On the surface, you’d think that “selling” and “asking” go hand in hand. In reality, salespeople at all experience levels often hesitate, tiptoe around, or dodge direct closes because they’re afraid of rejection, worried about coming across as pushy, or insecure about asking.
On this episode of the Sales Gravy Podcast, Jeb Blount explores why salespeople fear asking for the sale and what to do about it with author and Sales Gravy University instructor, Tony Morris
Every salesperson starts somewhere. Tony Morris started turning a profit buying 10 pounds of sweets from a shop and selling them for 20 pounds. Before that, he sold car washing door to door. But before all that, he spent hours watching his father prep for sales calls in the mirror, honing his language and mastering his message. It drove home one idea for a young Tony: To be a sales success, you have to practice, practice, practice learning how to ask for the sale.
The Fear Factor That Holds Salespeople Back From Asking for the Sale
There’s an underlying, deeply human factor that derails many capable sales professionals: The fear of asking for the sale.
Rejection stings, whether it’s a “no” from a potential client or crickets after your presented a proposal you believed was bulletproof. We fear hearing “no” because we interpret it, consciously or not, as a sign that our competence or worth is lacking. Ironically, the more empathetic and relationship-focused a salesperson is, the more they tend to shy away from scenarios that might lead to an uncomfortable refusal.
When you allow the fear of rejection for creep in when attempting to close the sales it often leads to:
Hesitation: You wait for the buyer to “signal” readiness, rather than proactively closing.
Defensiveness: If a conversation veers toward potential objections, you steer away or gloss over critical next steps.
Over-Explaining: To avoid a direct ask, you bury the buyer in details, hoping they’ll volunteer a “yes.”
Practice Is the Key to Asking Confidently for the Sale
Watch any top performer in any field—a pro golfer, a concert pianist, or an elite salesperson—and they often make it look effortless. People assume they were simply “born with it.” In truth, consistent practice is usually the reason they’re able to operate at such a high level without appearing scripted or nervous.
One reason salespeople hesitate to ask for the sale is that they don’t feel comfortable with what to say—or how to say it—when the conversation reaches its critical moment. Practice, especially under realistic conditions, engrains talk tracks, responses to objections, and emotional composure. Practice allows you to lean on muscle memory rather than fumbling for words or panicking at a curveball question or objection.
The more you prepare, the more comfortable you are in the moment. When you are well-prepared you come across as “unscripted” and fluid because you’re not scrambling to find the right words. You’ve internalized the dialogue, so it sounds like a calm, authentic conversation rather than a memorized monologue.
Make Peace with the Word “No”
Time and again, top sales performers cite a simple truth: a fast “no” can be better than a lingering “maybe.” It allows you to save time, refocus energy, and cultivate a pipeline of engaged prospects. Learning to handle “no” as a data point—rather than personal rejection—keeps you in motion.
Categorize the “Nos”: Some are “not now,” others are “not a fit,” and a few are “never.” Understanding which type of no you’re dealing with can shape follow-up strategies.
Seek Feedback: If appropriate, ask, “I respect your decision. May I ask what caused you to decline?” That insight can sharpen future presentations.
Stay Professional: Burn no bridges. A gracious exit can leave the door cracked open; circumstances often change.
Shift Your Mindset About What Asking for the Sale Really Means
Whether you’re selling software,
