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Mentor Relationship

Opinion piece by Kerry Morris, CEO of the Tower Group

Ah yes, the Mentor and the Mentee. A win-win solution to all the leadership problems of the world, right? Not so fast. My experience of seeking mentorship as a leader in my industry has been a tricky one, to say the least. What sounded like a pretty simple “swipe right” scenario a couple of years ago, wasn’t the easy mentorship journey I’d romanced it to be.       

In our modern world’s high-demand workplace environment, so many leaders are left alone on the battlefield to figure things out; for the longest time leaders in business were conditioned to believe that once you get to the top you should have enough padding and ammo to find the answers, lead your soldiers and get on with it. Until, of course, the Alpha boys like Richard Branson called their planes ‘Virgin’ and unashamedly announced “if you ask any successful business person, they will always have had a great mentor at some point along the road.” 

Thanks to stalwarts like Branson (mentored by Freddie Laker), Oprah and even Nelson Mandela – mentorship for leaders became cool, and everyone wanted one. Including me.

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Flashback to 2019. Climbing the ladder, ambitious as hell and just catching wind that Oprah had been mentored by the late Maya Angelou all along (and there I thought Gayle was her MVP), it became clearer to me than a Cape Town summer – I needed a mentor. 

How hard could it be? Think of someone that inspires you… call them up. No, don’t call them up, email them. No, first stalk them on social media, then email them. No, DM them rather. No, too soon. Okay, take a breath.

Firstly, it was highly irrational of me to think that I’d get through to Michelle Obama on the first try. What was I thinking? Secondly where would I begin to seek out a stranger that I could rely on to understand my psyche, offer me advice, steer solution and support me through my leadership journey as a high-performance player? 

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The going was tough. 

I knew I needed a sounding board; the pressures of business were becoming too heavy to carry alone. Therapy was not my thing – and so I took a few leaps of faith (most of them fails) to find my perfect mentor. And here’s what I found: there is no perfect mentor. Only, the perfect timing; the timing in your life. 

I discovered through many a trial that your mentor is not one of a kind – but a few different kinds that will change as your leadership seasons change; you will outgrow your mentors, as you grow; you will find who you are seeking only when who you are seeking aligns with what you need, and at the time you need it.

And if it isn’t Mish Obama, that’s okay too…     

The great misconception with seeking out a mentor or a life coach is that they must be 100% as you’d imagined, and that once you’ve picked one, they’re your ‘One’ for life. This is a far cry from the case. Finding a mentor who is the right fit for you isn’t an overnight train ride, nor is it “one size fits all”. It can take time – a long time – many coffee conversations and even a break-up or two before you meet your mentor match. And even then, there should never be only one.

The mentorship journey is exactly that: a journey. It’s ever-evolving as your needs as a leader evolve. There will be many that teach you, inspire you and even infuriate you; what matters is that you seek out all of these, and as many of these as you can, but with the right objectives in mind.    

To help you along, here’s what I know about finding a mentor who’s meant to be:

Gender doesn’t matter 

Often we think we need to identify with a mentor of our own sex for them to fully understand and appreciate how we operate in our environment. Wrong. Some of my most successful breakthroughs in business unfolded with mentors of the opposite sex. It’s refreshing, quite frankly, and empowering. When it comes to the mentor try-outs, open your mind to every gender. It’ll surprise you.  

The first date counts 

This is not like the time when your mom so desperately wanted you to settle for the neighbour’s nerdy son, nagging you to give him another chance. No – nothing like that at all. When seeking out a mentor, that first conversation counts; that first coffee matters; that first interaction is truly what will make or break your decision. Yes, it’s harsh. The hunt for a mentor relies heavily on your first instinct, so trust it. It’s your choice, nobody else’s. If the chemistry isn’t there – nod, smile and move up an aisle.   

This is not forever 

If the mentor is doing his/her job correctly, at some point along the process, the mentee grows confident enough to return to base camp alone. In other words, we can and often do outgrow our mentors, and hey, there should be no guilt attached to your Mentor-Mentee relationship, ever. If managed correctly, this relationship is one built on a predetermined knowing that when the student is ready, the teacher will leave the room. It’s par for the course. No strings attached.

Trust is a many-splendoured thing     

This is a big one. Trust is fundamental. Considering that the word “mentor” dates back to Homer’s Odyssey, where its origin refers to “he who is a wise and trusted friend”, this should be our first tick on the box in settling into a mentor-mentee relationship. It needs to feel that comfortable, like a friend over coffee. This is the person you’ll be confessing all your leadership weaknesses to; this is the person you’ll have bad days with; this is the person you’ll make some of your most strategic business moves with. They need to get you – and prove their integrity in the best interest of the mentorship. And if they’re any good, they’ll prove it quickly.

Yes, but could you climb Everest right now? 

It’s enough that you have to contend with hard-knock days, a trillion decisions at a time and beatings from clients and stakeholders on the weekly than to have to sit with a mentor that makes you feel lesser than. Constructive feedback aside (oh, and there will be that!), your mentor for the most part should leave you feeling empowered and enabled after each session – like you could summit the mountain. Not ashamed; never exhausted or insecure. This is not why you’ve come, and it’s never a good reason to stay.   

Her name could be Betty 

Not every mentor needs to be trending, referred or sought – this is a sweet truth I’ve learnt along the way. Some of my greatest mentors in my career were never mentors at all. Well, at least they weren’t paid to be, and they weren’t asked to be. They just were; these are the kind of mentors that teach you from afar, without fuss or expectation. These are the kind of “silent” sages that mentor you by example, over lunch, and without expectation; earning your trust and fluffing your wings so that you can and will become one of the greats someday. 

These kind of mentors are, in my opinion, the perfect kind – and they seem the hardest to find, because – well – they’re never found at all. They appear, rather – and you may never be the wiser. For me, her name was Betty – the woman who gave me my first job in recruitment. Strong, feisty and brave, Betty taught me big things, small things and those unconventional lessons in my life that have set me up to be the woman leader I am today. I recognise that. 

Funny how sometimes in our hardest search for the greatest learnings, we figure out we’d been taught them a long while ago already.   

Disclaimer: Just for the record, I did try DM Michelle Obama a couple times. 

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