Category: General

Fully Remote Organizations and the Prisoner’s Dilemma

There’s a part of working in a fully remote environment that I am still struggling to understand, as a reformed philosopher and general skeptic.

Automattic, where I work, works. We get an astonishing amount of shit done, and we do so across a number of product lines and continents. We all work from home, or wherever we can find a flat surface and a clear wifi signal.

One of the things that surprises people the most about Automattic is the immense level of trust that is placed in every employee; it’s baked into the culture. We are committed to transparency and communication. We’re trusted to do our very best work and to find motivation intrinsically, rather than having it nudged upon us by bureaucratic processes or micromanagement.

As a student of philosophy, especially social choices, something about this model has always seemed rough around the edges to me. It sounded good, and it seemed like people believed it, but in theory it seemed like it should not work.

We can parse this disbelief of mine in the terms of the classic prisoner’s dilemma, what’s called a collective action problem.

Shipping, supporting, and improving something like WordPress.com is a huge task. It takes lots of people working together, collectively, to get it done. There are problems associated with this kind of collective action – one of them, the basic building block, is the prisoner’s dilemma.

The prisoner’s dilemma goes like this:

  • You have two prisoners, X and Y. They’re kept separate.
  • They’re offered plea deals: if X rats on Y, he can get off with a reduced sentence. If Y rats on X, he gets the same deal.
  • Both X and Y know that the cops don’t have enough evidence without someone ratting.
  • If neither X nor Y betrays the other, they both serve 1 year for a lesser sentence.
  • If X and Y both betray each other, they each serve 2 years.
  • If X betrays Y but Y stays silent, X goes free and Y gets 3 years.

Short story long, in a prisoner’s dilemma, ratting leads to suboptimal outcomes in terms of overall jail time. The best outcome across both actors (2 total years in jail) require both to remain silent – but the only way to pursue your own maximal outcome (no years in jail) is, by definition, removing the best outcome for both prisoners.

Individuals acting rationally  to maximize their outcome ensures that the optimal collective outcome is not reached.

If your aim is to guarantee the lowest amount of jail time you get, the lowest possible jail time comes from the combination of your betrayal and your comrade’s remaining silent. The worst possible outcome results from your keeping silent while your erstwhile comrade betrays you. In the prisoner’s dilemma, betrayal always has the better calculus.

I’m cutting this short because this is a blog post, but collective action problems are super duper interesting.

If you want to dive down this rabbit hole (and if you do then we have the same kind of brain!), here’s a great place to start.

We can see the prisoner’s dilemma crop up all over the place, but especially when it comes to things like a public good. Let’s say your neighborhood wants to build a playground. You’d like a playground in your neighborhood and folks are taking up a collection (or possibly a Kickstarter, it is 2016 after all). The very best outcome for you would be if the playground gets built with no donation from you, if others contribute but you do not – because the good that is created is enjoyable for all and cost you nothing.

You’d be a free rider. But no one would know. Then you could spend your would-be donation money on champagne and Oreos.

It’s the prisoner’s dilemma that gives me pause about working fully remotely, because within the company, we have a bunch of really outstanding public goods. There are the obvious ones: unlimited vacation, being able to set your own schedule, outstanding health benefits.

When we dig a bit deeper, even more public goods come into focus; access to top talent who are generous with their time, the ability to work where you see the most impact – or to not work when you so choose.

When we think about these public goods, especially in the context of a results-only work environment with personally set schedules, we get to a place where it looks like the rational behavior is to not work that hard.

Stay with me, now.

Look, if we imagine a perfectly rational actor, who seeks to maximize their own utility at all times, and they see some benefit in the public goods on offer within Automattic, what is their course of action?

In this case, the public good that they’re seeking isn’t really relevant – if they want to move from design to development and want to maximize the time they can spend with a development mentor, or if they want to become the next World Champion of Hearthstone and as such simply want to minimize time spent in non-Hearthstone activities, whatever it is, the pursuit of it stays the same, right?

For our rational actor, to maximize their utility, it is in their best interest to do the amount of work that would get them fired, plus one unit of work. If they skate that edge, they will not get fired but will still enjoy the maximum utility available from the (awesome) public goods available within the company.

We can imagine on another hand, a different actor, motivated in some other way, who spends all of their time heads-down in their work, whether it’s live chat support or RSS feed debugging or expense reports or whatever – in virtue of the facts that a.) work takes time and b.) time is scarce, that means that our second actor here, a hard worker who is dedicated to the company, enjoys fewer of the public goods.

Unless the work itself represents the highest utility for an actor, according to the prisoner’s dilemma the rational actor at Automattic (and similarly organized companies) will always choose to skate one unit above being fired, gobbling up the public goods which are significantly less available to their more dedicated and harder working colleague.

And yet, it works. We work together. We ship software and support hundreds of thousands of customers. I can’t think of even one person I’ve worked with at Automattic who fits the description of the rational actor, above.

I don’t know if this is a problem with the prisoner’s dilemma, or if it should instead represent to me a sturdy underlining of a conclusion that I’ve always suspected:

Automatticians, and other folks finding success in the remote employment world, are by nature something other than purely rational.

I couldn’t be happier with this conclusion. Part of the secret sauce of Automattic is accepting this irrationality and letting each individual sit with it. This is what makes the trust so important. This is part of what makes remote work so special – it helps us move outside a purely selfish position of utility maximizing, and into something else.

Something better.

(Yep, we’re hiring.)

Finishing Lean In

I just finished Sheryl Sandberg’s Lean In, and I am so very glad to have read it. It was part of my push to read more books about business or leadership that were written by folks who were not old white businessmen.

Lean In was the latest one. Here are my some of my highlighted takeaways:

Despite being high achievers, even experts in their fields, women can’t seem to shake the sense that it is only a matter of time until they are found out for who they really are – impostors with limited skills or abilities.

 

One of the things I tell people these says is that there is no perfect fit when you’re looking for the next big thing to do. You have to take opportunities and make an opportunity fit for you, rather than the other way around. The ability to learn is the most important quality a leader can have.

 

Instead of blaming women for not negotiating more, we need to recognize that women often have good cause to be reluctant to advocate for their own interests because doing so can easily backfire.

 

We can joke, as Marlo Thomas did, that “a man has to be Joe McCarthy in order to be called ruthless. All a woman needs to do is put you on hold.”

 

Of all the ways women hold themselves back, perhaps the most pervasive is that they leave before they leave.

 

Now we know that women can do what men can do, but we don’t know that men can do what women can do … We need to encourage men to be more ambitious in their homes.

 

Mothers don’t want to be perceived as less dedicated to their jobs… we overwork to overcompensate. Even in workplaces that offer reduced or flextime arrangements, people fear that reducing their hours will jeopardize their career prospects.

 

If I had to embrace a definition of success, it would be that success is making the best choices we can… and accepting them.

 

In the future there will be no female leaders. There will only be leaders.

 

If this resonates with you at all, you should pick up Lean In. It’s entirely worth your time, and is an excellent perspective changer.

Next up for me is Berkun’s Confessions of a Public Speaker, since I need some more preparation before I speak at SupConf!

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?

 

 

Efficiency is Behavior

Working remotely and leading a remote team is not always so different from doing that same work locally. Many of the challenges are similar, if not exactly the same.

One thing that’s been on my mind a lot, and if you work in any sort of revenue-driven enterprise, it’s something you think about a lot as well, is the idea of efficiency, and how we can create more efficient situations.

I find a tension exists between traditional operations management ideas and approaches to efficiency gains (calculate throughput, build a sensitivity analysis, reduce waste) and my own approach to leadership, which is a sort of mix of servant leadership and hopeless romantic labor reformer.

That tension is the natural pressure that exists between the idea of employees, Workers, as a numerical input into a larger system (the average Subway sandwich maker can produce one point four sandwiches every five minutes. Reducing that to one point three would represent etc etc, just an example) and the belief that every person has creative value, that the folks working closest to the problem (the sandwich) are those most qualified to solve that problem better, or faster.

I’m not the first person to see this tension – we can read the massive acceptance of and growing excitement about Lean as an antidote to this very tension, if we’re generous, since we can see in the Toyota Production system great empowerment of what you’d call line workers to identify problems, repair, and improve their own Work.

There is a difference between efficiency on a spreadsheet (or, even worse, a Powerpoint presentation) and efficiency in action.

My team is fairly small – it’s me and eleven Happiness Engineers – and for us, efficiency is behavior. It’s actions – it’s not such a fungible idea, it’s not a board room topic. It’s about doing something One Way or This Other Way, and seeing which gets better results in the same amount of time – or the same results in less time, then going with it.

If you’re leading a team, especially a smaller team and double especially if you’re leading a remote team, you must recognize that efficiency comes from behavior, and by testing and changing behavior.

We will never get more efficient with a poster with a quote from Deming under a high res photo of a  fighter jet. The only way we’re going to get more efficient is by trying out new stuff, and chucking it if it doesn’t work.

That means leaving room for failure. That means kicking out the sacred cows and rejecting dogma. There is enormous value in reading and in discussing and in building spreadsheets – don’t get me wrong, I love spreadsheets – but all of those things have to result in action, in trying some shit out.

Otherwise, it’s just air, it’s just value locked up inside your head, and we’ve been over that.

Try something new today. Sleep one less hour. Sleep one more hour. Don’t check your email. Turn off Slack. Listen to one song on repeat.

Master List: 26 Resources to find a Remote Job

This is definitely the top comment I’ve gotten from folks:

“Yeah, sure, it really seems great to work remotely, but how am I supposed to find a job like that?”

or

“There are so many companies, how do I know which ones are remote friendly?”

or

“But Simon, I want to work from home but I don’t know where to start!“

Instead of commiserating and telling them my own story, I’m putting together a master list of every place you can find a remote job today. If I’ve missed a place, drop a comment below and I’ll update it.

I’m going to focus here on full time employment – if you’re interested in building a freelance or part time hustle, you probably already know about UpWork, HubStaff Talent, etc.

Here we go.

Continue reading “Master List: 26 Resources to find a Remote Job” →