End Every One on One the Same Way

I think about communication a lot!

It’s such a huge, and hard, and important topic for anyone trying to become a better leader. Especially in 2016, as the ideas of “management” and “leadership” become murkier and more difficult to nail down, and the tools we use to communicate with one another are exploding in number (if not quality) – it’s always on my mind.

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Research in the Right Order: When to Interview Your Customers

One of the parts of my work that I get the most satisfaction from, and the part that most consistently surprises me, is in listening to our customers.

WordPress.com has a lot of customers. When you are dealing with a B2C company at this scale, it gets to be important not just to learn to listen, but learn to seek information in the right order.

(If you were at my SupConf talk, some of this is going to be very familiar!)

I like to talk to people – it’s part of who I am. I am an unapologetic talk-to-think-er. My most successful side hustle was a thinly-veiled attempt to get incredibly smart and incredibly busy cutting-edge farmers to talk to me. It worked! I interviewed them (and other members of their industry) for over a year. I think the art of the interview is a subtle one, and I’m the sort of person who literally reads books about different types of interviews.

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Motivated by Big Ideas: Some SAO History

I have written some before about how I ended up specifically at Automattic, and what that process looked like for me. You can read that here.

I remember during my interview for the Happiness Engineer position (which was almost four years ago!), I told the interviewer that I wanted to work at Automattic because I was motivated by Big Ideas.

It wasn’t something I’d prepared – it sort of slipped out in the moment, the first thing that I thought of, a natural thing to bubble out of a moment of self-reflection. I’ve repeated it several times since, and I think about it a lot. I touched on this idea a little bit in one of my favorite of my own blog posts, Reformed Philosopher.

I studied philosophy as a young man, and even was a professional philosopher for a stint (a Google search for “Ouderkirk CCRI” turns up proof!) 

The process there went more like “Paying to study and talk about philosophy” to “Volunteer for AmeriCorps to live your philosophy” to “Have others pay you to talk about philosophy,” but each step of the way was motivated by different big ideas, different perspectives or insights.

The first, of course, is that philosophy, unlike statistics or biology or other more, shall we say tangible fields of study, rarely holds a correct answer. This means the focus becomes placed more on the process than in the result. The journey truly outweighs the destination. How you accomplish a goal can sometimes become bigger than the goal itself. These truths I find self-evident. They are in my bones in that way.

The second step, from school to community organizing, is outlined in more detail in the Reformed Philosopher piece. It’s a good one, I promise.

Moving from the community organizer piece to the professional philosopher is a little messier. I was in love, you see. I met the Doc, who at that time was not yet a Doc but a mere Graduate Student. The final piece of her studies was a practical year of clinical work – since she is much smarter than me, she was accepted into the program at Brown, in Providence, RI.

So, I moved with her. What idea is bigger than love, after all?

Rewinding a bit for some context; while I was in grad school myself for philosophy, I was also working at Starbucks and waiting tables. I was that kind of grad student! When we moved to Providence (the city which houses Brown University, the Rhode Island School of Design, Johnson and Wales, and of course, the Community College of Rhode Island), I cast a wide net; looking for waiting jobs, coffee shop jobs, teaching gigs, anything that might fit into my (even then) varied and disjointed resume.

I ended up slinging lattes and grading papers. It was not a bad existence! In time, I came to appreciate how high end coffee, what I still call progressive coffee, was both a force of deliciousness but also a force of economic good in the world. Progressive coffee was a non-coercive, delicious, delightful way to funnel the wealth of the West into some of the poorest areas on Earth.

This, this was a big idea. I worked in coffee for quite some time – I’d call it my first real career – I probably trained over one hundred baristas, for companies I worked with as well as for the Barista Guild of America. I was a regional barista competitor! I started a cafe professional community in Providence. I had a small but appreciative professional circle.

In retrospect, while what motivated me was the big idea, what really drove my success was the focus on process that my philosophy studies taught me. It wasn’t just the coffee – it was how the coffee was made, how we sold it, how we communicate with the customers, how we communicate with our space.

(You can see how these ideas manifest themselves in customer support for software products in this talk I gave with my a8cbff Daryl)

The focus on process combined with my experience teaching, helped me lead Seven Stars Bakery to be named the best cafe in Rhode Island. It was pretty cool! Even more cool was planting the seed of excitement about progressive coffee in the minds of tons of new coffee professionals – some of whom have gone on to outshine me in literally every way imaginable.

When the Doc got her first tenure track teaching job, and we moved to Saratoga Springs, where we still live, I was able to get a job opening cafes for a small regional chain – but it was clear that my values weren’t a great fit for their organization.

It was then that I discovered Automattic. Like many folks who end up working there, I had been a long-time WordPress user, but it had never occurred to me that I might work for the company behind WordPress.com – or even that there was a company behind WordPress.com. It had never come up.

Of course Automattic immediately rang my bell. A company whose primary driver, whose raison d’etre is to ensure that every human being has a voice, is able to express themselves on the primary mechanism of communication of our time, The Internet?

It was an obvious fit. It was a great fit. I made it through the trial, and have been on board for over three years now. Customer Support, Customer Success, Customer whatever, these are terms that describe in a big way what I’ve been doing my whole life; taking a big idea, and applying it on the personal level.

Sometimes that means reading Plato. Sometimes that means knocking on doors all day. Sometimes that means creating a curriculum (maybe Logic, maybe Espresso). These days, it means leading a team of Happiness Engineers, who put the power of the web into new hands every hour of every day.

I lead a live chat and email support team at Automattic, and this is my entry for the Week 1 SupportDriven writing challenge: “History: Our history shapes us — what path led you to Support? Was it a planned career? Or did you happen upon it?”

Customer Success in the Wild: Panoply Podcast Network Survey Teardown

What a title, am I right?

It’s a big title for a big article – strap in, this post is a long one, a question-by-question teardown of a Customer Success survey from a major media company, along with actionable take-aways. How’s that for clickbait?

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Packing a Conference Bag & Recommended Reading

Or, Packing a Carry On, 2016 Edition

I have a conference coming up next week, so I’m putting together my things, as one does. In prepping for the trip, I figured I’d do another What’s In My Bag post, since things have changed some since January of 2015!

Check it out:

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The last conference I attended was the first-ever SupConf (number two is coming up!) and it illustrated for me the allure and the failure (for me) of one-bag travel. I love the idea – go where you’re headed, have one bag and only one bag. The simplicity! The ease!

On the recommendation of my dear friend Clicky Steve, I went with the Osprey Porter 46 – it’s a great bag! I could backpack using it through all sorts of terrain and terroir for as long as I’d like and it would never let me down. It’s a great recommendation and it will be coming with me on this trip as well – but not as a solo bag.

The problem, for me, is that I don’t want to bring all of my luggage with me from the hotel room to a conference floor. Carrying a 46 liter backpack through a professional setting – it’s not a good look. At SupConf I settled on a reusable grocery bag to shuttle my laptop and conference materials from the AirBNB to the conference – and then promptly stashed it away from sight. I have some impostor syndrome around looking professional, I guess!

OK, so the Osprey Porter 46 will be acting as my clothes-and-sundries bag. Not a problem. That means that this faux-leather Timbuk2 will be doing double duty as my carry-on and my day-carry conference bag.

While it’s true that Automattic provides all of its employees a WordPress branded Timbuk2, and I absolutely adore mine, the lack of an exterior water bottle holder has come to be a consistent irritation on longer days – this bag, which I’ve had since my days as a community organizer for the City of Binghamton, has water bottle holders on both sides.

That means I can have a travel mug of coffee on one side, and a reusable water bottle on the other. What more could I need?

Here’s what’s going in my carry-on and daily-carry conference bag, for a 3-night conference trip with air travel:

1.) This is the bag itself. A quick look at the Timbuk2 website doesn’t look like they’re actively producing them anymore – it has the TSA compliant laptop compartment and notably fewer pockets and zip-ups than my WordPress bag. This will be its first big trip. This is your chance to shine, little buddy.

2.) A little notebook! It’s unlined, a sort of oversized Field Notes notebook. I’m 90% sure my colleague Timmy gave me this for doing QA testing on our new Editor. This is for various travel notes, potential blog posts, sketches, doodles, talk notes, etc. Your classic catch-all.

3.) It’s a Kindle! I left my last one on an airplane. This one, also, is secondhand. It’s full of books! Sort of! I’ll have to find my Kindle light before I leave, it’s not pictured but I would like to bring it – airplane overhead lights are too diffuse, and I always worry I’m keeping my seatmates awake with it on. A nice focused book light is key for late night and early morning flights.

4.) Fitbit Blaze! I did not think I was going to like this as much as I do – the latest update especially has added a few new front-facing templates. Being able to have the screen stay off until I’ve turned my wrist always gives me a sense of “Oh yeah we’re living in the future.” Plus, quantifying my heartrate, etc, is really interesting to see over time. This is the only small device I’m bringing that doesn’t charge using a micro USB charger.

5.) Stickerbombed Anker Powercore battery pack – this thing is seriously a lifesaver, especially in unfamiliar towns where I’m using GPS, wireless data, and other power-sucking functions. I can charge my Galaxy S4 up to six times with this beast!

6.) Karma Go Wifi Hotspot – Certified 100x better than airport wifi. Plus, it creates a wireless network that anyone around you can use, and when they do, you get some additional free data. Being friendly to strangers and getting free data is a nice combination!

7.) Dopp kit! This has toiletries, mints, an eyeglass repair kit, all that sort of stuff. Super handy to have on layovers! Once I get to the hotel this will stay in the hotel bathroom. I could do a whole post on the contents of this bag alone – it’s changed over time and is, I think, a pretty ideal balance of the necessary and the nice to have.

8.) 13″ Macbook Pro. Not pictured: the charger for this.

9.) Another notebook! This one is a slimmer Moleskine, specifically a Bullet Journal! The Doc has been following the format for about a month, and has been raving about it, so I’ve started giving it a try. I’m still undecided!

10.) I AM CRAZY ABOUT THIS THING! It’s a leather travel wallet made by a local company called Samwell Leather – I met them at a craft fair and they were the coolest folks. I’ve been complaining that I needed something like this for travel every time I came home from a trip – it holds a little notebook (how many notebooks do I need?), plus has space for your boarding documents and a pen. I am also the kind of maniac who likes to have hardcopy boarding documents, even with a massive smartphone battery pack.

(I’m skipping the pencils, pens, crayons and pencil sharpener – y’all know what those are, right?)

11.) Backup headphones! These are the in-ear headphones that came with my phone. They work, they fit fine, and they don’t need a battery to operate. They take up nearly no space, so I tuck them into a bag pocket and forget about them until I need them.

12.) These are the same on-ear wireless bluetooth headphones from Outdoor Pursuits that caused such conversation in the last Post! I still like them a lot for travel (since they fold up and don’t have a cord) and they’re holding up to lots of being thrown into and yanked out of bags, which is a good sign!

In addition to getting my bags ready, I’ve been doing a literature review of blog posts and other articles on maximizing my conference experience – I tweeted my way through them, but here are those links if you missed them in the information dump truck that is Twitter: