October 28, 2025
Welcome Back,
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Good morning! In today’s issue, we’ll dig into the all of the latest moves and highlight what they mean for you right now. Along the way, you’ll find insights you can put to work immediately
— Ryan Rincon, Founder at The Wealth Wagon Inc.
Today’s Post
Mastering Active Listening & Questioning in Sales
When you’re in sales, talking feels natural. But what if the real power isn’t in what you say, but in what you hear? That’s where active listening and smart questioning come in—they shift you from being a presenter to being a guide.
Why listening matters more than talking
Research shows top salespeople listen more than they speak—active listening creates trust, reveals real pain points, and makes your prospect feel heard.
When you ask good questions and genuinely listen, you avoid the common trap of pitching something that doesn’t match what your prospect actually needs.
“You don’t need more features, you need to understand the feature your customer cares about.” In other words: ask, listen, adapt.
What is active listening?
Active listening is more than simply hearing words. It’s:
Paying full attention to what the prospect is saying (and not saying).
Responding in a way that shows you understood (for example, paraphrasing their concern).
Asking follow-up questions that dig deeper into their motivations, challenges, and context.
Key questioning techniques that boost your sales game
Here are some techniques to use right away:
Ask open-ended questions:
Instead of “Do you have a budget?” ask “Tell me about how you’re budgeting for this initiative.”
These kinds of questions invite the prospect to share more detail rather than giving a yes/no answer.
Mirror or paraphrase what you heard:
Example: “So what I’m hearing is that your team spends 30% of time on manual outreach—did I get that right?”
This technique builds alignment and shows you’re listening.
Use silence wisely:
After asking a question, pause. Let the prospect think. Let them fill the space.
Silence is a tool, not a gap.
Focus on body language and tone (even in virtual calls):
Even over video, expressions, pacing, whether the prospect leans forward or seems distracted—they all tell you something.
Prioritize listening over waiting to speak:
If you’re already thinking about your next line while they’re talking, you’re probably going to miss something important.
How to apply this on a sales call or meeting
Before the call: Review any research you have on the prospect. Note possible questions, but be ready to change them based on what you hear.
During the call:
Start with a welcoming tone—“I know we’ve got about 30 minutes; I’d love to start by hearing what your biggest challenge is right now.”
Use an open-ended question to begin the conversation.
Listen, nod, paraphrase, ask deeper questions.
Avoid the temptation to launch into your product or solution until you have a clear understanding of their pain.
After the call: Send a quick recap email that includes something like: “What I heard you say…” This reinforces you listened and builds credibility.
Mistakes to avoid
Talking too much too early: If you lead with features and benefits without understanding the prospect’s problem, you’re missing the mark.
Asking closed questions only: “Is this a priority?” gives limited insight. Replace with “How does this priority show up in your daily workflow?”
Ignoring non-verbal cues: Prospects may say “We’re doing fine” but their tone or body language could indicate otherwise—listen to the sound as much as words.
Skipping follow-up questions: When the prospect says something vague like “we want to improve outreach,” ask “What does improvement look like for you?”
Quick checklist you can keep handy
Did I ask open-ended questions today?
Did I pause and let the prospect respond fully?
Did I paraphrase something the prospect said to confirm understanding?
Did I notice non-verbal cues and check for feelings behind words?
Did I avoid jumping into a pitch too early?
Final thoughts
Active listening and great questioning aren’t “nice-to-have”—they’re fundamental. When you shift from telling to asking, from talking to listening, you open up a world of insight, trust and stronger relationships. The next time you’re in a call, try this: listen more, ask well, then speak. You’ll be amazed at how much deeper the conversation goes—and how much closer you’ll come to closing.
That’s All For Today
I hope you enjoyed today’s issue of The Wealth Wagon. If you have any questions regarding today’s issue or future issues feel free to reply to this email and we will get back to you as soon as possible. Come back tomorrow for another great post. I hope to see you. 🤙
— Ryan Rincon, CEO and Founder at The Wealth Wagon Inc.
Disclaimer: This newsletter is for informational and educational purposes only and reflects the opinions of its editors and contributors. The content provided, including but not limited to real estate tips, stock market insights, business marketing strategies, and startup advice, is shared for general guidance and does not constitute financial, investment, real estate, legal, or business advice. We do not guarantee the accuracy, completeness, or reliability of any information provided. Past performance is not indicative of future results. All investment, real estate, and business decisions involve inherent risks, and readers are encouraged to perform their own due diligence and consult with qualified professionals before taking any action. This newsletter does not establish a fiduciary, advisory, or professional relationship between the publishers and readers.