Author: Simon

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 🙂

Customer Support is the Last Mile for SaaS Companies

Working as a Team Lead for one of the Happiness teams at Automattic has been a great opportunity for me to learn a lot about the Software as a Service ecosystem.

I’ve been thinking and talking about hospitality and its outsized value for software companies for a while now (here’s a talk I gave in 2014 on the topic) – there are a lot of ways that support is undervalued in a general way by software companies, but folks working in the SaaS sector especially are losing out on a ton of potential value by underutilizing their support staff.

There are lots of places where we as an industry could improve here, from recognizing the import of support in the classic Build – Measure – Learn cycle to admitting that UX research is essentially Hospitality 2.0.

I’ve made it pretty clear (I hope) that my position on software, and even really maybe all products everywhere, should Just Work. Having to contact support staff, or dig through documentation, or try to figure out which Stack Overflow commenter is the closest one to correct, isn’t something an end user should have to do. That’s really it. Full stop.

However, like you, I live in the real world, and I recognize that compromises have to be made – products have to do more than one thing, and deadlines and inefficiencies and sometimes simply economic necessity means that not everything we touch can be a perfectly tailored, intuitive non-interface.

Someday. Someday.

WordPress.com is a SaaS business. Our customers are largely non-technical, and our product is fairly complex, although powerful. There is certainly a learning curve, and while we provide some educational materials, a great many of our customers, especially new customers, lean on our support system to help them gain momentum in the right direction.

We’re not alone in this – many SaaS businesses, especially ones that offer many features and powerful suites of tools, share that learning curve. You can very likely think of two or three services that you use yourself that took some time to really figure out – imagine if someone less tech savvy than you were trying to figure out that product? Where would they head?

Note here that I’m talking specifically about SaaS companies who are by and large dealing with the public – B2B SaaS companies have their own tangled web of complicated issues that I am by and large unqualified to comment on.

For companies like WordPress.com, businesses that sell to the general public and have a not-insignificant learning curve, your support staff represents the last mile service for your company’s created value.

This idea of Last Mile service comes from (ugh) telecoms – Wikipedia Link , more context appropriate Investopedia explanation – the TLDR is that the last connection in the telecom chain tends to be disproportionately challenging and/or expensive, but it remains the crucial link between the end customer and the massive network of energy or information or water or whatever.

Imagine you were running a massive telecommunications company, and you had a geographically enormous physical network in place, fiber stretched coast to coast, fully prepared to bring high speed internet to the people. This is a massive, massive amount of value. Imagine that you are, for one reason or another, unable to connect that last mile, to make that switch between your vault of value and the customer who would absolutely love to buy it from you. That’s a last mile problem.

For many would-be customers of SaaS products, that final connection, that link between an enthusiastic customer and your stored value, is your support staff. When they are able to work effectively, a good support team can multiply the value of the product, because not only are they solving individual customer problems, they’re flipping the switch for that customer, creating that last mile connection that otherwise would never have existed, leaving a customer disconnected from the value that you can offer them.

Complicated, powerful products can bring value to customers in a way that punches way, way above their weight – folks who have never heard of HTML are building multi page responsive websites right now on WordPress.com. Think about that.

The issue is, if you’re selling to the public, some percent of them need a hand flipping that last mile switch – if you can’t or won’t provide that service for them, you’ll be missing out on a whole cohort of potential enthusiastic customers, because the fact is, so, so many companies today do not bother to invest in their support staff to the extent that maximizes the last mile service.

The insidious thing about this problem is that it can manifest itself in many different forms. It might be especially high first-day churn rates. It might be that a cohort of your customers massively underuse your product’s features (because they don’t really understand them, because the last mile isn’t connected), and as such they’re dissatisfied, and go dark. It might be that folks who DO contact support, but only once, tend to churn at a higher rate (that would indicate that your support staff may need to read closer, empathize rather than grind out emails as fast as possible.)

Only you can identify if your product’s learning curve is leaving people out in the cold, denying them access to the full value of your product.

If you think that’s a potential place for improvement (and it almost certainly is), you should take a long look at the way your customers are able to access support. Is it easy to find? Are operators thoughtful and thorough, rather than perfunctory and severe? Imagine you were deeply confused by a step in your signup and activation flow – can you get help right away?

Considering the metaphor of the last mile can be really helpful in improving your customers’ access to your company’s value – think about it, and get out there and flip some switches!

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!” →