Who’s Playing Ball? Five Ways to Know Where You Really Stand

November 11, 2025

What do you use to evaluate which prospects in your pipeline are truly playing ball?


How do you know if they’re engaged—or just being polite?


We’ve all been there: the opportunity feels good, the customer sounds positive, and your notes say, “They’ll definitely order soon.” But weeks later, you’re left chasing callbacks that never come and staring at a website that no one has logged into.


Before we jump into five ways to tell where you stand, let’s take a quick detour to the playground.


Think Like a Kid for a Minute

A few weeks ago, one of my new facilitators, Marcy, shared a story about her daughter, Isabella, that perfectly sums up persistence and clarity in selling.


Isabella,
Marcy’s daughter, wanted a pet—and not just any pet, but a dog.


Her first ask? Twelve dogs.


When that didn’t fly, she adjusted: “Okay, how about two cats?”

Denied again, she recalibrated once more: “Then how about a rabbit?”


The jury is still out on the rabbit, but here’s what’s brilliant about Isabella: she knows how to ask, adjust, and keep the conversation alive. She doesn’t walk away wondering where she stands.


If only more salespeople did the same.


Too often, representatives leave conversations thinking they’re “in the running” without ever confirming it. The best sellers don’t guess—they qualify engagement. They know who’s playing ball and who’s just holding the bat.


Here are five ways to know exactly where you stand:

 

1. Am I leaving this conversation knowing exactly where I stand?

Don’t let vague comments like “We’ll order when we need something” or “I’ll get you the list” end your conversation. Follow up with confidence:

  • Can you see yourself placing your next order with us?
  • Are there any concerns with what we put together?
  • If it were only up to you, would you start working with us?
  • Am I on the right track for how we can help your office?

We don’t know exactly where we stand unless we ask!

 

2. Interest is demonstrated by action! Has this customer shown interest through action, as evidenced by another meeting set with you?

A Next Set Time (NST) is tangible proof of interest. You’re not hoping they’re interested—you’re asking if they will talk or meet again to move to the next step. Time kills deals. Always ask for a Next Set Time, and you’ll get an immediate report card to gauge interest.

 

3. Are they giving me time and information to truly understand their needs?

Customers who make time for you—whether it’s ten minutes or an hour—are signaling interest. They’re investing their attention so you can ask better questions and tailor your approach.

 

4. Are they sharing specifics that show real engagement?

The more tangible the information, the better: product lists, measurements, specs, employee preferences.


When a customer offers details like these, it’s a clear sign they’re evaluating your solution seriously—not just browsing.

 

5. Are they giving me access to others—or keeping me at arm’s length?

Access equals opportunity. If your contact invites you to meet others or mentions additional decision-makers, the door is open.


If they block you, try pivoting your question:


“Who else cares the most about this?”


By asking “Who else cares about this?” rather than only “Who else makes the decision?” you’ll uncover others who could still say no.

Sales success isn’t just about having a full pipeline—it’s about knowing which opportunities are truly in play.


Be bold enough to ask where you stand. You may not get your “twelve dogs” every time—but you’ll walk away knowing who’s all in… and who’s just trying to take a quote and compare.

August 12, 2026
AI has changed how sales professionals prepare. In minutes, industry specific AI tools can help you research a company, understand an industry, organize your thoughts, and generate questions for an upcoming meeting including targeted categories. That is a real advantage. But it can also create a dangerous feeling: I already know this customer. You read the website. You scan recent news. You review a few LinkedIn profiles. You uncover lease renewal or contract renewal dates. And then, AI gives you a polished summary of the company’s likely priorities and challenges. The problem? “Likely” can quickly start to feel like “true.” AI should prepare you for discovery. It should never do the discovering for you. Here are five ways to use AI without losing the curiosity that makes great selling work. 1. Use AI to Prepare AI is excellent at helping you get ready. Use it to research companies and industries, brainstorm questions, organize your thoughts, identify possible decision-makers, and spot blind spots. Used well, AI saves time and helps you enter the conversation more informed. Try this prompt: “I’m preparing for a first meeting with [company name]. Using publicly available information, give me a brief overview of the business, three possible priorities or challenges, and three thoughtful discovery questions.” But preparation is only the starting point. The goal is not to prove how much you know. It is to learn what you do not know.  2. Watch Where AI Can Fool You AI can make assumptions sound like facts. It can also be incomplete, outdated, or simply wrong. Even accurate information can lead to the wrong conclusion. A company may be expanding, but growth may not be the customer’s biggest concern. The real issue could be staffing, service, cost control, or the time lost managing too many vendors. The danger is not using AI. The danger is believing you have learned everything before meeting the customer. Preparation should increase your curiosity, not replace it. 3. Remember: Curiosity Cannot Be Automated AI can tell you what a company does, what happened recently, and what trends may affect its industry. Only a real conversation can uncover why the customer is considering a change now, what is frustrating them, what success looks like, and what they are worried could go wrong. Use your research to open the conversation, not control it. 4. Ask the Questions AI Cannot Answer AI can suggest questions. The art of selling is knowing what to ask next. Try: “How did you decide on ….?” “Had we not called, what were you already planning to do about ______?” “What have you already tried?” “If you were sitting in a review six months from now, having personally made a significant impact on the business, what would success look like for you?” “What happens if nothing changes?” These questions move the conversation beyond surface-level pain. They also help you avoid pouncing too quickly. Whether the customer mentions delivery, cost, service, or vendor consolidation, slow down. The first answer is rarely the full answer. Ask one more question before offering one more solution. 5. Do Not Outsource Your Curiosity Everyone has access to similar AI tools. Not everyone listens well. Not everyone notices hesitation, follows an unexpected comment, or stays with an issue long enough to uncover what really matters. That is still your competitive advantage. Use AI to prepare, broaden your thinking, and identify what you may be missing. Then put it away and be fully present. Before your next customer conversation, challenge yourself to do three things: Prepare with AI. Verify with the customer. Ask one more question before offering a solution. Do not simply work through a list of AI-generated questions. Listen to the answer and follow where it leads. The question you did not plan to ask may be the one that uncovers the real opportunity. The more powerful AI becomes, the more valuable human curiosity becomes. AI can help you enter the conversation more informed. Your next move is to stay curious long enough to leave the conversation with a better understanding.
Sell like a Chameleon
May 24, 2026
Here’s a simple guide to recognizing four common customer speeds and how to adjust your approach.