Thoughts on mentors

3 min read

As a natural introvert, my mum sought ways of ensuring I could excel nonetheless.  She over strategised and over planned for every situation she could control.  I think she was humble enough to know she didn’t have all the answers on how to excel in Australia as immigrants, so she sought out mentors, tutors and teachers who could help me get to new heights.  So, thanks, Mum!  What she began, I then adopted as my own. 

English was technically my second language and I was in a debating team.  I was never a great debater so my mum sought out someone 1 year above me at school and pushed me to learn from him.  Matthew was the unlucky victim of our affection and he was very willing to pass on tips and tricks of the trade.  My mum then added on teachers and tutors who had won titles many years prior to coach me individually.  Within a few years, we had won our state’s championship, I had come 2nd in the country for public speaking and represented Australia in Model United Nations.  I learnt a very important lesson: learning from history allows you to accelerate much faster than learning from scratch.  In this case, this ESL kid was unlikely to win debating/MUN championships without Matthew having competed before and being able to explain how to win. 

Now I maintain a set of mentors that are kindly willing to teach me history so I can avoid mistakes and stand on the shoulders of giants.  It’s pretty simple and one of the most effective tools to accelerate your growth.  Simply, I keep a set of mentors that are 2, 5, 10 years ahead of where I am now.

10 years

The mentor 10+ years ahead is someone I really aspire to be one day.  He has already succeeded in the field I am in and has seen so many people walk the path that he can observe the pattern and tell me where I’m on track or off track.  This person can predict the future with surprising accuracy (though he’s 1 in a million), understand how people think and is an architect of situations so the situation falls in his favour.  This wisdom is hard to come by and having this parental figure guide the path is super helpful.  When you speak with him, it’s like Luke and Yoda – it takes a little while to unpack the simple sentences, understand the implications and the execution takes a while but is somehow always right.  

2 years

The mentor 2 years ahead and still remembers what it’s like to be me.  The advice is very actionable and he’s from the same context I am.  When I ask how to set culture in a 150-person org, he remembers what worked and what didn’t because they’re only now 300 people.  When I ask about scaling experiments, he can remember what kind of people he hired, what systems he set up and can tell great anecdotes about why certain choices failed.  

5 years

The mentor 5 years ahead is somewhere in between the 2 and 10 year mentors.  Sometimes the 2 year ahead mentor is wrong (they have fewer data points to explain), while the 5 year ahead one has worked at multiple successful companies and is building another so has more data points to explain a point.  When I ask a question, he can explain what he did in 3 different companies when they were at the same stage.  Sometimes the 10 year ahead mentor says something very wise but I’m not sure about the recipe needed to cook to action.  The 5 year one can break it down into small bite-sized steps for me.  

Take all 3

Why all 3? I’ll take whatever I can get.  However, if you have the luxury of choice, I’d take all 3.  Often, I keep multiple 2 years ones because some 2 year mentors we’ve surpassed in business size, e.g. our org is now bigger than theirs (their business is obviously more efficient) so some questions are harder to answer, e.g. culture at our size.  5 year ones are great because they’re far along enough to give you Yoda style wisdom and can turnn into actionable advice.  They tend to be more stable coz they’re far away enough that it’ll be hard for me to surpass them.  I often rely on them to turn the truism into wisdom.  The 10 year ones then have the experience and data points to succinctly give you wisdom to apply.  They have pattern recognition of time/geography.  They’re also scary coz they’re so successful.  

For example: take the YC adage “build something people want”.  

  • 10 years: Can tell you the truism.  “Moses, build something people want”  This is how Apple did it.  This is how my 30th IPO did it in India.  This is how my B2B portfolio company (aka Slack) did it.
  • 5 years: Wisdom comes in applying truisms at the right time and interpreting it the right way.  In this case, what people want = literally asking them what they want (faster horse) or reading in between the lines and predicting what people really want (car)
  • 2 years: Oh yeah, when I needed to build a faster horse, here’s what we did to build a faster horse.  Or yes, if you’re designing a car then here’s how we designed something that doesn’t exist.

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