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Feb. 28, 2018, 6 a.m.

Brent: 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. Hey, Aaron, get in here and play your jingle.


I'm your host, Brent Simmons. In the studio with me today is Ainsley Bourque Olson, OmniPlan PM at the Omni Group. Say hello, Ainsley.

Ainsley: Hello, Ainsley.

Brent: Thank you. Now you're the OmniPlan PM and I'm fairly sure, 'cause I don't know the answer, that PM stands for prime minister.

Ainsley: I mean it could. I am Canadian.

Brent: You are Canadian. Oh, wow, then certainly, it stands for prime minister.

Ainsley: No. In this case, that stands for product manager.

Brent: Product manager. So what's a product manager at Omni?

Ainsley: So at Omni, which might be very different from the way other companies work, our product managers are responsible for sort of the entire application. So as the OmniPlan PM, I'm responsible for OmniPlan for Mac and OmniPlan for iOS, more or less determining what work we do on the application, what bugs get priority, but also things like what needs to be documented within the app, helping support out with questions about OmniPlan.

Brent: Do you have a lot of say into what goes into a given release and that kind of thing?

Ainsley: Kind of depends on what else is going on. Following WWDC, we sort of have our marching orders from Apple, and Ken usually, but on the smaller scale of-

Brent: That's true. Apple tells us what to do then, yeah.

Ainsley: But I also have a lot of say in prioritizing crash fixes and bug fixes for a particular release, and whether something might need to go out sooner than we originally planned, that sort of thing.

Brent: Okay. Oh, that's pretty cool. So what is OmniPlan? It has something to do with project management?

Ainsley: Right. So OmniPlan is a project management application, which means I am the product manager of a project management app.

Brent: Cool.

Ainsley: Which is a little meta. And OmniPlan, unlike some of our other applications, has a pretty specific use case. So OmniGraffle might be used for diagramming, or wireframing, or laying out a floor plan, whereas OmniPlan is used almost entirely by project managers to help them schedule and budget their projects.

Brent: Is there a specific methodology or school of thought or anything that it adheres to? OmniFocus, for instance, was very GTD-focused, at least originally.

Ainsley: So OmniPlan started over 11 years ago with just a Gantt chart, which is typically used I think in more waterfall style project management. In OmniPlan 3, we also introduced a network diagram, as well as you can see your task outline. So it's fairly traditional project management that like a construction company might use for planning a project.

Brent: So it's certainly not just for software development. It's for any kind of planning and stuff.

Ainsley: Yeah, we see, yeah, all sorts of different types of use cases. It's pretty amazing when, occasionally a customer will email with a sample file because they have a question about their scheduling or why OmniPlan is leveling a project schedule in a certain way, to see it used for all sorts of things, projects big and small. It's pretty cool.

Brent: What does "leveling" mean? It's one of the apps I haven't worked on so I don't know that much about it.

Ainsley: So in OmniPlan, in an ideal scenario, you put a bunch of tasks in a project. You also put in the people that you have available, your resources.

Brent: Okay.

Ainsley: And any hard date constraints, like we can't start this phase until quarter 2," or "we can't start this task until this other task is finished." So you put all of that in your project.

Brent: So you have dependencies [crosstalk 00:03:49].

Ainsley: Right, dependencies, you're assigning resources, maybe you have a team of developers, if any one developer could do a particular task whoever's available first. So you put all that in and you say level this project.

Brent: Okay.

Ainsley: And OmniPlan gives you that ideal world, where everything goes according to plan, this is how quickly you can get your project done.

Brent: Oh, okay.

Ainsley: Which is a little bit like magic sometimes, and folks will contact us about why OmniPlan has chosen to schedule a particular task for a particular day, because you can get pretty complex with your scheduling needs.

Brent: Sure. Now I remember it was probably a couple of years back at a company meeting, there was a movie that our intrepid producer had made that featured a Las Vegas theme, and that had something to do with OmniPlan. What was that?

Ainsley: That is a trick question. No. It featured Aaron, OmniPlan's former PM, and it was about Monte Carlo simulations, which is-

Brent: Now that just sounds fun.

Ainsley: The video certainly is fun. It's a way of determining ... Basically, OmniPlan runs a bunch of simulations based on the information you put in and says, "We have a 50% confidence that this milestone will be hit by this date," and you can say you're more or less confident, that sort of thing. That's one of our Pro features that's fairly new.

Brent: Oh, wow. That's pretty cool though. Here's how things might go terribly wrong for you, maybe.

Ainsley: Yeah, exactly.

Brent: Right. Well, it's good to know, right. Is OmniPlan one of a kind or is there a lot of competitors? Are there similar apps?

Ainsley: That's a great question. I think there's a whole range of project management applications out there. The one that we're compared to most often is Microsoft Project, and we do import and export Microsoft Project files.

Brent: Sure.

Ainsley: And OmniPlan can be used for really similar things, but it's also its own app. Microsoft Project can be incredibly, incredibly complex and we've tried to make OmniPlan a bit more approachable.

Brent: I bet you, it's way nicer. I've never [inaudible 00:05:50] Microsoft Project, but ...

Ainsley: I certainly think so.

Brent: Yeah. I'd buy a Mac, just to use OmniPlan.

Ainsley: We often have folks who've just bought a Mac and really don't want to install Windows on it.

Brent: Yeah, right, okay, yeah.

Ainsley: That are looking at us as a potential alternative.

Brent: Cool. So how did you get into product management?

Ainsley: So I started at Omni a little over five years in customer support and then ... But 2-1/2 years ago, Omni was looking at switching to full-time product managers so for a long time, we had PMs who were say part time in support, part time managing OmniFocus or part time in test, part time managing OmniPlan.

Brent: What surprised me at the time, 'cause I remember that change, I thought everybody was a full-time PM already, yeah.

Ainsley: Yeah, I think it was ... I mean I didn't do it, but I think it could be tricky to juggle both sets because as a PM, things can jump out at you. It's hard to predict exactly what your day's going to look like.

Brent: I'm picturing the things like little monsters hiding behind the doors jumping out at you-

Ainsley: Yeah. Little bugs.

Brent: ... during the day.

Ainsley: Yeah. So when that position opened up, I applied and here we are.

Brent: Yeah. Cool. Did you need any training or did you have any experience with this before?

Ainsley: Looking back, I was surprised at how little I knew for the first part of the ... I mean when I first took off in the role. I did take a 9-month project management application through U-Dub's continuing education program, which was interesting because it was a project management training course so a lot of the folks who were going through it might be OmniPlan users, which was pretty —

Brent: Really? Cool.

Ainsley: So I both learned techniques for managing a team and prioritizing and that sort of thing as well as I think got a pretty interesting insight to who our users might be.

Brent: Uh-huh. Wow, that's just perfect, yeah. That's awesome.

Ainsley: It worked out pretty well.

Brent: Yeah. We get a lot of feedback from Plan users outside of that class. I think you mentioned we got anonymized files and things like that.

Ainsley: Yeah, we get all kinds of things. So we'll have someone send in a fairly complex project and say, "Hey, why is it doing this?" Which is really cool to see that they're halfway through a project and they're using OmniPlan to get them there. Or we'll get feedback from customers who are just starting to use the application and some of them are tried and true project managers who are looking for a new piece of software to use and some folks have no experience with project management, but they've heard OmniPlan's the tool to use-

Brent: Right.

Ainsley: So they're both trying to learn how to be a project manager and how to use the software at the same time. Our support team has really great conversations with them about how to do that.

Brent: So we've solved at least a little bit. It's an ongoing process, right? Something like OmniFocus, everybody in the company probably uses it because it's super general interest, but OmniPlan is way more of a niche-

Ainsley: Exactly.

Brent: ... product so yeah, that makes it interesting. So we have to talk to people outside all the time, yeah.

Ainsley: And I do feel like when I give demos at the company meeting, which I really like doing, OmniPlan's features are maybe a little more of a surprise than some of our other apps-

Brent: Yeah, right. Yeah, yeah.

Ainsley: ... to the folks who don't use it daily here.

Brent: That's cool though. How long's Plan been around?

Ainsley: I'd looked right before this, I believe it's been around for a little over 11 years.

Brent: Oh, okay.

Ainsley: We launched OmniPlan 1 in 2006.

Brent: Okay.

Ainsley: Now we're on the version 3 of both the Mac and the iOS app.

Brent: Okay. So you're also the prime minister of our internal tools, which I think is cool. We have a bunch of internal tools from Omni ... Well, and some external tools still, OmniPresence, OmniDiskSweeper, but you also do BugZapper, CrashSorter, OmniWarble. What's OmniWarble?

Ainsley: We have an internal tool for interesting tweets that our support team uses for making sure they're not trampling on each other's replies and keeping track of how many times we tweeted back at a particular customer and maybe we should encourage them to email. We've got more characters now, but Twitter's still a hard platform to provide support on.

Brent: Yeah, for sure.

Ainsley: Those are basically the apps that aren't our four big shipping apps. OmniPresence is our sync mechanism. It's customer facing.

Brent: That's our document sync mechanism, right.

Ainsley: Right. And it's a-

Brent: It's [meant 00:10:00] for Outliner and Plan and Graffle.

Ainsley: Yeah, it's a free application that you can sync with the Omni Sync Server or with your own custom WebDAV server, and anybody can use it regardless of whether or not they're using one of our applications.

Brent: Oh, okay.

Ainsley: Then OmniDiskSweeper is our other free app that we're still distributing externally.

Brent: What does it do?

Ainsley: OmniDiskSweeper is a tool for helping you ... I believe our tag line is "Delete with an iron fist," for finding and deleting files on your Mac's hard drive.

Brent: Okay. Just like caches or things that have been uninstalled and [crosstalk 00:10:34] stuff?

Ainsley: Yes. I mean it'll find everything. It won't tell you what's safe to delete. It'll let you delete it all, as our support team will let you know. That's an app that Omni's made for a long time, and I believe we used to charge for.

Brent: Okay. So OmniBugZapper, I think we all kind of live in there it seems like. That's our bug tracking tool.

Ainsley: Right. So that's our internal bug tracking tool. We go through a release cycle much like we do with our external apps. It's slower as we don't have as many folks with as much time to work on it, but we do try to test it before we set it up for the entire company to use, which works for the most part.

Brent: Except?

Ainsley: I think it was maybe a year or so ago, someone wondered what happens if you put an emoji to bug title? So we tried, and it turns out putting an emoji in an Omni Bug Zapper bug title will crash the application for every user currently using it.

Brent: Did it crash the database server or-

Ainsley: I think so.

Brent: Yeah.

Ainsley: I believe Ken had to get in there and make maybe a database change. I'm not sure where exactly the change came in.

Brent: Okay.

Ainsley: But it did need to be fixed pretty swiftly.

Brent: Yeah, yeah.

Ainsley: And that's not the kind of bug that we would hope to ship in one of our shipping apps.

Brent: Certainly not, yeah.

Ainsley: We probably would've caught that-

Brent: Especially not an emoji related bug. People love emoji.

Ainsley: So we probably would've caught that before it made production in one of our other applications.

Brent: Yeah. There's SupportLoad and OmniAutoBuild. OmniAutoBuild is the one that tells us which builds are currently not working-

Ainsley: Exactly.

Brent: That's always ... I don't like using that app 'cause it's bad news.

Ainsley: Yeah, and it's an app that only a specific department uses much like our SupportLoad tools, the tools that only our support team members sees. They're pretty niche apps I'd say.

Brent: Yeah.

Ainsley: Using inside the company.

Brent: So you're from Nova Scotia.

Ainsley: Yeah.

Brent: Or as I like to call it New Scotland.

Ainsley: Exactly.

Brent: 'Cause Nova Scotia is a Latin name, which makes no sense.

Ainsley: They didn't ask my opinion on it so ...

Brent: You would've said New Scotland, right?

Ainsley: Exactly.

Brent: Yeah, okay.

Ainsley: Yeah. I was born in Nova Scotia, and then my parents moved to the States when I was 3. Then I grew up in Eastern Washington and then went to University of Washington and never left Seattle.

Brent: Cool. Were you lucky enough to use Macs growing up?

Ainsley: I was.

Brent: Wow. Good.

Ainsley: So our first computer was a Mac. I think my second computer was a Bondi Blue iMac-

Brent: Oh, cool.

Ainsley: ... that I remember very distinctly and my dad still has in the garage. And I actually used OmniGraffle well before I came to Omni.

Brent: Nice.

Ainsley: It must've been installed. We used to ship OmniGraffle with, I think it was a standard edition of OmniGraffle with some Mac hardware, and I needed to make a ... I think it was some sort of like family tree diagram for my 9th grade Biology class.

Brent: Wow.

Ainsley: And everybody else had these hand drawn diagrams with wonky lines that were arms width in size and I used OmniGraffle to create this nice, tidy diagram turned in.

Brent: You got an A+.

Ainsley: I can assume as much.

Brent: Yeah, I would think so.

Ainsley: I did not become a biologist though.

Brent: No. So you went to UW. What'd you major in?

Ainsley: I have a poli sci degree-

Brent: Cool.

Ainsley: ... with a minor in Math.

Brent: All right.

Ainsley: So very applicable to my daily work.

Brent: Yeah, sure. That's an interesting combination. I don't think that comes up all that often.

Ainsley: Yeah, I don't think too many folks are writing political science essays and proving algebra theories at the same time.

Brent: Yeah, right. They ought to be though, but that's a whole other topic.

Ainsley: I enjoyed it.

Brent: Yeah, yeah. Then you went to work after school, during school?

Ainsley: Yeah, I needed -- my junior year of college, I needed a job. I think as my dad said, "Well, you know Apple computers pretty well and there's an Apple store in University Village right by the UW. Why don't you apply?" So I did and I spent two years there as a sales specialist working part time while I was in school. Then when I graduated, I didn't necessarily have a plan and the Apple store offered me a full time role as a Family Room Specialist, which is basically a technician that does iPhone and iPad tech support appointments and provides workshop training and One to One training for their One to One program members.

Brent: Okay.

Ainsley: So teaching folks to use Pages and Numbers and that sort of thing.

Brent: Cool. How to do their family trees in OmniGraffle, right? Yeah.

Ainsley: Exactly. No, we actually trained on Apple software.

Brent: Oh, I see. I see.

Ainsley: So OmniGraffle would have been well outside what I was permitted to teach at the Apple store.

Brent: Apple. All right. You're not the only person to come from Apple retail to Omni.

Ainsley: No, there's, I would say a good chunk of us that came from Apple retail at some point. Some folks much longer ago than I did, but when I decided I was done with Apple retail, I was ready to move to a 9 to 5 sort of job. My friend, Steve, had just gotten a job at the OmniGroup, as well as somebody named Rachel who used to work at the Apple store with me and then, a gal named Robyn who the years before also worked at the Apple store, all three of them were working at Omni, as well as my mom's husband's friend.

Brent: Yeah, right.

Ainsley: I had all these connections at Omni. So when a support role opened up, I applied. About probably halfway through the process, I learned that my friend, Aaron Cherof who does our music for the podcast, had also applied.

Brent: Oh, no! Face off.

Ainsley: And we were not aware that there was more than one role available. So here we are thinking we were both competing as Apple retail employees looking to work at the Omni Group, and it was a pretty great day when we learned we had both been offered the roles here. So him and I started about a week apart and celebrate our Omni-versaries together.

Brent: Oh, that's pretty cool. Yeah, right on. Now you're on a podcast and he makes the music for it.

Ainsley: Exactly.

Brent: That's pretty cool. I asked Aaron if he would be next actually. And he said no 'cause he's got pneumonia or something?

Ainsley: Yeah, his voice isn't quite in podcast form at the moment.

Brent: Geez. Poor guy. Things have been going around. It's been a tough season.

Ainsley: Yeah, it's a gnarly flu bug.

Brent: Yeah. So I heard a rumor that you not only got married, but you used OmniFocus to plan your wedding.

Ainsley: Yeah, I used-

Brent: What a good employee you are.

Ainsley: I'd say I use our apps all the time, so OmniFocus-

Brent: Yeah.

Ainsley: Especially -- it's interesting, when you're in the support department, you find yourself testing things in OmniFocus all the time so it could be tough to use OmniFocus as your day-to-day task manager when you also have a task that says "repeat three times, due next Friday," because you've been testing something for a customer while you're on the phone. When I moved from being full time support to being a product manager, I switched fully to using OmniFocus as a task manager.

Brent: Cool.

Ainsley: So I had projects upon projects for wedding planning. I used OmniGraffle for-

Brent: Seat diagrams?

Ainsley: And return labels and all sorts of things.

Brent: Yeah, sure. Yeah.

Ainsley: But I did give my day-of wedding coordinator a nice little OmniGraffle diagram with exactly where the tables needed to be, when it was time to set up.

Brent: Cool. And the family trees of all attendees I would hope-

Ainsley: Exactly.

Brent: Yeah, right. Because that information is critical.

Ainsley: We actually, both my grandfather and my husband's grandfather, have pretty extensive family trees.

Brent: Oh, yeah?

Ainsley: I think we recently found out that my husband is a 6th descendant of a King of Norway or something.

Brent: Wow. That's pretty cool.

Ainsley: We were told to brag.

Brent: Yeah, yeah. You're a prime minister and related to an eventual king I assume.

Ainsley: Or something like that.

Brent: The rules of ascension declare that he will be king of Norway.

Ainsley: I plan to take full advantage.

Brent: And you live in Ballard, which is the Norwegian section of Seattle.

Ainsley: Exactly.

Brent: I've often joked, my wife's maiden name is Erickson, and that's how I get in, 'cause Simmons is not a Norwegian name.

Ainsley: No. Yes, we were told to use our Norwegian heritage as clout if we needed to in the neighborhood.

Brent: Yeah, yeah, that's cool.

Ainsley: Although I think Ballard is a little less Norwegian than it used to be.

Brent: Possibly true.

Ainsley: I do enjoy the parade every summer though or every spring.

Brent: Oh, Syttende Mai.

Ainsley: Yeah.

Brent: Yeah, absolutely, yeah.

Ainsley: It was the first year I lived there, I tried to go home after my shift at Apple, but there was a parade between me and the apartment. So I sat down to watch it instead.

Brent: Yeah. When you're not getting married or being at work, you knit [crosstalk 00:18:35] knitters.

Ainsley: I do knit.

Brent: Do we have a group of knitters?

Ainsley: We have quite a collection of knitters here at Omni, all sorts of skill ranges, from the advanced to folks who are just picking it up. Sometimes, we bring our knitting in at lunch. I don't do it quite as often because I'm not great at grabbing it to bring it here with me, but it's great. There is ... when I first started here, I was doing something wrong in my knitting and I couldn't quite figure out what.

Brent: Okay.

Ainsley: And I brought it in and somebody showed me I was twisting my stitches funny and I was set to go.

Brent: Nice.

Ainsley: So it's a really great sort of small community that we have here.

Brent: Yeah. Yeah, how big is that small community though? It does seem sometimes like half the company is knitting now.

Ainsley: I do think a lot of people have picked it up.

Brent: Yeah.

Ainsley: I'm not really sure there's-

Brent: It seems to be contagious.

Ainsley: Yeah, there's probably at least a dozen folks who are knitting on a regular basis.

Brent: Dozen knitters out of 60-ish people, that's a lot of knitting.

Ainsley: Well we've certainly had people learn to knit from the experienced knitters here and it's really cool to see what everybody else is working on.

Brent: Yeah, that's awesome. So you live in Ballard, but you live in what we're now calling the Brewery District of Ballard, right.

Ainsley: I saw that online the other day that somebody was calling that area the Brewery District. It's an industrial part of Seattle where a lot of local brewers have found they can, I believe, get pretty affordable brewery space and I think we have close to a dozen breweries within a mile or two from our apartment, which is, as far as I'm concerned, a pretty ideal place to live.

Brent: Right. Your biggest problem now is choice, like which one do we go to?

Ainsley: Exactly.

Brent: We went to Stoup yesterday. Let's go to whatever.

Ainsley: Yeah, what order should we do our little brewery crawl rotation?

Brent: Oh, yeah, yeah. So you'll hit three or something in a night sometimes?

Ainsley: Depends on how ... For a while there, especially in the summer, we'll go for a little walk about on a Saturday afternoon and stop by a couple.

Brent: Yeah.

Ainsley: Especially on a nice day where they have outdoor space and delicious local beers.

Brent: Oh, yeah.

Ainsley: Hard to complain.

Brent: And the food trucks come up and ...

Ainsley: Yeah, delicious food trucks.

Brent: Yeah.

Ainsley: It's a pretty ideal neighborhood in my opinion.

Brent: Yeah. It's pretty cool. Are you a dog person? Everyone here's a dog person it seems like.

Ainsley: I actually would say I'm much more of a dog person now than I was when I started Omni. I've gotten to really love them.

Brent: Yeah.

Ainsley: But I've always sort of been a cat person.

Brent: Yay. I'm a cat person.

Ainsley: We have two cats, Linus and Lucy. I like to say we got them both for free. They were cats that didn't work out for someone else.

Brent: Yeah.

Ainsley: One's quite fluffy.

Brent: But they liked you better.

Ainsley: I mean they seem to like our apartment quite a bit.

Brent: Cool.

Ainsley: Actually for our wedding, Derek, who's the PM for OmniOutliner, painted us two really great cat portraits of Linus and Lucy as their Peanut characters.

Brent: Cool.

Ainsley: But they were pretty accurate photos of our cats. [Inaudible 00:21:23], I absolutely love them.

Brent: Cool. Can I have pictures for the show notes?

Ainsley: I think we can arrange that.

Brent: All right, people, there will be pictures in the show notes.

Ainsley: I believe Linus once made it into an OmniGraffle feature video.

Brent: Oh, sweet.

Ainsley: I think Mark was-

Brent: Well, that's the big time.

Ainsley: Yeah, I think Mark was looking for some sample photography and I just happened to have a cat photo ready to go.

Brent: Well, thanks, Ainsley Bourque Olson.

Ainsley: You're welcome.

Brent: You pronounce it Bourque Olson as if there's a hyphen, but there's no hyphen.

Ainsley: Yeah.

Brent: Just so the world knows that.

Ainsley: Yeah, they'll let you do it.

Brent: Ainsley Bourque Olson.

Ainsley: Yeah, if you don't want to get rid of a maiden name and you really enjoy spelling it out -- it has a Q -- you can keep it and add an extra last name.

Brent: That's great.

Ainsley: The lady might look at you funny, but sure can do it.

Brent: Yeah, whatever. So how can people find you on the web?

Ainsley: I am on Twitter and Instagram as @ainslaw.

Brent: Where's the "law" come from? ... or the "aw"? "ainsl-aw"?

Ainsley: It's kind of a silly story. So I, years and years ago was a day camp counselor, and there was a little kid who half the time would say "Ainslaw" instead of Ainsley. So I told the story to a college friend, right around the time that I set up a Twitter profile for the first time, and he started calling me Ainslaw so that became my Twitter handle.

Brent: All right.

Ainsley: And I didn't realize I was going to keep that for the rest of forever probably.

Brent: Yeah, yeah, it seems likely now.

Ainsley: So you can find me on many social networks with this fairly random username.

Brent: Well, I'd also like to thank our intrepid producer, Mark Boszko. Say hello, Mark.

Mark: Hello, Mark.

Brent: And especially I want to thank you for listening. Thank you. Music.