Mentor Moments That Shape Character

Why Do So Many Mentorship Relationships Fail Before They Ever Work? “You can't be more committed to somebody’s success than they are.” That insight comes from Colleen Stanley, author of Be the Mentor Who Mattered, during a recent conversation on the Sales Gravy Podcast. It's a simple statement that cuts through all the noise about mentorship and gets to the heart of why most mentoring relationships fail to deliver results. Sales professionals constantly talk about wanting mentors. They want access to someone who's been there, done that, and can show them the shortcuts. But when they get that access, they squander it. They show up unprepared. They argue with advice. They never implement what they learn. On the flip side, experienced sales leaders say they want to give back and mentor the next generation. But they get burned out after investing time in people who don't follow through. So they stop offering help altogether. The problem isn't a lack of willing mentors or eager mentees. The problem is that nobody understands their role in making mentorship work. What Mentees Get Wrong About Mentorship Most people treat mentorship like a magic pill, assuming that simply being near someone successful will transfer that success to them. It doesn’t work that way. Getting real value from a mentor requires more than just showing up. You need to actively do the work that makes their guidance worthwhile. Start by focusing on these key actions: Ask Directly The biggest barrier to mentorship isn’t that successful people won’t help you. It’s that you never ask. You assume they’re too busy, too important, or too far removed from your situation to care. You’re wrong on all three counts. Successful people got where they are because someone helped them along the way. Most of them want to pay that forward. But they’re not mind readers. If you want help, ask for it directly. Respect Their Time When you do ask, come prepared. Don’t ask for “15 minutes to pick your brain.” That’s code for “I haven’t thought about what I actually need, so I’m going to waste your time figuring it out.” Instead, be specific. “I’m struggling with qualifying early in the sales process. Could you share how you approach qualification conversations?” Specific questions get specific answers. Vague requests get vague responses—or none at all. Do What They Tell You to Do This is where most mentoring relationships die. You ask for advice. You get great guidance. Then you come back with a list of reasons why it won’t work for your situation. Stop that. If you’re going to ask someone for their expertise, try their approach before explaining why your situation is different. You’re there because they know more than you do. Acting like you know better defeats the entire purpose. Your mentor’s reward isn’t money or recognition. It’s watching you take their advice and succeed because of it. When you implement what they teach and come back with results, they’ll invest even more in your development. When you make excuses, they’ll move on. Take Tough Feedback Without Getting Defensive Not every mentor has read the latest book on constructive feedback. Some of them are direct or blunt. Take it anyway. When someone cares enough about your success to tell you the truth—even when it’s uncomfortable—that’s a gift. Don’t reject it because it wasn’t wrapped perfectly. The best mentors don’t sugarcoat feedback because they respect you enough to be honest. They see potential in you that you can’t see yet, and they’re not going to let you waste it by staying comfortable. What Mentors Get Wrong About Mentorship If you’re in a position to mentor others, you already know the frustration of investing in someone who doesn’t follow through. It’s exhausting. Eventually, you start to wonder if it’s worth your time at all. Before you close yourself off completely, it’s important to understand the common patterns that cause mentoring relationships to stall. Waiting for the Perfect Mentee There is no perfect mentee. Everyone who asks for your help is going to be rough around the edges. They’ll make mistakes. They might waste some of your time. That’s the cost of mentoring. The real question isn’t whether someone is polished. It’s whether they’re committed. Are they showing up prepared? Are they implementing what you teach? Are they making progress, even if it’s slow? If the answer is yes, keep investing. If it’s no, redirect your energy elsewhere. Just don’t let one bad experience make you cynical about everyone. Trying to Control Their Path Your job as a mentor isn’t to create a clone of yourself. It’s to help someone develop their own approach using the principles that made you successful. They might take your advice and apply it differently. They might adapt it to their personality, their market, or their selling style. That’s not wrong. That’s the point. Stay unattached to the outcome. You can’t be more invested in their success than they are. Give them your best insights, support their growth, and let them own the results. Mentoring the Wrong People Not everyone needs your specific expertise. Some people need tactical help with prospecting. Some need strategic guidance. Others need coaching on emotional intelligence. Look for the multipliers. Mentor people who will take what you teach them and use it to help others. When someone you mentor goes on to mentor others, your impact grows far beyond what you could achieve alone. That doesn’t mean only mentoring future executives. It means finding people who are genuinely committed to growth and generous enough to share what they learn. The Real Value of Mentorship Mentorship isn’t a transaction. It’s not about what you can get from someone more successful or what you owe someone less experienced. It’s about creating a community where people help each other get better. Where progress matters more than perfection. Where tough feedback is welcomed because everyone knows it comes from a place of care. Having someone in your corner who believes in your potential—even when you don’t—can be the difference between quitting and breaking through. But that only works if both sides understand their role. Mentees must show up ready to learn and willing to act. Mentors must show up ready to tell the truth and willing to invest. Find the mentors who will challenge you. Be the mentor who changes someone else’s trajectory. Ready to take the next step in your development? Finding the right mentor or coach can transform your sales career—if you know what to look for. Learn how to identify the coach who’s right for you with our FREE How to Find the Right Coach for You Guide.