Tag: automattic

If You’re Not Preparing for Your One on Ones You’re Wasting Everyone’s Time

I’m working on a massive opus of my thinking on one on ones, how important they are to remote teams, and a bunch of tall tales about the times I’ve messed them up, and how to avoid my mess ups in your own life.

(Note: This massive opus¬†will not be a list of questions to ask during one on ones. We have enough of those ūüôā )

If I were writing for an actual publication and not my personal blog, it would have an SEO optimized, click-gravity headline: “The Ultimate Guide to Remote One on Ones” – “You Won’t Believe What This Dude Said in a Remote One on One!” – “56 Ways to WOW your Boss!” etc etc.

( You can see my first ever post about one on ones here: Communicating with a Remote Team: One on Ones)

One thing that doesn’t fit super well into that piece, but is still something I want to talk about, is that one on ones are¬†important, and they are¬†hard to get right.

Continue reading “If You’re Not Preparing for Your One on Ones You’re Wasting Everyone’s Time”

Create Leadership Workshops at Your Company!

One ongoing project that I have at Automattic that I am especially proud of are our Developing Leadership Workshops. 

The workshops take place once per month, and last about an hour each. So far it’s been almost entirely Team Leads from within the company, with one guest speaker, Kevin Goldsmith of Spotify.

The workshops are stolen directly from Work Rules and Google’s similar practices – the idea, broadly, is to help individuals unlock the value in their own experience and practices to the rest of the folks¬†at the company.

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Remote Work, Scheduling and Serendipity

Something I’ve been thinking about quite a lot these days is the role that structure and discipline play in the life of a remote worker, and¬†a downside I’ve noticed to becoming too structured.

I wrote a little about the import of creating your own signals – in some way we can see that through this same conversation, right? We have to make our own signals in order to keep things running smoothly, to ensure we have the discipline or structure to work the way that we would like to work.

There is a definite tension when it comes to the idea of structure and the idea of working remotely: I think personal freedom is a huge part of what attracts people to a remote lifestyle.

I often find when chatting with others who work remotely, that there is a certain sense of reluctance around creating more structure in their day, or in their approach to work. This Post isn’t all about freedom and structure, although I do think that’s a topic 100% worth really taking a bite out of.

For today, let’s take a look at how I think about structure in terms of what helps me work most effectively, and then we can move on to this bigger topic of going a bit too far in terms of structure.

I structure my work time entirely around my calendar (Google Calendar that is) – I move everything from my to-do lists and legal pads to my calendar as quickly as possible. It’s where I keep everything.

If it’s not on my calendar it doesn’t exist.

That’s from Ramit. He and I agree on this one.

Especially when working remotely, having things laid out very clearly, in a structured and time-bound manner, helps me ensure nothing slips through the cracks, and allows me to see what my day will be like without having to check a dozen different places or processes.

It has been working really well, for years now. It’s kept me focused and successful and impactful in the ways that I have envisioned and planned out ahead of time.

As an aside, do you remember Blockbuster video, or other video rental places? I have really fond memories as a kid, high schooler, and even into college, going to the video store and just sort of wandering until something caught my eye. There wasn’t an algorithm or selection mechanism at play, other than the ones in my own mind, I guess.

I watched some awful movies, but also some really great ones, ones that wouldn’t ever show up on my Netflix queue today. This was a little bit of serendipity, a minor act of finding something that I wasn’t looking for.

The same thing happened in public libraries for me a lot growing up. That’s how I first found and read¬†Stranger in a Strange Land, which was my absolute favorite book for decades. In fact, my first tattoo was from another Heinlein book, TANSTAAFL.

Before our last Grand Meetup, I told the newest folks on my team, joining Automattic for their first ever Grand Meetup, that the most important thing they could do was to leave room for luck – to avoid overpacking their days, to leave room to decompress, to engender chance; meet someone new, join conversations you’d otherwise rush by.

For some reason it never occurred to me, at least until now, that this advice is actually very important for everyone who is engaged in remote work, all the time Рnot just during a once-a-year workcation.

I would argue that not only is it important for remote workers to try to leave time for serendipity, you actually must find and create space for it. Teams and departments and approaches being siloed is bad enough when folks are in different offices – when you’re on different continents, the odds of a serendipitous meeting of the minds at just the right moment, well, it’s unlikely.

If you work remotely, you need to not only leave space in your day for chance, you also need to get out there. You need to ask folks in the design department to lunch – yes, maybe it’s a voice call while you’re eating breakfast and they’re eating lunch. You need to see if your HR rep would join you for a coffee – maybe they’re in a Starbucks in London and you’re having Cheerios in Chicago, but it’s still a coffee!

When we’re not physically close to one another, we lose something without the chance meetings of mere proximity. To recapture this, we have to make time, and make friends.

Get out there and meet someone new.


Motivation, Money and Freedom

Some of you may recall that my personal mantra for 2015 was “Create selfless value,” and it worked out wonderfully.

I made some pretty cool stuff, I got to know a lot of people I wouldn’t have otherwise, and I think I really made a difference for a lot of folks – mostly at very little cost, but without the nagging question in my mind, ‘How will this come back to me?’

Rejecting that thread has been surprisingly freeing, and it has fundamentally changed the way I think about social capital (a topic I’ve been pretty interested in for a little while) and the way that small nudges or introductions can end up creating a lot of value.

We’re near the end of January of 2016, and I still don’t have a solid idea as to what my mantra will be for 2016, but I think part of it will be about gaining¬†or retaining¬†or maybe generating freedom in my own life.

That’s still a big bite. A huge topic. It’s not enough structure, but I’ll work on it. One thing I’m certainly trying to be better about is being transparent about things that are important to me – as illustrated here.

A surprising piece of feedback I’ve gotten regarding my goals for 2016 is about my goal around producing side income.

I’ve been a ¬†fan and vocal supporter¬†of both company creeds in general and Automattic’s creed in particular. Matt writes a little about the creed (along with its full text) here, but the relevant¬†part is:

I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation.

The feedback I’ve received is about the apparent tension between my own goal (to produce¬†side¬†hustle¬†revenue¬†equal to 50% of my take home pay) and the above line.

I would hate to give the perception to any of you, dear readers, that my motivation to increase my income has anything to do with the money itself. Money itself is not worth anything to me Рbut the fact is, my family and I (like you and your family I would expect) are restrained by money in many ways.

Like a lot of young folks of my generation, I have a pretty significant student loan burden – I pay more for student loans each month than I do toward our¬†mortgage. These two chunks of debt, student loan and home loan, represent a weight on our ability to flourish, to save for Mango’s future – Mango being the toddler that lives with the Doctor and I – to give to charities or politicians we believe in, to even pursue our interests.

In fact, I would turn this argument around Рmy desire to work more, to build more value and to really delight folks outside of my (awesome) job Рis motivated by a desire to avoid being driven by money.

With heaps of debt, all financial decisions come with that looming burden – it becomes a weight, mentally, emotionally, creatively. It’s a problem!

I want to escape having money be a part of my motivations altogether; I want to be able to live without that concern. That there is a certain twisted irony to the fact that the pursuit of this dream involves additional money is not lost on me.

Sometimes in the chase for freedom we’re taken on paths we don’t expect. Like Walt, I contain multitudes.


Working Remotely, Thinking Globally, and FOMO

You’ve heard of FOMO already, right?

This is for all of you folks at home who would never click that link to Wikipedia:

Fear of missing out or FoMO is “a pervasive apprehension that others might be having rewarding experiences from which one is absent”.[2] This social angst [3] is characterized by “a desire to stay continually connected with what others are doing”.[2] FoMO is also defined as a fear of regret,[4] which may lead to a compulsive concern that one might miss an opportunity for¬†social interaction, a novel experience, profitable investment or other satisfying event.[5] In other words, FoMO perpetuates the fear of having made the wrong decision on how to spend time, as “you can imagine how things could be different”.[4]

Working as a team lead at Automattic, on our flagship product, WordPress.com, is a wild experience for a lot of reasons.

Continue reading “Working Remotely, Thinking Globally, and FOMO”