5 Characteristics to Look For in a Mentor

How to look beyond the Cult of Personality to find meaningful mentorship

Yana Yevsiyevich
THE Co.
10 min readFeb 5, 2018

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There is a near defeaning amount of noise today.

It is the sound of digital tidalwaves ripping and rippling with the fractious voices of those who know better. And who are willing tell you about it through their podcast, their e-book (originally £456,000.00 but now a mere £39.99) and a tour (tickets for 3 days only one gabagillion pounds — snacks not included).

It is the sound of failed, corporate professionals who decide they will coach others on success principles — because that makes sense. It is the sound of the 22 year-old barrista, who learned an “important life lesson” from a family member passing away, and has decided to become a life-coach as a side hustle. It is the man in his mid-30s with an impeccable suit, a microphone attached to his face, a humble stage presence, and a charmingly empathetic personality who promises a program of unparalleled success. It is the millenial instragramer posing next to a (hired) jet in the background with a (hired) lambourghini in the foreground, flashing the obligatory (hired) bling on whichever limb won’t collapse under the weight of their debt. It is the 19 year old girl who survived a hangnail and a patch of eczema that will now kindly become your WebMD and motivational coach.

It is as hilarious as it is infuriating.

Melissa McCarthy in The Boss.

As I write this article, the irony (or perhaps even hypocrisy) isn’t lost on me. One could raise a suspicious eyebrow at me and challenge my motives; and that is worth clarifying. I am not a life-coach (oh good grief, that would be the day). I am not a coach. I am not a mentor (despite some people kindly and curiously giving me such a moniker). I have yet to develop the very characteristics that I look for in a mentor, which is what this article explores.

Rather, I am in the fortunate position of receiving extraordinary mentors in various stages of my life and through various forms — no, not like Yoda appearing all hologram-like. It is from being spoilt by phenomonenal mentorship that I write this; in the hope that it will help others avoid the ‘Cult of Personality’ mentorship that seemingly exists.

It’s also worth noting that I value mentorship as one of the most fundamental aspects of a deeply meaningful life; to find one good mentor in life is a blessing — to find a few is the rarest of gifts. And to discern between the genuine and the charlatan takes some thought. Over the years, these have become my non-negotiables.

NB: I believe that mentorship may come in direct and indirect forms (i.e. someone directly mentoring a person who occupies the same physical space is as influential as someone gleaning mentorship from a book or audio). I do not discriminate on the form of mentorship, but certainly discriminate on the basis of value added and the five non-negotiable characteristics I expect.

The Genuine: The Five Characteristics

№5 Fruit on the Tree → This characteristic weeds out nearly 97% of the nonsense one finds on Instagram and Snapshit — I mean, Snapchat. In order for someone to be a geunine mentor, they must have fruit on the tree. In other words, for me to even give them a passing glance, they must be able to prove that they nurtured, grew and harvested in their life that which I would like to do myself. For the same reason that I would not ask a football coach to teach me waterpolo, it doesn’t make sense to take advice from someone who has not achieved that which you would like to attain; oh, if you could only hear my husband laugh at my use of sports references. Why in the world would I take advice from a child pyschologist whose children are sociopaths? Why in the blazes would I take advice from some well-dressed, well-meaning kid whose greatest achievement is shaving in the morning? Why in the hoo-ha would I take advice from a consistently failing entrepreneur or writer or [insert objective here] as they’re still figuring it out? Now, don’t misunderstand me, I believe in failing foward and I definitely believe in people supporting each other in this process — learning together, absolutely; that does not mean, however, that they are ready to be mentors. They need to achieve the objective before speaking in to my life about it.

This also means that, for the majority of us, our parents and friends are not suitable mentors. Out of love and respect, I try not to disagree or argue with friends or family who give me advice, but I certainly don’t act on it. You may love your siblings and parents, but why would you take finacial advice from those who may work 80 hour weeks and are yet to be financially stable?

As such, I ask the following questions:

  • Has this person successfully achieved (and already traversed) that which I’d like to emulate in my life?
  • Have they done so ethically and without compromising moral convictions?
  • Have they failed forward and are able to speak from humility and experience?

№4 Objective & Honest → I like my mentorship like I like my alcohol — a metaphorical punch to the face. As a Russian, that would be with vodka; cold, straight and to the point. If you like your mentorship like a hot pink Strawberry Daiquiri (that will erode all layers of your enamel from sheer saccharine), then we certainly have a difference of input — and that’s okay! Regardless, the expectation should be that the information and guidance is objective as well as honest. And, that may become tricky.

Ideally, if you are seeking direct mentorship in your life, the relationship must have the dynamic strength to demand objectivity. This means that your mentor will not speak from a basis of emotion or subjectivity; rather, it will be information that is required. It may not always be easy to hear or action, but it is necessary truth.

And that’s also when you know that you are capable of being mentored. It’s that awkward moment when your mentor tells you to go right, when every fibre of your being tells you to go left, but you listen to your mentor because you know they are speaking objectively and have a multifaceted, informed view of your situation. In genuine mentorship, there will inevitably be moments of inconvenient truths.

Interestingly, this characteristic also does not lend itself inherently to family or friends. It is nearly impossible for friends and family to speak from a place of objectivity because, well, they probably like you a little bit; or worse, they subconsciously love seeing you struggle as it maintains status quo. Struggling to cope? Tell your Mum and she’ll stroke your ego and remind you of what a special little snowflake you are (bless). Successfully achieving mediocrity? Tell your best friend and he’ll throw you a beer whilst reminding you that you don’t need to achieve any more! Drowning in debt? Tell your Dad and watch him explain every horrific financial principle (as accepted by 97% of society) known to mankind and expect such principles to somehow work for you (certainly didn’t work for him … with a 75,000 year mortgage at 85% variable interest rate).

So, when seeking a mentor, I will always ask:

  • Is this mentor capable of objectively assessing situations in my life?
  • Are they capable of being compassionate, but separating emotions from the necessary advice?

№3 Self Aware → Any mentor who speaks in to my life is self aware in two specific ways: (1) they have the humility to know their own limitations and (2) they have the humility to remember their path and process.

There will be times when a mentor may not have the answer or even advice as you may be in a unique circumstance. A good mentor will tell you this. An exceptional mentor will find other associates to confer with in order to provide you with guidance. Every exceptional mentor I have understands they have limitations and have the humility to ensure that does not affect your growth or stability.

Any mentor worth their socks remembers the struggle. They remember being in the trenches and fighting for their vision, whatever that may be. And they can balance the “no nonsense, objective truth giving” with the empathy of someone who remembers what it means to battle on.

№2 Continually Growing → Whenever I meet a self-proclaimed mentor or life-coach or career-coach or whatever-coach, I always ask them one question: who is your mentor? Incredibly, and this never fails to shock me, many of them hem and haw, have a surprised look on their face, and shrug — “Gosh, I don’t really know” or “I find mentorship everywhere” (the worst) or “I have tons, actually” (even more the worst). I smile politely and walk away immediately.

If my mentors were not actively being mentored by those who came before them, then I wouldn’t trust their judgement. How could I possibly? If a mentor does not have active mentorship in their life, I cannot help but think: (1) do they no longer value a growth mindset ?(2) do they no longer believe they require one? (3) do they believe they have it all figured out?

Again, any mentor worth their socks has a dream bigger than themselves and the humility to recognise that they will always require guidance and growth. Could you even imagine someone like Elon Musk or Oprah Winfrey or Tony Robbins not engaged in active mentorship themselves? Nonsense.

So, when seeking a mentor, I will always ask:

  • Who is your mentor?
  • What books are you currently reading and which audios are you currently listening to?
  • How do you choose your mentors?

The final question is particularly important as I do not know a solitary successful person that is not discrening when it comes to seeking mentorship. They don’t simply choose the mentorship because it is free or available at a discount. Mentorship is an investment and they view it as such. This brings me to my final characterstic.

№1 Vested Interest → This is both the most important and the most difficult characteristic to find.

I attended an Entrepreneur’s MeetUp about six months ago and was met with the most curious situation. Two rocket scientists (seriously, this is not the start of a joke) stood in front of the audience to explain their venture idea, which isn’t important for our purposes, and their dilemma: the service they were developing did not require them to earn a profit, so they wanted to offer their services for free; however, they also recognised that some people may have a bias against free services and not value it as much as they would if they paid for the service. To test their hypothesis, they prompted the audience “raise your hand if you would use our service and take advice on your tech start-up from us free of charge.”

Nearly everyone raised their hand.

I did not.

They found this curious and surprising, so they asked why I would not. I explained that although they are clearly VERY clever, talented and good-hearted gentlemen, I wouldn’t let them near my startup with a ten foot barge pole. How, in good conscience, could I allow my most precious (hypothetical) idea to be sculpted or molded by the advice of anyone who (1) did not have a background or knowledge specific to my field; (2) would provide advice that was not vetted for the scenarios I would encounter; (3) would not provide bespoke advice or guidance to my mentorship needs and; (4) would have absolutely no incentive to ensure I succeed. “Would it make a difference if we charged you?” Only in that I’d laugh harder and run away faster.

No thank you. Whether the service was free or paid for was not the issue. The real issue, I explained, was that there was no vested interest between themselves and myself — a financial reason to ensure that every piece of advice, research, guidance and support would lead to our mutual success. It’s very easy to give advice with no skin in the game; I’m not interested in that and you should have higher standards.

So, when seeking a mentor, I will always ask:

  • If I can prove to you that I am ready for mentorship and will invest wholly in to myself and this enterprise, will you invest your time and resources in succeeding together?

Now that will separate the genuine mentors from the charlatans.

Pilot and Copilot

“One of the greatest values of mentors is the ability to see ahead what others cannot see and to help them navigate a course to their destination.” — John C. Maxwell

If any of this resonated with you, give a girl a slamming high five. It’s always comforting to know when one person’s crazy matches another. Or join me in the Twitterverse!

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Yana Yevsiyevich
THE Co.

Aspiring human | Aspiring coder & writer | Aspiring towards freedom |