Alex MacCaw

JavaScript programmer, O'Reilly author.

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The style of a leader

When I was a kid, my dad and I would make a weekly pilgrimage to the television and tune into the next episode of Star Trek The Next Generation. We sat glued to the screen as Captain Jean Luc Picard would make heroic sacrifices and grand speeches about the Prime Directive. It was my first taste of what a leader should be, and it made an impression.

Picard showed that a leader should demonstrate no fear, no weakness, and never shed a tear. A leader should command from a place of authority and be fervently obeyed by his crew members. A leader should compartmentalize his work and personal life. And don’t even think about socializing with your subordinates!

As I grew up, my idols only seemed to reinforce this impression of leadership. Steve Jobs was famously autocratic, the lone genius bending Apple to his will. The same goes for Bill Gates, Andy Grove, and a whole host of CEOs that I...

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A value driven life

We all have values that we live our lives by, whether we realize it or not. Our values are what we use when evaluating big decisions, and determine how we sit with the consequences of those decisions. Decisions like should I go back to grad school? Should I move cities? Should I propose to my partner?

However, what we often don’t do is do this intentionally. We internalize values at a subconscious level and they surface as gut feelings. For the most part we don’t use them with intent.

By really understanding your values, you can turn these gut feelings into an intentional framework you can use for evaluating decisions and behaviors. Your values can be your north star, your guiding principles, and the bedrock of how you live your life.

Understanding your values

I originally titled this section, ‘choosing your values’, but in actual fact you already have a set of values derived from...

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How I learnt to program and dropped out of high-school

Like many kids, my first interest in computers came through games. My parents had been persuaded to purchase me a laptop when I was fourteen (relenting, I suspect, because my handwriting was terrible), and I quickly got to setting up massive Call Of Duty LAN parties between the boarding houses at our school.

I was at a relatively unacademic private school in the south-west of England. This school was not my first choice, as I had been bullied out of a more prestigious school, but the silver lining turned out to be that I was left mainly to my own devices.

In England, we don’t have mandatory conscription, but some of the private schools do have army training (in case we ever need to quell some sort of class revolution I suppose). As a bit of a nerd that preferred warm places and sedentary activities, marching up and down outside was my last idea of fun.

So I came up with a plan: I...

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Conscious Leadership

Conscious Leadership is about being more interested in learning than being right. When our egos make us afraid to be wrong, that fear leads us to defend our ideas at all costs, and to work too hard to convince others that we are right—often with anger.

Conscious Leadership is about recognizing when these emotions (fear, anger, sadness) have gripped our thought processes, releasing these emotions, and shifting back to a state of curiosity where we are receptive to all ideas and creativity, even if they seem to contradict our own.

It is in a state of playful curiosity that truly elegant solutions are achieved.

At Clearbit, we practice Conscious Leadership. Everyone joining the company is asked to read The 15 Commitments of Conscious Leadership. We also regularly get the leaders of the group behind the movement in to present to our office.

When I discuss these principles outside the...

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How we run our entire company out of Asana

Over a three month period last year I was lucky enough to have Matt Mochary, who I consider to be the world’s best coach, come around Clearbit and teach me everything he knows.

Together with the folks from Bolt, we developed a system for running a company out of Asana that has transformed the way we operate.

I’m going to break down how we use Asana to run two of our most important meetings, the One on One and our bi-weekly Leadership sync. I’m also going to show you how we reserve most of the meetings for reading, rather than verbally getting people up-to-speed, for optimum efficiency.

Caveat emptor

The company I run, Clearbit, is only 60 people. This system may break down at larger company sizes (we will see). Also you’ll notice that sometimes we’re forcing Asana to do things it wasn’t quite built to do. This works for us, but perhaps someday someone will write a dedicated tool...

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Feedback is not a dirty word

Feedback, performance reviews, appraisals. A collective shiver just went down all of your spines. These words are so highly politicized in today’s work environments it’s no wonder people can’t stand them.

For many years I too dreaded the idea of getting critical feedback. I sought recognition and praise, but avoided anything critical like the plague. I was self-aware enough to have some idea of my own failings, but shame and defensiveness kept me from exploring and discussing them.

For a long time such was the status quo. I was a talented engineer, and people let me do what I did best: hack away in the corner and build new products. Anyone who gave a hint of feedback was met with such derision that no more was forthcoming. In retrospect, a lack of feedback during that period stunted my growth.

This all came to a head when I founded a company and started building out a team. Suddenly...

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CEO Coaches

Every world-class athlete has a coach: every tennis player at Wimbledon, every golfer in the PGA, and every hitter in the MLB. An athlete without a coach is incomplete.

So, why don’t we think the same way about coaches for CEOs? Perhaps it’s because of the idealized notion that strong leaders should be stoic and invulnerable. Perhaps it’s because it’s harder to quantify the impact of coaching on the health of a company and the bottom line. Perhaps it’s because we don’t value mental health the same way we do physical? I’m not sure, but it is my experience that coaches are absolutely crucial for growth in all areas of life.

At the start of this year, I was squarely in the ‘no-coach’ camp. So, when our COO Luke broached the subject of me getting a coach, my initial reaction was negative. Things were going well, the business was growing, and people were happy. What could I learn that I...

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My life is random

All the best parts of my life are due to pure chance. From life-changing relationships to the closest friends, it’s all completely random.

Sometimes I think back to some of the single actions that ended up changing my life forever.

That time I danced on a specific side of a room and met a cute girl that I ended up dating for four years. Or that time I pushed myself to attend a dinner I wasn’t looking forward to and met a mentor that changed my entire perspective on how companies should be run.

I even met a good friend through whois when I was trying to buy a domain-name he owned. That friend would later introduce me to my co-founder and many of the key people in my life. What if I’d bought a different domain? Or hadn’t offered him brunch as payment? My life would be substantially different that’s for sure.

It can be scary prospect, the idea that one’s life is random and that you...

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Motivation

I’ve been experimenting with building a few ‘life-hacking’ tools that help motivate me and optimize for perspective in my life. One of these tools is a Chrome extension called Motivation.

Motivation replaces your new tab screen with a counter showing your age incrementing in real time. It seems to have a struck a chord–22,000 people use it weekly. It’s a simple tool, but it helps me think about perspective a bit more, which in turn helps me optimize my time.

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Clearbit

I’ve always believed that improving tooling and basic infrastructure is an incredibly valuable way to spend time. Some of the companies I admire most – GitHub, Stripe and Twilio – are founded on these principles. By improving basic building blocks, you can enable a whole new generation of companies to innovate.

To take one example, combine three APIs - Google Maps, Twilio and Braintree - and you enable a company like Uber. Clearly there’s a lot more to Uber but I think it’s safe to say they would have struggled building out all three APIs at the same time as bootstrapping a driver marketplace. Infrastructure is crucial for innovation.

Which brings me neatly onto what I’ve been working on for the last year - Clearbit. For most businesses getting quality and accurate data is incredibly painful. Often it means relying on APIs designed before the modern web was even conceived, or...

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