One Secret To My Success

I'm lucky to have read a couple books this year that have seriously impacted my way of thinking: Nassim Nicholas Taleb's Antifragile is probably the heaviest read I've ever taken on a vacation, but ideas like optionality, iatrogenics, and black swan events have had a big influence on me. Another that I recently finished was Superforecasting by Philip Tetlock and Dan Gardner. One impact that the latter book has immediately had on me is that I talk way more in probabilities.

I'm thinking about working on Parliament Hill now that I've put in the work to get an MP elected. I think it'd be fun, I think it'd be a feather in my cap, and I think I'd be good at handling anything thrown my way. I believe the odds of me getting an offer are fairly high, but I've been really hesitant to say it's a sure thing, because I don't have enough information to know for sure. Maybe there are so many better qualified people applying that bringing me in would actually be a negative. I know that the party's looking to hire about 1,000 people and has received around 12,000 applications. Being able to move to Ottawa immediately, my experience both on the campaign trail and in the private sector, etc., all works in my favour, and probably puts me in the top 10% of candidates, but looking at the openings and the applications, it's clear that only about 8% of applicants are going to end up with jobs. So when people have asked "are you working on the Hill now?" my go-to response has been "I think it's got about an 80% likelihood of happening, but it's not yet certain."

Another thing that's been asked of me a fair bit is how I came to the decision to work with Marco Mendicino in Eglinton-Lawrence. I don't live in the riding. I had strong candidates running on either side of my street (Chrystia Freeland to the north, Adam Vaughn to the south), and both had pretty solid chances of winning. So why would I spend the money on a TTC pass and the time on a commute to volunteer so far from home?

The answer involves the application of a process I used extensively when I was working at Shopify. I call it The Graph.

At the start of the election every single riding had projections and polling aggregations that suggested the likelihood of a given riding going Liberal. If we took the percentage odds of a Liberal win in every riding and turned them into a bar graph, it'd look something like this.

That's one column for each of the 121 ridings in Ontario. If we sort that distribution, we get a graph like this.

This isn't representative of the actual distribution of odds in Ontario at the start of the campaign because I just used a random number generator, but for illustrative purposes, it works. Ranking all the ridings like this lets us split them into three categories.

  1. Sure Things. Ridings that are sufficiently likely to go Liberal that short of a massive scandal or screwup, the Liberal candidate's going to win.
  2. Lost Causes. Ridings that are only going Liberal if we come close to a sweep.
  3. Coin Tosses. Ridings that we will lose if we sit around instead of campaigning, but which we can win if we're out hustling and knocking doors every single day.

You can think of anything over 70% as a Sure Thing, anything under 30% as a Lost Cause, and anything in the middle as a Coin Toss. What I wanted to do on the campaign was find a Coin Toss between the Conservatives and Liberals that was on a Subway line, and the closest viable option was Eglinton-Lawrence. It certainly didn't hurt that Marco's a fantastic guy who's going to be a great MP, but that was my thought process. It's a process I wound up reusing over and over again over the campaign.

Every time I'm at the door giving my spiel, I'm doing my best to read the person I'm talking to. If the first words out of their mouth are "Marco's got my vote!" then they're probably a Sure Thing. If they say "The Liberals are a bunch of pederasts, teaching sex-ed to children, and forcing 6 year olds to have anal sex!" which is an actual thing someone said to me, they're a Lost Cause. In either case, I really just want to get out of the conversation as quickly as possible. Coin Tosses might say something like "Marco's a great guy, but I'm terrified by the idea of Justin being Prime Minister." and they're the most fun, because they're the ones I can really work on persuading by making the case for our platform. When I'm out knocking doors with Marco, one of my objectives was making sure Marco spent as much time as possible speaking to Coin Tosses. This didn't always jibe with the broader goal of getting Marco to speak to as many people as possible, but you do your best to strike a balance based on the time of day, how likely people are to be home, and so on.

This is the exact same approach I took at Shopify in the days when I was onboarding new merchants. A merchant replying to me to say it was their third Shopify account and they knew what they were doing would get a quick "Sounds great, XXX - let me know if you have any questions or need assistance!" while someone saying they wanted to launch a business but had no idea what they would sell or what distinct value they'd bring to the table would get a copy-pasted list of resources on starting a business. Someone who had the value prop down but needed help with implementation... that's the kind of person I wouldn't hesitate to schedule a half-hour call with in order to get them up and running. Of course, we don't have data when a person signs up on the odds of them converting to a paid customer, but one of the skills I developed in my time at Shopify was the ability to make those predictions. I never tracked my success, but I remember feeling like I was pretty good at it by the time I had been there for a year or two. Spending as little time on the Sure Things as I spent on the Lost Causes meant I could speed through tickets, and I set more than a couple productivity records in those days.

This basic model of probability and prioritization is not the only thing that's contributed to the successes I've had in life. It probably isn't even the biggest one. But it is one that's fairly easy to grasp and apply to tons of things in your own life. If you do, you might start noticing you can accomplish a lot more in a lot less time.

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