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How to make mentoring matter: 11 fundamental steps

Updated: Sep 27, 2022

Many of us want to be mentors but don't really know how to mentor successfully. Mentoring is not a skill we are necessarily ever taught - but mentoring is often something we feel called to do, to make a difference, to pay it forward. So often we get caught up in a mentoring relationship, as the mentor, only to find that we actually have no idea how to mentor meaningfully. Not only does it erode our confidence, but sometimes it means that we remove ourselves from the mentoring system and deny mentees the opportunity to fast-track their learning.

So often we get caught up in a mentoring relationship, as the mentor, only to find that we actually have no idea how to mentor meaningfully.

In the process of having mentored students and young professionals over the course of my career, I've made no shortage of mistakes in mentoring including:

  • taking on too many mentees at one time and not being available when I said I would be,

  • not being clear on what I was competent to mentor on,

  • trying to have all the answers instead of facilitating my mentees through processes through sharing of my experiences,

  • missing the opportunity to learn from my mentee,

  • not setting clear expectations upfront,

  • not having expectations of my mentees and then being disappointed at the lack of reciprocity,

  • not spending enough time reflecting on what it is like to be learning something new,

  • letting a mentoring relationship run on longer than it served its purpose,

  • listening so that I could share my pearls of wisdom, rather than listening for what my mentee was actually saying.

Based on my experiences, I believe there are 11 fundamentals to making mentoring matter. I see this as a dynamic list, so if I've missed some that you think are important, I would love to add them to this list so please get in contact!

1. Set the framework upfront

It all starts with developing a clear social contract between you, as the mentor, and your mentee. So often we start mentoring relationships because we want to help, but we don't start out with a clear set of expectations, values, and boundaries that will guide the relationship.

Set the mentor-mentee relationship up for success but agreeing upfront on how you both want the relationship to work. Here are some questions to help you set the framework.

Think about your respective roles in the relationship.

  • What do you expect of each other - in preparation for the mentoring sessions, in the sessions, and after each session?

  • What do you not expect of each other?

Be clear on the mentoring scope.

  • What are you able and willing to mentor on?

  • What's outside of the boundaries of your mentoring abilities?

Set time boundaries.

  • How often and how and for how long, will you meet with each other?

Clarify methods of communication.

  • What's the most effective way for you to communicate with each other and what do you both expect in terms of response times?

What's your why?

  • What does this mentoring relationship mean to you?

  • Why are you both in it?

  • What does it help you to achieve?

Hold each other to account.

  • How will you hold each other accountable to your social contract?

Start with the end in mind because mentoring relationships can and should have a finite end.

  • How will you know when the mentoring relationship has run its course and how will you end it?

How do you want the relationship to be?

  • Together discuss the qualities that you want the relationship to have. Fun? Formal? Relaxed? Honest? Challenging? Honest? Reciprocal? It could be all of these and more.

  • Once you have a list of qualities talk about how you both will show up to uphold these qualities - in other words what behaviors will you need to adopt?

2. Get conscious about what you have learned

Your mentee doesn't know what she doesn't know - it's your job to help her identify what she needs to know and mentor her towards becoming competent. The tricky part of this is, if you have become so automated in how you do things, you may no longer be conscious of what you know - you may not know what you know because how you do your job has become habituated in the process of mastering your competence. Get conscious by reflecting on some of the transition points in your career.

  • What do you wish you had known when you transitioned from university into the world of work, from managing yourself to managing others, from managing a team to managing a business unit, from being employed to starting your own company?

  • What did you now know when you started the transition process, what challenges did you experience in the transition process and what did you learn, what new competencies did you develop, what insights did you gain as you mastered the transition journey?

3. Mentoring is more than telling and asking questions. It's listening too.

People open up when they know they are truly being listened to. But so often we listen through our own filters and are so caught up in our own internal chatter that we actually aren't listening to the person right in front of us. Deepening your listening skills as a mentor can make mentoring really matter. When your mentee feels truly seen and understood, the conversations deepen, and the value that comes from those conversations increases.

Kimsey-House et al tell us that most conversations skim along the surface - that our conversations have the equivalent depth these days as pressing the like button on a social media post. Imagine having a conversation with your mentee, and your engagement with them is the equivalent of a "thumbs up"... not a lot of growth and learning is going to come from that relationship.

To truly engage with your mentee, your listening needs to be active and intentional move beyond the first level of listening which is where we mostly get stuck listening to our internal chatter.

Three levels of listening

Kimsey-House et al talk about three levels of listening:

  • Level 1: Internal listening - this is where your awareness is on yourself. You are listening to your mentees words, but you are filtering them in relation to what they mean to you. If this is the only kind of listening you’re doing in a mentoring conversation, you are probably going to leave your mentee frustrated, disappointed, and feeling unseen and unheard.

  • Level 2: Focussed listening - your awareness shifts from yourself, to being focussed on your mentee. At this level you are listening not just to her words, but also her emotions, her expressions, what she values, her worldview, what energizes, and what de-energizes her, what she says, and what she doesn't say. In Level 2, aren't thinking ahead to what you want to say next or what you’re going to ask, you are holding the space to let your mentee verbalise her thoughts and learn in the process. This level of listening requires conscious practice. As Kimsey-House et al state, "when you connect at Level 2, it’s as if the message is I have time for you. Not just I have time to address the problem but I have time for you".

  • Level 3: Global listening - at this level you are receiving information from all your senses - not just what you can see and observe, but what you can feel in the space around and between you, your gut intuition kicks in here. At level 3 you trust your instinct to read the room and listen to the information that the environment around you is sending.

"It’s as if the message is I have time for you. Not just I have time to address the problem but I have time for you". - Kimsey-House et al

Fluidly moving through all of these levels, being aware when your internal chatter (Level 1) is louder than your mentee, trusting your intuition to read the room, and being brave enough to offer what you are sensing (Level 2 and 3) - that's when what truly matters will enter the mentoring conversations.

4. Stick to open-ended questions that open up the conversation

I can think of multiple occasions where I have ended off a conversation with "Do you understand what I mean?", had the response "Yes", and then weeks later experienced that my mentee quite clearly did not know what I meant, but was saying what she thought I wanted to hear.

Any question that can be answered with yes or no, is likely to end the conversation. Rather than opening up the conversation and giving the opportunity for further inquiry, any question that starts with Have you, Do you, Can you, is going to end the conversation or at the very least result in uncomfortable follow-up questions.

But questions that start with How did you, What did you, When did you, Where will you, Who could you, all open up the opportunity for further exploration and more importantly the opportunity to check your mentees' understanding and ability to think things through for themselves.

5. Cultivate curiosity - yours and your mentees'

A curious mentee can be a very rewarding mentee to spend time with. But it's worth knowing that we aren't all curious about the same things, and that curiosity can have different dimensions, some of which can raise more anxiety and therefore fear than others. Helping your mentee to cultivate their curiosity by normalising the anxiety, can be a useful skill to develop.

5 dimensions of curiosity

Todd Kashdan talks about five dimensions of curiosity:

“Joyous Exploration” Curiosity:

It's the curiosity that grows from a sense of awe and wonder in experiencing or learning something new - for some, it may be the awe of experiencing snow for the first time, for others it may be the wonder in cresting a hill and experiencing the awe of a new landscape or view.

Kashdan says "This is the prototype of curiosity — the pleasurable experience of becoming interested in something and wanting to discover new information, learn, and grow".

“Need to Know” Curiosity:

This is the curiosity that drives a need to know, to research to find solutions, to problem solve, to fill a knowledge gap that makes you uncomfortable because until you have that knowledge you are unable to solve a specific problem.

Kashdan says "When there is something you want to know, and you don’t have the answer yet, an itch lingers that needs to be scratched. Getting a piece of information that closes the gap that bothers you rarely offers pleasure, instead it’s the reduction of discomfort".

“Social” Curiosity:

This is the type of curiosity that drives some of us to want to know more about the people around them, different cultures, different belief systems, people who are different from us in some way, shape, or form. It's a curiosity that can bridge differences and create connections and relationships. The underlying motivation is to understand what makes people tick.

It's worth being conscious that there is another concept, and that is covert social curiosity - it's the dark side of social curiosity where the underlying motivation is to be surreptitious in learning more about someone with the intention of perhaps wielding that information against them - often gathered by snooping, gossiping and other indirect means.

Kashdan says "Social curiosity is a gateway to the reservoir of knowledge and experiences held by people with diverse experiences, views, and perspectives."

As mentors we need to be intentional in modeling overt social curiosity.

“Accepting the Anxiety” Curiosity:

This dimension of curiosity enables us to tolerate the stress that comes with getting out of our comfort zone to learn something new, to be a beginner at something, to accept that there will be great discomfort in a new experience, but not letting that hold you back - transitioning into a new phase of your career would fit into this dimension and it's likely to be where your mentee is right now.

Kashdan says "This dimension is about the willingness to embrace the doubt, confusion, anxiety, and other forms of distress that arise from exploring new, unexpected, complex, mysterious, or obscure events ... it's what mobilizes our energy to push forward and act on our sense of intrigue".

“Thrill Seeking” Curiosity:

People with natural thrill-seeking curiosity may take bigger risks because the anxiety that comes with the newness and the excitement of the experience actually feeds them.

Kashdan says "You do not have to be a big thrill-seeker to be high on the other dimensions. Knowing that you are willing to accept large tradeoffs for some variety offers useful information into what you value".

6. Encourage and empower your mentee through a journey of low-stakes risk-taking

Taking ever greater risks is part and parcel of developing your career, but being thrown in the deep end can all but break your confidence and desire to ever try something new again.

I will never forget the approach my first boyfriend took to trying to get me to start mountain climbing. I wanted to impress him (I was very impressionable back then...) and so the stakes were high for me. Back then, I believed that impressing him was my way to be liked by him. That's a completely different story though.

A trip to Waterval Boven early in our relationship and a clear expectation that I would be able to climb alongside him and his mountain climbing friends was something I wanted to live up to. He was an avid abseiler and mountain climber with a natural ability to excel in these sports. I was not. I didn't have the technique, the muscle tone, the equipment (climbing in takkies is not to be recommended), the physique, or for that matter love of heights, for climbing - I had never climbed before.

I got a few meters off the ground and was so far out of my comfort zone that I froze. My arms ached (poor technique), my toes were sliding in my shoes and my confidence was gone - I was a jibbering wreck and after I was belayed back down to earth I stormed off to the car and refused to ever try again. There was no joyous exploration, no thrill-seeking curiosity, no acceptance of the anxiety on my part. Despite being quite safe (I was on a rope), my lack of exposure to climbing made this a terrifying and confidence-crumbling experience.

There was no journey of low-stakes risk-taking to increase my comfort with something completely new to me. We often expect our mentees to climb mountains before they have learned the basic techniques on a climbing wall. Our job as mentors is to take them step by step through a learning journey - sometimes stretching them, sometimes keeping them safe, always exposing them to situations that will build confidence and competence.

Delegating tasks is much the same – so many of us struggle to delegate because we delegate too much in one go and in the process, learn that we are the only ones who can get it right first time. Unfortunately we teach our mentees that they aren’t good enough and shouldn’t take a risk.

Start small and progress at the pace of the mentee with a little push and some words that convey confidence so that the mentee can take on a bit more each time. Remember what we said about different dimensions of curiosity – the objective is to encourage rather than diminish curiosity.

Low-stakes risk-taking includes starting small and slowly relinquishing more responsibility as and when your mentee demonstrates competence. So often we delegate things that are too high stakes to get wrong and when a mentee does just that, we take back everything. In the process, the mentee learns that they aren't good enough, and the mentor learns that delegating is a waste of time because no one does it well enough.

Low-stakes risk-taking could include things like:

  • writing a section of a report rather than the whole report and slowly being given additional sections to write once the first section has been completed comfortably

  • mapping out a process with your mentee instead of leaving her to map it out entirely on her own for the first time

  • presenting a small section of a meeting rather than running the whole meeting

  • liaising with a client who you know to be tolerant and accommodating, rather than the company's highest-stakes client who won't tolerate working with anyone but you

  • coordinating a simple project rather than taking on a complex multi-disciplinary project

7. Get conscious and intentional in what you model through your words and actions

You are a mentor all the time - not just in your mentoring sessions. This means you have a responsibility to make sure that you are conscious about how you show up, intentional in what you model through your behaviours and courageous in modelling the behaviours that you are influencing your mentee to adopt.

This is a lesson that became abundantly clear to me the day I was encouraging my mentee to step up for a leadership role and she said to me that she had no desire to position herself for leadership because the way I was demonstrating what it meant to be in leadership, was that it was just about sacrificing myself for long hours, exhaustion and little to no time for family or fun.

  • Have you just had a conversation with your mentee about cultivating overt social curiosity? Make sure you aren't unintentionally modelling covert social curiosity.

  • Have you been encouraging your mentee to step out of her comfort zone and stretch herself with some public speaking, or to put her hand up to present at the next client meeting. Make sure you aren't visibly shying away from opportunities to stretch yourself.

  • Have you talked with your mentee about building a skill around delegating tasks to her team members, but demonstrated your lack of trust in your own team by holding on to work and fixing their mistakes for them?

Everything you do, everything you say, and everything you don't do and don't say, is part and parcel of your role as a mentor.

8. Speak to your mentees potential

At any given moment we are the best we can be, as well as the fears that hold us back. Sometimes in equal measure. Most often not.

It's more than likely your mentee is at the edge of her comfort zone, learning new things and being stretched, and so she is probably experiencing a degree of anxiety. That anxiety can help her or hinder her.

As a mentor you have the power to influence that in how you speak.

You've been in her position before - what did it feel like for you when you were out of your comfort zone and have a session with your line manager/project manager or mentor. You probably felt some fear.

Now, if your line manager homed in on your fear and instead of asking you for your thoughts on how to resolve an issue, she told you how to sort out the issue, it definitely accentuated those fears subconsciously and probably pushed you to play small, to shrink back to try take less risks.

But what if your line manager showed confidence in your potential and said "I believe in you, I believe you can solve this. So let's talk about this. Let me hear your thoughts on solving this and then together we can figure out a way forward."

Wouldn't that make you curious about her confidence in you? Wouldn't that make you want to rise to the occasion? Wouldn't that give you the courage to embrace the doubt and push forward?

9. Help your mentee develop an enterprise perspective

Everything is connected and the sooner your mentee understands how the organization works and how her work impacts others' and vice versa, the faster she will be able to contribute value and be perceived as a valuable member of the team. This isn't merely about putting the enterprise ahead of her own needs, this is about securing her own needs through a bigger perspective of her role in the system. Similarly there is a connectedness on a time dimension – how show up in career and in organization now has an impact and connectedness later on in ones career.

A really great exercise to do with your mentee is challenge her connection to the enterprise and to her career.

  • Make two columns on a piece of paper – in the left hand column get her to list all the living breathing values that she can see in the organization – you can do this together as an exercise in observing behaviors that are evidence of values). In the right hand column get her to list her values.

  • Then together look for overlaps in values – how do the business values reinforce and enable her to uphold and live her values and equally how do her values contribute to upholding the values of the organization?

  • In a third column you could map out what behaviours would be evidence of those overlapping behaviours.

  • In a fourth column you could bring a time dimension to this to discuss how those behaviours now might contribute to her career at some point in the future.

10. Facilitate your mentee's network and relationships

Networking is probably one of the toughest tasks for most young professionals – if you re comfortable with networking its probably the most valuable skill you can transfer to your mentee.

Make introductions, invite your mentee to join you in everything that involves networking. Introduce your mentee as your mentee in your social media networks – LinkedIn, if you are talking on a webinar or at a conference or anywhere introduce your mentee by name. Shine a spotlight on him or her.

I remember sending my mentee to accounts to get foreign currency for a site visit we were doing. I was too lazy to go to accounts with him and asked him to introduce himself to the accounts manager. In retrospect it was a mistake because she was the proverbial dragon lady and I made it unnecessarily traumatic for him. He came back without petty cash and what looked very close to PTSD.

I realized I needed to go downstairs with him and take the time to make the introduction. I learned three things that day:

  • making an introduction personally lubricates the relationship – it’s a worthwhile investment of time

  • I’d forgotten what it's like having to introduce myself to people who have worked in an organization 'forever' – they can either be welcoming or terrifying.

  • Your mentees' network are not just professionals – they are support staff and people that make the business run in the background. If you take them for granted, chances are your mentee will too, and will come short.

11. Be open to the possibility that you too will learn something

Everyone is a possible mentor. Through mentoring I have learned so much about myself and others – there have been no shortage of light bulb moments. I’ve learned:

  • how my competence is deepened when I transfer my skills to others,

  • how I become conscious again of things I had forgotten

  • how the world has changed since I was a young professional and yet how so much has stayed the same.

I get new perspective, I am humbled by the experiences of young people and their questions and I am calibrating who I am in relation to others.

I’ve literally learned something from every one of my mentees – some things about their worldview, some things about my worldview, sometimes very practical skills and most often a confirmation of why I like to mentor and be involved in the development of young professionals.

These days I ask my mentees what is one thing they think they can mentor me on and I also tell them that I expect to learn something from them. It very quickly confirms that they have value to bring to the relationship and levels the playing fields.

I hope this list offers food for thought and ultimately leads to mentoring that matters, mentoring that is meaningful. If you enjoyed this blog, please share it with mentors and mentees in your network.


I recently did a 45 minutes talk for a women's business group on "What's the fuss about mentoring". If you would like to watch it, you can find it on my Youtube channel.


I love conversations and would love to engage with you on your career and how you are managing yourself and your career like a business.

I believe "managing your career like a business" means having insight on where you want to go in your career, the agility and resilience to change track when necessary, competence to navigate transition points, and self-awareness to manage yourself.

I help you do that through one-on-one coaching, CV and LinkedIn profile writing, topic-specific workshops and a suite of blogs and other materials available on my website. Want more information? Drop me a message and I will get back to you asap.

In addition to my coaching work, I am a committee member of Women in Mining South Africa (WIMSA) and lead the WIMSA online peer-to-peer mentoring programme.

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