How to Create Authentic Sales Conversations

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 ☠️📞

Stop Solving. Start Selling. Traditional sales advice says, "Stop selling and start solving." While that approach isn’t entirely wrong—you shouldn’t push—jumping straight to a solution isn’t helpful either. In my sales workshops, I see this trap all the time: A client shares a challenge, and sales professionals immediately shift into problem-solving mode. Their instinct? Offer a solution right away because they have come prepared with a bag full of solutions and want to bring them out with pride. Show up and throw up! The problem? The client isn’t always ready for it. Here’s what great sales leaders do instead: •Pause and listen – Clients don’t just want answers; they want to feel heard. •Dig deeper – Ask: “What impact is this challenge having on your business?” •Resist the urge to pitch – A solution offered too soon feels generic, not strategic, and specific to the issues that the client is trying to solve. •Co-create the way forward – Help the client connect the dots instead of handing them the answer. Then it becomes a co-created solution from just being your solution. The best salespeople don’t just sell solutions—they guide the conversation in a way that makes the client want to buy. It’s known to the world as consultative selling, but I call it the trust-building conversation as the idea is to move from being an expert to a trusted advisor and that requires patience and resilience. So, Slow down. Listen more. Sell smarter. Build Trust #Sales #Leadership #SalesStrategy #ListeningSkills #Trust #valueconversations

“Yeah, but for you… it was easy.” I hear this all the time. And my response is always the same: “Yes, and it can be easy for you, too.” Here’s the truth: things look easy when you’re only seeing the result, not the process. But behind the scenes, there’s a simple framework I follow that makes things feel easier over time. My guiding principle. “Meet as many people as you can, without expecting anything in return, instead ask what you can do for them.” The key? It’s not about me—it’s about them. 👉 1. Research & Personalize Success starts with preparation. I don’t go into a conversation blind. I research the person, their business, their challenges, and their wins. But it’s not just about gathering facts—it’s about finding a meaningful connection. I tailor my approach to them—referencing their latest project, a shared connection, or a recent post. It’s not about what I want; it’s about what they need. When you show up informed and intentional, you stand out. 👉 2. Reach Out I don’t sit back and wait for opportunities to come to me—I create them. I send a thoughtful, authentic message that reflects my research and personalization. No copy-paste templates. No generic outreach. Just a genuine effort to start a conversation. Authenticity opens doors that strategy alone can’t. 👉 3. Virtual Coffee This is where the magic happens. A relaxed, no-pressure conversation where I show up prepared, curious, and genuinely interested. I’m not trying to close a deal—I’m trying to open a relationship. When you focus on connection instead of outcome, the right opportunities naturally follow. The reason it looks easy is that I’ve built a process. I’ve done it so many times that it feels natural—but it didn’t start that way. You need to work the process until it feels comfortable. So yes—it can be easy for you, too. You just have to be willing to put in the reps and make it about them. What’s your process? 👊 If you are in sales or leadership and looking for more ways to drive performance, 👥 follow me and send me a 📩 message. When I started my journey as an entrepreneur, I thought I had a pretty good handle on business.

Last week, I was talking to a sales rep who felt trapped by rigid sales scripts. It's a common problem. Following a script too closely can make you sound robotic 🤖 and alienate your prospect. That's where ethnographic-style questioning comes in. ⁉️ Instead of asking closed-ended questions like "Are you the decision-maker?", try open-ended ones like "Can you walk me through how decisions like this are typically made in your organization?" This approach, inspired by cultural anthropology, encourages prospects to share more about their processes, challenges, and motivations. I'm not advocating you abandon structure, but rather, enhance your sales playbook to foster genuine dialogue. 👉 Have you experimented with more open-ended questioning in your sales calls? #SalesStrategy #CRMAdoption #B2BSales #SalesCulture