Sales Meeting Best Practices

Most AEs fail on the phone for one simple reason: They’re cold calling people who’ve never heard of them. In 2025, that’s just lazy. Here’s how I would book executive meetings without sounding like a desperate sales rep: I used to teach cold calling techniques. Tonality. Pacing. Objection handling. And while that still matters... It’s not the reason I consistently get meetings with C-level buyers. The secret? I never cold call anymore. I warm call. Here’s how I do it: Step 1: Start with a personalized, relevant email. Do some quick research. Make it about them. For example, if I’m reaching out to a CRO, I’ll highlight a drop in quota attainment from RepVue and explain how I can help upskill their team in tough times. Step 2: That same day—a few hours later—I call their cell phone. (ZoomInfo or LinkedIn can get you that. No excuses.) DO NOT call the office. DO NOT waste time dialing assistants. If you can’t get a cell, send a LinkedIn connection request with a DM or video message. Step 3: When I call, I say: “Hi, this is Ian Koniak—did you happen to see the email I sent this morning?” If they say no: “No problem. I sent it because I saw your team’s quota attainment is down since 2022. I think I can help based on what I’ve done with other clients. Do you have a couple minutes now, or should we find time to connect on Zoom?” It’s not a pitch. It’s a reference to something you already sent that’s about them. That’s what makes it warm. Step 4: If they don’t respond, wait 2–3 days. Then reply to the original thread with more context: – Mention the training or workshops you offer – Share real results (e.g., 20% increase in quota attainment) – Ask: “Is this something you’d be open to learning more about?” Always lead with interest, not a hard ask for time. Step 5+: Stack 6–8 touchpoints total. Each one builds on the last—adding more insight, examples, testimonials. Mix in: – LinkedIn videos – Client stories – Relevant frameworks Each message = more value. That’s how you break through. It can take 8-12 touchpoints to get a meeting. Most reps quit after 1-3 touchpoints. Or worse—just send the same “following up” message. No value. No relevance. No shot. This process works. It’s not magic. It’s just real sales effort with a real strategy.

So...you’re talking about money too soon with your clients. Most advisors are trained to prove expertise quickly, so first meetings become presentations instead of conversations. An opportunity to "wow" with technical acumen. But wealthy folks usually aren’t trying to solve a spreadsheet problem first. They’re asking themselves things like: “What does success look like now?” “Will this wealth help or hurt my kids?” “What kind of life am I actually building?” The best advisors understand that people don’t want to feel analyzed, they want to feel understood. That’s why great first meetings sound less like a pitch and more like curiosity: “Tell me about your family.” “What’s changed recently?” “What worries you most?” BeFi teaches us that people decide emotionally first and justify intellectually second. If you miss the emotional driver, you’re probably solving the wrong problem. Before clients trust you with their money, they need to trust you with their story.

How I run sales meetings that lead to next steps 90% of the time. Running a successful sales meeting involves clear communication before, during, and after. Often, attendees aren't sure what to expect, so we have to make sure to set the tone before the call even happens. So I send an agenda 24 hours prior to the call and include the following. • What topics will be discussed • Questions to answer beforehand • Use cases if applicable Also, make sure to do some research about the company so you have context. No one likes an unprepared sales rep. During the call immediately set expectations. • Ask if they have a hard-stop • Refer back to the email to set the agenda for the call • Mention that you did some research and tell them what you found Be an active listener and ask deep discovery questions to uncover pain. As the call wraps up, make sure to leave 7-9 minutes to guide them through the next steps. Here is an example: "Typically, when we see a problem like this, we would most likely include (x person) and (y person) on the next call to discuss how we help in that area. Would Thursday at 10am EST work for you?" I book these meetings directly from Calendly's browser extension while still on the call because it's quick, smooth, and instant. Calendar invites are sent before we end the call so you remove the possibility of being ghosted after. We still have work to do after you nail down the next steps. We ain't done yet. Send a summary email, not to do more selling but to recap for accountability. • What their main goals/priorities are • Timeline • Next steps When you have a system to run better meetings, it leads to great results. P.S. Do you agree with this framework? #BetterMeetings

Do NOT end a cold call without a calendared next step Look, you did the hardest part. There's a 95%+ chance the prospect doesn't pick up the phone. Don't waste that opportunity. Prospect can't talk right now? Schedule time to follow up. Prospect asks you to send an email? Schedule time to follow up. Prospect says they're in a meeting? Schedule time to follow up. Here's an example of how you could handle "Send me an email." ✅ 1) Agree Prospect: “Can you send me an email?” Rep: “Sure thing, happy to.” Doing so disarms the prospect. And that’s all you can ask for when objection handling during a cold call. Genuine conversation. That’s the goal. ✅ 2) Get more info Now it’s time to dig in. Your goal is to anchor back to a legitimate reason for the prospect to meet with you. Prospect: “Can you send me an email.” Rep: “Sure thing, happy to. So I can get the right info to you—are you like most HR leaders in that your team is absolutely swamped with manual tasks running payroll, benefits, etc. across five different tools?" Then dig in for as much as the prospect is willing: - Find out their current solution - See if they have similar problems that your clients have ✅ 3) Ask for the meeting Now it’s time to anchor around what you just learned to the reason for meeting. Rep: “Got it, this is exactly what we’ve helped ABC and XYZ companies with. Their HR teams were getting bogged down with manual admin. work across the five solutions they pieced together for payroll, benefits, onboarding, etc. How about this—most of the material we send over can be very generic and unhelpful. A more effective use of your time would be to spend time with one of our HR specialists to look at this through a lens that’s more specific to your business. Do you have your calendar handy?” This usually does the trick ✅ 4) How to handle resistance Still getting resistance? Try this: Rep: “Okay, no worries. How about we put 5 minutes on the calendar for tomorrow when you’ve had a chance to look over the email? If you like what you see, we keep the meeting. If you don’t, you can cancel. Sound fair?” ~~~ The 5-minute placeholder works like a charm. You can use it anytime you can get the prospect to nail down time with you.

The best deals are not won by the best talkers. They are won by the most prepared people in the room. And most people in that room are not prepared. They have a pitch. They have a product. They have a hope that the conversation goes well. The best people have something different entirely. They know who is sitting across from them. Their industry. Their pressures. Their culture. Their language. And they speak it before anyone asks them to. That is what changes everything. Not the pitch. Not the product. The moment the other person realises this is someone who actually did the work to understand me. Nobody does that anymore. Most people show up and perform. The best people show up and connect. The difference between those two things is preparation. And preparation is a choice available to everyone in the room. Most deals are not lost because the product was wrong. They are lost because the person never felt understood enough to say yes. Trust is not built in the meeting. It is built in the hours before it begins. 💡 Try this: ↳ Notice how much time you spend on the pitch versus the person ↳ Research one cultural detail before every important meeting ↳ Find one challenge specific to their industry before you arrive ↳ Watch what happens when someone feels genuinely understood ↳ Track how quickly trust builds when you speak their language first ↳ Ask yourself if you are preparing to sell or preparing to serve Preparation is not extra effort. It is the thing that makes everything else feel effortless. The deal is not closed in the meeting. It is closed in the work nobody sees before it begins. What is one thing you do before an important meeting that most people skip entirely? #Sales #Preparation #BusinessGrowth #CustomerSuccess #Communication #Leadership #KnowYourCustomer #Mindset #ProfessionalDevelopment #Winning

He thought He WON THE DEAL But... A few months ago, I was coaching a young sales rep. Let's call him Rohan. Smart. Driven. Great with people. He came to me one day, frustrated. “The client loved the demo. They said it’s exactly what they wanted. But now they’ve gone completely silent.” I asked him, “What was the next step you both agreed on before you ended the meeting?” He paused. “Uh… we said we’d stay in touch.” And that’s when I smiled, because I knew what had happened. He didn’t lose the deal in the follow-up. He lost it in the meeting itself. I told Rohan something I’ve learned the hard way: “Never end a meeting with excitement. End it with commitment.” Now, every time he finishes a meeting, he locks in these 3 things: 1. Next Step: A concrete date, time, and action. Because “let’s stay in touch” is where good deals die. 2. Involvement: Who else needs to be part of the next conversation. Because hidden decision-makers are silent deal killers. 3. Value Alignment: What was most valuable for the client in today’s discussion. Because if you don’t know what clicked, you won’t know what to build on next. Two weeks later, Rohan texted me after a big client call: “Got all 3 commitments. Deal closed in 10 days.” That’s when he realized, Sales isn’t just about convincing people. It’s about keeping momentum alive. If you’re a sales rep reading this: Don’t let enthusiasm fool you into thinking a deal is WON. Until you have commitment, you only have a conversation. Remember, “Never end a meeting with excitement. End it with commitment.” #sales #salestips #salescoaching #b2bsales #salesleadership

Your POC process is probably why you're not closing enterprise deals.   After analyzing POC outcomes across our portfolio, the data is clear: Companies with structured and priced POCs close 3x more deals than those running free pilots.   Why charge? Price signals seriousness. Even nominal fees filter serious buyers from tire-kickers. Frame your pilots as fixed-fee engagements: Say "we structure this as a 4-week, fixed-fee engagement to quantify value and build your business case."   Be sure to clarify pricing expectations in the process: If your pilot costs $5K but commercial deals are $100K-$300K based on the value unlocked, state this explicitly to avoid anchoring.   Here are 5 best POC best practices we see:   1. Define success criteria, not scope Align on specific KPIs, business outcomes, and who signs off before writing a line of code.   2. Time-box ruthlessly with weekly checkpoints POCs should run 30-90 days max. Set weekly or bi-weekly checkpoints to maintain urgency.   3. Pre-commit the path to commercial discussions Before starting any pilot, confirm that hitting the success metrics will trigger stakeholder presentations and commercial negotiations.   4. Demand access to the full buying center Technical users alone can't close deals. Ensure you meet decision-makers and budget holders during the POC, not after.   5. Document like a contract Formalize scope, terms, and deliverables in the agreement. Include specific responsibilities for both sides, data access requirements, success metrics, timelines, and post-POC commitments.   --   POCs are where your enterprise motion gets built. Treat them that way.   I wrote a guide to AI pricing with Madhavan Ramanujam and Joshua Bloom that discusses these ideas in more detail. If you're curious to dive deeper, I'll leave that link below. Also, Madhavan just released a new book called Scaling Innovation that also explores these topics. Highly recommend!

"Let me know if you have any questions." "Happy to discuss further." "Looking forward to your thoughts." Every time you end a follow-up with these wimpy closes, you're asking busy executives to do work they won't do. They're not going to think of questions. They're not going to schedule a follow-up call. They're not going to send you their thoughts. They're going to delete your email and move on with their actual job. The fix is making the next step so easy that a drunk executive could do it. Instead of "let me know if you have questions," embed your calendar link directly in the email. One click to book time. Instead of "happy to discuss further," Create a simple yes/no decision box: "Ready to see the ROI calculation? Yes | No" Instead of hoping they'll respond with their availability, give them three specific time slots to choose from. The most powerful follow-up technique? Use their exact words from your call. When Jessica said she's "bleeding money on software licenses," don't paraphrase it. Quote it exactly. Reference her Thursday board meeting. Add one insight she didn't know. There's nothing more impossible to ignore than hearing your own words reflected back with new value attached. Your generic templates sound like every other vendor they're ghosting. But your personalized follow-ups that reference specific moments from your conversation get responses. Stop making prospects do the work of figuring out next steps. Start making it obvious how they move forward. Every follow-up is life or death for your deal. Most AEs are committing suicide with their own emails. Don’t be like most AEs.

Here’s how to have a conversation with a human being. As salespeople, we’ve been taught to never end a meeting with a prospect without booking another one. The demo ends. The prospect says, “I’ll let you know.” The seller jumps in: “How long do you need to decide?” The prospect says, “A week.” The seller, trained by the gospel of “always set a next meeting,” replies: “Perfect. Let’s get 15 minutes on the calendar for a quick check-in so we can get to a yes or a no. How about next Wednesday at 10 or 11 Eastern?” The prospect, not wanting to be rude, says sure. The seller logs the next step in Salesforce and pounds their chest. Then Wednesday rolls around. And the prospect ghosts. Why? Pressure. The meeting wasn’t a mutual commitment. It was compliance. The prospect agreed because it was easier in the moment than saying no. When you push for a next step that isn’t earned, you get politeness instead of progress. You get calendar clutter instead of clarity. Here’s what I suggest instead. At the end of the meeting, see if the prospect is motivated to continue the conversation: “You probably have a sense of whether this is worth exploring further.” If there’s interest, gently suggest a next step that benefits the prospect, not you. Something like this: “After seeing the demo, some folks like to try it out for themselves in their environment. Is that something you’d like to do?” If they say no, that’s okay. “Sounds like the demo missed the mark.” Then shut the front door. And ask, “Where would you like to go from here?” That small shift changes everything. It replaces pressure with permission. And when people feel safe, they’re more honest. The best next meeting isn’t one you push for. It’s one the prospect asks for. You don’t create motivation, you align with it.

If you’re in B2B sales and struggling to book meetings, this post will show you exactly why—and how to fix it. In the next 90 seconds, you’ll learn: ✅ Why your outreach is being ignored ✅ The cold call script that worked—until it didn’t ✅ One rule that flipped my results and rebuilt my pipeline ✅ How to trade value for access and stop sounding like every other rep This is field-tested and Fortune 500-proven. No fluff. Just what works. Let’s be honest: most salespeople are asking for time like amateurs. They’re dialing, interrupting, and begging—without offering anything worth trading for the meeting. I used to say: “Hi, this is Anthony Iannarino with [Company]. I’d like to introduce myself and my company. Would 11:30 Tuesday work for you?” That line booked hundreds of meetings. Until it didn’t. Because once every salesperson starts saying the same thing, it becomes noise. Then I made a shift.I stopped asking for time. I started trading value. I created something I called an executive briefing—a strategic, high-level conversation offering insight on market trends, industry risks, and the shifts leaders needed to prepare for. I wasn’t pitching. I was delivering perspective. That single shift changed everything. Executives started saying yes again. Not because I asked better—because I offered better. I call this the Trading Value Rule: Never ask for a meeting without offering something worth more than the time you're requesting. It flips the script. You go from salesperson to strategic partner—before the meeting even happens. This isn’t just how I prospect. It’s how I sell. It’s why The Lost Art of Closing works. If your meetings are down, your value isn’t visible. Fix the offer—and the doors open. Want the cold call script I used? Drop a in the comments and I’ll DM it to you. #B2BSales #ColdCalling #SalesStrategy #ValueBasedSelling