Author: Simon

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 🙂 )

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” →

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!

Sheryl Sandberg, Iran, and Leading Well

I can acknowledge that I am late to the party, but I’m reading Lean In. It’s fantastic.

There is a ton to think about in this book, and I have a few pieces brewing on the topics within, but there was one passage that has really struck a chord – it fits into something that I’ve been wrestling with myself, the kind of idea that has a few pieces, and they don’t quite come into focus until suddenly, they do.

Let’s start with that passage, it’s on page 132 in my copy:

After the married women spoke about how hard it was to balance their lives, the single woman interjected that she was tired of people not taking her need to have a life seriously. She felt that her colleagues were always rushing off to be with their families, leaving her to pick up the slack. She argued, “My coworkers should understand that I need to go to a party tonight – and this is just as legitimate as their kids’ soccer game – because going to a party is the only way I might actually meet someone and start a family so I can have a soccer game to go to one day!”

(Just a sidebar here, I thought about cutting the last part, from ‘because going to a party…’ because I think it subsumes the agency of the single woman and sort of reduces her desires into an early-game version of the married womens’ desires, but I’m leaving it since that’s how it was in the book.)

One of the other pieces of this suddenly-in-focus idea comes straight from the headlines of January of this year. Remember when the French President Hollande turned down a State Lunch with Iran because they demanded that the meal be served without wine?

Here’s a New Yorker piece on the event. It’s a good piece, and approaches this event from the perspective of hospitality – to what do we owe our guests? It is, after all, that the Iranian delegation placed their request out of religious observance – not merely to inconvenience or to bully the French.

As I do, around this time I grilled my friends about the topic – have you heard about the French Lunch? What do you think about the Iranian argument? They were mostly avoidant, being very polite and generally pretty proper. The impression I got was that in a general way, it’s assumed that religious beliefs tend to trump social norms in cases like this.

One voice that really resonated with me with David Plotz, speaking on a podcast (the part I’m referring to starts at 1:00:08) – Plotz sees this debate not as one of religious freedom, but rather in terms of what it means to lead a Good Life; “…the things that you claim as fundamental to you.”

I don’t always agree with Plotz, but here I think he is on the right side.

This idea of a Good Life is a highly personal one, and not something that we can quantify or really lend objective judgment to. A person’s life, and the goals that they have for that life, and the things that they hold dear, are deeply personal and generally not subject to debate – especially not at work, and especially not by someone who thinks seriously and deeply about leadership.

Like most of what I write here, this is geared toward folks leading teams remotely, working with people who they rarely see in person, how to make that work in a way that works. This piece is applicable to folks in traditional workspaces as well, but is especially important for remote teams.

What Iran, Sandberg and Plotz have helped to show me is that I’ve been making big assumptions about what a Good Life is, and in bringing my own sensibilities into my work, I think I’ve probably failed to serve some of my peers as well as I could have.

I think that many of us unintentionally give preference to certain ideas of the Good Life in a way that unreasonably ranks other ideas of the Good Life lower on the totem pole. Imagine at your workplace a colleague says that they cannot make an off-hours meeting because their little boy has a recital. Now imagine the same colleague says that they cannot make an early meeting because they have a brewery tour to go to.

We give preference to a particular vision of what a Good Life is – it’s kids, it’s a mortgage, it’s the picket fence and a rescue dog. This is not everyone’s Good Life.

There are arguments to be made to prefer or reject any vision of the Good Life over another – maybe having children and raising them well is good citizenship. Maybe having children contributes to the global overpopulation problem.

As a leader it is not your place to give preference to anyone’s conception of the Good Life.

Unfortunately, you probably are, though. I know I have. How many times have I assumed that a single member of my team will work on a holiday because other folks have kids out of day care? In simple terms, I was bringing in my own idea of a Good Life and using it to give preference to folks on my team.

On one level, giving up my own idea of the Good Life is in part setting aside my own ego. After all, I chose my own idea of the Good Life, I want to believe it has value; to accommodate other ideas of success means acknowledging that at the worst I might be wrong or, (gasp) there may be multiple ways to be right.

In addition to ego, there has to be a rejection of judgment – and this is probably the hardest part of all. In making space for and allowing for folks on your team to conceive of and pursue their own idea of the Good Life, it means defending that pursuit in ways that, at least at first, may seem very strange to other folks who are coming to work with their own ideas around the Good Life.

You can see more clearly now why that last part of the Sandberg quote does not really advance my argument – if the single woman had simply said,  “My coworkers should understand that I need to go to a party tonight – and this is just as legitimate as their kids’ soccer game,” she and I would be more simpatico.

Using the party as a route to marriage, etc, simply acquiesces to the existing status quo Good Life.

If a member of your team is productive, and efficient, and creating the results that the team needs to find success, as their leader it is not only your job to allow them to pursue their own vision of the Good Life, but to defend that vision against other members of the team, and even other people within your organization.

The reason this is more important for remote teams than for geographically co-located teams lies in the trust remote teams need in order to be performant. Working without daily schedules or shared office space means that, as a leader, you have to trust your team explicitly, and believe that they’re making the best choices for themselves and for the organization.

The pursuit of the Good Life has to be included in that trust. In a remote environment especially, knowing that you respect their choices and will stand up for them is a big piece of serving your team well.

I don’t have a great call to action on this one. It’s hard to step outside of my own idea of the Good Life. I’m starting to see things more clearly now, and I hope that you’ll think on this too, and try to recognize when you’re unintentionally bringing in your own idea of the Good Life in a way that’s reducing the Good Life of others.