Year: 2018

Thinking in bets

As a kid I’d occasionally watch World Series of Poker events on ESPN. During the broadcast they’d show the percentage likelihood each player had for winning the hand. I remember thinking, “How in the world do players remember all of this information…”

It certainly didn’t occur to me that some of the betting strategies players applied would also be effective in the business world. That’s part of why I found Annie Duke’s Thinking in Bets a worthwhile read. Duke is a professional poker player and her book is a guide to making decisions within uncertain environments.

She views a bet as, essentially, a decision about an uncertain future. To make effective bets we have to learn how to separate outcome quality from decision quality. The quality of our decisions is all we’re able to control. Yet we tend to evaluate our decisions by their outcomes; if the outcome is good then we made a good decision. The problem is it doesn’t work that way. A bad outcome can stem from a logically sound and effective decision.

Duke doesn’t advocate that we try to change this cognitive tendency through willpower alone. She holds that our capacity for deliberative decision-making is already maxed out. Instead she frames it this way:

The challenge is not to change the way our brains operate but to figure out how to work within the limitations of the brains we already have. 1

A path toward better decisions is to leverage our competitive drive to change our routines. We can change the features by which we compare ourselves (e.g. work to be the best credit giver rather than work to receive the most credit).

If we approach the decisions we make as bets then we can explore alternative reasons for why a given outcome came to pass. If we dismiss another’s good outcome as simply luck then we close down opportunities to learn from their expertise and skill. And it’s those lessons that we can apply to our own decisions.

A big part of what helped Duke in her career was having a decision group to deconstruct and debug situations with. It’s the Mertonian values of such a group that matter most. As she writes:

As a rule of thumb, if we have an urge to leave out a detail because it makes us uncomfortable or requires even more clarification to explain away, those are exactly the details we must share. The mere fact of our hesitation and discomfort is a signal that such information may be critical to providing a complete and balanced account.2

  1. Thinking in Bets, pg. 14.
  2. Ibid, pg. 154.

Support Operations Webinar

At Automattic we recently started building a support operations team. We’re wrapping up hiring for a Director-level position and will add a handful of roles within the team after that. Formalizing this work will help us strengthen many of the behind-the-scenes processes that power our support. It’s been a great learning process to go through as well.

Later this week I’m joining the fine folks at Help Scout along with pros from SmugMug and FreshBooks to chat about how we’ve built our various operations teams. We’ll cover how we structure our teams, why we started building them, and more. It should be a great conversation!

You can find all the details for the webinar on Help Scout’s site. It’ll also be recorded, so if you can’t make it live they’ll send you the recording if you sign up.

New Hampshire

Last month Leah and I spent a week in Plymouth, New Hampshire. It was more of a work trip than a vacation. But we did take advantage of some perfect fall weather to hike the Welch and Dickey Loop Trail. A great trail with some views over the surrounding valleys.

Stressful customers

In support we often write to confused and frustrated people. After all, they likely got in touch with us because they’re confused and frustrated with our products. That’s okay, we’re expert communicators. We can help them get set up.

One thing we can do as part of that is not presume a customer is “abusive” or “rude” or “unreasonable” at the first mention of profanity and frustration. We want to resist our first impulse, which can often be to admonish the customer on their tone. This will more often than not aggravate their frustration.

Instead, when confronted with a profanity-laden message, our first instinct should be to give the customer the benefit of the doubt.

We must treat their frustration as a signal that we should invest more in our understanding of their situation. We need to pause, step back, and focus on the issue at hand. That means fully understanding the history of their interactions with us and their issues with our product.

It also means keeping the conversation focused on resolving their issue. We can recognize their emotion without condemning it nor playing into it. Every person we interact with is, well, a person. We all have moments when our frustration gets the better of us and we’re harsher than we mean to be with a company.

I believe our role in support is to help people be successful. And to see every conversation as an opportunity to change someone’s impression about our business and our product. Even the angry, profane, and ALL CAPS people deserve our help. After all, it’s typically our product or our missteps which have pushed them to frustration. That’s alright, our world-class communication can turn things around.

Replacing Instapaper with Pinboard

After Instapaper’s odd GDPR-related decision to (temporarily) block EU access I decided to re-evaluate what tool I use for my reading list. I’ve used Instapaper every day for the better part of a decade but something about their recent decision didn’t sit right with me.

I’ve had a Pinboard account since 2009 and decided to try it as a read-later tool. So far so good. If you’re interested you can see what I’ve recently read here.

The import process to Pinboard was a bit of a pain. It’s supposed to be automatic but for some reason my export files weren’t importing. I didn’t have that many articles in my backlog, so I ended up migrating these manually.

On the settings side Pinboard has a bookmarklet you can add to your browser for one-click article saving. I also set it up to mark everything as private by default. That gives me a private to-read list and a public already-read list.

iOS is where Pinboard is the least competitive with Instapaper. What’s worked well enough for me is the Pinner app (on both iPhone and iPad). That makes it easy to read articles through Safari’s reader mode. Plus it’s then much easier to turn articles into bookmarks. The main downside is that there’s no offline storage, though I rarely used that with Instapaper.

The bonus feature is that Pinboard has, for a fee, built-in archiving. For $25/year it will crawl every bookmark you add and save a cached version for as long as you have an active, paid account. It’s a nice protection against link rot.


Allerton Gardens.

Leah and I just got back from 9 days in Kauai. This was our second trip to the island and we enjoyed it just as much as the first. On the activities side of things we went for a hike along the south shore, did two intro SCUBA dives, and more. Plus, this was our view for the week. No complaints.

I also read my way through 5 books: Leonardo da Vinci by Walter Isaacson, Museums: A Visual Anthropology by Mary Bouquet, The End of Average by Todd Rose, A Guide to the Good Life by William B. Irvine, and Anathem by Neal Stephenson.

I recently joined Fletcher Richman on his new Support Leaders podcast to talk about Automattic’s support team. The episode is live now. It’s a quick 38-minute listen where we talk about how I came to work in support, how we work at Automattic, and some of my favorite books.