝘦𝘦𝘥𝘦𝘥 𝘢𝘯𝘥 𝘮𝘢𝘬𝘦 𝘴𝘶𝘳𝘦 𝘸𝘦’𝘳𝘦 𝘣𝘶𝘪𝘭𝘥𝘪𝘯𝘨 𝘵𝘰𝘸𝘢𝘳𝘥 𝘵𝘩𝘦 𝘰𝘶𝘵𝘤𝘰𝘮𝘦𝘴 𝘵𝘩𝘢𝘵 𝘮𝘢𝘵𝘵𝘦𝘳 𝘵𝘰 𝘺𝘰𝘶.” You don’t need to beg for goal alignment. You need to earn it with clarity and confidence teaching the customer why it is valuable for them to share that information with you. Stop asking if they want to talk strategy. Start leading the conversation in a way that makes it a no-brainer. What’s helped you unlock goal-setting conversations with customers? #customersuccess