106: Software and Soft Skills with Artie Jordan

Pete Mockaitis
Artie, thanks so much for being here on the How to be Awesome At Your Job podcast.

Artie Jordan
Man, thanks so much for having me. This is great.

Pete Mockaitis
Oh, I’m glad to have you as well. But I want to make sure that I get out there first of all I-L-L.

Artie Jordan
Yeah. Illinois, baby.

Pete Mockaitis
That’s right, that’s right. University of Illinois. Respect, that’s very cool. Can you tell me about your organization CSTUY – what it is and why you feel passionate about it?

Artie Jordan
Yeah, sure. So CSTUY is a non-profit some folks and I started in New York City, the computer science technology for urban youth. And the goal there is to take some computer science curriculum from one of the high schools here that a guy by the name of Mike Zamansky or just Z, developed that inspired a pretty big generation of folks to go into the technical field and bring that curriculum to the broader New York City area. And it’s a big passion for me ’cause I definitely am a true believer when it comes to the empowering nature of learning how to program, how to do system administration, how to just use computers. I think it gives people a huge leg up, so it’s been a real pleasure working with those folks.

Pete Mockaitis
That does sound really cool. Yes, absolutely. And so I’d also like to hear a little bit about one of your historical experiences, because right now as we’re speaking we’ve got a president transitioning into the White House, and you’ve use technology to help Barack Obama do just that. Can you tell us a bit about that experience?

Artie Jordan
Indeed, yeah. So in 2008 I was living in Chicago and I had the opportunity to go volunteer for the headquarters team for the “Obama for America” ‘08 campaign; joined the team full-time that summer and led the telethoning roll out for what’s called “Get Out to Vote”, which is this big period during any big campaign where folks just try to engage with voters and figure out who’s going to go to the polls.

And then on election night my boss pulled me aside and said, “So, looks like we’re going to win. Can you get in your car and drive to Washington tomorrow and help with the transition?” And all big campaigns prepare for this kind of thing. So, worked in D.C. in a big group of people, basically trying to assist with all the interviews for all of the staff that were going to work for the new administration. They call it “The Plum Book” – it’s this plum colored book that has all the appointments that the incoming administration can make.

So, for us it was putting together a big database if folks remember change.org. And putting together a big sort of application system for folks to apply and helping folks set up meetings and just meeting a lot of really interesting folks.

And then on the side I kind of went around D.C. and went to a bunch of conferences and heard from a bunch of folks and wrote a couple of memos basically talking about what could be done using lot of the new technologies that had come in and that had debuted between administrations. So I learned a lot about cloud computing around that time as well, and during the last eight years I think the federal government has done a lot of work to prepare more traditional organizations like federal government to be able to utilize less traditional software as a service type – services like Salesforce or Amazon.com or things like that. Or Amazon Web Services, I should say.

Pete Mockaitis
Excellent. Cool. And so, some of the stuff you wrote up has gotten some traction – folks have been using and doing it.

Artie Jordan
I like to think so. To be perfectly honest, some of those memos might’ve just gone into a file somewhere, a circular file of some kind, but I certainly learned a lot and I know that the mission was definitely still carried out over the last couple of years. I’ve certainly personally seen governmental organizations grab SaaS with both hands and really try to learn a lot of lessons about how to do things better and more efficiently in government and beyond, utilizing a lot of these services. And I’ve seen a lot of these services mature, in terms of being able to provide organizations like the federal government or universities or other places that are trying to follow some ethical or security guidelines, and these businesses have mature their products to be able to offer those services to these groups that have tighter controls around their business process.

Pete Mockaitis
That’s cool. Any interesting stories in terms of being in the heat, the thick of it all by doing that?

Artie Jordan
The one thing I’ll always remember is: We all showed up in D.C. and kind of had to pack into a couple of apartments together kind of overnight, and we would all be walking around town with these ID badges for the presidential transition team or PTT. And not a lot us had worked in D.C. before so we all had to buy suits and start to learn the ropes. And I think there was a lot of secrecy around it, or at least not secrecy, but they certainly didn’t want us giving off the cuff interviews around that time. And so we would only be allowed to use our badges when we were onsite at the office, and so whenever anybody would just sort of walk out of the office and meet up for dinner later and still have their badge out, someone would say “You’re PPT is showing.”

Pete Mockaitis
Zing! Oh, that’s fun, that’s fun. So now let’s talk about sort of a more recent experience. Alright, here at 2U you had the experience of building the IT department from the ground up. And so, I’d like to hear maybe some fresh lessons learned, in terms of when you have that responsibility and you get to establish a team from scratch. What is that like and what are some things you learned doing that along the way, in terms of smart moves versus your mistakes that you would rather others not repeat?

Artie Jordan
Sure. So when I joined 2U about seven years ago, the company had only been running for a year before that, and kind of went upstairs and helped my boss fix the WiFi in the office and he almost offered me a job on the spot. And he said, “You’re going to be in charge of everything with electricity running through it.” So, great, okay.

And so when I started out, I knew that this was going to a pretty fast growing company with a really smart business model and a real mission. So everything that I sort of tackled from the beginning I thought to myself, “If this is going to be a place where I’m going to be able to grow a team, I need to think about everything that I’m doing as a process that somebody else might take over some day.”

So the classic sort of IT trick at first is obviously to create a help desk – that’s your first step. Don’t just email me, ’cause it might not always be me in this position. Email a queue and even if I’m the only one taking work off of that queue, make sure you email that queue. Or if you come by my desk and you need some help, then I’ll email the queue for you, this kind of stuff.

Pete Mockaitis
Yeah.

Artie Jordan
And the process of seeing what is taking over all of my day today, this year? At first it was a lot of helping students, it was a lot of helping employees, it was setting up offices and things like that. So, first big split was making sure that I had some help helping out employees with their day-to-day tasks, and again having that queue there from the outset was super helpful, and then sort of dividing from there.

So maybe a year later it was clear, “Okay, this business is really taking off; we’re getting a lot of employees now. What am I spending all my time on now? Okay, office infrastructure. Let’s package that up and create a job description for the types of stuff that I’m doing there.” And each year there it’s sort of been new set of things that have really been the focus, whether it’s been back-end server management, security is obviously on everyone’s minds these days, telephones for us because we have a lot of folks – admissions counselors and like – talking to students all the time, or student support folks helping students with their process.

So for me the lesson from all that was something that actually was put very nicely by this woman Patty McCord couple years later when I ran into her, and she said, “If I can’t fire you I can’t promote you.” Or I think put another way – if you’re indispensable at this task, then you’re unpromotable. And for me making sure that anything that I was getting myself into, I had a mind towards packaging up and potentially handing off at some later date – that was the big key.

Pete Mockaitis
That’s great, yes. And so I’d like to get your take then – you said each year there’s been a different focus. And so in the midst of rapid growth and change, I’m thinking sometimes when people encounter change, they get kind of irritated, “Argh, we were in a good groove, it was working fine. You changed everything around on us.” So, what are some of your perspectives on how you and your teammates stay sort of nimble and ready to switch to something new without too much feet-dragging and belly-aching?

Artie Jordan
Sure, sure. I know you’ve had a couple of other guests talk about “Agile” at times, and in the tech world there is capital ‘A’ “Agile”, which is some lessons around software development or business process; and then there’s sort of the more lower case ‘a’ “agile”, which is just what people think about, in terms of the word “agility”.

And when you work in technology, you’re either learning new stuff or you’re falling behind. And I think that that’s sort of a benefit that comes natural to this part of the industry at least. We don’t see a lot of folks come in applying for jobs that aren’t interested in learning new stuff. So for us that focus on capital ‘A’ and small ‘a’ agility has been a big importance. I think a lot of the agile practices are designed to keep that lower case agility in place, focusing on allowing teams and individuals to do what they’re really good at, which means allowing them to make a lot of decisions that are very progressive and that keep us moving forward with the changes.

A big part of it also has been focusing on using solutions that will grow with your business and focusing on what you do best. I think a lot about competitive advantage. We want folks here to be working on stuff that will provide better outcomes for students; we don’t necessarily want them to be working on new ways of racking and stacking servers. We’re going to outsource that part to the folks that do it the best – to someone like Amazon Web Services or we’re going to outsource it to someone like Salesforce.

And I think something else that’s really kept us rolling with the changes is this notion that it’s tough to hire folks in an industry where the software development skills are in very high demand, system administration skills are in very high demand, data analysis skills are in very high demand. And the folks that are good at that type of stuff, they want to work at progressive organizations.

It’s a big selling point to hiring when you can say, “Look, here’s all the sort of tools that we have in our tool box, and we’re going to keep you learning while you’re here. It’s an education company and it’s a learning organization to boot.” And those two things I think create that sort of what we think of as a virtuous cycle of the tools that we use that help keep us at pace to handle scale, are also the tools that help us hire folks that are interested in working towards the mission that we work towards.

Pete Mockaitis
Got you, that’s great. So now I want to talk a little bit about some skills beyond the technical part. That’s one of your specialties, is talking about soft skills and developing those for technical staff. Could you maybe start us off by sharing maybe the case for why that’s even necessary or helpful, just in case we have a hardcore technical, “This is optimal” kind of a listener. Why is that important, to begin with, even if you are an engineer, a coder or developer who is ostensibly there to build cool stuff?

Artie Jordan
Yeah. I think it’s a fairly well-known thing by now, that the myth of the lone coder is that – it’s a myth. And the best pieces of software out there that everyone uses, the best services that everyone uses are created by highly collaborative teams. And so, I don’t think it’s that much of a hard sell to talk to someone about their career in an engineering field or in a technical field or any other sort of specialized field, where you otherwise might think that you’re going to have your head down all the time, to sell them on the notion that their best work is going to be the work that they do collaboratively.
When you look around at a lot of the most famous technologies in the world and when you look around at in particular technologies based on or that utilize open-source technology, particularly web applications or any sort of website businesses or web services or SaaS services, you see these massive open source projects. And those open-source projects are entirely collaborative, and the decision making that goes into those open-source projects is entirely collaborative, and I think the notion that soft skills aren’t important is either dead or almost dead, at least in the software field, because folks really do recognize that all these projects are collaborative.

Pete Mockaitis
Okay. So, when you talk about soft skills, could you maybe delineate a few of those – what are some key things that you’re talking about here within that broader term?

Artie Jordan
Yeah. I think a lot about Linus Torvalds, who’s the creator of the Linux operating system that basically the whole world runs on now, at least the Internet. And one of the biggest projects besides Linux that he’s known for is this software called “Git”, which is a collaboration software for software developers. It’s where people store their code and it’s how people work together on code in particular.

And I have this kind of theory that even if Linux were to disappear tomorrow, Linus Torvalds would go down in history as a genius for inventing Git, because it is this revolutionary way of unlocking the potential of collaborative teams through the exchange of code in a very orderly fashion. And anybody who’s ever contributed code to an open-source project or worked on code in a business environment can see that it takes a lot of communication to effectively create anything of real value.

Pete Mockaitis
Okay, so communication and collaboration indeed. So I’d love to hear then what are some maybe common pitfalls or shortcomings you see when folks are doing some communicating, they’re doing some collaborating, and it’s sub-optimal?

Artie Jordan
Sure. Well, I think it’s obvious that the value of communication is there, I think the obviousness is there for everybody. I think a lot of folks do get into some of the STEM fields, either coincidentally or maybe in some cases because of an introversion or an interest in things besides… That are often asocial or at least the research of which don’t always promote communication. So I think you can find folks that think that they can kind of get it all done on their own, or fix the problem from their desk, or solve a technical dispute from the command line without any sort of discussion.

And that’s where I think a lot of these conversations come up, where we talk about how important it is to build a consensus and how the consensus-building comes not just from showing folks that you can make the best thing or do the best thing or make the best choice, but also being able to talk it out. And I think the plethora of manners in which people can communicate today really helps with this.

For folks that don’t feel that they’re as eloquent say in person or don’t feel that they’re as eloquent in email, things like Slack or communicating via ticketing tools or the ease of use of some collaboration, like meeting technologies helps lower the barrier of entry I’d say for a lot of that kind of, I guess, skittishness around communication.

But I think it also goes beyond just the tools or just even face-to-face encouragement. I think a big part of what we’ve seen with a lot of the focus, especially in technical fields on creating really good, positive cultures, kind of revolves around that, and sort of recognizing that it’s not just on the individual to create that kind of safe space, but it’s also on the organization.

Pete Mockaitis
Okay, certainly. And so I’m thinking with you’re coaching your team day in – day out, are there some particular things that you find yourself saying frequently, like, “Hey, do this” and, “Hey, don’t do that.”

Artie Jordan
The main thing that I find is helpful is anything that can promote empathy, and I think that there’s just a laundry list. So I think it differs for different people, but we talk a lot about business process analysis, and I think there are some folks that specialize in it, there are some roles that that’s all folks do. So on a team of software developers, you’ll have software developers, you’ll have business analysts and you’ll have product managers and these types of things.
And certain people might just specialize in business process analysis.
So, when I’m talking to folks about business process analysis, I’m really talking about having empathy for your client, and if your client is internal or external or another developer or a team member, it’s basically trying to remind folks about having that curiosity about who they’re communicating with, who they’re collaborating with, who they’re serving in that sense.
When you have that level of empathy, when you have that level of mutual understanding, when you can see the other person’s challenges, all this stuff gets easier. And I think there’s been a lot of soul searching in the technology industry that I’ve seen over the last couple of years around this type of idea. So one of the groups that I manage here is a team called DevOps, and this is a group that sort of combines some of the lessons of server operations as well as the lessons of software development – Dev and Ops.

And the whole notion there, the whole movement around DevOps is tied very closely to some of the Agile movement, is this idea of seeing each other’s worlds as being this relatable set of challenges, this relatable set of goals, this common mission, this type of thing. So that’s something that we talk about a lot here.
And then I also find myself when I’m coaching other managers, really challenging them to dig deep into folks’ day-to-day kind of frustrations and what not, that a lot of times people really just need to talk stuff out. It seems super basic and it definitely is, but I’m sometimes surprised at that basic sort of disinterest I guess that you can see. Or it’s not even a disinterest; I think it’s just that folks forget. They get a little bit too much in the weeds at times and just being able to lift your head above a little bit and see other people, again, is super important.
A real easy trick too is to try to get people to have more actual face-to-face communication, even if that just means going over some sort of video conference as opposed to a phone call. I think that level of empathy really heightens and I think a lot of the literature recently around cognitive behavior really reinforces this – being able to see actual human faces drastically improves the empathy that people feel for each other, even when they’re talking about things that they might have disagreements about.

Pete Mockaitis
Okay, cool. Thank you. Well, is there anything else you want to make sure that we cover off before we hear about some of your favorite things here?

Artie Jordan
One of the things that we talk a lot about here also is this notion of Conway’s Law, which is a software development truism. And it basically says that any sort of thing that you design will inevitably end up resembling the org chart or communication structure of the team that designed it. It’s super applicable when it comes to software development; I mean it’s hilariously applicable. But I think it also is applicable to other business processes or other designs that are created by other types of business units.
And for us we think a lot about it because it really governs how we want to set up our structure communication, and if we want, say, a piece of software that works very very closely with another piece of software, we might want to sit those two teams together. If we have two pieces of software that we need to be more transactional in how they interact with each other, then we might want to separate those teams a little bit more and do more structured communication between them. I find that that’s a really helpful thing when it comes to talking to people about how their communication is actually important to the technology that they’re working on. And bridging that gap between the soft skills and the hard skills.

Pete Mockaitis
Got you, thank you. Well then, could you start us off by sharing a bit about a favorite quote, something you find inspiring?

Artie Jordan
Yeah. I guess the quote that probably rings through my head the most is just from a book – it’s “Show some adaptability.” I’ve thought about that a lot over the last couple of years as I’ve learned how to do a lot of these different jobs in order to be able to manage folks doing them, and I think about it a lot. “Show some adaptability.”

Pete Mockaitis
Alright, thank you. And how about a favorite study or a piece of research?

Artie Jordan
I’m a huge podcast junkie. Your podcast is great by the way.

Pete Mockaitis
Oh, thank you.

Artie Jordan
The one I listen to the most is EconTalk, and so I’ve read a lot of economics lately; it’s maybe a lost calling. I’m expecting a daughter in February, so I’ve been really pleased by the research by this woman, Emily Oster, who wrote a book called Expecting Better. Super interesting I think for parents and non-parents alike, in terms of evaluating a lot of expert opinion and then making decisions around what kind of trade-offs you’re comfortable with, which I think is kind of important for everybody.

Pete Mockaitis
Cool, thank you. And how about a favorite book?

Artie Jordan
Far and away my favorite book is called Cryptonomicon by Neal Stephenson. It’s one of those books that I think about a lot and then I go and I read one or two passages. And if I read more than six passages, I end up re-reading it.

Pete Mockaitis
Wow.

Artie Jordan
Very very heavy on the theme… It’s a fiction, it’s a novel, but very heavy on the theme of the combination of soft and hard skills actually.

Pete Mockaitis
Cool, thank you. And how about a favorite tool, whether that’s hardware, software or a product you like?

Artie Jordan
I actually was originally born in Louisiana, so I am one of those folks that carry a pocket knife, I have a Kershaw Leek. Gets me some funny looks up North, but I think it’s good to have – be prepared and all that.

Pete Mockaitis
Cool, cool. And how about a favorite habit or personal practice that you found useful?

Artie Jordan
I was thinking about that. Besides coffee first thing in the morning, one of the things that I really like to do is try to make every conversation that I have interesting to me. I think as an introvert I find that small talk can kind of drain my batteries the fastest. I was thinking about the interview you had the other day with the drill sergeant who was talking about, “Don’t plan your time; plan your battery, plan your energy.” So I find that trying to find something interesting in every conversation I have actually replenishes my batteries, and it’s super fun.

Pete Mockaitis
That’s awesome. Thanks for the little trick; I’m going to dig into that a bit. And is there a particular thing you share that gets your teammates or others you’re communicating with really kind of nodding their heads, like, “Yes, Artie, that is brilliant!”

Artie Jordan
Probably one of the things I say a lot is – I totally stole this from a friend – but he said to me once, “Honest work is the gift you give yourself.” I work for a great company, but I basically always try to remember that I work for myself first and try to look for that alignment.

Pete Mockaitis
Okay, cool. And what would you say if folks want to learn more or get in touch with you, what’s the best place that you’d point them to?

Artie Jordan
Yeah, so at 2U I do a lot of recruiting so I’m out all over the New York meet-up scene for technology. And then besides that I’m @ajordan just about everywhere. I guess Twitter’s probably my big one. And I do write blog posts occasionally, but I probably need to listen to a few more episodes of the podcasts to get over some of my writing perfectionism.

Pete Mockaitis
Oh, okay. Well, I’ll be thinking about that actually as a topic. I appreciate it, thank you. And do you have a final parting word, a challenge or a call to action you’d issue to those seeking to be more awesome at their jobs?

Artie Jordan
Well, I think it’s just because it’s timely and maybe a little bit tangential, but relevant, given some recent, current events – I would give a challenge to everybody to enable two-factor authentication on as many services as they can. Google it: two-factor authentication. It’s super simple, one of the easiest ways to start securing a lot of stuff and prevent some big disasters that we saw this year. So I guess that would be my plea as a security-minded person.

Pete Mockaitis
Okay, thank you. That’s very specific and unique. Thank you. Cool. Well, Arty, this has been a lot of fun, and I wish you tons of luck as your team and 2U continues to grow, and keep on rocking!

Artie Jordan
It’s been a pleasure. Thanks, Pete! Keep up the good work!