The Journey from Mentor to Sage

Growing Fruit on Other People's Trees

Caring mentors do not view themselves as superior to mentees but rather view them as fellow travelers on the road to making good decisions. Similarly, the best mentors view less experienced mentors as equals and fellow travelers, when they seek to grow as mentors. Lloyd and I have developed a pathway for mentor growth. It consists of five stages for highly accomplished entrepreneurs and/or CEOs, who have rapidly scaled organizations.

Lloyd administered self-assessments with highly accomplished entrepreneurs/CEOs regarding their mentoring capabilities. Many had done a fair amount of mentoring. They typically rate themselves a nine on a 10 scale, and sometimes 10 on a 10 scale. When Lloyd shares some of his learning from having mentored over 23,000 hours, the entrepreneur/CEOs regrade themselves typically with a five or six on a 10 scale.

Although we have named the first level as “Basic”, keep in mind that is not referring to someone who has little life experience but rather highly accomplished people with little training in mentoring. The world’s best tennis players, Olympic athletes, professional baseball pitchers and hitters, etc. all have coaches, even at the peak of their careers. We believe highly accomplished people can often become remarkably better mentors, if they approach developing mentoring skills with some of the same diligence as in developing their management or other professional skills.

We hope that the five stages below inspire you to progress through the levels and become the best mentor you can be, benefiting as many people as possible. We formed Sage Stage for exactly that purpose.

As you read the below, please keep several principles in mind re the five stages:

• Developmental Nature: Each level builds on previous ones; advancement requires mastery of lower levels

• Bi-directional Flow: Higher levels inform and enhance lower-level practice

• Contextual Flexibility: Effective mentors can operate at multiple levels as needed

• Biblical Foundation: Integration of wisdom principles and spiritual development

• Continuous Learning: Even transcendent sages continue growing and adapting

• Exponential Impact: Higher levels create multiplicative rather than additive influence

  
  

Stage 1: Well Intentioned 

Basic Level: Advice-Giving | Experience-Based | Reactive

The Reflexive Mentor represents the natural starting point for most successful leaders entering the mentoring space. Having achieved significant success, they are eager to share what they've learned and genuinely want to help others succeed. Their approach is characterized by generous availability and an abundance of advice drawn from personal experience.

These mentors can be over talkative during sessions, measuring their effectiveness by how much wisdom they have dispensed, rather than how much the mentee has grown. They rely heavily on storytelling from their own journey, often beginning responses with phrases like "When I faced this situation..." or "Here's what worked for me..." Their primary tools are personal experiences and basic analytical frameworks like pros-and-cons lists.

Reflexive Mentors can excel at providing tactical solutions, especially when it comes to issues in their personal areas of expertise. They can offer valuable shortcuts based on lessons they have learned the hard way. They tend to respond reactively to immediate problems, jumping in with solutions as soon as challenges are presented. Their guidance tends to be prescriptive, assuming that what worked in their context will work for their mentees.

However, this stage has significant limitations. They may not distinguish between their personal preferences and universal principles, and they rarely address the mentee's deeper development needs or leadership growth. When mentees don't follow their advice exactly, these mentors may feel frustrated or unappreciated.

Because they often receive positive feedback from mentees, some mentors remain in this entry level stage for decades.

The growth edge for Reflexive Mentors lies in recognizing that effective mentoring requires more than sharing success stories. They can develop patience to truly understand each mentee's unique situation before offering guidance. The transition catalyst typically comes when they realize that despite their best intentions, their prescriptive approach isn't creating the transformational results they hoped for.

As Proverbs 20:5 reminds us, "The purposes of a person's heart are deep waters, but one who has insight draws them out." The Reflexive Mentor's journey toward sage-level impact begins with learning to draw out rather than pour in—shifting from telling their story to helping mentees discover solutions, problem-solving skills, and important insights.

The biblical foundation for growth beyond this stage rests in understanding that true wisdom isn't just about having the right answers but about asking the right questions that lead others to discover their own best path forward.

Stage 2: Developing 

Growth Level: Active Listening | Tool-Building | Growth-Minded

The Developing Mentor has discovered the transformative power of curiosity over certainty. They have moved beyond the reflexive style -- immediately offering solutions, to recognizing that understanding must precede advice. This stage is characterized by a genuine commitment to growth—both their own and their mentees'—and a willingness to develop new skills and frameworks.

These mentors actively seek feedback on their mentoring effectiveness and invest time in learning better approaches. They have begun building a toolbox of analytical frameworks beyond basic pros-and-cons lists, incorporating tools like SWOT analysis, Stephen Covey's four quadrants for time management, and basic personality assessments. They're learning to read body language and emotional cues, understanding that effective mentoring addresses both rational and emotional dimensions.

Developing Mentors create safe spaces for mentees to think aloud without immediate judgment. They've learned to hold back when the urge to interrupt with a solution arises, instead asking follow-up questions like "What assumptions are you making here?" or "What would success look like for you?" They begin to understand that the process of articulating challenges often helps mentees discover their own solutions.

Their growth mindset extends to their mentoring relationships. They maintain notes from sessions, track which approaches seem most effective with different types of mentees and actively work to improve their questioning techniques. They start to recognize patterns in their own biases and blind spots, seeking to minimize their influence on mentees' decision-making.

The growth edge for this stage involves developing discernment about when to transition from listening to more active guidance. The transition catalyst often comes when they realize that while questions are powerful, there are moments when their hard-earned wisdom and direct feedback could prevent mentees from costly mistakes or accelerate breakthrough thinking.

Esteemed management professor Peter Drucker said “Asking the right question is 50% of the way to the best solution.”

James 1:19 provides the biblical foundation for this stage: "My dear brothers and sisters, take note of this: Everyone should be quick to listen, slow to speak and slow to become angry." The Developing Mentor has learned that wisdom often emerges not from having the best answers, but from creating the space for truth to surface through patient, skillful inquiry. 

Stage 3: Skilled 

Competency Level: Deep Listening | Selective | Whole-Person Focus

The Skilled Mentor has achieved a level of competency that transforms both the depth and selectivity of their mentoring practice. They speak only about 25% of the time during sessions, having learned that their most powerful contribution often comes through the quality of their listening and the precision of their questions. They've developed the ability to hear not just the immediate challenge being presented, but the underlying patterns and root causes that create recurring issues.

These mentors have become selective about their mentoring relationships. They have learned that their most valuable contribution comes from working with mentees with strong track records, who demonstrate genuine commitment to growth and implementation. These Mentors use clear criteria to evaluate potential mentoring relationships, looking for entrepreneurs who take notes, follow through on commitments, and demonstrate the capacity to receive and act on feedback.

Their toolbox has expanded significantly to include sophisticated frameworks like decision trees, risk preference curves, enterprise risk management mapping, comprehensive personality assessments, and systematic approaches to strategic planning. They understand how to apply different tools based on the specific situation and the mentee's learning style. They've also developed skills in reading organizational dynamics and helping mentees understand how personal leadership patterns affect entire enterprises.

Skilled Mentors excel at addressing the whole person, not just the business/professional challenge. They recognize that sustainable success requires growth in multiple dimensions—leadership capacity, emotional intelligence, spiritual grounding, and life integration. They are comfortable discussing how a mentee's family situation might be affecting their decision-making or how their spiritual practices (or lack thereof) might be influencing their ability to handle stress and uncertainty.

Their approach becomes more systematic and intentional. They prepare for sessions by reviewing previous conversations and thinking strategically about what questions might be most helpful. They follow up between sessions and help mentees track progress against agreed-upon goals. They've learned to balance encouragement with honest feedback, understanding that constructive criticism is one of the most valuable gifts they can offer.

The growth edge involves learning to adapt their sophisticated approach to meet mentees where they are while maintaining the depth that makes their mentoring transformational. The transition catalyst typically comes when they recognize that their individual impact, while significant, could be multiplied through systems and approaches that extend beyond one-on-one relationships.

Proverbs 27:17 captures the essence of this stage: "As iron sharpens iron, so one person sharpens another." The Skilled Mentor has learned to create the kind of constructive friction that produces genuine transformation in both thinking and action.

Stage 4: Transformational 

Mastery Level: Synthesizing | Catalytic | Systems-Thinking

The Transformational Sage operates at a level of synthesis and systems thinking that transforms both the scope and impact of their mentoring. They have developed the ability to see patterns across multiple mentees, industries, and contexts, enabling them to provide insights that transcend individual situations. Their thinking has become chess-like—they can see multiple moves ahead and help mentees understand how current decisions will affect future options. They deeply listen to mentees and often speak only 20% of the time.

These sages have embraced technology as a force multiplier for their wisdom. They maintain sophisticated databases of insights, frameworks, robust toolboxes, and case studies that allow them to quickly access relevant experience from across their extensive mentoring portfolio. They use AI tools to enhance their preparation, identify patterns they might miss, and even simulate potential outcomes of different strategic approaches.

Transformational Sages excel at multiplying mentors. They don't just mentor individuals; they think systematically about how to create frameworks and approaches that can be replicated and scaled. They often mentor other mentors, teach at conferences, or develop curricula that extend their influence far beyond direct relationships.

Their cross-cultural and cross-industry perspective allows them to bring insights from unexpected sources. A strategic sage might help a healthcare entrepreneur by sharing lessons from a successful education technology company, or assist a US-based social entrepreneur by applying frameworks developed in emerging markets. They've learned to abstract principles from specific contexts and apply them creatively to new situations.

The Transformational Sage has also learned to create and leverage networks. They regularly connect mentees with each other, facilitate collaboration between organizations, and orchestrate partnerships that multiply impact. They think beyond individual success to ecosystem transformation.

The growth edge involves learning to package their sophisticated insights in accessible ways while maintaining their systematic approach to multiplication. The transition catalyst typically comes when they recognize that their ultimate impact lies not in the breadth of their influence but in the depth of their spiritual wisdom and its transformational power.

Proverbs 14:8 anchors this sage: "The wisdom of the prudent is to give thought to their ways." The Transformational Sage has learned to think systemically about ways that multiply wisdom across time and context.

Stage 5: Transcendent 

Peak Level: Long Lasting Impact | Spiritual | World Changing

The Transcendent Sage represents the pinnacle of mentoring effectiveness. They have many thousands of hours mentoring highly accomplished people. Their impact extends far beyond individual mentees to shape entire movements, fields of endeavor, or areas of practice. They have transcended ego concerns to focus entirely on multiplying their wisdom through others, finding deep fulfillment in what Bob Buford described as watching their "fruit grow on other people's trees." They are thought leaders and create original work advancing the field of mentoring.

These sages have developed sophisticated discernment about where to invest their time and energy. They actively seek what Jesus called "pearls of great value"—those rare mentees whose character, capacity, and calling position them to transform thousands or millions of lives. While they may have casual relationships with many, they invest most deeply in these catalytic leaders, understanding that their mentoring will compound across generations.

The Transcendent Sage has mastered what Lloyd Reeb and Chris Crane call "the Miracle of Compound Mentoring." They understand that by mentoring one leader who goes on to mentor others, who also goes on to mentor others, their wisdom can multiply exponentially, creating impact that lasts for decades or even centuries. These sages find their greatest joy not in seeing what their direct mentees accomplish, but in witnessing what their mentees' mentees achieve.

The Transcendent Sage embraces mentoring as a spiritual journey and sacred calling. They have learned to integrate prayer, spiritual discernment, and Biblical wisdom into their mentoring. They understand that the most important guidance often comes not from their accumulated experience but from their ability to discern God's leading for each unique situation. They regularly engage in spiritual disciplines—prayer, fasting, solitude, and Scripture meditation, especially in the Bible’s “Wisdom Books” such as Proverbs —as essential preparation for their mentoring work.

These sages have developed comprehensive toolboxes and systems for sharing and capturing their wisdom. They maintain curated databases of insights and stories, create frameworks that can be taught to other mentors, and often write books or develop curricula that extend their influence far beyond direct relationships. They think futuristically how to preserve and multiply their wisdom for future generations. Their AI databases can ask mentees prescient questions, the answers to which allow real time mentoring to be conducted on a higher level. The databases preserve the sage’s wisdom long after they leave this world.

The Transcendent Sage has achieved what Terry Looper calls "sacred pace"—they've learned to slow down enough to hear God's voice clearly and to help others do the same. Their mentoring sessions often include times of prayer, reflection, and spiritual exploration. They understand that the most important question isn't "What should I do?" but "What is God calling me to do?"

They have also transcended the need for credit or recognition. They mentor other highly experienced mentors. They genuinely celebrate when their mentees surpass them, understanding that this multiplication represents the ultimate success of their investment. They have learned to hold their influence lightly, recognizing that their role is to be faithful stewards of the wisdom God has entrusted to them. They exemplify, “The instruction of the wise is like a life giving a fountain” Proverbs 13:14a NLT.

However, even at this stage, Transcendent Sages continue to grow and learn. They remain humble about their limitations and actively seek feedback and course corrections. They understand that wisdom is not static but must continue evolving to remain relevant. They embody, “Instruct the wise, and they will be even wiser” proverbs 9:9a NLT

The growth edge at this stage involves continuing to deepen their spiritual formation while finding new ways to systematize and multiply their approach so that others can learn to mentor at similarly transformational levels.

Proverbs 11:30 provides the biblical foundation: "The fruit of the righteous is a tree of life, and the one who is wise saves lives." The Transcendent Sage has learned that their ultimate legacy lies not in what they've accomplished directly, but in the lives they've transformed through the multiplication of divine wisdom.

Their journey represents the fulfillment of Jesus' promise in Matthew 13:8: "Still other seed fell on good soil, where it produced a crop—a hundred, sixty or thirty times what was sown." The Transcendent Sage has become good soil that yields a hundredfold return on the wisdom invested in them, creating exponential impact that extends far beyond their earthly life.

We invite you to embark on a journey to become a world class mentor: to become someone who will transforms the lives of many people directly and many more indirectly with a long-lasting legacy.

A PDF of Chapter 5 of Lloyd Reeb and Chris Crane's newest book, Sage Stage, also dives into "The Progression to Sage Mentoring." You can download and read it here:

Sage Stage Chapter 5.pdf

Download PDF • 347KB