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June 1, 2021, 6 a.m.
How Thomas Vander Wal Uses Omni Software

On today’s Omni Show, we welcome information architect, Thomas Vander Wal. He's currently in charge of DevSecOps strategy and planning at a large aerospace company, and utilizes OmniGraffle & OmniOutliner to easily wrangle and visualize complex data quickly.

Show Notes:

In this episode, Thomas and Andrew chat about how tools like OmniOutliner and OmniGraffle interact to build a more accurate, coherent picture of your data- regardless of the situation.

Some other people, places, and things mentioned:


Andrew J. Mason: You're listening to The Omni Show. Get to know the people and stories behind The Omni Group's award winning productivity apps for Mac and iOS. My name's Andrew J. Mason, and today we talk to Information Architect Thomas Vander Wal on how he uses OmniGraffle and OmniOutliner.

Andrew J. Mason: Well welcome everybody, to another episode of The Omni Show. I'm so excited about this one, because we are honored to be able to have Thomas Vander Wal with us currently today. He's a brilliant mind and information architect, and he's currently leading the DevSecOps, strategy and planning at a large aerospace company. He's held many roles in the past, from leading product design and architecture to new product efforts in R&D labs, or running skunkwork teams. He's been mentoring cross-functional teams to modernize and improve their work methods and patterns. And, he's lead and mentored information architects and knowledge managers. He's best known for coining the term folksonomy and initiating the term InfoCloud, with its personal InfoCloud and local InfoCloud framings. Very smart guy.

Andrew J. Mason: Thomas, we are honored to have you with us today. Thanks for joining us.

Thomas Vander Wal: Thank you. It's a great pleasure to be here. I've been a huge fan for a long, long time. Between OmniGraffle and OmniOutliner, I do an awful lot of thinking in those tools. They help me think and work through things.

Andrew J. Mason: One might have a general idea as to how OmniGraffle or OmniOutliner might be used in information architecture. OmniOutliner I could foresee as being something more sequential and OmniGraffle a lot more associative. But, let's back up before we even hit that direction and talk us through what is an information architect? What do you actually do? How do you even get started down that career path?

Thomas Vander Wal: I'd somewhat stumbled into it backwards. So in the late '90s, it was the days of the webmaster, where you did everything. One of the things that I had learned in grad school in public policy was dealing with large datasets, being able to understand data, how the flows work so you can do analytics. But, being able to understand the systems and the data, and what you need to tell a story, or to understand something, that training in grad school bubbled up into how I dealt with the web and web applications, so making things easy to find.

Thomas Vander Wal: One of the skunkwork projects that I did, starting in '99 and ran through 2001, was taking all the data that US Department of Transportation captured and was required to capture, and building a front end to all that data where you could mix, match and marry datasets and get information about the datasets, as well as run some lightweight analytics on datasets that you were mixing and matching, as well as being able to put that onto maps [inaudible 00:02:47]. We had one of the first versions of Esri's web interface for GIS.

Thomas Vander Wal: So being able to take all that information, bring it forward, being able to have metadata viewers that you could pop up as you were working with the data to understand analytics for continuous data, understand the different cardinality. As well as being able to understand changes in regulation, because a motorcycle is not a motorcycle every year, a pickup truck is not necessarily a truck every year, and the weights and all the different things that come into play shift. So if you are trying to have a good dataset and analysis, you need to understand, "I need this description of a motorcycle for this year, something that is equal to it, to be able to run time series."

Thomas Vander Wal: So digging into data, complicated datasets, complex datasets, a lot of that was in my training and how I viewed things. But then, also just looking at information systems, how something flowed through a system, what are the touchpoints. And then, over the years of being able to work with two-sided systems, where you have either internal customer service or citizen service, and then external customers or people out in the field in your own organization. What are the touchpoints, who is helping what, what systems are involved, and being able to take a schematic and a workflow of a system and understand where they go to, customer facing systems or using facing systems, where they are a support side system. Essentially, you're trying to tease out and understand how the people who are going to be using the system think about things, understanding their mental models, but also what are the terms that they use and how do they think about it in their own perspective. I've worked on systems where you can have vastly different interfaces and vastly different terms, based on whoever is using the exact same system.

Thomas Vander Wal: It's essentially information architecture is making those understandings. Understanding how people think about the system, how it fits into their life and their needs. And then, being able to connect to whatever the system is and what is in it, and what service you're trying to provide.

Andrew J. Mason: How much of an art versus science do you find this to be? Is pattern recognition a very sequential process for you, that you go step-by-step and then you figure it out? Or, do you see patterns just start to emerge in a more artistic fashion? And intuitively just say, "Nope, that's what people need to bring forward and visualize in a certain way."

Thomas Vander Wal: It's yes to both of those pieces. One of it is being able to have there are patterns and being able to tease things out, but part of building systems and understanding an organization's or a customer's need and what their problem sets are, quite often those are not well defined. I've done an awful lot of work with large enterprise, which quite often have really poorly thought through and poorly developed tools.

Thomas Vander Wal: Every now and then, someone will ask what I do and it's just, "I make work tools suck less." People are hired to do a job, and they are given tools that get in their way of helping them do their job. So being able to, essentially, tease apart what those pieces are, understand the underlying patterns, and the underlying theory and framework for the social or complexity lenses. Which is just taking the small pieces as they standalone, what are they, what are the ground truth underneath them, and being able to ask people, "Does this describe your problem? Is there anything here?" If there is, good. And then, being able to, if there is something, hold onto it, pick up another lens, walk them through that. And then, just start layering the things that are relevant.

Thomas Vander Wal: You can start seeing problems in things that are complicated, where you can solve things from various grids or complexity, where when one thing shifts everything shifts, once you take an action and the paths change, so being able to see those. Quite often, when you're dealing with people who are interaction with a system to interact with people on the other side, humans are incredibly complex. Everybody has their own understandings and framings of the world, what the tools are, what their roles are, how they do things and it's usually different than the person on the other end. You may think that you're making a nice gesture on your side to the other person and they're getting poked in the eye, and you really don't have that understanding.

Thomas Vander Wal: So being able to frame that, and tell stories, and go into the most important things is being able to essentially have a map that you can point to and talk about something. OmniGraffle is one of the tools that helps me do that very, very quickly and is incredibly helpful for that.

Andrew J. Mason: There is this ... We're humans, there's an emotional component here. And to be able to say, when you see information that pokes the box or messes with somebody ... To be able to say and look at it in a third party way and say, "It's not you, it's not me, we're looking at this objective third party thing," that's got to be really helpful.

Thomas Vander Wal: Yeah. One of the things that comes into play with a lot of organizational work systems is that they're collaborative. Office 365, you can have two people working in a spreadsheet at once, two people working in a document at the same time. And how do you do that, or when you have multiple people being able to have comments and other things, being alerted when someone has made a comment in a document or made a change to it, so you can go directly to that and see that. And, have built up frameworks around those pieces and the distance that you are from a document, and having a point system. If you're in the document seeing something, you get five points. If you're getting a notification about that in Slack or some other system it's, "The word then was changed to this." Well, what's the paragraph, where is this? You have no idea.

Thomas Vander Wal: So it's being able to bridge those together and seeing that distance, seeing it represented. What are the things that you need to close that gap and have a better understand? It's the visual framing, but then also understanding all the components that come into it. Quite often, we'll start doing round trips in a workflow between OmniOutliner and a mind mapping tool. Quite often, you use MindNode or iThoughts. Save things out as OPML, pick them up in OmniOutliner, flesh things out, move them around a little bit. Pick it up in the mind mapping tool, rearrange, looking to see if there's sub-components. And quite often, as they get larger, the mind map becomes problematic and you really need to start working just in the outline. And the outline becomes the framework for writing things out as well, and building presentations and building stories that need visualization as well.

Andrew J. Mason: So OmniGraffle and OmniOutliner, this is crazy, I'm looking at my notes. You have over 220 OmniOutliner files dating back to the early 2000s, and over 550 OmniGraffle files dating back to the early 2000s. In what ways have these products assisted you?

Thomas Vander Wal: With OmniOutliner, a lot of it's building a framework for telling a story, understanding the various components, being able to see what is connected to what and what are subsets, whether it's a mental model and understanding, if you're looking at social scaling and the different social scaling.

Thomas Vander Wal: One of the things having public policy background is it comes with an awful lot of social science, at a grad school level. And, understanding encampments or you've got 20 people living in a small community, community grows and gets up to about 500 people. The needs for 500 people are different than 20 people. There are certain tipping points and inflection points that surface along the way, so being able to frame all of those as you're working along really helps. One of the things that understanding social scaling, from an urban planning or an encampment model, is that pretty much those exact tipping points are the same things that happen inside organizations, the same tipping points happen.

Thomas Vander Wal: You can walk into a company or meet somebody for lunch and not know the size of their company and the problems that they're having, the things that they're adding to their organization are really good clues as to the size of their company. They can mention something and they're like, "Oh, you're about 75 people." They're like, "How do you know?" I'm like, "You just said you had these problems. Those are problems that you hit between 50 to 75 people." It's just pretty much a doubling to a tripling, with the gap between the double and triple as that room for error.

Thomas Vander Wal: Different organizations and different models, when you hit those tipping points, the pain gets much worse at different points, depending if you're distributed or remote. Or, if you have a company over two floors, you're essentially getting things that if you're having two different offices in two different locations. Because the vocabulary starts shifting, how people work on different floors can drift quite a bit.

Andrew J. Mason: That's wild. So entire cultures encapsulated within one floor of an office.

Thomas Vander Wal: Yeah, it's nuts. When you know that it's a possibility, you start seeing it everywhere. You're like, "Oh yeah, of course." People talking about problems that they have in their organization, how do you start solving it, and some of their problems, "It sounds like you have two offices." They're like, "No, we have one office. We're just on two floors." Well, that's part of what's driving it.

Thomas Vander Wal: I had done work with a large bank in the Northeast. Their headquarters was downtown in the city, their second largest office was 20 miles away, and people could hot desk and work from either location. People would say that it would take them about a week or two to adjust to the different vocabulary for, "Where's the supply closet? Where's the copier? How do I get this done?" Just the vocabulary was drastically different in 20 miles. They're like, "It's like working in a different country, or a completely different company in a completely different country, using the same language."

Andrew J. Mason: So when you're helping somebody out and you have all of this complexity in front of you, do you go for the lowest hanging fruit, the most obvious pain point first? Or, is this more like the jar of salsa that fell from the kitchen cabinet onto the floor and shattered, and you just, "We've got to pick some corner somewhere, it doesn't really matter where. Let's just start cleaning."

Thomas Vander Wal: Yeah. In the lenses that I have, you usually start off with about three to six different lenses, and part of it is just helping people realize, and more importantly see, what they have going on. A lot of people are like, "Oh, it's just work. We're looking for a solution that does this." They're looking at the end point and not wanting to understand the materials or your building environment. When you're dealing with people, people are the materials and you need to understand the materials really well. So it's, "Okay, here's the social scaling, here's how teams work, here are the nine to 12 core tools or elements that people need to do their work in a team."

Thomas Vander Wal: It's just, "For a good team function, here are the pieces," and you can walk them through those, you can walk through the social scaling piece, how teams work with teams, what's the ecosystem inside an organization of somebody on a team asking a question, nobody on their team knows, going out to a community of practice for that domain asking a question, getting good responses back. But, you may have somebody else on the team going to a different domain, asking the same question and getting slightly different things back, which is quite often good. And then, taking those two different domains and then bridging them together around that similar idea. And then, being able to take that from the top down, where you have a community of expertise, which is usually managers, and highlighting things that are coming up and bubbling up from the bottom for good solutions, and highlighting them across the company, tucking them away in a knowledge base or a learning environment.

Thomas Vander Wal: So you're essentially sharing your lessons learned across the whole company, and making them easy to find.

Andrew J. Mason: Thomas, do you find that, once awareness is brought to a given situation where change is needed, that change just naturally emerges? You can't unsee it, there it is, and it's a lot more obvious now.

Thomas Vander Wal: Yeah. A lot of times, there is so much change and there's so much differentiation in tools and working environment, and the people running things and needing to make decisions around tools and how things work, having that depth of understanding of what is needed, it just isn't there. An awful lot of the large consulting companies are not going to that depth as well.

Thomas Vander Wal: So being able to bring in understanding of here's how teams function, being able to run it, pairing with a jobs to be done model. And saying, how do you coordinate things, how do you manage a schedule? How do you know when things are due and where your shared document's stored? And being able to give rating points, "Hey this is done really well, this is not really done well." And then you're able to say, "Okay, here are the things that you need to focus on for tools, and particularly in a collaborative environment like a team or teams working with other teams and other groups." Being able to understand that, but also being able to see it in example, really starts helping as well.

Andrew J. Mason: Okay. This might be a horribly worded question, but I think you'll get the spirit of where I'm headed with it. We recently had Harvard Professor Alyssa Goodman on the show as well, talking about your path to Newton Diagram that she created in OmniGraffle. And, the level of complexity and detail that was visually communicated with just one image was mind blowing. When I go in to create a diagram myself, I tend to think very linearly or one-dimensionally. How do you get to a spot where you get the off-ramp of that circular thinking and see the multiple dimensions layered on top of each other? How do you have that holistic view of multiple layers of complexity? Does that make sense?

Thomas Vander Wal: Yeah. Some of it is walking back to finding a good metaphor, and being able to take things out of the norm and making it really simple. Quite often, in workshops and talks around complexity model and social work environment have a very high level framework called the Social Progression of Fire. Where you just start out with sparks and sparks of ideas in a Slack channel or Twitter, and you're running across things. And people are saying, "Hey, did you see that this is going on?" Or, "A competitor's looking at this." Or, "Some of our customers are saying that they have a big need, and I think we can solve it." You have eight people that are talking about it and they may not be connected, it's just surfacing. And saying, "Hey, we'll take these sparks and build a campfire."

Thomas Vander Wal: So have a safe place where you're essentially just doing a brain dump, sharing things with each other, capturing things. Figuring out, "Is there something here? Should we build a new product? How do we support this?" It could be as simple as bringing your dog to work, "Should we be doing this?" But, you have a small group that's looking for something, figuring out if there's something there. Essentially figuring out, also, if they have enough of an understanding of the subject. And if they don't, add a couple other people to it.

Thomas Vander Wal: But, it's essentially just a very small group that has interest in a subject, bringing them together, brain dump capture it. If there's something there and you want to move forward, you're essentially adding more fuel to it and turning it from a campfire to a bonfire. You're essentially opening it up to more people, you have a legal review, you have people who are working on packaging, you have people who are working on logistics, thinking how you can deal with global trade issues. Just all these different things start coming into view and you're like, "Can we do this? Do we want to do this?" And then going, "Okay, yeah we can build this." It goes from this campfire where there's a lot of people involved, back down to a small team that can build it, and that last piece is you're building a torch.

Thomas Vander Wal: So you're having something that's safe, reliable, repeatable, that you continually can turn out. So you've gone from the spark, to the campfire, to the bonfire, to the torch. And you have different social models, different interaction models around essentially the same thing in the idea building, and following that spark of a flame, and getting it all the way to a torch where you can hand it off to other people, it has function, you can add it to a building or a street post, and it becomes something that's really helpful.

Thomas Vander Wal: So taking a model like that, people start seeing that there's different interaction models and different scales, and then walk it back to some things that are more closer to less metaphor and more reality and actual structure. And, looking at small group dynamics, how do ideas come in. Or, if there's pain points or other things that are surfacing, how do you collect them, gather them, bring them together in a group. And quite often, you're using very different tools.

Thomas Vander Wal: An awful lot of companies, and particularly large companies, they'll want to have one tools that's easy to manage, which doesn't necessarily exist. If you can get a tool that can cover all those different social scales, and dimensions and interaction models for work, that's a good thing. But, they don't exactly exist so you have to start thinking about how do we inter-operate between things, and being able to have essentially a link when you're at the torch and be able to track it all the way back to the spark. It's like, "Oh yeah, there was this one piece on one of the sparks that came up that we didn't really capture along the way. We could iterate on it."

Andrew J. Mason: Thank you so much for walking us through one of those lenses as a for example, I think that's really helpful.

Andrew J. Mason: Let's talk a little bit about this idea of folksonomy. This is a term that you had coined in the early 2000s, about what was happening with traditional structure online as people were starting to give labels and names to things themselves. It was like taxonomy, this idea of cataloging things, as it related to just everyday folks doing it. When things like Flickr and Delicious were coming out, you really saw tagging starting to come to the forefront. How has that changed over the last decade or so? How has the vision shift or morphed in any certain direction? And, what do you see happening right now with that idea?

Thomas Vander Wal: There's a few different things. One, I still see around, and quite often seeing it inside organizations and inside groups where the folksonomy is essentially a person tagging something. They're tagging an object in their own vocabulary that's shared out. So most taxonomy systems are two-dimensional, you have an object and a tag, you don't know who put it on there. One of the things that I had framed out really early on was the benefits and the detractors of having a taxonomy, and then the benefits and the detractors of folksonomy.

Thomas Vander Wal: The thing with the folksonomy is that it's always updating. You're essentially doing it for free, because people are putting things on there so that they can re-find it later and re-find it themselves, and doesn't mean that it's necessarily good for everybody. But, you also can start understanding somebody in engineering is working on something, they have a certain label, somebody in marketing is working on the same thing and they have different labels and tags for it. You could have somebody in, taking that same concept, and working business models around it and they're using different vocabulary and terms on it. But essentially, they're talking around the same object.

Thomas Vander Wal: So being able to take that object, look at what one person has put on it, find other things with that term, and then being able to take another term, look at it from somebody else's perspective, other tags that they've put on it and other things that they've tagged with that term. You start getting this relatively rich synonym repository for bringing people together, to essentially reduce error but also being able to build out the taxonomy so that people can find what they're looking for.

Andrew J. Mason: Can I ask, what are you seeing emerge as this trend takes a more personal direction?

Thomas Vander Wal: One of the things that's been interesting is there's enterprises that are doing this internally. When I saw Delicious in late 2003, early 2004, it didn't click as to what it was doing, which is somewhat ironic because it was essentially the solution to a problem that I had working for a legal trade association in the mid '90s. And we were using CompuServe as the internal member social platform, and allowing people to share briefs and share experiences from different cases, or looking for help, and there was the ability to add categories or tags to things. But, it was a flat field of 255 characters.

Thomas Vander Wal: One of the things that became quickly apparent is that there was three different groups within the organization with three different mental models for what things should be called. And then, you also had was this something that the organization put out there? Is there a preferred, authoritative term that's out there? We were talking to CompuServe an awful lot and their product folks and it's like, "What we really would like to do is put something out there, be able to add categories, or organizational tags or labels to things, but then individuals tag it in their own vocabulary and terminology for their own collection." This was '96, '97 and CompuServe was like, "Oh, this will be coming when we move from the desktop to the web and that'll be in 12 months." And 12 months turned into three to four years, and they didn't quite have it then, and people had moved off to AOL and to all sorts of other places.

Thomas Vander Wal: When Joshua Schachter had built Delicious, I wasn't thinking in that model, that he was building essentially what we were looking for. But, I didn't really understand Delicious until I was looking for something, and I couldn't remember ... I was looking for something from an information architecture term, and there wasn't a whole lot there that had been collected or shared, but I knew that the knowledge management community had just huge volumes and background. But, I couldn't remember the term that the knowledge management community used. And, I finally found a resource that I was looking for in Delicious, and somebody had tagged it with both the information architecture term and the knowledge management term. So I clicked on the knowledge management term, and all of a sudden I had 30 resources. It's like, "Ah, this is phenomenal."

Thomas Vander Wal: And then, we got into ... There was an information architecture newsgroup and listserv. One of the things that information architects like to do, and spend an awful lot of time and attention doing, is naming things and trying to figure out what something is called. People were like, "Well, what do we call this thing?" I was like, "Oh no, this is going to be months of what do we call this. I want to talk about what it's doing." I had just thrown out folksonomy just to keep things moving, because it's regular folks essentially doing taxonomy, and it stuck and the conversations moved on.

Thomas Vander Wal: But, just had such a deep fascination, going back to the needs in the '90s, having a tool like Delicious. And then, everything from Amazon had tagging on it, which got to be very performative and sometimes insanely funny. There's a whole lot of different ways that self-tagging that's openly shared out, ways that it can work. But, one of the things that I'm finding interesting within the last year or two is where it has morphed to, somewhat in personal knowledge management tools, things like Obsidian and things with back links.

Andrew J. Mason: And as certain tools morph and change, how are you carrying this information with you? As hardware gets updated, there's new software, how do you carry this stuff along with you for the journey?

Thomas Vander Wal: Over the last probably 10 years, 10 to 15 years, I'd been keeping text notes and then, about 2010, I'd turned to markdown notes, for all sorts of different things. I thought I had around 1200 notes that I had been keeping with nvALT, but I also had some sub-directories underneath that, and it's probably around 4000, 3-4000 notes. Some of it will be early ideas for things that turned into blog posts or articles. I layered Obsidian over that and that became my vault. And all of a sudden, little by little, I will search for something and it will find different pieces. I'm like, "Oh, that's connected to this term or this mental model." One of the things I also have in there is one of the directories is around the social lenses and complexity lenses. So I'm now taking all these different ideas, tying them back, being able to tie them together a bit. But also, being able to see connections that I hadn't really been able to see before, which is one of the things I really like an awful lot.

Thomas Vander Wal: I have used DEVONthink as well. I've been using DEVONthink since about 2005, and have around 70,000 objects in there. So anything of potential interest gets putting into a PDF and tucked into DEVONthink. And have done some expert witness work and canonical pieces that are linked to from Wikipedia, that are just completely gone from the web, they're not in the Wayback Machine or anything else, but I have copies of them. Copies of the white papers, copies of companies' marketing materials, all sorts of different things, as well as discussion groups. Anything of potential interest, I just tucked away and can search it, and it does this relevance, fuzzy relevance engine work.

Thomas Vander Wal: So I use DEVONthink to find things. Quite often I'll go to OmniOutliner, and then in the notes underneath a piece, I'll link back to something in DEVONthink. One of the things I have in my directories that Obsidian is sitting over and correlating, and connecting things, is my OmniOutliner files and my OmniGraffle files. So now, I can take my graphics in OmniGraffle, put a file link to them where it's relevant. Oh, I've got six different versions of this visualization of a story that's related to this idea, and now I can find them easily, and then open them up and be able to pull them into presentation, or when I'm trying to explain something, pull it together more easily.

Andrew J. Mason: I see this really cool story arc emerging where you have all the thumbtacks on the map, and over time you're just trying to figure out, "Okay, how do I draw all the strings that connect these things together in a new way, or a fresh way, that helps me see things in an up-to-date way."

Thomas Vander Wal: Yeah. Every now and then, it's getting to about once or twice a week, where just going through and adding back links into a blog post or a note from eight to 12 years ago, and that will connect to other things. And then, I'll out to the graph view, which I didn't place much value in, I just thought it was a neat little thing ... I'm like, "Wait, what's this node connected to this other large node?" It's an interesting way to start exploring and just connecting ideas, and finding things that are relevant.

Thomas Vander Wal: It goes back to that listening to people talk about Obsidian and other things with the back linking, it's very, very similar to that folksonomy model, and personal information management and personal knowledge management, that essentially, using your own terms and using those back links as hooks to pull things closer to you that are connected. And then, taking that to the next step for the folks that are doing Evergreen notes and publishing them out to the web.

Thomas Vander Wal: There's a woman, Maggie Appleton, who just has a really, really nice collection of Evergreen notes and really nice visual explanations of things, taking that very personal collection, and then making it more public and sharing it. And then other people are picking up those, putting them in their own collections and sharing those out. It's the early days of folksonomy, early Web 2.0 of being able to have this nice web of knowledge that's interconnected, and being able to find facts, being able to find proof and the foundations for things somewhat easily, and being able to understand them. Going back to the Vannevar Bush days, all of that, "One day we will have this," it's getting close to being that day where we have it.

Andrew J. Mason: It's so cool to catch the circular nature of this as well. You know, how web used to be one thing, and then a Web 2.0 made it kind of the same thing but with some fresh ideas attached to it. And, this idea of InfoClouds become a very personal information repository that's tagged. And then now, all of a person's personal thought clouds can be tagged and then shared with another person. It's almost like repositories of information, it's just so cool to see.

Andrew J. Mason: One or two more questions. Can you tell me about an instance where either OmniGraffle or OmniFocus, you've been working one of those pieces of software and there's something missing. You're looking in all these different systems and levels of complexity, and by taking all of that information and externalizing it, suddenly something just popped out of you like, "Oh, that was the missing piece, that's what I've been looking for."

Thomas Vander Wal: Yeah. Bouncing between a mind map and OmniOutliner in early stages of discovery or trying to work something through, and thinking something is just a two-sided problem set, and then realizing that we need to connect not only people to things and stages of work, but we also have automations and different systems. It's like when you're moving across different systems or different stages of your work, you may be touching different tool sets. You get to a certain point and it's, "Oh, we hand off to another team, this team is out." How are we tracking across these things? And it goes from being a two-dimensional problem, or an easy set of two things of person and roles, roles and tools, to being what type of person are we looking at, or what type of individual. Is it a system, is it a person? What roles, how many different roles? Are roles tied to different stages of the development and the workflow process?

Thomas Vander Wal: Okay, now we've got to think about, this went from something really easy to describe, and to draw and to explain, to something that gets all bit more complicated and takes a little bit more thinking. But, when you can take that next step, and embrace the very complicated emerging into complex, it really helps everybody understand things. And you're able to say, "Oh, this process, we thought it would matter here. It doesn't come into play for three or more steps in our workflow process. We don't need to think about that now."

Andrew J. Mason: Oh yeah, switch those layers off. It cracks me up too, because it's like how many new insights did you have? "Oh just one, just one new insight." And, how much did it affect on that drawing? "Oh, a whole lot."

Thomas Vander Wal: Yeah. Yeah. One of the nice things about OmniGraffle is I can ... Sometimes I'll start sketching in pencil on paper, and you have legal copy paper sitting landscape in front of me. I'll just start taking notes and sketching things and then it's like, "Forget it, I've got to go to OmniGraffle." And then, just being able to move things around, "Wait, there's different layers," so start working with turning layers on, turning off. Okay, there's another dimension to this, and you start working with those different dimensions.

Thomas Vander Wal: I can get something done in OmniGraffle in about a third of the time that I can get something done in Visio. And, without the swearing.

Andrew J. Mason: I love it. I don't know if that's an official tagline we could use, but I love it.

Andrew J. Mason: Before we wrap up, I'd love to hear just a little bit more about how do you think with multiple layers and this idea of lenses. When you're looking at data and trying to get that perfect picture, I guess it can't be perfect, but that accurate picture of what's going on, and you're turning on and off layers and seeing multiple dimensions, how do you think in that way?

Thomas Vander Wal: One of the things, when I go back into the social elements list or the social lenses list in OmniGraffle, it's now up to 76 objects and it had started from ... One of my friends on Twitter, saying that he was working on a 3D project with data. He's like, "Oh, data and 3D is really complicated and a headache." I'm like, "Oh, you should try social, it's 7D or 8D." Which led to people asking on Twitter, "What's the 7D or the 8D?" Over three or four days, I was up to 12 or 15 high level dimensions. People had long been asking, "How do you think?" Part of it is I think in these smaller components and just do deep dives. "Oh, I need to understand this."

Thomas Vander Wal: Around 2010, I think it was about a year and a half later, I had around 40 social lenses and was stick around that for a while. And, it was about the time that Dave Gray reached out and his company had been bought, and the company that had bought him focused heavily on social. He's like, "I really could use a good understanding of your social lenses." He's like, "A lot of the social stuff just isn't making any sense." And walked him through all 40, somewhere between 40 to 44 lenses, but it took about four full days and he went through two cases of note cards. We would do a five-hour or six-hour session and he's like, "We've got to stop because I just finished a case of note cards. I've got to go out and buy some more." But, it was just walking through that.

Thomas Vander Wal: And then, looking in it now, it's up to 76 lenses, probably about 15 of them or so are other people's work that I find really helpful and continually point to other's work so I don't need to create it and it's really helpful. But then, also I've got pieces that are highlighted in yellow that I don't know where it fits with everything else, other people's work is in blue. But, when I do a full expansion of it, I'm coming up on 1000 rows in OmniOutliner.

Thomas Vander Wal: A couple times, I've started down the path of doing a book and realized that I can probably take a workshop, a half-day to full-day workshop, a half-day is about 12 lenses, a full-day is about 15, and do a book on that. And then, there's some where this one thing could turn into a book, just because there was so much in it. It's just capturing that accretion of knowledge and understanding, and just having a way to structure it. Even in 1000 rows, it is insanely high level and doesn't begin digging into anything. That's why I tie things back to my markdown notes that I keep in my note directories.

Thomas Vander Wal: So I'll flesh something out that'll maybe start toward an article, or a blog post or something, just keep track of it, keep the state of it. And, have a checkbox for yeah, this concept is written up. I look at it, and there's not a whole lot that I've fully written up, and maybe have about 20 things or so. A lot of it is just for memory, and presentations and workshops. We'll go back to those and we'll link keynote presentations to it, and other things that I've created and OmniGraffle files to it.

Thomas Vander Wal: So it's trying to find the connection between how Obsidian and lines in the outline, how to better connect those two. But, not quite there yet. I get sidetracked with what's in my notes.

Andrew J. Mason: Thomas, this has been an incredibly fruitful conversation for me, I imagine for our listeners as well. Thank you so much for joining us. If folks are interested in catching up with you or connecting with the work that you're doing, how can they do that?

Thomas Vander Wal: I'm trying to figure out what I pay attention to. Sending email to is probably the easiest way. Then, on Twitter I have @vanderwal, that's a private account, and @infocloud, those two accounts. I look in those a little bit, but also they push out to email and also push into Slack as well, so we'll usually notice it eventually there.

Andrew J. Mason: That is excellent. Thomas, it's been a great honor of mine and all of ours to be able to have you as a guest on the show. Thank you so much for joining us.

Thomas Vander Wal: Great, thank you. Keep up making great products.

Andrew J. Mason: And, thank all of you for listening today.

Andrew J. Mason: Hey, we're curious. Are you enjoying the shows, are you enjoying learning how people are getting things done utilizing Omni software and products? Drop us a line @theomnishow on Twitter, we'd love to hear from you there. You can also find out everything that's happening with The Omni Group at