Seven, Mostly Disconnected, Thoughts on Leadership I had while watching the Double Fine Documentary

| 6 min read
#engineering #creativity #leadership #game-design

I’ve been making my way through the Double Fine Psychodyssey series. It’s a THIRTY TWO episode documentary series looking at the SEVEN-YEAR making of Psychonauts 2. It’s an absolute whale of a show, and also probably some of the best art produced this year, and maybe the best look at how creative and tech work actually happens.

So many parts hit home, and I’d so so so recommend you just go watch it. But here were a few parts that especially stuck out to me.

1. Thought Leadership Doesn’t Exist

There are people, leaders, whose primary value to a company comes in the form of the things they say. The uh… thoughts they have. But it’s not “thought leadership”, thought leadership is someone who wants you to pay them money for an abstracted notion of value without them having to do any actual cultural work.

Nonetheless, the value that gets invoked is the tip of the iceberg of what’s actually happening. The real work is in the social connections they have made, the trust they have built, and their technical understanding of the problem at hand. Tim Schafer, the head of the company, puts this so well when he talks about how two people can say the same thing, but one gets ignored and the other is appreciated. That means your value isn’t just in the ideas you have, it’s in your ability to be heard by the people you’re trying to tell them to. That’s a social thing, not a purely intellectual activity. Yes, the output is “thought”, but the work is pretty nuanced.

2. Double Fine’s Documentary is Probably the Best Piece of Media on Psychological Safety I’ve Ever Seen

The term “psychological safety” gets thrown around so much these days that it seems like a vague description for letting people enjoy their work. Like it’s just something you think about once, make some adjustments, and then you’re good to go. What’s so powerful about the documentary is how it lays bare just how hard it is to develop and how easy it is to accidentally break, and how hard it can be to recover once it’s gone. DoubleFine as a company is an industry standout in terms of caring about their employees, working conditions and trying to do the right thing. And it’s still incredibly clear that they struggle with it, and they still make mistakes.

The line between good and bad leadership is, still in my opinion, so slim. There just aren’t many opportunities to see other teams grappling with it in a real and meaningful way. It was nice to see the reality being represented as this active process that requires constant energy and attention over time, and not this one of thing that you implement, and then you’re good to go forever.

3. Semi-Permeable Boundaries are Everything

One of the most interesting points of tension in the show is overlap and roles and responsibility. Much of the toxic and reasonable tension comes from the overlap in who gets to make “design” decisions about the game.

Game Design is such a great microcosm of this because when you think of “design” you often think of the people making the challenges and building the levels. But as the series makes clear, artists get to make design decisions with the themes they pick, and systems engineers get to make decisions by what they decide is easy and difficult, and writers get to make design decisions. So, it’s all ostensibly a place that everyone plays in, even if everyone doesn’t own it. And collaboration happens when everyone gets to have some say in that. But, collaboration also stops happening when everyone has every say in that. And finding those boundaries is a challenge that changes from project to project.

4. Being a good leader means people will still be vaguely frustrated with you all the time, and you just get to deal with that

In an unsurprising amount of time, employees shared frustrations on ways that Tim Schafer was or wasn’t getting involved enough in the project. What was interesting wasn’t that these occurred, it was mostly that… regardless of how good or bad things were going, the level of frustrations remained fairly consistent. The number of times Tim’s tics get called out, interpreted or diagnosed is pretty often. This isn’t some sort of “gosh, people should be kinder to their leaders”. Hardly. It’s the idea that as a leader, you will frequently get very specific responses that can be informative, but that you can’t interpret as direct causal feedback. The goal isn’t to never frustrate anyone or to be well liked in all situations.

Being a good leader means people will still be often vaguely frustrated with you and think you could do a better job DALL-E Rendering of Being a good leader means people will still be often vaguely frustrated with you and think you could do a better job

It’s an acknowledgement that most leadership is judged moment to moment based on how that person made them feel. And every so often, many times, it will rightfully not be great. And also, sometimes, and many times, that feedback is both true, and not useful because doing the thing that felt less great in one moment leads to a better outcome overall. There’s that quote about the stock market being a voting machine in the short term and a weighing machine in the long term. I think leadership is clearly similar, it’s judged by popularity in the short term, but its true value is determined by trust in the long term.

5. Discomfort is Where the Good Stuff Happens

I’m probably alone on this one, and god knows a terrible meeting is, in fact, one of the circles of hell. But working with other people on tough problems and executing them in a timely manner is, in fact, the best part of it. Half the reason solo projects are such a grind is that there’s no one else to bounce ideas off or to collaborate with. The Human part of technological work, is in fact, the fun part. You can see this in the followup interviews about the group discussions about levels or timelines. So much of the important work actually happens when people are uncomfortable or have to push back against each other or grapple with challenging concepts.

The friction of working with other people is also the reason that working with other people has multiplicative benefits. So leaning into the situations that feel like you might be calling someone out or that you might be nudging too hard, or asking uncomfortable questions. That’s the stuff that moves projects forward.

6. Discomfort is Also Where the Bad Stuff Happens

The counterpoint to this is that capital-b Bad things also happen with what looks like discomfort. When the team goes through what is transparently a very challenging time, it was clearly hard for company leadership to distinguish the types of discomfort. Task-based discomfort, we have a sincere disagreement about the direction of this project and identity-based discomfort, this person isn’t listening to my ideas about the direction of this project can look very similar at the moment.

When we imagine toxic work environments (or really just failure states in general) we think of catastrophes, or situations where it’s obviously just so bad that there are warning signs going off anywhere. But often people are good at normalizing the positives and the negatives. So good stuff can seem mundane (and even uncomfortable) and terrible stuff can also seem mundane (and really uncomfortable). The number of people in the episodes who were basically muddling through but also admitted to feeling super burnt out was incredibly telling.

7. The Whole Leading versus Managing Thing is Kinda BS

The company hosts what it calls “Amnesia Fortnights”. It’s a two-week period where everyone pauses what they’re doing and focuses on small hackathons to develop new projects and ideas.

These episodes are so heartwarming because you get to see new people take the lead on projects and get a chance to exercise their ideas and guide teams through execution. On the one hand, each of these people clearly has exerted some informal influence within the company previously, both because their pitch got voted to the top, and also because they feature somewhat prominently in the docuseries. But the interviews with each of them (and with Tim) about the experience are telling. It’s a new set of challenges, opportunities, and ways of thinking about the world. For some people, it’s an opportunity to take on new responsibilities in the future, and for others it’s a recognition that maybe they’re not as interested in that type of role. But in both cases it’s an opportunity, and an important one, that Double Fine uses to expose leadership to a broader array of people.

The idea that you’d need to expose this sort of ad-hoc “not real” leadership opportunity runs counter to the idea that leadership is management without the BS. If all you had to do was “lean in” more or “lead from the bottom”, specific leadership moments like this, especially at such a caring and thoughtful company, simply wouldn’t be necessary. But, they, in fact, are because often the little tasks, the blocking, and tackling of management, are what make actual breakthroughs possible. And from an equity perspective, leading through influence is a poor substitute for being the one out in front.

Occasionally It's Nice Not Having any Clear Answers

So much of writing about business and leadership traffics in clear, definitive answers about what to do to make things better. You should create emotional safety, listen to your employees/coworkers, and eliminate crunch. But actually doing that in the context of trying to make money, meet industry demands, and also produce good work is a complex challenge. Seeing people take it on, and mostly succeed, is helpful, even if there aren't any clear answers or takeaways.