Rapping Your Way To Team Happiness And Success – Miles Orkin


BY Sam Davies


19 November 2020

Reading Time: 11 minutes

In this podcast:
Psychology • Teams • Culture • Pausefest

I had such a fun time talking with Miles Orkin. Miles is a UX lead at Google and spends a lot of his time thinking about how he can empower teams. Miles started his career writing for Thrasher magazine (which basically makes him my hero!) I am really interested in the thread between a youth spent in music and sports, like skateboarding that have a high degree of autonomy, and a DIY community ethic and successful business leaders. I had a great chat with Matt Minear from BAD last year on this topic, and I know that personally for me, skateboarding taught me many of the skills I use as a leader today.

I can’t teach you how to skate – only the pavement can teach you how to skate

Miles had some fantastic insights into how to create an environment in your workplace, that is geared towards maximum happiness and success from teams. We touched on:

  • Building a psychologically safe workplace
  • Allowing people to fail
  • Learning in the boardroom
  • How FUN is one of the key ingredients in work
  • Sub Cultures at work
  • UX RAPS!

I really enjoyed this one, thanks to Miles and Pausefest for making this chat possible and we hope you enjoy it!

Miles Orkin - Sam Davies



Transcript of Sam Davies in conversation with Miles Orkin

(00:05) Welcome to another episode of Humans Aren’t Robots. The series of conversations with designers and creative thinkers uncovering the human elements of teams and modern business practices. I’m your host, Sam Davies. A conversation I had at Pausefest earlier in the year with Miles Orkin. Miles is a UX leader at Google leading something like a team of 500 UXers. What he spends most of his time doing is thinking about ways that he can lead, motivate humans at Google so that they do a better job. A lot of that which we spoke about in this conversation, is providing a space of psychological safety. Google did a study around this, which they called Project Aristotle and it’s five components: Make it safe to speak the truth, make the tough calls, constantly seek clarity and make it line up so ensuring the team see the connections between purpose, and number five is to do it, review it and adapt. But number one making it safe to speak. Miles has a background in journalism, skateboarding and punk rock and hip hop.

(04:08) How is the Internet going to shape our lives, having been without it for years and then coming into it and that discovery element?

Yeah it was a big shift when the Internet made those connections so much easier to happen. My first real job was at Thrasher skateboarding magazine in the late eighties, dawn of the street style era. We had that sense of speaking to marginalized people in their voice, in the context that they wanted, it gave a lot of satisfaction that was actually something that carried through my whole career and I still focus on.

(07:02) Between Thrasher and a few surfy magazines for a 12 year old in Australia, it helped define my worldview and was a kind of gateway to another part of the universe.

(09:16) There’s something about the culture of punk or skateboarding where there is this strong sense of autonomy, strong passion, creative freedom, not giving a fuck and just going out and making shit happen no matter what, that breeds very well into the modern business world?

I think it does. At Google now in my role, I work with really large UX teams on creativity and culture and inclusion and organizational enablement. But one thing I do is a lot of different workshops on sort of peripheral skills or soft skills. I do a UX rap at Google, it’s part of my presentation. I’ve got a generic UX rap, a designer UX rap, a UX culture rap. I’m working on a full length album.

(11:28) What was the pivot then from writing the recipe, the Thrasher, then did you go back to school and study creative writing?

Yeah at some point I thought if I don’t go back to college, I’ll probably end up writing about skateboarding my whole life. And I like skateboarding, but I want to do more than just that. I went back to school and had to get part time work. So I started contracting. At Thrasher, I learned graphic design and typesetting, it was before the Internet, before desktop publishing. I would work in the production department or the art department or the copy department and then the Internet happened and there was the big dot com boom.

(13:30) So kind of a writer on the left bank? No, I became a UX account lead for a Swedish web consultancy in their Barcelona office, and I did that for two years. Then eventually we went back to the States. I ended up getting a job at American Cancer Society as digital and regular communications, I actually worked there for ten years.

(14:07) I had lost my brother to cancer earlier on and had other family members. That meant a lot to me personally. I did a lot of traditional communication and creative services work, but also led a lot of digital initiatives and ended up being their national director for web and mobile. It was a great education in how you mobilize people around a mission and a cause. It had this weird connection to skateboarding.

(15:40) I’m more interested in doing programs or initiatives that are focused on people rather than on products. And so when I came to Google, I was doing a lot of operational leadership, but also, Google UX or the one I’m on now is six hundred and thirty people.

(16:07) Now I’m in Reach UX which is the biggest UX team at Google. What I learned in the nonprofit world was directly applicable at Google. Everyone’s kind of a volunteer, because it’s really decentralized. The decision making is very consensus-based, it’s not a typical hierarchical company.

(17:17) What was the role of a user experience designer at that time?

Early 2000’s I don’t think it was called UX at the time. That was the dawn of the era of user centered design. I think my perspective on UX is very holistic. I’m much more of a generalist than a specialist. I have a lot of visual design background from various roles, but I didn’t go to design school. What I’m good at is being able to articulate a design point of view, because I have good word skills. I understand methods for design thinking.

(19:21) Agile is another big one, be agile and not stress about whatever the framework might be. And I think it’s the same with a lot of design thinking practices?

(19:31) Yeah, exactly. And you see it play out and you’re trying to roll some new way of doing things out to 5000 people, you need to put it into a playbook. If you map out the steps you can teach anyone a dance, you can teach them the samba or the salsa. But that doesn’t mean they’re a good dancer. Let’s find your groove and naturally dance that way.

(20:27) You work for the largest tech companies in the world, but it all comes back to having those passionate people that can find their groove. How do you start empowering that as a leader?

(20:43) I draw on my background in punk rock and skateboarding culture. Whether you have a company of one hundred thousand people like Google or a company or team of 100 people, it’s not just a monoculture. It’s really a mix of micro and macro communities. How do you enable all the subcultures in a way that feels open and fluid?

(22:34) You have to work top down and bottom up. The story that you shape from the top down has to be something that is applicable to a lot of different kinds of people. What’s the common thread that you can tell them that makes them feel part of something special? It is creating an organizational narrative that feels authentic and not overly thought, it should be straightforward and we care, we all matter.

(23:43) The notion of bringing your whole self to work. But what I really work on encouraging people to do is, is to think of the responsibility on the other and place a burden on others. If you are looking at the people around you as essentially stereotypes, then try harder to know what they’re really like.

(24:39) A big part of that is psychological safety. Do you feel safe in your team? Do you feel connected? People’s lives are so interesting. You need to find out about where they’re born and about their lives. And if you have that connection, then when everything goes crazy or people are mad, you can get through it because you care about this person.

(25:40) So is that sort of top down, bottom up, as a leader, you can show vulnerability and you can have those conversations and ask some of those deeper questions?

At some point I had a role where I was leading teams in Google Cloud, which includes G Suite, but also Google Cloud platform, that if you look at the total number of UXers, it was like seven or eight hundred people, when I’m one person. What I started doing was meeting with directors and saying what do people need help with? So I built modules that were hour long workshops. People like edutainment, fun, engaging. So it’s team building and skill building and connection building all at once. And it’s but it’s like putting spinach in a milkshake with your kids, like they don’t even know it’s there. That’s the key.

(28:15) Let’s say you’re running a design sprint and it’s a daylong thing I’ll come in l do a UX rap and then do a little activity where I say talk to each other about where you’re born, what you were like as a kid, and one experience that really shaped who you are and just break into small groups and talk. And you watch that start happening and like it’s quiet for a few minutes and then it just goes like it lights up.

(30:12) There’s an element of putting people out of their comfort zone a little bit. How do you see fear sort of playing a role in development as a human?

Fear is natural and it’s healthy, but it doesn’t have to inhibit your decision making. So part of overcoming fear is making sure teams understand how to have conversations when things go wrong. I talk to teams about learning from failure. Making sure that you’re helping managers know that it is hard to do design work. It is emotional. I can’t teach you how to skate, only the pavement can teach you how to skate.

(33:25) How do you learn to process the feelings and have the space to process them? Sometimes when you’re working in creative material, you have to listen and you have to look at how it’s landing with people. You have to train yourself to absorb feedback beyond just the verbal cues and when you can do that, you end up making better iterations.

(34:59) I think that’s really pertinent in design in that a lot of people that are giving feedback don’t have the vocabulary to actually talk about it, because often it’s an emotional connection with design?

(36:52) Most good designs get better and better when you ask more questions and clarify, because everyone’s got a different vocabulary for expressing an emotional response. A big part of influence and persuasion is not just thinking you figured it out, but actually knowing you figured it out because you did all kinds of espionage, basically recon.

(38:29) From the junior to the senior, showing people that you’re listening to them is really important.

(38:37) The more information I can find out about the person I’m going into a room with, especially on a human level too, creates an instant connection that you can have that totally changes the whole conversation.

(39:09) Yeah. And a lot of that can come from your recon and you’re not just coming from a place of insincerity and really like curiosity because people are interesting.

(39:55) And it basically becomes more interesting for everybody, for you, for the person, for anyone listening to the podcast, because then you’re more engaged in what makes us tick as humans. It’s anthropology, it’s not business strategy. Humans care about humans. When you look at the research around storytelling, for instance, our brains light up when we hear a real story.

(41:16) I feel like education in the United States over the last twenty years has changed a lot. Nowadays kids are so focused on jumping through the hoops of academia that they get out of school and everything feels like a test. And when everything feels like a test, you think that there’s a right answer and a wrong answer. And you don’t realize that this is not a test.

(42:28) And that I think getting people to change their mentality about that is really helpful for having a more productive, creative conversation.

(42:34) Is that something you’re obviously working in a high performing environment with a lot of people? Because I imagine it is quite a different sort of mindset. A lot of them probably weren’t skating or playing in bands, because they were so focused on studying.

(43:15) I will literally tell people that, I have a one thing that I’ll tell people – this is not a test.

(43:32) If you get into these corporates, especially the big companies, they’re like corporate thought ecosystems. And you forget like, no, I’m a whole person. It’s kind of back to be your whole self, see the whole person. So I think it’s just having conversations. I think I would say my general approach is try to create a lot of opportunities for having conversations with people in small to medium sized groups, meeting up to like 50 people, because even up to 50 people, you can have a conversation, you can have back and forth and you can do some stuff, break them up and make them have small conversations, then bring them bring them back together and have a big conversation. And it’s really through dialogue that people learn more.

(46:15) I often find that within organisations, people with cultural differences, different backgrounds, coming into a largely white Anglo-Saxon culture here in Australia, I feel, I don’t know, ashamed or that they hold that back and don’t fully embrace it. For example, at the office, we do team lunches where we will bring stuff and cook things. And it’s often the people that have had different backgrounds, they come with the best food. And that’s a really great pathway. Food is a great pathway to some of those conversations.

(46:42) Yeah, definitely. You’re not going to cook something too experimental. You’ll probably cook that thing that your parents made when you were a kid. And that’s like so close to your heart and yeah, and if people really feel it, it’s a very sort of tangible sense of who someone is and where they’re what their backgrounds like. And it’s really fun to learn that about somebody.

(48:05) Websites are really focused on efficiency and short attention spans and how can we get someone to a funnel as fast as we possibly? What do you see is the scope for full creativity and new design systems and layouts on the Web?

(49:20) It used to be just compiling information. Everythings just exploded. So what makes websites compelling and effective now is the sense of immediacy. How can the web property that you’re developing fold into people’s lives seamlessly?

(50:01) Cognitive fluency is something they talk about on the Web. As soon as something sits outside of what cognitive fluency is essentially just my brain is used to seeing things like this, a long scroll that vertically down the page. As soon as something changes out of that, all of a sudden the brain’s going I don’t understand this anymore. The way we engage with digital these days is, that’s a lost sale as opposed to that sense of sort of exploration or trying something different?

Yeah, it’s delicate for people who are working on designing web experiences, new or different is not always better, especially depending on the behaviors you’re looking to, to sort of engender. But the thing that I think gets more and more important in a lot of different kinds of experiences on the Web is context. So you will accept a bigger change in gestural modality or more steps in a flow, if you know why really clearly and how you explain context can often be not just with words, it can be visual, it can be audio.

(52:15) It comes back to storytelling. So you have a story that you want to tell.

Yeah, there’s ways to give hooks that let people comfortably engage with the content. So it could be a visual hook that’s relating to other parts of their lives that are super ingrained and comfortable. How might people interpret the story? Who are the people and how we want to talk to or tell the story to? What can we learn about how people are interpreting our story? And so I think people often will focus too much on writing the perfect story when really like you, that’s kind of back to context.

(55:37) And podcasting is a really good way to do it?

Yeah. I pay attention to mindfulness in schools of thought that are more influenced by like Buddhist thought and things. And the idea of listening in a selfless way is incredibly stressful for people.

(57:44) Empathy is one of those words that gets kicked around all the time in design teams. And it’s really empathy in the context of UX is often just another methodology for getting data points about users. What I talk to people about is you need to think more about compassion. I’m not so much focused on the user research, but on the team dynamics.

(59:09) Symbolic gestures can be really meaningful. And I talk to leaders about this a lot.

(01:00:10) People struggle sometimes when they cross over into this leadership beyond just management. The symbolism, I think it happens at the leadership level, but also in your day to day and making sure that you make the gestures that show you care. People abuse power dynamics unconsciously. That’s a culture thing you see at your workplace.

(01:01:07) I really thank you so much for the conversation. So if I want to find you online where can they look? I’m not good at social media. LinkedIn, Miles Orkin that’s the place that I look the most. I think I have Twitter. I have a Twitter handle. I make a Twitter post once a year. Thank you. Cheers.

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Sam Davies

Sam has been running a Digital Agency in some form or another for almost a decade. He loves the internet and the positive changes it has brought to the world but still loves time away from the glowing cubes. Surf, Fish, Drink, Cook, Laugh….Drink! You can follow him on Instagram @samdaviesdn and on Snapchat @digitalnoir