Chris Dent

From Faster Than 20

Chris is a hacker-philosopher, who prizes good tools designed to support good practices. In addition to co-founding Blue Oxen Associates with me in 2002, Chris worked at Socialtext (the first enterprise wiki company) and osmosoft (the creators of TiddlyWiki and TiddlyWeb, which Chris created).

He was the ideal partner for me as I first ventured into the collaboration business. Chris has a very clear point-of-view, which he is good at articulating, but he is also devoted to testing and modeling those ideas, not just espousing them. Our conversations and work together were particularly generative at a time when I was taking a lot of ideas and trying to put them into focused practice.

How I Met Chris

In 2000, Doug Engelbart taught a 10-week colloquium at Stanford called, "Unfinished Revolutions." I had the good fortune of taking that class (which led to me working with him), and the mailing list — unrev-ii — attracted followers from around the world. One of those people was Chris, who at the time was getting his masters degree at Indiana University's School of Library Information Sciences (SLIS).

Chris's posts tended to resonate with me. I was also extremely interested in the tools he was experimenting with for himself, especially Warp, a wiki-like tool that automatically created links to concepts. He and I shared a sensibility for architectures that supported knowledge work as well as incremental changes that could actually move us toward our shared vision.

In addition to his research and projects like Warp, Chris worked as a system administrator and programmer at IU, focused on a open source knowledge base project called Arts. Arts itself was interesting, but what was particularly fascinating were the team practices that accompanied these tools, practices that ended up influencing me in our work together. Chris also attracted, worked with, and mentored a bunch of awesome hackers from the midwest, who became part of my tribe, and who have all gone on to do really cool things.

In spring of 2002, Chris reached out to me on a whim about doing an "internship" with me for SLIS credit. As it turns out, I was in the process of starting up what would become Blue Oxen Associates with another person, and I thought Chris would make an amazing addition, even if it were only temporary. My original partner and I were going through a rigorous planning process, which worked so well, we decided not to start a company together. Our values were too different. Chris and I, on the other hand, immediately clicked, and we worked very well together. I asked if he would join me as a co-founder instead, and to my delight, he agreed.

We framed our business as a "do-tank." We wanted to create a paid infrastructure to support high-performance communities. Those communities would act as (willing) test subjects for our research, and we would integrate what we learned back into our infrastructure. The core technical component of our infrastructure consisted of a tool we developed together called PurpleWiki, which combined Ward Cunningham's wiki with Doug Engelbart's purple numbers.

Our year and a half working together was incredibly generative, but we weren't making any money, and Chris decided to leave Blue Oxen Associates. We continued our generative relationship, and he acted as a virus for our ideas, injecting them into other communities and bringing other great people into our world.

My time with Chris was incredibly rich. It took me seven years before I found another conceptual partnership as generative as the one I had with Chris. That was with Kristin Cobble, with whom I not coincidentally co-founded my second try at a company — Groupaya — focused on helping groups collaborate more effectively.

Lessons Learned

I'm not sure I learned anything entirely new conceptually from Chris — we found each other largely because we were already largely aligned philosophically — but Chris had a way of distilling ideas clearly, and his unique perspectives helped shape mine. More importantly, Chris was very good at certain practices, and his discipline and insistence around those practices not only helped me improve my craft, but also helped ground and further refine our shared philosophy. I tried to boil down our shared philosophy (AKA the Blue Oxen Way) in this blog post, but I'll try to go deeper here.

Be less dumb. A great example of Chris's way of words was his explanation for why he cared about this work. He wanted to "be less dumb." Even though some complained that this had a negative spin, I liked the everyman aspect to it. It's the same thing as "developing collective intelligence," said more accessibly and — in my opinion — impactfully.

It's all about shared understanding and shared language. This is obviously a common takeaway from my time with both Doug Engelbart and Jeff Conklin, but Chris and I talked about this and practiced it relentlessly. Our work with wikis emphasized the fact that wikis help surface shared language. This was one of Ward's intentional design principles (the first wiki was meant to support a pattern language repository, after all), but it's not well understood — less so today — and the vast majority of developers have ignored this important capability.

Stigmergy. Chris introduced me to this term, which describes collaboration via leaving and following trails, which is what ants do. It's what enables networks to behave collectively intelligent, and it is central to how we believe high-performance collaboration is practiced. Most of the practices we espoused were in service of stigmergic collaboration. These included things like...

Think out loud. The simple act of doing what you're already doing — thinking — in an open and transparent way has so many benefits. Thinking out loud is a form of synthesis, which helps you crystallize your thinking. It's also a low overhead way of leaving trails, and it potentially leads to all sorts of powerful collaboration.

In my year-and-a-half of working with Chris, we were only in the same room together for one week. Although we did talk regularly over the phone (on my insistence; Chris hated it), the vast majority of our engagement was asynchronous. Both of us were disciplined about thinking out loud, which gave us plenty of fodder to build on. If you look at the first four years of my blog (almost 400 posts), many of them started off with me responding to something Chris had written. Speaking of which...

Blogging! Chris convinced me to start blogging, and that became my primary channel for "thinking out loud" for several years. It came at a particularly generative time, when there were lots of other great thinkers and doers blogging, and we were all following and responding to each other's blogs. Back then, blogging was much more about thinking together than it was about broadcasting or demonstrating expertise.

If it's not captured, it didn't happen. We were on the same page about the digital infrastructure needed to do this well (e.g. fine-grained addressability), but at the end of the day, it still required that people actually do it. Chris was much more disciplined than I was about making sure that there was some record of every interaction, which helped instill in me the importance of and intention to do it. To this day, one of the hallmarks of my teams is our discipline around note-taking. That all started with Chris.

Synthesis is part of the work. We all too often look at synthesis as "something extra." One of our shared beliefs was that synthesis was part of the work, a necessary component of critical thinking and stigmergic collaboration. Again, Chris was more disciplined about this than I was, but working with him helped me develop greater discipline. In many ways, I've been missing someone like Chris on all of my teams since, as I tend to be the sole person setting the example when it comes to capture and synthesis. (My HyperScope team was just as good at overall information hygiene, and we were collectively decent at synthesis, but I still carried the team in that regard.)

Develop a rhythm. One of the reasons Chris and I worked so well together asynchronously was that we had an excellent work rhythm. We were in different time zones, and when things were working well, I would wake up in the morning, read something new that he had written, and build on that. He would do the same. Chris named this rhythm as being super important, and would often talk about the little things needed to re-establish it when things got out of sync.

Practice good information hygiene. Everybody I've worked with has not only heard me talk about information hygiene, they have adopted the term easily (although sometimes reluctantly). Chris, obviously, coined it. He was an expert practitioner at it, and he helped me get better at it.

Better tools enable better practices. On describing what brought us together, Chris wrote, "We clearly shared the idea that good tools combined with good use of those tools was an important aspect of being good collaborators." From a technical perspective, we zeroed in on a set of fundamental knowledge practices that would help us be less dumb — capturing content easily, citing specific content, supporting reuse — and tried to identify simple ways to support them. For many years, we were known as the "purple number" people. On the one hand, this seemed ridiculous, since purple numbers were such a simple, "obvious" concept. On the other hand, the simplicity sometimes belied the power, and so we were happy about the association.

Never let a big, overwhelming idea get in the way of doing something. In the early days, we talked a lot about how to do transclusions "right." It was not on our near-term roadmap, because it would be complicated to do. Then Chris decided to just do it. It wasn't the "right" way to do it. It was a total hack. But it was beautiful and important, because it was simple, because it demonstrated the concept, and because we were able to learn a lot from actually using it as opposed to just thinking about it.

Invest in story. One of Chris's observations / critiques of me was that I am the type of person who wants ideas to simply speak for themselves. It's not that I'm not willing to evangelize an idea, it's that I sometimes don't understand why I need to. Just look at the idea! Isn't it obvious?! It's clearly not obvious to everyone, and if I want to make the world a better place, I need to invest in explaining what I see and understand to everyone else in an accessible way. When he first told me this back in 2003, I knew he was right, and it's a battle I've been fighting (and mostly losing) ever since.