Category: Remote Leadership

Finding Your Own Structure

On the recommendation of my friend and colleague Andrew I recently picked up a leadership book called Extreme Ownership. Here’s his take on it.

There is a lot to talk about in this particular book, but the piece that really stands out to me is the idea that structure and discipline can help an individual to a life of greater freedom. This idea is especially germane to remote workers or folks otherwise enjoying highly flexible schedules and workplaces.

Having travelled in some pretty radical circles, I am familiar with the usual backlash against structure, process, and limitations on behavior – there is definitely a mindset that rejects these things in a wholesale way, and while I don’t agree with it (or find it to be particularly coherent as a political philosophy), there it is.

I can acknowledge that on its face, the idea of adding structure in order to increase personal liberty may sound counterintuitive. Stick with me. We’ll go on this journey together.

When I was studying philosophy one of the works that somehow found its way into all of my other classes was a paper called Two Concepts of Liberty.

If you’re so inclined, and have about sixty pages of time to dedicate, I totally recommend giving it a read in its entirety – it’s dense but brilliant, the kind of work you’ll get through and just nod, because it’s simply intuitively correct, something you understood before you even read it, but put into the very words you never could have.

The TL:DR of Two Concepts is that we can think of liberty as falling into two buckets: Positive Liberty and Negative Liberty. 

Negative liberty is essentially freedom of movement or freedom of choice. If I stop you from eating a donut, I’m infringing on your negative liberty. If I tell you to work on this project and only this project or you’re fired, I’m infringing on your negative liberty.

Positive liberty, Berlin says, is self mastery. Being able to make decisions for yourself in an informed and critical way means you have high levels of positive liberty.

When you answer Berlin’s question, “What, or who, is the source of control or interference that can determine someone to do, or be, this rather than that?” – if the answer is “I am the source of control,” then you’re enjoying positive liberty.

These two ideas are often at odds in ways that will help us to understand my above assertion, that through some structure and some discipline, we can ourselves become more free.

Consider driving. I live in the US, so I’ll be referring to US-based road rules – please substitute whatever is appropriate in your region of the world.

Driving in a car requires following certain rules – you stop at red lights, you drive at an appropriate speed, you stay to the right hand side of the road. These are necessarily restrictions on our behavior and as such, limiting factors of our negative liberty.

However, even as our negative liberty is constrained, we’re able to exercise greater positive liberty, as driving becomes a safe activity, it becomes reasonable to engage in, rather than some sort of Mad Max terror situation. We’re able to effectively self govern.

By creating a more structured environment, we’re all able to thrive more fully and accomplish our personal goals. What is the end goal of liberty if not to accomplish our personal goals?

In Extreme Ownership, they talk about a very serious level of discipline, but they’re also dealing with very serious personal goals; kill or be killed. For somewhat less severe goals (decrease churn, make our customers happier), less serious discipline is probably OK.

One of the things that remote workers gain is an open day. There are pros and cons, and the freedom at hand can be thrilling, to be sure.

When you consider your work, and the way that you approach your work, let me encourage you not to mistake negative liberty for positive liberty. Creating structure around your goals and around your day allows you more freedom, not less.

When you’re your own boss, or when you enjoy the freedom to essentially behave as though you’re your own boss, creating your own schedule, etc, one of the best things you can do is to create some boundaries for yourself, to intentionally limit your own negative liberty.

Maybe that means getting up at 5AM to go to the gym, taking away your own ability to stay in a warm bed. Maybe that means always shutting off the laptop at 5PM, because you know you’ll let work creep into your personal time otherwise.

Self mastery, positive liberty, is best accomplished when you impose your own restrictions on your negative liberty – but you do so intentionally, with an eye to your own broader goals and aspirations. A lack of organization will also surely fill your time, and surely will keep you occupied – but will it move you forward in the right ways?

 

 

Working from Home and Phatic Communication

Working from home, being what’s called a remote worker, is a really fascinating frontier of Work. It’s fascinating both because as a paradigm, it creates new challenges, and it also makes visible ways in which more traditional work spaces overcome old challenges.

Working remotely has helped me understand traditional work places much better – if only because in stepping outside of what we see as the usual way of doing business, many of the previously invisible advantages of shared space come into stark relief.

Something I’ve been thinking about quite a lot recently is the idea of phatic conversations – that is, talk whose whole purpose is the talk itself, and not to a larger end (find something out from a colleague, accomplish a shared goal, communicate time away from work.)

I’ve written about communication with remote teams a couple other times lately:

Communicating with Remote Teams: One on Ones

Work from Home but Still Eat with Friends

This term, phatic conversation, is a new one for me, and I should say that I heard it for the first time via a podcast. It was one of those moments when someone else touches on and explains something that immediately brings your own thoughts from a mess into order. This is the thing I’ve been wandering around the outside of.

In a traditional workplace, phatic conversations happen in virtue of being around people, and they serve as a real social lubricant that is mutually beneficial and builds trust and sociability over time.

You have tons of these interactions: not all with colleagues, and not even all verbal. That neighbor that checks the mail at the same time as you? Those nods and waves are phatic communication.

We can even see things like small talk as part of this: when you engage in small talk with a stranger or with someone you’ve known for a long time, part of the purpose of that talk is the talk itself. 

It outlines a safe space. It’s a little back and forth to establish shared norms, we-are-the-same-tribe-right? 

The same is true of colleagues; when a meeting goes long due to some inane banter on an off topic, sharing a joke and a laugh on the way to lunch – this counts, there’s a real value there.

When you work next to someone, in the same building or the same floor, you sort of get phatic conversations for free.

When we think about this concept in a remote environment, where some or all of the folks working in an organization are scattered here and there geographically, this calculus changes.

Remote workers have to get our phatic conversations on purpose – we have to reach out to one another, to grab a virtual coffee or a video-conferenced lunch. It’s really interesting, right? When I was working in more traditional environments, I would have never identified small talk or waiting in line at the copy machine as ways my workplace solved a problem.

Phatic conversations are still important – they grease the wheels and create more shared experiences, and help to humanize folks you maybe don’t work with all that often. This is important!

It’s important not just socially, not just because it’s good to get to know your colleagues for your own sense of belonging and social in-grouping. It’s important because it opens up streams of communication, it gives you and your new connection access to more and different viewpoints and parts of the company (and, if you’re sufficiently distributed, different parts of the world.)

There’s value there – real, demonstrable value for the company or organization. Getting fresh eyes and fresh ears on problems is where innovation comes from. It’s by combining diverse viewpoints that we’re able to approach our problems and obstacles in new and exciting ways.

I have a few scheduled lunches every week where I sit and eat my lunch on camera with someone else (they’re not always eating, time zones means that lunch is relative!) – it’s a really nice way to spend lunch, and I’ve gotten to know folks a lot better this way.

Over the next few months, I’m going to start reaching out to folks specifically to have a coffee, and make it clear that it’s a chat to have a chat. Not people I already count as friends, but really intentionally folks I wouldn’t otherwise ever have face time with.

I don’t want to pull their developers away. I don’t want their designer to work on my project. I just want to have a coffee, to see how their day is going. It feels like this is a way to stoke the fires of serendipity a little, allowing space for unusual combinations to surface and flourish.

If you work in a remote environment, I encourage you to do this, too – it’s just coffee 🙂

Iterating on One on Ones

I know, I know – I’ve written about one on ones before.

If you’re not familiar, a one on one is a short sit down between a team lead and a member of the team. Folks much smarter than me have written some really insightful stuff about them, why they’re important, what they’re for. Here’s a great one, from Rands.

I do them once a week, for about thirty minutes, with every member of my team. I’ve been thinking about one on ones quite a lot recently – some feel really productive, some feel like I’m really getting to know the team member, and some feel functional, perfunctory, useful not maybe not productive.

This coming week, we’re starting a new structure of weekly updates. Since Athens’ inception we’ve done roughly weekly updates with our sister team (Sparta, obviously) on Wednesdays.

These updates weren’t really structured at all – folks would write about their home being remodeled, or their recent projects, or their ticket or chat count, or maybe an upcoming vacation. They were nice, but not especially helpful, as someone trying to understand how folks were doing, what they were working on, etc.

We didn’t even have a great reason to be doing them on Wednesdays – at one time, all of the teams at Automattic did updates on Thursdays, so it made sense to schedule internal team updates on Wednesdays.

Our company wide updates are still called Thursday Updates, but they are usually posted on Fridays, sometimes the following Monday, depending on what time zones the team’s members tend to work from.

The time we scheduled the updates didn’t make sense anymore. Our internal stats for chats and tickets run Sunday > Saturday, so to do any kind of regular volume updates meant folks had to do some math by hand, which was a point of friction.

Wednesday was also suboptimal because it was right about the point in the week where folk started to catch their groove – breaking it up with unstructured reflection (or being ignored, or populated with throwaway content), wasn’t the best we could do.

Short story long – starting this coming week we’ll be doing our updates on Monday morning, with a consistent structure for each person on the team, including me. There are expectations for clear and transparent reporting of individual volume, as well as how it compares to our team baseline, which is a sort of cooperative understanding of what a day’s work looks like for us at this time.

This brings us around to the obvious question; what does this have to do with one on ones?

In considering the one on ones that I really enjoy, that I feel are Working, they’re consistent in that they are not simply status updates – they’re not “I did X. This week I’m doing Y.”

Instead, they’re about experiences and approaches, friction and family. They’re about building a relationship rather than communicating things I can easily find elsewhere, especially with our commitment to communication and transparency.

As our weekly personal updates become more focused, I think it’s entirely possible that they could take the place of the more status-update-like one on one conversations. This isn’t to say that I’ll stop doing them (I love one on ones), but rather I’ll have a chance to start doing them correctly – using them to get to know my team, rather than getting to know the stuff around them.

I think it is probably also a good move for me to start being more clear to my team how I think about one on ones – if they are meant for talking about bigger career thinking, about navigating the waters within Automattic, about finding the right way to be impactful, there is likely a better way to structure that.

I’m not sure what that structure will look like – I have been reading about OKRs quite a lot, and it seems like they could fill that not-daily-work-but-still-important-work structure.

I am also trying to be more aware that my natural inclination toward more structure is not always the right move – although, I think I’m probably right about this one!

 

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.

Continue reading “Create Leadership Workshops at Your Company!”

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 – not 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.