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There’s a sales skill that requires almost no training. You don’t need a script. You don’t need a new methodology. You don’t even need another question. You just need to pause. Ask a question. Then wait. It sounds ridiculously simple. But watch what happens in a real sales conversation. The salesperson asks: “What’s your biggest challenge right now?” The prospect pauses for two seconds. And the salesperson jumps in. “Is it finding people? Retention? Getting enough new busines

Most salespeople know they should ask open-ended questions. That’s not the problem. The problem is actually doing it. Try this exercise. For the next five minutes, have a conversation with someone and only ask questions that start with: What How Tell me Describe Sounds easy. It isn’t. Within a few questions, most of us slip back into: “Do you…?” “Are you…?” “Have you…?” “Is that…?” Closed questions are incredibly natural. And there’s nothing inherently wrong with them. The pr

One of the simplest ways to get better at selling is to stop thinking like a salesperson. Think like the buyer. Before you make the call, send the email or walk into the meeting, ask yourself: If I were them, why would I care? Not: What do I want to tell them? Not: What product do I want to sell? Not: What do I need to get from this meeting? What matters to them? Salespeople spend a lot of time thinking about their own objectives. I need to get an appointment. I need to uncov

“How’s your day going?” It sounds like small talk. But it can be one of the best questions you ask. The problem is what we normally do with the answer. “How’s your day going?” “Crazy.” “Yeah, me too. Anyway…” We asked the question. They answered. And then we completely ignored the answer. What if instead you got curious? “Crazy?” And then stopped talking. Now they might tell you. “We’re short-staffed.” “We’ve got a huge project that’s behind schedule.” “My boss just dropped s

“Build rapport.” It’s one of those pieces of sales advice everyone agrees with. But what does it actually mean? For a lot of salespeople, it means a few minutes of small talk at the beginning of the meeting. “How was your weekend?” “Did you watch the game?” “How’s the weather?” Then we mentally check the rapport box and get down to business. But that’s not really rapport. Rapport is connection. And connection comes from curiosity. If you want to build rapport with someone, le

Most people think listening is something that just happens. Someone talks. You hear them. Therefore, you listened. But hearing and listening are two very different things. Listening is a choice. You have to choose to stop thinking about what you’re going to say next. Choose not to interrupt. Choose not to solve the problem before the other person has finished explaining it. Choose to stay curious. That’s harder than it sounds. Especially in sales. A prospect says something th

f I could give a salesperson just one question to add to their discovery conversations, it might be this: “What else?” It’s ridiculously simple. And ridiculously effective. Ask a prospect: “What’s the biggest challenge you’re dealing with right now?” They give you an answer. Most salespeople immediately start exploring that answer. Or worse, they start solving it. Instead, try: “What else?” And then: “What else?” Something interesting happens. The first answer is often the ob

One of the most valuable meetings you can have at the beginning of a project has nothing to do with timelines, tasks or deliverables. It’s a vision meeting. Before everyone starts doing the work, get the people involved together and ask: What does great look like? Imagine we’re six months down the road. The project has been a huge success. What happened? What changed? What are people doing differently? What results are we seeing? What would make us look back and say, “That re

Great sales conversations aren’t scripted. They’re improv. You need a plan. You need to know where you want the conversation to go. You need good questions. But then you have to listen and respond to what’s actually happening. That’s where many sales conversations fall apart. The salesperson asks a question. The prospect answers. And instead of responding to the answer, the salesperson asks the next question on their list. That’s not a conversation. That’s an interview. Think

If you want better sales conversations, start by looking at the questions your salespeople are asking. Because the quality of the conversation is usually determined by the quality of the questions. Too many salespeople ask questions they already know the answer to. “Are you happy with your current supplier?” “Would you be interested in saving money?” “Is service important to you?” These questions don’t make the prospect think. And if the prospect isn’t thinking, you’re probab

There’s a question I hear from sales leaders: “Why would we outsource sales training? Shouldn’t our managers be doing that?” Ideally, yes. Your managers should be coaching. They should be reinforcing skills. They should be helping their people get better. But there’s a difference between coaching the work and building the skills required to do the work. Think about professional sports. A great head coach doesn’t personally teach every specialist skill. They bring in experts.

I’ve been thinking about this question: Would therapists make good salespeople? Think about what a good therapist does. They don’t dominate the conversation. They don’t rush to give advice. They don’t hear the first answer and immediately move on. They ask questions. They listen. They notice the words you use. And when you say something interesting, they stay there. “Tell me more about that.” “What do you mean by that?” “How does that make you feel?” They’re curious. And perh

Most salespeople know they should build rapport. The problem is, they often confuse rapport with small talk. “How was your weekend?” “Did you catch the game?” “How’s the weather over there?” There’s nothing wrong with those questions. But there’s a difference between being friendly and actually building a relationship. I call it Strategic Rapport. Strategic rapport is being genuinely curious about the person in front of you. Not because you’re trying to manipulate them. Becau

There’s a tiny habit I’ve been practicing lately that makes a big difference in face-to-face conversations. It’s so small, I almost hesitate to share it. But the impact? Big. Here it is: When you’re talking to someone, try to notice the color of their eyes. That’s it. Not in a creepy way. Not staring. Just long enough to really see them. When I do this, something shifts. The conversation gets deeper. There’s more connection. More trust. More presence. It's like both people dr

Part of my job is to watch salespeople in action. You can learn a lot by observing how sellers operate. Recently, I rode with a salesperson who could not find a current customer’s office. (Awkward) Over four meetings, the same seller never set an agenda, and client interactions seemed to have no point. Ride-alongs are an opportunity to observe, coach, and learn. Done right, they can uncover best practices and problems. Here’s how I get the most out of these experiences: 1. O

On a Sunday visit to a car dealership, I experienced a common but ineffective opening line from a salesperson: “How is your day going so far?” At first glance, this might seem like a warm, friendly question to break the ice. But if I were training a sales team, I’d strongly advise against it. Here's why. The problem with “How is your day going?” is that it doesn’t lead anywhere. The response is almost always generic: “It’s great,” “It’s fine,” or “I can’t complain.” None of t

If there’s one phrase I would purge from every salesperson on the planet, it’s: “I’m just following up.” It sounds harmless, and feels polite. But it sends the worst message to buyers: “What I’m about to say isn’t important.” "I don’t have a real reason for calling.” "Feel free to ignore me.” You might as well say, “I’m just wasting your time.” When you start with “just following up,” you put yourself in a one-down subservient position before the conversation even begins. You

Why “Is Tom Available?” is the Worst Question You Can Ask When Cold Calling When cold calling, many salespeople fall into the trap of starting with questions like: "Is Tom available?" "Can I speak to Tom?" "I’m looking for Tom." These closed-ended, permission-based questions are a recipe for rejection. Think about it: if you ask, "Is Tom available?" and the gatekeeper says "no," where do you go from there? You’ve handed the gatekeeper control of the conversation, and their jo

Salespeople, take yourself back to the first time you asked someone to dance. Maybe you were 14 or 15. Remember how nervous you were? Boys on one side of the hall, girls on the other. Finally, you pluck up the courage to make that long, lonely walk across the dance floor. And when you got there, what did you ask? "Would you like to dance?" Or maybe, "Do you want to dance?" For 50-70% of us, that question was met with a dismissive "no." And it felt awful. Now, with the wisdom

Most people ask closed-ended questions without even realizing it. Are you? Can you? Did you? Do you? Have you? Will you? Would you? It makes sense—this is how we’ve been asking questions our whole lives. But when you become a manager and need to get your salespeople talking, those same habits hold you back. Closed-ended questions don’t do useful work for you, because they lead to short answers, surface-level conversations, and you doing most of the heavy lifting. Making the s