A few pieces of advice on great leadership

This is an email I sent out to the dubizzle team after leaving operations at the end of 2013.  To my knowledge, it hasn’t been shared publicly before.  I re-read it from time to time to remember the lessons I’ve learned.  I’m putting it here because I think it’s important that it has a place to live (other than my archived sent box), and so I can share those lessons with other aspiring leaders.

Parting advice for dubizzle leaders – Dec. 9th, 2013

Hi all,

As I make my journey back home, I wanted to leave you all with some of the lessons on leadership I learned in my time at dubizzle.  Before jumping straight into it, however, I wanted to say a few words about leadership.

Some of you without the word director or manager in your title may have read the subject and wondered if this email applies to you.  It does.  Leadership is not something that is bestowed by means of a title.  It’s not something that is bestowed at all.

Leadership is simply having a vision that others buy into, and being someone who people want to work with in order to achieve that vision.  It’s a skill, and like any other skill, it must be learned.  Every one of you has the capacity to be great leaders, if you didn’t, you wouldn’t be here.

I refute the idea that people are either leaders or followers.  We are all both at different times and in different situation.  We lead where we have vision, and follow where there is someone else’s vision that we buy into.  Like most things, however, there are several different ways to get buy in and to have people decide to work with you.  Some of them are bad (e.g. fear), and others are good (e.g. inspiration & love).   I’ve done both good and bad.  I’ve made some mistakes, and I’ve had some successes.  Along the way I’ve learned a few things about good leadership that I didn’t know when I started.  Based on those experiences, here are a few pieces of advice on dubizzle leadership that I’d like to leave you with (in no particular order):

Make yourself redundant.

As a leader you are not judged by your individual achievement, but by the achievement of your team.  Achievement not only in what that team does, but in how they do it.  Have you cultivated a culture of values?  Have individuals within your team experienced great personal growth?  Have you, as a leader, developed great leaders below you who could take your job?

If you were to disappear, would your team continue to achieve without you?  The test of a great leader is not only the success your team has achieved while you were in charge, but that team’s continued and sustained success once you have moved on.  Making oneself redundant should be the primary goal of every great leader.

Hire people that scare you.

The best hires I’ve made scared the shit out of me.  They are the ones where deep down inside you worry that this person is too good, too smart, too driven, and all around too senior to report to you.  You fear that, although they might not know it yet, they should be your boss and you’re not qualified to lead them.  If you’re lucky, you’re right.  You will learn a tremendous amount from people like this, and you will be constantly challenged to keep them challenged.  As a result, you have no other choice but to push yourself to become a drastically better leader.  Endeavor to only hire people that scare you.

Do what you are curious and passionate about.

If you’re not curious and passionate about what you do, discover what it is that you are curious and passionate about, and do that.  Life’s too short to spend the majority of it doing something you don’t feel passionate about.  To be truly great at something, you must truly love and be curious about it.

Sometimes, simply allowing your passion to drive how you work can make you exceptional and fulfilled (e.g. someone in customer service who is passionate about comedy, becomes passionate about making the users they help laugh).  Other times, the two things are simply too far apart to overlap.

Dubizzle has always endeavored to hire people who we believe are curious and passionate about their area of work.  Don’t let that passion wither.  Follow it.  Stay hungry for more.  Constantly seek and discover it.  Let it guide you in life (in and outside of work).  Others will be inspired by your passion, and they will want to be a part of your vision.

Remain humble.

If you were to chart a line graph of an individual’s growth and success over time, the moment that line peaked and started coming back down is the moment in which they lost their humility.  It’s a bit of a catch 22.  Humility allows you to observe, learn and grow at great speed, but growing at great speed makes it more difficult to remain humble.

No matter what it is, and how good you are at it, there is someone out there better than you.  The arrogant person denies that such people exist, and avoids them lest they undermine their achievements.  The humble person seeks those people out, surrounds themselves with those better, and in so doing, becomes ever more humble, while learning and growing at ever greater speed.  Facebook says “we’re only 1% of the way there.”  Humility is remembering that no matter how far you’ve come, no matter how much you learn and achieve, you still have 99% left to go.

Own your failure.  Share your success.

Easy to say, yet difficult to do.  It is in our nature to crave recognition for our achievements, and to want to deflect blame for our failures.  To be a great leader, however, you must do the opposite.

If I’m the leader and my team fails because someone on my team dropped the ball, there are two possible causes.  One, I didn’t give that person the proper context, support, structure or environment to succeed – and therefore it’s my fault.  Two, I did do all of that, but I had the wrong person in the role – also my fault.  When a team fails, no matter what the circumstance, the great leader raises their hand and takes that failure on the chin.

As a leader, your job is to get the right people in the right roles, to inspire them and include them in the vision, to set a structure of freedom and responsibility, to cultivate a culture of values, and to be constantly setting context.  Nowhere in the job description does it call for your own individual achievement.  If a leader is taking credit for their team’s achievements, they’re either not acting as a leader by focusing on achieving things themselves, or they are acting arrogantly by taking credit for the achievements of others.  Since a leader’s success is measured by the growth and achievement of their team, the clearest sign of a great leader is one who’s team is packed with rapidly growing individuals whose achievements dwarf their own.

Talk too much, and listen even more.

Communication is crucial to leadership, and communication is two ways.  If you have four people on your team, that means you should be listening four times as much as you’re talking.  (And you should be talking a lot.)

At dubizzle, you are working with some of the best people in the world.  They are all smarter than you in their area of expertise.  All they need is the context (to know what you know), and they will achieve far greater things than you can imagine right now.  Context, however, cannot be over communicated.  If they understand it the first time, they will remember it the 3rd or 4th time, and by the 10th time it will become reflex.  When giving context, talk until you’re sure you’ve talked too much, and then talk some more.

Then listen.  Ask questions.  Listen some more.  Ask more questions.  Repeat ad infinitum.  Given the proper context, it should come as no surprise that this group of people, all of whom are smarter than you, will blow your fu**ing mind.  Then you just let them do.

Be emotional.

Your team will only ever care as deeply about the vision as you do (and you show them that you do), not more.  Dig deep within yourself and find that vision to which you can emotionally connect to the point that it could bring you to tears.  Once you have found that, make it central to everything you do.  Talk about it in every discussion you have.  However uncomfortable, force yourself to speak about it to the point that your voice shakes.  Let others see the vulnerability of emotion it evokes in you.  They will feel it too.

The source of all inspiration is emotion.  Great people want to be inspired, and inspired people achieve beyond what’s possible (yourself included).  The extent of your inspiration is only limited by the extent of your emotions.  And your team’s inspiration is only limited by your own.

Have some fun.

Next time you’re on the beach, pick up a handful of sand.  Out of that handful, pick a single grain.  Then imagine all of the millions of atoms that make up that single grain, and the many more millions of electrons orbiting around those atoms.  Although you can’t see it, on one of those electrons there is a population of billions of miniscule modified apes going about their busy lives (all of which are relatively very short).  And now focus on one of those modified apes.  Like all other miniscule modified apes, this one takes its life very seriously. She views it as the epic drama that it is, and despite all scientific evidence to the contrary, she suspects that she might just be the center of the universe.  That miniscule modified ape is you.  It would be a shame if you didn’t take every opportunity to laugh about it and spend this blink of a life having fun.


Despite the fact of our absurd and insignificant existence, what you’re doing is of paramount importance.  Perhaps those miniscule modified apes’ suspicions are correct, and each one of them is the center of a vast universe.

At the core of our vision at dubizzle is simply a desire to make the world a fairer and more just place.  We do this through bringing transparency and efficiency to nearly all types of trade.  We have the ability to drastically change economies, empower the un-empowered, dissolve long standing lines between have and have-nots, and open up avenues for badasses everywhere to own their own destiny.

However, we can only do this if we win – and every win is a vast universe that we’ve just made a bit better.  So never forget why you’re here, and what you’ve decided to do.  WIN EVERYTHING!

If you can do half of these things, you’ll be twice the leader that I ever was.  But that shouldn’t be too hard, I only ever made it 1% of the way there;)

Good luck!

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