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Jan. 31, 2022, 6 a.m.
The 2022 Omni Roadmap with Ken Case

Today, we hang out with the CEO of the Omni Group, Ken Case.  He talks us through all of the exciting details of the Omni 2022 Roadmap Blog Post.  Discussion covers the OmniFocus 4 TestFlight, Omni Automation, application support for Shortcuts, and more.  At some point, Ken may or may not also divulge a few additional upcoming OmniGraffle spoilers.


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 The Omni Group's 2022 roadmap with CEO, Ken Case.

Andrew J. Mason: Hey, everybody welcome to another episode of The Omni Show. My name's Andrew J. Mason, and we have seen some rumblings around the Omni Slack channel. In case you're wondering, yes this show is that show. The Omni 2022 Roadmap Show. I couldn't be more thrilled to talk to Ken Case, CEO of The Omni Group. Ken, how's it going these days?

Ken Case: Oh, it's going great. Thank you.

Andrew J. Mason: That's so good to hear. It's tough out there.

Ken Case: One of the things that I nod to at the beginning of the roadmap is actually the situation that we're all still in, this pandemic situation. It's not a great situation. So I shouldn't say great from that point of view, but we're settling in at least to adjusting to life in this state, and I'm really hoping that once we get past this Omicron wave, we have life returned to some semblance of normality, we'll find out.

Andrew J. Mason: Yeah, absolutely believing that the best is still ahead. And it's a great point that you mentioned because everything that we're going to talk about today is in the context of a distributed work environment. And once you look at this list, it is so amazing how much our team got done this year. Everybody deserves a back pat because 2021...

Ken Case: It's been a busy year.

Andrew J. Mason: It has. And I think sometimes we don't sit there and take the time to celebrate the accomplishments that happen because life comes at us fast and furious. So let's wind back the clock back to the beginning of 2021, the first item or milestone had to do with OmniPlan. Talk to us about that a little bit?

Ken Case: Yeah, absolutely. So, this time last year we were putting the final touches on OmniPlan for the iPad and iPhone. In the past, our product releases between the Mac and other platforms... In fact, all of our platforms started out being completely independent ports of each other, right. They were independent development efforts, where we of course originally developed all of our apps on Mac and then the iPhone shift, and we brought on the focus there. And then the iPad shift, and we saw an opportunity for some of our Mac apps to come to this much more mobile touch experience and started bringing our apps there. But they were new SKUs, they were new products and we were selling them separately and they had their own product cycles, and we started over with version number one as the version number that we were using for all of them.

Ken Case: So even though at the time when OmniGraffle was in version 5, it was OmniGraffle 1 for iPad, and fast forward, now we have OmniGraffle 7 on the Mac, we're at OmniGraffle 3 on the iPad. We ended up bringing the iPad app over to the iPhone as well and then unifying them, so it was one universal app. Which was not a big deal for the apps that were previously iPad-only apps, but it was a big deal for OmniFocus, where we had that merge going on. Long story short, we wanted to get to a simpler experience, where people didn't have to worry about where have I already purchased this product? Where can I use it? Where am I allowed to use it? And instead know that anywhere that you buy one of our apps, you can use it on any device where that app runs.

Ken Case: So OmniPlan 4, last year was our first app to become truly universal for every purchase of the app, now unlocks it everywhere. We do have universal purchases available of all the other apps in the form of our subscriptions. So if you subscribe to OmniFocus or OmniGraffle right now, you get it across all devices. But as time goes on, we want to make it so that every purchase, including the traditional licenses, where you're buying once and you don't have to pay over and over again every year, work the same way. You buy it once and now you have access to it on any device, so that's the start of last year.

Andrew J. Mason: Which is not a shabby start mind you. And so many people look for parody in their apps and their ecosystem, like I want to pay once and have this app show up everywhere. And that simplicity isn't for free, it's hard one. It's something that I believe this team has fought for, and I so respect that. It's not something that comes for free. So all of that's happening, and then around May, right before WWDC, the team decides to set their sites somewhere new, let's talk about this.

Ken Case: Well, the big thing that we announced and launched in May, we started an experiment really, a set of experiments. Which was that we announced OmniFocus 4, which is the upcoming new version of OmniFocus, but every major version of our apps takes a while to develop. And by a while, I mean these are multi-year projects, they're not something that happens in just a few months. Often they will take three or four years between one release to another, and if you look at our release history, OmniFocus is now almost 15 years old. You can see that there's this time between each release as we do this development cycle. But with OmniFocus 4, we announced that we were starting a TestFlight and that people were invited to check it out and come help with this test. With this version, we are redesigning and rebuilding the app.

Ken Case: We wanted to take a step back and think about what were our goals when we originally designed the app? What sort of feedback have we received from customers about how well that's worked out and what decisions would we make differently if we were doing it from scratch again now? And because we're stepping back and reimplementing on top of Apple's latest technology, SwiftUI, their new framework for doing this sort of development. We had the opportunity to say, well, if we're rebuilding everything anyway, what would we build differently? Maybe let's try a few of these different experiments.

Andrew J. Mason: And how was that received?

Ken Case: Well, the feedback we got was overwhelming. We had thousands of people sign up, saying that they would love to start the test flight and we weren't ready for that level of feedback right away. So we started inviting people in batches over several months. It took before we got to the point where we were caught up on everybody who had signed up, was now invited, and from then on, we would just have open enrollments, all you have to do is sign up and you're immediately in the TestFlight. And now, of course, we're over 7,000 testers.

Andrew J. Mason: 7,000 testers. I can barely manage seven people giving me feedback, so 7,000, there you go. I think we've mentioned this before, this idea of co-creation that happens with the users. I think it's so cool that we look to the broader ecosystem of what's going on in current Macintosh trends that informs our design. But then also down to the individual user level, what is it that the customers really want and working in tandem in the middle with all of them, I think, is what creates as good products as we have.

Ken Case: Yeah. This time we wanted to recenter the experience and make it much more approachable, much easier for people to just dive in and start using. The goal that I had in mind was, let's make it as easy to start using as Reminders is. And that's a pretty aggressive goal for something that's as complex as OmniFocus is. It's not complex just because we love complexity, it's complex because we're trying to make it powerful enough to solve some real needs that customers have, but we don't want everybody to be faced with that right off the start.

Ken Case: And we've really appreciated having this broad set of customers testing out as we go along week by week and make changes, and not every step is the right step. We might try an experiment for a week and quickly back out, or sometimes we'll try it for a month and it'll lead to something totally different, then we realize, oh, this can do it, we can solve our problem even better. But really, centering that experience back around the task list itself, the outline, being able to edit things in line, being able to build more flexible perspectives, and present the content in different ways. And then making the navigation itself more efficient, particularly on the iPad and iPhone.

Ken Case: Yeah, there's a lot of fun stuff in this release—and if anyone listening is intrigued, we invite you to check out the edit test line.

Andrew J. Mason: Absolutely. Jump in and give it a whirl if you haven't already, and we're excited to keep creating this. Let's talk a little bit more about WWDC, what happens there? You have fresh challenges implementing whatever OS-level changes are thrown your way. I personally like to call this the mini-game because it's like, who knows? What could it be? And so in September, October range, we have brand new versions of macOS and iOS, and what happened there?

Ken Case: So, as I mentioned earlier, we had decided that we were going to rebuild this version of OmniFocus using SwiftUI, which is a new framework from Apple. So we knew that was going to require at least macOS Big Sur, macOS 11, because SwiftUI wasn't really supported before that. So that gave us a baseline and i0S 14, so that was sort of what we were planning on, and then we listened to Apple at WWDC and discovered that they had made a number of additional improvements to SwiftUI, for things that would address feedback that we were already getting from customers about things that they were wanting in the app and wondering why it didn't support drag and drop as much as they wanted... Or there were bugs as well, they were performance issues and so on.

Ken Case: This is relatively new framework for Apple, and relatively new framework... And so we made the decision, okay, well I guess let's stop building for this old platform that is already shipping. We're only going to develop for this new platform that hasn't even released yet. And that's kind of a risky move, right? Because you don't know how well that platform's going to turn out, that's part of the reason we didn't do it upfront in the first place. But when we saw just the amount of attention that Apple had given to new SwiftUI framework and how many improvements and bug fixes they had made, it became clear that we didn't want to spend the rest of the development cycle, trying to work around the same problems that they'd already fixed. Let's instead build on top of the fixed foundation.

Ken Case: And that meant we would have to wait a little bit longer maybe before we would be on that foundation, for sure, and before some customers could use it. Of course, that meant some people that had signed up for the test flight and were in it were now left out of it because they didn't want to jump onto Beta during the summer. But, after a few months, Apple did ship iOS 15, of course, in September. And then everybody was able to jump back onto a released operating system and hop back into the test flight, and it definitely felt like the right move.

Andrew J. Mason: I want to pause too and give a nod to something that has been happening, I don't want to say behind the scenes. It didn't necessarily get the roadmap nod, but it has been a multi-year project, and that's the Omni Automation framework. If you haven't heard of it yet, or this is your first episode listening with us, You're going to find out a lot of cool things about how to give new superpowers to Omni products through scripting. Do you mind just giving us a few words about that Ken?

Ken Case: Sure, absolutely. One of the initiatives that we've had over the last several years now, has been to try to bring the power of the apps and make it available to the user in more flexible ways. Let users kind of customize the apps to meet their needs. And in order to do that, we built this Omni Automation framework that people can build their own plugins and scripts and really drive our applications, creating their own interfaces, creating their own keyboard shortcuts that match their particular workflow... Customize it to whatever they need. And then of course you can share that with other people, maybe you can find somebody else's workflow that saves you some time or use that as a template to build your own thing or to customize. And so we've seen people use that in so many different ways to improve all of our apps, really. Especially OmniFocus, I think is where a lot of people spend a lot of time recently in building all sorts of different Shortcuts options.

Ken Case: Well, over time we've been trying to make that API richer and more flexible, so people can continue to do more and more with it. So we've added features like being able to open files or present more interface elements, store passwords, connect to web services, on and on. And now you can have a plugin that you write for OmniGraffle that would connect to a web service and scan a network, and then draw a diagram of it on your canvas. That's now possible with the technology that's built today. I haven't actually seen somebody build that yet, I would love to... For somebody to do that. I keep thinking maybe it would be a fun spare time project for me to do because I do have a network that's worth scanning—enough pieces to it. But anyway, things like that I think really again, bring the power of these applications out to where the user can do more with them.

Ken Case: And of course, a part of that, we don't want that just to be available to people who can program JavaScripts. So we've also been implementing better support for Shortcuts, [inaudible 00:12:28] shareable, easily for people... Somebody can write a shortcut. Our recent shortcuts have support for Omni Automation JavaScript code in them, so you have all the power available from JavaScript, but it's as easy to use and share as shortcuts are and can be triggered along with anything that shortcuts works with, in the iPhone or iPad platforms or the Mac now in macOS Monterey. So yeah, it's been a fun time to see all of this ecosystem grow and to know of different ways people are putting this power to use and we want to continue to extend that ecosystem, just to make it even easier for people to do things.

Andrew J. Mason: That's so great. And it reminds me of Joe Buhlig, who we were talking to last episode, how I found out that there's a script I was using that was giving my OmniFocus install a brand new superpower. And I had never even met the guy that had coded it, and it's so cool that I don't have to know JavaScript, I get to extend the power of this app, it's a very neat thing to see.

Andrew J. Mason: Let's fast forward over to this year, and as I'm reading through your post and you're turning your sights toward the future, I came across one line buried right in the middle of the post and as soon as I saw it, I double took and I'm just going to read what you wrote. You said, "We continue to work on OmniFocus 4 and we'll of course be making it a universal app, the first of our apps that will be universal right at launch. This means, that we plan to ship all additions of OmniFocus 4 simultaneously across all of Apple's platforms, that will be a huge milestone for us." And as I read it, I had that cartoon character response, [inaudible 00:13:57] what!

Ken Case: Well, this is kind of the natural outcome of making the app universal. It does take longer to sync all of this up, and it does mean some waiting on one platform or the other, perhaps. But we think this story is a lot more confusing if we say that OmniFocus 4 is available, but oh, right now it's all only available on the iPhone, and now it's also available on the Mac. That's kind of hard to explain and… what should I be buying? Do I need to wait? Is it sync compatible still? All these sorts of questions that make for a confusing customer experience, really.

Ken Case: So when it came down to it and we thought about it, we decided, well, it's not ready to ship today, of course for the iPhone and iPad. But if it were, we could then just turn all of our attention to the Mac and finish it up there. We would still want to wait until both sides were completely done and then say, All right, it's time to ship because that means that OmniFocus 4 is really OmniFocus 4 everywhere at the same time, not in this half-world or that it's still a lot to do.

Andrew J. Mason: I love it. OmniFocus 4 isn't all for the future, coming down the pipeline after OmniFocus 4, what's the next software that we're turning our sites towards?

Ken Case: Yeah, absolutely. So I mentioned that we would be doing this process of rethinking our apps and really redesigning and rebuilding them on the latest technologies across all of our product line. We started the process with OmniPlan 4, which was already in progress at that point, so it wasn't quite as dramatic a rethink... We didn't rebuild everything there the way we might in some of the other apps, but that was sort of the start of the process where we brought some of the outline and time blank chart of OmniPlan 2, the iPad and iPhone that hadn't ever been there, by making this outline code in SwiftUI. For OmniFocus of course, that's now the next step... That's the one that's in progress. And after this, then our attention will be turning to OmniGraffle. OmniGraffle was next up in our product schedule, anyway. We're a small team, so we can only focus the majority of our attention on one thing at a time, really.

Ken Case: And at the moment that's OmniFocus 4, in the future it'll be OmniGraffle, in the past it was OmniPlan, and before that, it was actually OmniOutliner, version five. We're just doing this cycle through the apps, and after we go to OmniGraffle, then we can take a look at the next OmniOutliner and so on.

Ken Case: But for the moment, the next step in line will be OmniGraffle, and we've already started looking back at the last 20 years of feedback because this app has been out since macOS 10 launched, and looking back there are some things on the wish list I realized, oh, this is something that we have been thinking about and wanting to do for a long time. And in fact, there's a request in here that was filed back in 2001 from a customer, and we're finally addressing this bit of feedback. But we would love to hear from all of our Graffle customers now that are using it and have wishes for the future, because this is a great time to be hearing from you and finding out what you would like to see in this next version because we look forward to making it the best ever as we do this redesign.

Andrew J. Mason: I'm curious, so I'm just going to go ahead and ask. Possible spoiler alert here, I know that this wasn't really written about in your post, but is there anything that we can look forward to in terms of features?

Ken Case: Oh yes, possible spoiler alerts. So one of the features that people have asked for, for decades, literally decades now, has been the ability to not just copy and paste to shape, but to copy and paste the shape and have them still be linked. So that when you make changes to one shape, it makes changes to the whole collection of shapes. And we've had some workarounds involving things like our link back feature, where you can copy something as PDF and then paste it, so you have this PDF representation you can scale and go back and edit the source. It will sort of take that form, but doing it right this time with true objects, the shared references is a feature that people have asked for, for decades, and that we think now is the right time to do it.

Ken Case: But I'll also give another example of how a redesign can help with OmniGraffle. The same process that we were just doing with OmniFocus, where we wanted to make the basic experience simple and easy and make the app as approachable as possible from the start, also of course applies to OmniGraffle. So we want you to be able to sit down open OmniGraffle, you see a blank canvas, but what do you do with it? Well, you should be able to see, here are some of the shapes that I can drag onto it, here's how I might connect with them and have that feel intuitive and natural.

Ken Case: And there are some great, simple diagramming tools out there now that you know, we're looking to as some inspiration... Okay, how should this look when you start out using the app? Now, of course, OmniGraffle has much more depth and complexity when you need those advanced features, you need to be able to get to the steeper part of the interface and get to more things, but you shouldn't have to start out being confronted by all of that. So again, yes, progressive disclosure is one of my favorite interface design concepts. And we plan to apply that to OmniGraffle as we've been applying it to OmniFocus.

Andrew J. Mason: And this early in the process too is also when the blue sky dreaming sessions happen. So if there is a killer feature that you're looking to see happen in OmniGraffle, we'd love it if you'd send an email to to let us know what you're thinking. Now, something else to pay attention to is that there's a very special anniversary coming up, talk to us about that.

Ken Case: Well, the domain, we registered 30 years ago, in this upcoming September is when we will be celebrating its 30th anniversary. Of course, at that time, there wasn't a website involved with that. If you can imagine an age where the domain name did not mean a website, it mostly meant an email address or maybe an FTP site or things like that.

Andrew J. Mason: Wow. So a domain name without a corresponding website.

Ken Case: The worldwide web was invented on the platform we were working on at the time, the NeXT platform. And that month was the month that NeXTSTEP 3.0 shipped on the platform. So that was one of the reasons we decided, all right, it's time to get serious about this, not just work independently as different independent contractors on the next platform. Let's form a little company, and let's call it the Omni Group, and went from there.

Andrew J. Mason: 30 years. I feel like the Internet's like dog years, it just goes by faster or something like that. And yet not only is it still here, but like we said at the beginning, I truly do believe that the best is yet to come for this team. Ken, as always, I enjoy our time together. Thank you so much for hanging out.

Ken Case: Oh, absolutely. Thank you for taking the time with me and thanks to all of our listeners for hanging in through this episode. And especially again, I want to thank all of those people who signed up for the test fight this year. Your feedback truly has been invaluable and has helped us guide where the next version of this product is going to go. And we appreciate your input.

Andrew J. Mason: Fully agreed. Thank you, Ken.

Ken Case: Thank you.

Andrew J. Mason: Hey, and I'd also like to add at the end too here. As crazy busy as you think Ken probably is as the CEO of Omni Group, and he's a busy guy. He loves hanging out with and communicating with the larger community. So you can follow him on Twitter @kcase, and you can also see him hanging out at the Omni Group Slack channels, and we'll throw a link to that in our show notes. Hey and thank all of you for listening today too. As always, you can 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