Exposing Our Own Biases: Why I Err Wildly Towards Over-Documentation

SpotlessMind article 2024-12-30

One of the goals of Spotless Mind is to understand how we work, and as such, to fully develop our system, we’ve been using yours truly as a guinea pig for our system. This has led me to think hard about how I work (I had already written a book on that topic as well).

One clear and overwhelming bias of mine—as anyone who has worked with me for more than twenty minutes within the last twenty years knows—is my strong bias towards over-documentation. I always coach my teams, “If it’s not written-and-shared, it didn’t happen,” and many, many of my other work approaches focus on that. In fact, one of the reasons I am obsessed with using Basecamp as a work platform is because it promotes easy and natural documentation.

So there’s an interesting twist to that. Very interestingly—let’s peek inside the sausage factory for a moment—early versions of our Briefings on Individuals explained my documentation obsession by saying that “context” is important to me. Our own system deduced that I love understanding the context behind everything—why is it happening? What are the motivations? What are the details about it? And so forth—and I can’t deny it. It is true. I do love context and suck in as much of it as I can get.

However, I realized upon reading early versions of my own guides, while we were in the process of making them more sophisticated (and they’re pretty awesome now, I would observe in an unbiased way!), that my obsession with documentation has a few reasons beyond merely being a sucker for context. I think they are worth explaining because these reasons together amount to a Defense of Documentation.

For these reasons, as the court-appointed attorney for the Defendant (named “The Documentation Dictator”), let’s articulate the reason why Documentation might just possibly be underrated. Let’s go:

First: Let’s repeat the most obvious reason, and the one in my own Briefing, that I mentioned above: documentation provides greater context, as well as longer-lasting context, to, well, anything. Documentation adds clarity as well as subtlety, for example, by choosing to preserve what is most important (what is least important is least likely to be written down). This context helps you understand what is really happening in the situation, to get a better grasp of the underlying reality of things—including the parts hardest to codify, such as the personalities of those involved and what each of those is trying to accomplish. A hard task!

But not just that: the mere act of making people write it down forces the individuals involved to think about the context, what’s important, what’s not, and them being forced to think is only a good thing.

Second: Information gets lost far more often than you think. My CTO once died, and he was the only one with access to key information, such as passwords to encrypted drives, code, data, and so forth. Information gets lost in more informal ways as well; people forget. Backups, copies, and other people knowing—even knowing the informal things—go a long way. I would argue that people are biased and don’t realize how much important information is lost. But hopefully, now that Google doesn’t even let us see more than the past 20 results and has removed most old sites from its public repository, maybe people will start realizing that what they counted on Google to be able to find forever, they no longer can. And that’s just a very obvious example of this deeper pattern.

Third: A wise lawyer once taught me that, in court, documents written at the time things happened are considered acceptable, first-hand evidence (in a very strong way that documents written much later about events long ago are not considered; those are merely second-hand), and I always think it’s a useful way to think about it. All the time, outsiders to the team need to come into situations and try to figure out what’s happening. You hire a new employee—they need to figure out how the company works. You bring a team member from a different division into a project—they need to figure out the project very quickly. And documents go a very, very long way toward helping do that. Even with very high-trust partners that have perfect integrity and great memories, it’s surprisingly frequent that you need to go back and double-check key details, just to make sure. Having a “historical record” is too undervalued by everyone these days.

Fourth: There’s a funny characteristic of human nature: we tend to remember everything in a way that’s biased towards ourselves. Having Human DNA in me, I fall victim to that as well. When two people commit to some dollar number between them but remember it differently—even for cases as simple as, I’ll pay you back my proportional cost of the dinner we shared—when people disagree, isn’t it funny how the person who has to pay always remember a cheaper number that he needs to pay and the recipient always remember it was a higher number? With to-do items in the workplace, this happens endlessly, day to day: who committed to what, who said what would happen by when? By not writing it down, it’s easy to turn everything into a “tomorrow, tomorrow, tomorrow” (creeps in this petty pace from day to day until the last syllable of recorded time!) and that’s how things never happen.

Fifth: It really helps with managing employees and team members, especially remotely. If you’re not side-by-side and working on the exact same document or details together, it’s hard to know what they’re even doing. If they’re even doing anything at all! But a culture of documentation and transparency goes a very long way toward solving that. If the corporate culture is to document everything that happens, then you know what is or isn’t happening! Fun story: multiple times in my life, not recently, I’ve worked with extreme geniuses who couldn’t produce anything or get anything done, and my culture of documentation exposed that early.

Sixth: As a leader/manager, I value ENORMOUSLY making sure my employees/team are comfortable sharing BAD NEWS with me (I love the Godfather line: “The Godfather is the sort of man who insists that bad news is told to him immediately,” and that’s exactly how I am). By making people feel comfortable telling me bad news, I need to make them feel comfortable telling me EVERYTHING—even if it means I need to practice the yoga “mmmm” to make sure I always respond positively. By insisting on overcommunication and overdocumentation and talking about everything (and my always responding in a healthy and positive way, no matter how difficult), I’ve found that it makes them much more likely to share bad news (hey, it’s just documented like everything) as it happens, rather than wait and wait and wait until the last possible moment, when it’s already too late. Said more simply, it’s hard for me to convince under-communicators to share bad news with me. There’s a variation of this point: this strategy exposes people’s Achilles’ heels (such as if they’re lazy or if they’re working hard but making huge mistakes) very, very quickly as well, which is an added plus.

Seventh: Also, as a leader/manager, by being overly transparent through overdocumentation and insisting on extreme “99% transparency” as I call it, I’ve found that it really helps in an incredible way to build trust in me. And that’s one reason why I can manage people so quickly and effectively: because this helps them trust me very quickly. And similar to trust, I’ve found it helps motivate people as well.

Eighth: I love how Amazon has a famous policy to start every meeting by reading a meeting document written by the meeting leader for 15 minutes. My first point above was that documents force the individual (doing the documentation) to think through the issues; but Amazon does this because it forces even those attending the meeting to think through the issues! Part of the genius of this policy is that it forces everyone to think during every single meeting.

Of course, we have to mention the core argument against documentation: it’s a trade-off with speed. And while on a certain level, that makes sense—it, by definition, takes time. But on a deeper level, I don’t think that’s a real pattern. My experience has overwhelmingly taught me that competent people who work fast and do good work will always find time to document (at least when made to), or find someone else on their team to do it for them (having meeting notes does not mean you yourself need to take the meeting notes). And if the most competent people can do it… then so can you. It’s a bit like one of my mother’s favorite sayings: “If you want to get something done, give it to a busy person.” There’s a reason why Amazon insists that its insanely-busy employees take the time to write up their context and argument before every single meeting.

And for these reasons, I turn to the court of public opinion—and I rest my case! If you have any questions or want to discuss this issue in more detail, feel free to drop me a line. I’m always open to other arguments against my position that I haven’t yet thought of or heard!

If you’re interested in getting A Briefing on You: A Roadmap to How You Work Best, or Your Personal User Manual to give to colleagues, you should try SpotlessMind.io.
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Morgan F

Morgan tries to understand humans using ancient Greek and Latin classics as his guides. Seneca said all that needs to be said.

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