How Do I Earn Respect When Selling to People Older Than Me? (Ask Jeb)

Elli in Galveston, Texas, faces a scenario that many young sales professionals know all too well: How do you earn respect and project confidence in selling when you’re dealing with people who are older and more experienced than you? Ellie’s question highlights a universal issue in sales. Whether you’re dealing with age differences or expertise gaps, it’s easy to feel anxious if your buyer is decades older or has been in the industry for a long time. Below, you’ll find practical strategies to bridge that confidence gap, project authority, and demonstrate a relaxed assertiveness that resonates with prospects of any age. 1. Recognize That It’s Mostly in Your Head A significant part of Ellie’s challenge stems from internal dialogue rather than external facts. As I reminded her, rarely will a prospect openly declare, “I don’t respect you because you’re young.” Instead, we often impose that narrative on ourselves. Negative Self-TalkTelling yourself, “They’ll never take me seriously,” can become a self-fulfilling prophecy. When you believe you lack standing, that energy radiates, and prospects pick up on it. Flip Your MindsetMost professionals—older or otherwise—care primarily about whether you can solve their problems, save them time, or increase their revenue. Your birth year is less important than your ability to address their business needs. 2. Win Through Questions The simplest way to defuse insecurities about age or experience is to ask better questions. Listening is far more powerful than talking in most sales situations. Tap Into Their ExpertiseIf they’ve been in the business for decades, demonstrate sincere curiosity: “How have you seen this industry evolve since you started?” or “What are some of the biggest shifts you’re preparing for next?” By making them the expert, you earn respect through authentic engagement. Use Youth as a StrengthBeing new or younger often means a fresh perspective. Admit what you don’t know and say, “I’d love to learn from someone with your track record. What advice would you give to someone like me?” You’ll be amazed at how many seasoned pros want to mentor enthusiastic newcomers. Don’t Fear “I Don’t Know”If you get a technical question you can’t answer on the spot, say, “That’s a great question. I’m not 100% sure, but let me check with my team and get back to you.” This approach does two things: it proves you’re honest (rather than bluffing), and it gives you a solid reason to continue the conversation later. 3. Relaxed, Assertive Confidence—The “Jedi Mind Trick” If there’s a secret weapon in sales, it’s projecting selling confidence. But this isn’t about memorizing every rebuttal or faking bravado. It’s about becoming relaxed and assertive enough to handle anything that comes your way. Rely on Frameworks and Processes Know the steps you’ll take to open a call, overcome objections, or ask for the business. When you trust your proven framework, you’re less likely to freeze under pressure. For instance, if you have a system for handling objections, you’ll approach objections with calm anticipation rather than dread. Practice and Role-Play Just like athletes rehearse plays, sales pros need to rehearse calls. Role playing with a manager or teammate builds “muscle memory.” When real-world situations or questions arise, it’ll feel familiar—something you’ve already navigated. Overcome Obstacle Fear Face the age-gap issue repeatedly until it no longer feels daunting. Think of it as exposure therapy. The more you engage with senior-level buyers, the more you realize they’re just people with specific needs and pain points. Keep Your Pipeline Full Nothing nurtures confidence like having multiple deals in progress. A robust pipeline means you can approach each conversation without desperation, which projects a sense of calm authority. 4. Rewiring Your Internal Scripts Even the best frameworks won’t help if your own thoughts tear you down. Here’s how to realign your mindset: Self-AwarenessListen to the messages in your head. Are you mentally telling yourself you don’t belong, or that you lack the expertise to help a big-name prospect? Recognize those thoughts for what they are—self-imposed limitations. Positive AffirmationsReplace negative chatter with empowering statements: “I’ve prepared carefully, and I know how to ask the right questions. I’m here to help.” Simple but effective. Visualize SuccessBefore stepping into a meeting, picture the conversation unfolding smoothly. Imagine asking incisive questions and guiding the prospect to a positive next step. That mental rehearsal can soothe nerves and raise your confidence. 5. Making “Older” Prospects Feel Familiar Intimidation often stems from the unknown. When you deal with a large, entrenched prospect, it’s easy to see them as unapproachable. But frequent interaction turns intimidation into familiarity. Aim for Micro-CommitmentsInstead of pushing for a big purchase right away, propose a short introductory meeting or a quick product demo. Build the relationship gradually, letting familiarity replace doubt, and boost your selling confidence. Don’t Confuse Longevity with RigiditySome of the most established companies are eager for fresh ideas. If you display genuine interest in helping them innovate, you’ll stand out among reps who assume older clients won’t consider new solutions. 6. The Bottom Line: Confidence Is Contagious Whether you’re talking to a brand-new entrepreneur or a CEO with decades of experience, confidence is a feeling people sense and respond to. If you walk in unsure of yourself, that doubt can quietly poison the interaction. But if you arrive calm, prepared, and sincerely invested in understanding your buyer’s world, you’ll find that even the most seasoned executives lean in with curiosity and respect. Remember: You don’t need to know everything. You just need to show genuine interest, have a reliable process, and let your passion for helping them shine through. That’s the real secret to selling confidence across any age gap—making the other person feel heard, validated, and supported. Got a Burning Sales Question? If you’re wrestling with a tough scenario—whether it’s about age gaps, prospecting woes, or tricky objections—I’d love to help you tackle it. Head over to salesgravy.com/ask, fill out a short form, and our team will reach out to schedule you for a future Ask Jeb episode.