Singapore Government

The Classical View of Mentoring

Article by Patrick O’Brien, Managing Director of The Amanuenses Network Pte Ltd

The Origins of Mentor

In a world that craves for effective Leadership, the word Mentor is nowadays ubiquitous; some people wish to become one, others want have access to one.

Yet, Mentor is an ancient term that dates back to the time of the Trojan Wars, well over 3,000 years ago.  In Homer’s Odyssey, one of the heroes Odysseus, left his family to sail from the shores of Ithaca in Greece, to the city of Troy in Turkey.  He placed the future of his son Telemachus under the wing of his good friend, Mentor.

Mentor’s role was to guard, guide and grow Telemachus, to keep him in his care, awaiting the safe return of his young protégé’s father.  Twenty years later, Odysseus returned home.

What a Mentor Provides

The Odyssey crafted the classical view of the modern-day Mentor; a wise old man, who willingly, nobly, and over a long period of time, imparts knowledge in the service of others.  In this view, the Mentor performs differing roles for their Mentee, the person in their charge.

First, they act as guardian and protector, providing safety and security to enable their Mentee to countenance change.  For instance, the Mentor may look out for the Mentee, raising awareness of possible issues to consider, such as changes in regulatory policies, or corporate strategies.

Next, a Mentor provides structure and accountability, providing shape to the track in which their Mentee wishes to head.  For instance, they may act as a sounding board, helping their Mentee set broad direction, find appropriate headings, and choose relevant destinations.

Finally, they bring experience and connections, providing advice and guidance to help their Mentee grow. For instance, the Mentor may share specific skills and open specific doors, cultivating the competences the Mentee requires for the next stage of their life’s journey.

Mentoring Differs from Managing

Both aspects are important in effective Leadership, yet each draw on different behaviours.

The focus of a Manager is to drive current business performance.  It’s the ends that matter, so they’ll invariably lean more toward completion of the tasks, than the perspectives of the people.  The focus of a Mentor is to cultivate personal growth; the future means are more important.  They’ll therefore tend more toward people development, than specific task achievement.

As a Manager works to ensure that desired results are delivered, they usually have direct line responsibility for a team.  With their delegated authority, they’ll plan, organise, direct, coordinate, and control.  Providing direction and telling others, dominates their actions.

In contrast, as a Mentor works to share their experiences, they cultivate deep relationships with their Mentee.  They’ll set time aside to build trust, deepen the dialogue, and bring their wisdom to bear.  Providing personal support and guidance, dominates their actions.

Finally, the efforts of a Manager are business related, and typically transactional; they ensure that jobs are executed well, so focus on stability, process, and preservation of the status quo.  Conversely, a Mentor is personal, and, transformational; they foster growth in others, so focus on enabling personal change, and creation of a safe, motivating environment for its realisation.

Three Essentials Ingredients for a Mentor

In order to provide guidance and cultivate growth, a Mentor needs to be able to curate strong, trusting relationships within which their Mentee can flourish.  This requires a Mentor to hone their Leadership skills in three critical areas.

First, they need strong communications skills.  This allows them to build healthy dialogue with their Mentee.  They’ll be empathetic to the core, naturally build rapport, have great listening skills, able to ask good questions, keen to probe where necessary, and, confident to provide real-time feedback to their Mentee.

Next, they require good EQ (Emotional Intelligence).  This allows them to relate well to situations as they manage themselves and others.  They’ll use social skills to build relationships, that honour and respect differences, as well as garner trust.  They’ll also clarify responsibilities, encourage Mentee self-awareness, and keep Mentees accountable for their own growth actions.

Finally, they need relevant wisdom.  This allows them to contribute positive accelerants to their Mentee’s growth journey.  They’ll reflect on their own first-hand experiences, share life stories, package nuggets of wisdom, and suggest relevant options too.  They may also be able to provide access to information, bring their connections to bear on projects, perhaps even, open doors.

Positioning Mentoring as a Process

An effective Mentor wields influence; they have the ability to help their Mentee realise transformational change.  They need to be able to build safe, trusting relationships, that allow dialogue to flow.  They need to treat their Mentee with respect, and feel comfortable to share.

An effective Mentee embraces change; they have a mindset that’s open to learning.  They need to set their desired direction, commit to the course, and invest the time required to realise their future successes.  They need the courage to be a little vulnerable; attitude is important.

To achieve such fruitful outcomes, it does take two parties to act harmoniously and in concert.  Mentoring is less about positions, titles, tasks and roles, and more about creating a collaborative learning process for two individuals, who are both committed equally, to personal growth.

When the Mentoring process is constructed well, it’s never a zero-sum game; both people grow in substantial ways.  The Mentor especially gains, as they strengthen core soft skills for their own Leadership journey, in areas covering coaching and communications.

They also gain deep satisfaction as they see their Mentee’s grow.  The value of a well-intended, heart-felt, and personally spoken “Thank You” from their Mentee, is truly priceless.

In the next Article, we’ll switch from the classical to the contemporary, and explore how Mentoring is changing; it’s more fluid, Mentoring has Morphed.


The Article was originally commissioned by the Institute of Singapore Chartered Accountants (ISCA) and the Singapore Accountancy Commission (SAC), as part of their CFO Mentoring Programme.  It was written by The Amanuenses Network Pte Ltd ( and republished on their websites and the IS Chartered Accountant Journal, with all rights reserved.

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