Success Story with Scott D. Clary

Lessons – The #1 Thing Great Mentors Do Differently

Guest: Scott Miller (6x Bestselling Author)
Date: November 18, 2025

Episode Overview

This "Lessons" episode focuses on the real value and function of mentorship—dispelling myths, highlighting the importance of vulnerability, and offering actionable strategies for both seeking and becoming a great mentor. Host Scott D. Clary and Scott Miller (author and leadership expert) discuss how great mentors rely on wisdom, not authority, and openly share both successes and failures. They unpack what healthy, mutually respectful mentorship looks like, the wide-ranging benefits of having diverse mentors, and pragmatic advice on finding the right fit.

Key Discussion Points & Insights

What is a Mentor? (00:26–03:25)

• Scott Miller shares:
  • Mentors can be formal ("Will you mentor me?") or informal (a wise friend).
  • A true mentor shares wisdom—not just successes but also failures—with an abundance mentality.
  • Emphasizes learning from experiences:
    • “I learned more about having a successful marriage from those who are divorced. I learned more as an entrepreneur growing my business from those who've had bankruptcies...” (C, 00:42)
  • A mentor is “more concerned with what is right than being right...Can any of my journey, mistakes and successes, be helpful to you? That’s what a mentor is.” (C, 01:20)

Misconceptions About Mentors (01:48–03:25)

• Many mistake mentorship as seeking an all-purpose ‘guru.’
  • The best approach is to have several mentors for different life domains.
  • “If you find multiple people who’ve done different things in different areas of your life...that’s probably the best way to leverage what a mentor is.” (B, 01:58)
• Consuming books and interviews can offer mentorship at scale, but it’s not the same as a true, reciprocal relationship.

Building a Genuine Mentor Relationship (03:25–06:11)

• Formalizing the relationship is important—clarity of intent matters.
  • “A mentor is someone who is in a relationship with you...It’s someone who’s pursued a path similar to the one you want...that has enough confidence to demonstrate humility.” (C, 03:34)
  • Don’t manipulate: “Don’t manipulate someone into thinking they are your mentor, and then all of a sudden you ambush them for a different reason. That’s just called duplicity and disingenuousness.” (C, 04:31)
  • Honor boundaries. Mentors are not therapists or constant cheerleaders.
• Be clear when you reach out:
  • “My intent is to try to learn from your experience. Would you spend some time with me over the next six months? One call a month for 30 minutes...” (C, 05:01)
• Respect their time and don’t overstep with unwarranted communication.

Key Benefits of Having a Mentor (09:05–12:20)

• No one succeeds entirely alone; mentors show “blind spots” and help “look around corners.”
  • “I don’t know a single person that’s successful that’s ever figured out their life without a mentor...they may not realize it, but...it might be a rabbi, it might be a priest, it might be a father-in-law...” (C, 10:05)
• Mentors ask powerful, open-ended questions, helping you discover your passions, mission, and fears.
• “A great mentor is someone who listens more than they talk.” (C, 11:13)
• Not all mentors are older or more experienced in every way; some “mentor me on how to get on Clubhouse and TikTok...I’ve got mentors that are half my age.” (C, 11:50)

How to Find & Approach a Mentor (12:20–15:03)

• Start with your network; look for wisdom, not just “success.”
  • “When I say accomplished, it might mean that they’ve had the most bankruptcies, because the people who have had the most failures probably have the deepest lessons to teach.” (C, 12:49)
• Don’t hesitate to reach beyond your immediate circle—most successful people are willing to help if asked respectfully.
  • “Most of my success has come because I was willing to ask...sometimes they say no, sometimes they say yes.” (C, 13:27)
• Avoid “scope creep”: Don’t treat mentors as friends, banks, or therapists.
  • Critical red flag is when mentors try to “turn you into them” rather than helping you find your unique path.

Recognizing Red Flags in Mentorship (15:03–17:38)

• Self-awareness is key: understand what it’s like to coach or mentor you.
• Be practical and incremental—like dating, start small (a few short meetings), see if it’s a fit.
  • “Incrementalizing: it’s like dating. Are you going to know in the first date whether or not you want to invite this person back?” (C, 15:53)
• Be gracious if it’s not working—thank the mentor and move on without burning bridges.
  • “Can I tell you, Scott, I have so appreciated your investment in me. I’m going to actually release you from any further commitments...Would you be willing, if I needed some more time, to ever give it to me?” (C, 17:09)

Notable Quotes & Memorable Moments

• On true mentorship:
  “A mentor is someone who is more concerned with what is right than being right.”
  — Scott Miller (C), 01:16

• On vulnerability and failure:
  “I learned more about having a successful marriage from those who are divorced. I learned more as an entrepreneur growing my business from those who've had bankruptcies than from those who made their first million by age 30.”
  — Scott Miller (C), 00:50

• On boundaries:
  “Most mentors, if they’re valuable, they’re probably successful, they’re probably in demand...Be respectful of your mentor’s time and boundaries.”
  — Scott Miller (C), 05:40

• On mentorship diversity:
  “I have several people that are mentoring me on how to get on Clubhouse and TikTok...I'm not afraid to say I've got mentors that are half my age.”
  — Scott Miller (C), 11:50

• On seeking mentorship:
  “Most successful people have an abundance mindset. They’ll help you out as long as there’s not this sort of mission creep.”
  — Scott Miller (C), 05:18

• On ending mentorships gracefully:
  “I have so appreciated your investment in me. I’m going to actually release you from any further commitments...Would you be willing, if I needed some more time, to ever give it to me?”
  — Scott Miller (C), 17:09

Important Timestamps

• [00:26] – "What is a mentor" defined and demystified
• [03:25] – Emphasizing relationship, vulnerability, and intent
• [05:01] – How to formally approach and honor a mentor’s limits
• [10:05] – “Nobody succeeds without some form of mentorship”
• [11:50] – It's okay to have younger mentors and learn cross-generationally
• [12:49] – Practical steps for finding a mentor, starting with your network
• [15:53] – “Incrementalizing” mentorships and treating the process like dating
• [17:09] – How to graciously conclude or pause a mentor relationship

Summary Takeaways

• Mentorship is rooted in wisdom, vulnerability, and the ability to share both successes and messes.
• The ideal mentorship involves candid guidance, clear intentions, and healthy boundaries.
• Don’t expect one mentor to be your guide in all areas—seek multiple mentors with domain-specific knowledge.
• Success rarely happens in isolation; mentorship helps reveal blind spots and accelerates growth.
• Be intentional, respectful, and grateful—mentorship is a two-way, evolving relationship.