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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

There’s a tiny habit I’ve been using lately that makes a big difference in face-to-face conversations. It’s so small, it is tiny, I feel stupid sharing it, but the impact is big.  Here it is: When you’re talking to someone, try to notice the color of their eyes. Not in a creepy way. Not in a long weirsd start way. Just long enough to really see them. When I do this, I find something shifts. Conversations are deeper. There’s more connection. More trust. More presence. More hum

A friend of mine admits he’s a terrible listener. His words, not mine. He says his brain runs a million miles an hour, he interrupts, he jumps topics like he's on a pogo stick. And honestly… he's not wrong. But here’s the twist: we went to an event with a great speaker—funny, compelling, told stories that really stuck—and this same friend? Locked in. Not just present, but later, he replayed those stories back to me. He remembered the message, the tone, even the punchlines. So

The first few seconds of a sales interaction matter—whether you’re in person or on the phone. Getting people on your side quickly is important. When we first meet someone, our brains are doing a quick scan: Do I like you? Do we agree? Do I feel safe here? That judgment happens fast—within seconds. And if you’re in sales, your job is to stack the deck in your favor. You can increase your chances of being liked—and trusted—by using Strategic Rapport. Not small talk. Not the wea

I stole one of my favorite closing tools from a therapist. It’s now my go-to when someone’s on the fence—undecided, unsure, caught between “maybe now” and “maybe later.” I used it recently with a sales leader who wasn’t sure whether to move ahead with a series of workshops or push it out a quarter. Instead of convincing, I asked four simple questions—each designed to shift the thinking from “should we do this?” to “can we afford not to?” Here’s how it works: The Impact of Ina

“Most salespeople think rapport is about being friendly. It's not. It’s about making the other person feel understood.” Over the past 20 years training thousands of sellers, I’ve learned this: People talk to people who listen well and ask the next RIGHT question. Here are 5 rapport-building mistakes I see all the time—and how to fix them: 1. They ask “How are you?” instead of “What’s keeping you busy today?”  → One is polite. The other starts a real conversation. 2. They talk

Most companies wouldn’t dream of building their own HR platform or designing a CRM from scratch, yet many still try to create and deliver sales training in-house. It’s well-intentioned, but often ineffective. Here’s why smart organizations are moving in a different direction—and choosing to outsource their sales training to experts. 1. It Costs Less Than You Think Outsourcing doesn’t mean more expensive. In fact, it often means no salaries, no benefits, no internal coordinati

Up to the moment a concern surfaces, most customer conversations are puppy dogs and roses, they’ve got a need, you’re asking good questions, and you’re making a solid recommendation. All good. Then it gets real. You quote a price or propose a next step, and they counter with: “That’s too expensive.”  “Your lead times are too long.”  “I want to think about it." That’s when tension creeps in. Even if everyone stays friendly, the conversation shifts—just enough to throw you off

You’re not sure when it started. You’re not sure who’s running it. You’re definitely not sure when—or if—it’s going to end. I sat in one recently where, 45 minutes in, I still didn’t know the purpose. No agenda. No structure. Just people talking. At one point, I was wondering: “Has this meeting even started? Or is it already over?” That’s what happens when no one sets the agenda. And it happens way too often! No structure. No purpose. No clear roles or outcomes. Just people s

I’ve worked on 150+ sales improvement projects. Different teams. Different industries. Same pattern: Salespeople aren’t asking great questions. If I were a sales manager today, I’d start by listening — not to the pitch, but to the questions. Because here’s what’s happening: Too Many Close-Ended Questions Salespeople default to safe questions:  • “Do you want to add anything to the agenda?”  • “Do you need anything else?”  • “Have you used this before?” They sound polite. But

You never know where a conversation will go. That’s what makes them powerful. Every time we talk to someone, we’re making hundreds—maybe thousands—of small choices. Do we stay with what they just said—or pivot to something new? Do we ask a follow-up—or share a personal story we were reminded of? Do we circle back—or move forward? Conversations aren’t scripted. They’re improv. And great improv follows a few powerful rules. Rule #1: Yes, and… Accept what’s offered and build on

In my last fifteen coaching sessions, every client said the same thing: “I want to be more proactive.” Different industries, different roles — same story. Everyone feels buried in urgent requests, unexpected fires, and endless interruptions. No one is getting to the work they actually need to do. The world has shifted from doing work to reacting to it. Here are five practical ideas to help you shift from reactive to proactive. 1. Start with Three Take a leaf out of Mike Willi

I grew up in Ebernoe, a tiny hamlet in West Sussex, England that had a cricket pitch with a road running through it. On Sundays we would watch the matches. Every so often, someone would shout “Car!” and play would stop while a driver passed through the pitch. Then everyone reset, and the game carried on. It was a strange setup, but it worked — people adapted. It’s a lot like sales management. You rarely have a perfect team. You take the players you have, turn them into top pr

During COVID, many inside sales teams were flying. Phones rang off the hook, customers answered, and every rep was busy. But now? It’s different. Email has taken over. Inbound calls are down. And when the phone does ring, most conversations are quick and transactional, solve the problem, hang up, move on. Teams that were once thriving now feel flat. It’s not effort that’s missing — it’s depth. As I listen to hundreds of calls across industries, I keep hearing the same things:

It’s the simplest question in sales… and almost nobody asks it. Managers spend their days forecasting, reviewing past performance, running one-on-ones, prepping decks, and sitting in meetings. They’ve never been this busy. And most were promoted because they were great sellers, not because they were great teachers. So teams get motivation instead of ability. “Ask better questions.” “Run a tighter meeting.” “Dig deeper.” Good advice… with no practice behind it. If you want beh