099: The Knowledge You Possess with Stephanie Morillo

In this episode, Stephanie Morillo talks about content strategy, technical writing, organizing and optimizing company internal systems, and that you need to give yourself more credit for the things you’ve already accomplished!


Jamey Hampton | John K. Sawers | Coraline Ada Ehmke

Guest Starring:

Stephanie Morillo: @radiomorillo | stephaniemorillo | #WOCinTechChat

Show Notes:

02:40 – Stephanie’s Superpower: Intellectual Curiosity

13:06 – On Being a Content PM, Technical Writer, and Ruby Together Core Team Member


Ruby Together

19:44 – Validating Open Source Software Contribution

Write the Docs Slack Community

24:27 – Filtering Feedback

28:14 – The Importance of Content Strategy

Greater Than Code Episode 088: The Safety 2 Dance with Steven Shorrock

43:24 – Don’t Minimize Yourself! (Psst: You’re awesome!)

Coraline’s low-friction task management system

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John: Understanding the teams you’re working with better.

Coraline: The power of dreams.

Jamey: The value of being able to know when people in your life are interacting with you in good faith.

Stephanie: Figuring out the “why”.


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JAMEY:  Hello everyone and welcome to Episode 99 of Greater Than Code. We are so close to 100. It’s very exciting. I am one of your hosts, Jamey Hampton and I am here with another one of your host, John K Sawers.

JOHN:  Thanks Jamey and I am here with Coraline Ada Ehmke.

CORALINE:  That’s a blatant lie and you know it.

JOHN:  I only lie when I’m on a podcast.

CORALINE:  Okay. I am happy to introduce our guests today, Stephanie Morillo. Stephanie is a content PM at Microsoft and an empress of documentation at Ruby Together. She first got into tech in 2012 when a fellow Dominican developer from the Bronx taught her how to code. In the time sense, she’s been employed at various startups working at the intersection where developers and communicators meet. In 2015, she co-founded the Women of Color in Tech Chat with Christina Morillo and through the initiative, they released a collection of hundreds of free stock images of women of color technologists, which I have used to my slides. Thank you.

She’s spoken at various tech conferences, written a number pieces on the tech industry. For Model View Culture, serves as a copy editor for an O’Reilly title, is guest editing an upcoming issue of the Recompiler Magazine and is currently a member of the Bundler core team. She’s also finishing up a master’s degree in user experience design. Stephanie is passionate about open source, good food, reading fiction and constantly learning.

Well, I can say Stephanie that your bio isn’t quite up to the caliber of people that we usually have on the show. We like people who actually do things and it sounds like you’re just like sitting on the couch, bingeing Netflix all day long. I mean, what the hell?

STEPHANIE:  That is actually what I do but I knew that a three-sentence bio would probably not be the most exciting, so I had to dig through the archives and give listeners just a sense of the fact that I’m not actually binge watching Netflix all day and I do stuff. I’m glad that that is exactly what came across.

CORALINE:  Absolutely. You’re a very busy woman and it shows and you’re doing a lot of good in the world and I’m so excited to be talking to you.

STEPHANIE:  Thank you. Same here.

CORALINE:  We’ve been in overlapping circles for quite a while and it’s nice to actually have a chance to have a nice conversation with you, so welcome.

STEPHANIE:  Thank you.

CORALINE:  As you know, we start out every show by asking our guest one very important question, “What is Big O notation?”


CORALINE:  Alternately, we have another question if you don’t feel like going to the Big O notation, you could tell us what your superpower is and how you developed it.

STEPHANIE:  Okay, great. That is a question that I can answer. I would say that my superpower is intellectual curiosity. I feel that the trajectory that my life has taken in all of the different tangential past that I’ve gone on have come about because I tend to dream a lot and I think that really came about just from being a kid in the Bronx in the 90s that didn’t really get out much. My parents were really over protective. The Bronx in the 90s was not such a great place but one thing that I was able to do was read a lot.

I was really fortunate to go to an elementary school that knew that a lot of kids from the area that I grew up in, statistically speaking, our chances were not that great, so they really instilled in us the power and the love of reading and through reading, it’s really where I just let my imagination go wild and I knew very much as a kid that the things that I jumped about I wanted to be able to make come true one day. I think that that is probably where that intellectual curiosity comes about. It’s just from that deep need to be able to live out something that perhaps, people didn’t think would be available to someone like me.

CORALINE:  Do you feel like if elementary-school-Stephanie saw grown-up-Stephanie now, that she would be surprised or she would just like, “Fuck, yeah. I did it!”

STEPHANIE:  I think she would be surprised. I think she’d be stunned. When I was a kid, I wanted to travel, I wanted to be a musician, I wanted to learn different languages and I really took advantage of that. Right after I left elementary school, I went to performing arts high school. I got the opportunity to be classically trained. I interned at the Metropolitan Opera and then when I went to college, I took every opportunity that I could to just get out, to leave the country.

I studied abroad a few times, did a Fulbright afterwards and really, I think that just stems from adult-Stephanie fulfilling the dreams of seven-year-old-Stephanie. I think she wouldn’t even know what to say like, “Wait, you actually did this? What does this mean?” which I think is kind of nice.

JOHN:  Yeah, it’s great.

JAMEY:  I love the idea of fulfilling the dream of a seven-year old you. Do you like to think about that a lot when you’re making decisions about what to do and stuff?

STEPHANIE:  I did. It’s funny because the whole idea of being an adult, the whole purpose of being an adult is fulfilling the dreams of yourself when you were seven. That’s something that Guillermo del Toro, the director once said and that’s why he does all of these fantastical films is because that’s a representative of everything he wanted when he was a child.

I think that a lot of the decisions that I have taken in life really came from that but you also have to be careful because one of the things that was really hard for me was letting go of certain dreams that I couldn’t do. My dream when I was a kid — it sounds really silly now but this was something that I held very dear — was wanting to be a musician and wanting to be a professional musician and that’s something that I wanted to be since I was a child and I took it very seriously.

But I had to learn as I became an adult that you don’t have to hold yourself accountable to dreams that you had as a kid, especially when the reality is a lot different and there are ways that I can incorporate musicianship into my life that are probably more reasonable than anything but I do think also that just real life and experiencing things, as they are allowed me to explore other things. I think the dreams of my childhood were a springboard for just about everything else that I’ve been able to do since.

CORALINE:  I wanted to be a musician when I was a kid too and I actually remember the lyrics to the first song that I wrote and it’s really embarrassing. I’m not going to share it, though. It would damage —

JAMEY:  Coraline, how are you doing this to us?

CORALINE:  It would damage my credibility. Maybe, I’ll do it off-air. But yeah, I understand what you mean. I found ways to incorporate musicianship into my life and it’s a hobby that I’m really passionate about but I have no delusions of ever making more than $2.37 that Spotify pays me every month or whatever but it’s still part of what makes our lives rich and those childhood dreams can really inspire us in ways that are often surprising.

STEPHANIE:  Absolutely.

JAMEY:  I think in some ways having a hobby that you are really passionate about is more special than doing something like for a career. People talk about doing something you love and I think that there is value to that. It’s not completely valueless but I find that in my experience, starting to do something in a more career-y way or a way that’s making you money can ruin it. There are some things that I’ve been starting to do. I learned to be a writer when I was kid and I actually am starting to do like freelance writing and writing for anthologies that I might be starting to get paid. It’s exciting and rewarding and I feel like I’m doing it and I’m fulfilling something but I also feel like I’m worried about ruining it and I have to be very careful about I don’t want to turn this thing I love into a stressful thing instead.

JOHN:  Yeah. Having no goals or requirements or hard responsibilities in your hobby can be so liberating.

STEPHANIE:  It’s funny because it reminds me of a tweet that I saw earlier this week about someone and I’m paraphrasing very loosely but they were basically alluding to what you just said that the moment you do the thing that you love and you turn it into a career, the thing that once calmed you, no longer calms you. It’s no longer calming. Basically, it’s no longer a form of escapism because now it is something that you are obligated to do for whatever reason.

Definitely, being protective over the things that we love but without trying to suffocate our dreams or our hobbies by always thinking about them in terms of an opportunity. It’s an opportunity for you to submit to an anthology because it’s something that you enjoy but perhaps, if you were to make that a career or try to make them to a career, it might be differently because now the stakes are different, so yeah, I always find that really interesting.

JOHN:  I know with intellectual curiosity, it’s something that isn’t necessarily rewarded when you’re growing up. It sounds like you had an environment that supported that.

STEPHANIE:  Yeah, I did. My parents are both immigrants from the Dominican Republic and both of my parents were definitely on focus a lot on the day-to-day and making sure that my brother and I had everything that we needed and for the most part, I think they were like, “Stephanie is fine. She does her homework. She doesn’t need to be told what to do,” so I was kind of left to my own devices to create this world, this inner reach, inner universe for myself and parents — well, my parents anyway — were like, “They’re kids. You got to just let them do what they do,” and because it looked like a healthy hobby, wanting to read and write all the time, they were definitely supportive of that.

I don’t think they thought about it from the point of view of like, “Wow, you know this is very enriching for our child.” It was more like, “This is a good hobby to have and hopefully, it’ll translate to better grades,” which will translate to a whole bunch of other things down the line. I think my parents trusted me to know and do kind of what was right and I lived in my head, for the most part.

CORALINE:  Stephanie, forgive me if I insist your personal but are your parents still with you?

STEPHANIE:  Yes, but I grew up with my father. My parents got divorced when I was very little, about six years old and my parents were co-parenting for a few years and then my brother and I moved with my father when I was about 12 or 13 years old. He’s been the primary parent in my life ever since.

CORALINE:  I’m curious as to whether he understands how successful you are now and understands the work that you do.

STEPHANIE:  He does not understand the work that I do and I think he understands the success now. Because of where I work, it’s a name that’s recognizable. When I told him that I was going to work there, he was immensely proud. My dad was always a little bit worried about my career choices because he didn’t quite understand how it translates into a real job. The idea of working remotely, he thought I was going to get fired.

Unlimited PTO, what does that mean exactly, you have to let your boss know in advance that you want to take a few days out and then, just letting him know that I was making a good living from doing content from writing and editing. That was something that didn’t quite compute for him because he comes from a background where the good jobs are the ones that are very easily defined and readily understood: lawyers, doctors of some form, engineers and then of course, by extension, developers. He understands that I work in the tech space and I’m adjacent to developers in some way. I think that’s what’s really helped orient him or really help him understand exactly where I am kind of in the lay of the land.

I know he’s really proud of me in how far I’ve come and it means a lot to me because being the child of immigrants, there are many sacrifices that they had to make in order for me to be where I am. Even though I was able to observe, simply by being the child of immigrants, it wasn’t a lived experience for me. Everything that I do, I always do it with my dad in mind specifically because I want him to know that his sacrifices meant something and that they were rewarded somehow. Making sure that I make my dad proud is always a priority.

CORALINE:  Do you want to talk about what it is you do day-to-day, maybe what you do with the Bundler team or what you do with some of these other projects that you’re involved in?

STEPHANIE:  Yes, sure.

CORALINE:  What is a day in the life?

STEPHANIE:  A day in the life. I’m a content manager on the Azure Cloud developer team, which the easiest way to define it is that I get to be a hype woman for a lot of really dope people. Basically, it’s myself and another colleague. We’re basically conduits between the cloud developer advocates and a lot of them, they’re on the conference circuit. A lot of them speak not just at conferences. They host workshops. They write blogs on their own blogs, for third parties. They speak on podcasts. They do video tutorials. They contribute to documentation, etcetera. They generate a lot of content and my job basically, is to help connect everything that they’re doing with the internal Microsoft marketing teams and making sure that all of the cool stuff that’s coming out of my team is being amplified by the greater Microsoft marketing teams and then similarly, helping the Microsoft marketing teams identify cloud developer advocates that would be great for a really cool marketing campaigns and stuff like that.

It’s basically just trying to help communicate what the role of the cloud developer advocate is internally to the rest of the organization and just making sure that all of the great work that’s being done on the ground by people who are at conferences, at meetups gets relayed back into the internal organization. That’s what I do.

It’s been a learning curve because Microsoft is a huge company. It’s the largest company that ever worked at. I worked at startups for five years before this, so there’s definitely having to learn the lay of the land in that way. But what I really enjoy about my job is that I get to really discover what people working in different stacks are doing because the cloud developer advocates, they all come from different programming languages. We also have a bunch of people in the IT space doing like cloud ops and I really get to learn a little bit more about what it is that they like, what it is that they enjoy, what it is that they think is important which is really cool, which is really I think inspired me to try to level up my game. It’s cool because I basically just get to hang out with people that are creating really cool stuff and making sure that I can help plug them into things internally so that people know how awesome it is that they are. That’s what I do day-to-day.

On the Bundler side, the way that I came about joining the core team was that about a year and a half ago, André Arko invited me to join Ruby Together to help the Bundler team and the Ruby Gems team with documentation. When I joined, I wrote two guides for Bundler and then one about just trying to figure out ways to make the docs more accessible to people. It was a lot of content strategy, just trying to say like what kind of traffic are we currently getting, who goes to our pages, which pages do they visit, is there a way that we can make our titles more reflective of how people search for stuff, how to use Bundler to do ‘blah’. The chances are that’s probably how somebody is going to search for something in Google just to make clear what it is that we’re doing.

Then I just started talking to André a lot, just asking a lot of questions about Bundler, about where Bundler is going and just trying to think of ideas of how to get ahead of the curve, how to anticipate some of the needs of Bundler documentation in the future and then I would just go into the issue tracker in Bundler and if I’d see something documentation related that a user raised, I would try to work with the team to write that or even encourage that particular user to update the documentation themselves.

It seemed that the rest of the maintainers on the Bundler core team really appreciated my responsiveness and how I was trying to work with the community that way, so I was named a member of the core team last month. It’s basically what I already do with Ruby Together with Bundler through Ruby Together, just that the relationship has been a little bit more formalized.

CORALINE:  Just to define some terms for people who maybe aren’t in the Ruby community, Ruby Together is a non-profit devoted to funding open source work on critical Ruby infrastructure projects like Ruby Gems and Bundler. We try to make sure that we are offering opportunities to otherwise marginalized developers to also participate in our paid open source work. Bundler is the tool for creating and managing Ruby libraries, so it is definitely a core piece, essential component of the Ruby infrastructure, the Ruby ecosystem. The work on that is so important that I couldn’t over-emphasize. I’m really glad that you’re part of making that more approachable, more friendly and more available to more people.

STEPHANIE:  I am too. I never anticipated that I would be as involved in open source as much as I am now and just going beyond the kind of day-to-day responsibilities as somebody with Ruby Together, I was always really inquisitive so I would always message André and ask him just for more context or just bounce ideas off of him. I think that through my work through Ruby Together, I’ve developed a real deep appreciation of open source and I think of certainly a better understanding from when I started just of the opportunities but also the very real and significant challenges that exist in open source and knowing that I’m one of the very few women, I’m one of the very few people of color that are very active in the open source community is something that I definitely don’t take for granted and understand.

What I also appreciate very much so is how I’m in an environment where non-coding contributions count and matter. Something that I want to emphasize is that I’m a non-coding contributor and that doesn’t mean that I’m not at all technical. It just means that my purview is very different or the scope of my work is complimentary to the work that other folks are doing on the more technical side. Just along all of those fronts, it really gave me a space to explore even beyond the stuff that we’re working on at Ruby Together with Bundler and Ruby Gems, just wanting to branch out a little bit and try to figure out ways that I can bring more writing and editing to open source work. That’s been very rewarding.

CORALINE:  I have to mention this. A lot of people who so still subscribe to the notion of meritocracy have this mantra of it’s all about the code. I think that’s very dismissive of all of the other sort of work that goes into managing an effective open source project. There’s documentation, there’s user guides, there’s a fucking ReadMe for… you know, there’s community building, there’s community management, there’s peacemaking, there’s so much more that goes into a successful open source project than just the code. Is that something that you find yourself having to fight to validate?

STEPHANIE:  Yes. Oh, yeah. Absolutely. I don’t have to fight it very often but I imagine that people who learn that I am a non-coding contributor, there are some people who probably respond to that with a roll of the eyes like, “Not only is she woman but on top of that, she’s not a developer,” which what I worry is that people would further use that to validate what I think are negative and terrible stereotypical notions of what it is to be technical and also a woman in the space and I’m sure you can speak to this also. Women aren’t taken as seriously technically or otherwise or in other roles that are kind of adjacent to the core development space, project management or anything like that.

I think because a lot of the specific contributions that you named aren’t captured easily in a contribution graph on GitHub, very frustratingly enough, there are people who are responsible for UI, for interaction design, for a whole bunch of other things that can’t easily be tracked or even worked on in the GitHub ecosystem, which I think further pushes people to this point that you mentioned. Just about not being taken seriously or not being viewed as technical enough and it’s something that I struggle with every day, not even open source but just in general.

I think I always have to check myself with regard to what it is that I know and not minimizing my brilliance and my contributions simply because I’m not writing code and that’s actually something that’s really hard because I’m in a space where a lot of the people, not just developers but people with ops experience or whatever, just like people who are like in the trenches actually working on the more technical aspects of this work and knowing that that’s not the kind of contribution that I bring. It’s very easy to feel like you’re not always up to snuff or even to associate intelligence and brilliance with that, simply because that’s the space that I operate in and I realize that that’s something that I’ve internalized, that I have to work on myself.

It is definitely a fight on the… Not a fight but a challenge that I constantly want to address externally and also, internally with myself so that I don’t put myself in the position where I’m actually minimizing my efforts or I’m not viewing myself as less technical than anyone else simply because the nature of my work is different from somebody who’s actually working on new features and new releases in that fashion.

JOHN:  Yeah. The system really erases that work. There’s no way to quantify or even make visible a lot of that sort of stuff.

STEPHANIE:  Yeah, absolutely. I think with documentation, it’s probably possible to do that more with documentation than it is with some of these other types of contributions and one of the things that I like focusing my open source work on is on developers getting to understand what technical writing is and what documentation is and how technical writers work on that stuff.

I’m a part of the Write the Docs Slack community and these are highly technical people. They might not all be developers or come from an engineering background, even though over the last 10 years, the documentation space has been moving more toward that particular model simply because of the need for API documentation, like the growing need for API documentation versus end user documentation but these are people that have questions that are not all that different. Not just questions but also work flows and processes that are not at all that different from developers and now using dev tools for a lot of their work. I think that it’s really important for the wider developer community to develop an understanding and an appreciation of that.

JAMEY:  I think it’s thankless too because we keep talking about had difficult it is to quantify this kind of work and I think the best way to quantify it would be to be like, “Oh, this project doesn’t have it and it sucks,” but so I think it’s one of those like you only hear about it when it’s bad kind of jobs which is really difficult.


JAMEY:  Thank you. I appreciate you.

STEPHANIE:  Oh, yeah. I appreciate you too.

JAMEY:  Do you struggle with that? Do you experience that, only getting negative feedback from people and no positive feedback? How do you kind of deal with that in your career?

STEPHANIE:  Well, with regard to documentation or just like in general?

JAMEY:  I guess I didn’t mean documentation specifically but I also didn’t necessarily mean in general. I mean like with the things you do, you’re feeling undervalued because people only notice them when they want to complain.

STEPHANIE:  Yeah. I don’t know if it’s more negative feedback to be honest. I think that in general, I’ve received a lot of positive feedback for the work that I do, thankfully —

JAMEY:  I am so glad to hear that.

STEPHANIE:  Yeah. That’s not to say that there aren’t moments when people just ignore your contribution or whatever, just to let you know but we talk a little bit more about how it is with documentation. When it works, nobody is even going to give you any feedback. It’s like, “Okay, it works,” and that’s fine because we understand that a user is usually trying to access documentation when they need to do a thing or fix the thing and if it works, that’s great. There was no friction there.

When something isn’t working, it’s usually when we hear about it so I actually value that feedback a lot because the purpose of writing good documentation or at least, maintaining documentation is to make sure that the documentation doesn’t prevent a user from actually accomplishing their goal so if we find that there’s an obstacle or something that’s not clear, then that’s definitely something that we want to address.

In that particular instance, critical feedback versus like negative feedback, critical feedback is definitely really important in that particular space but I’ve been lucky in that. People give me positive feedback when asked but sometimes, it’s kind of like, “Okay, the thing works,” and I don’t hear much from it. I don’t know if that answers your question.

JAMEY:  I guess my question is like how do you handle that for yourself, maybe emotionally or in a way that doesn’t burn you out?

STEPHANIE:  Oh, yeah. If we go back to things a little bit, I don’t always get the feedback that I feel I need or if I go a long time without getting any kind of feedback of any sort, I’m not sure if I’m doing too much or too little, having a check in and explicitly ask for feedback, suggestions, things that I should work on are really important for me because self-doubt happens to be a thing that I experienced like many people and without that external feedback, it’s really easy to just tune into the voice in your head, which for whatever reason, the more you focus on it, sometimes the things that it will start saying are really out there.

I try to ask for a feedback and make sure that it’s, I want to say that I tune this out but filter for feedback that I know is coming from a good place that has been contextualized properly and that isn’t really about putting me down but making sure that I do the best work. Everything else for the most part, I try to just get whatever I think is useful and then let it go. I always try to make sure that I’m doing the same for whoever I get feedback for. Communicating feedback is really important and we know that the delivery is just as important as the message, so I always try to keep that in mind.

JAMEY:  That’s a really great advice.

CORALINE:  Just to switch a little bit, I have a situation at my work where we have about 175 engineers and we don’t have external-facing documentation because we’re a consumer-facing company but we have a lot of internal systems. We have what we call the [inaudible] which is just a collection of markdown documents in the GitHub repo. I have advocated for hiring someone with strong content and editorial skills to structure these documents in some kind of way so that they’re easily searchable, so that they’re not scattered between multiple document, so that they have a cohesion and are kept up to date.

This idea kind of got shut down and the main reason was that writing good documentation should be part of every developer’s job, so if we’re not doing it that means we have to level up. I agree with that but I also see the value in someone who specializes in content management, in writing in technical documentation and in information architecture. What I’m going to do is I’m going to ask you if you agree and I’m going to play that back to my management so the pressure is on, to get this exactly right, Stephanie. You have to help me out.

STEPHANIE:  Okay, I absolutely will do. It sounds like your team needs a content strategist, someone who has experience on the editorial side but also on the UX side in terms of the information architecture that you were talking about, someone that’s really good with building out information systems who can see things, who knows who their users are, who know how to define the user and the user in this case would be your engineering team and to get a better understanding of how they conceptualize and think about content and categories and even organizing content.

It’s interesting that one of the things that has been told to you is that documentation should be a part of every engineers job and that’s definitely true but it’s also that technical writing and documentation and keeping good documentation is a skill that a lot of people have not been properly taught how to do. It’s actually very difficult. A lot of technical writers will tell you themselves that what it takes to write something that is what we consider straightforward and clear and concise actually takes a lot of mental energy and people think about things differently. I would recommend that.

You go back to your engineering group and suggest that they hire a content strategist on a contracting basis for an X amount of months, for discovery to find what kind of documentation exist, to do like a full-content audit, to discuss how everything is structured right now, what are the categories that exist, how can we organize this better, how can we optimize for discoverability and findability and also, for helping your team create a strategy around maintenance.

This person, actually can help build that out for your team but that also handed off to you and say, “In order for this to continue to work, this is how this should be done. This is how that should be done, etcetera,” so that way, it’s not one person’s job forever. The engineering teams could still be very involved but they have the opportunity to actually learn that from a professional for whom this is their entire job. They’re content strategist for whom this is their entire job. This is the reason for their existence, working on knowledge bases and wikis and internal documentation and all of that stuff. That would be my recommendation to the Stitch Fix’s engineering team — hire a content strategist. They would be awesome.

CORALINE:  Awesome. I will try that.


JOHN:  Even if the individual developers are creating useful, well-structured documents, someone still has to organize those documents and that’s nobody’s job right now. There’s no one doing the architecture like you said.

STEPHANIE:  Yes. I’m doing my degree in user experience design and I’m actually taking a course in information architecture right now and I took a course a few semesters ago on knowledge organization structures and it’s really fascinating. We look at site navigation and all of the different ways that a site organizes content and we don’t really have the vocabulary, really understand exactly what the decisions were that created the system, this navigation. It’s funny. It’s something we take for granted but it’s not something that everyone knows how to do and learning how to do it is actually very hard.

That is why I’ve said this before that librarians are the information architects we need because this is definitely right up their alley like how do you classify things, how do you categorize things, how do you organize things and it is a lot harder than what it looks. It’s not very intuitive either but when you have that vocabulary and when you understand what goes behind it, it makes it a lot easier to them communicate the ‘why’ behind that to people who don’t have that same understanding. To your point, the engineer could write the documentation and that’s fine but where does this actually go and how do we control the taxonomy of the system that we’re building, so that it’s actually usable.

JOHN:  Library science is a real degree.

STEPHANIE:  Yes, it is.

JAMEY:  I think it’s really important to talk about these kind of things because I agree with you. That is taken for granted and I think it’s very easy for people to be like, “Well, that’s not as difficult or as important as what I do,” but then the thing they’re saying that about, would they be able to do it? I don’t think… Maybe they would.

STEPHANIE:  Yes, very true. When somebody actually points that out and says, “Oh, by the way. This thing that you totally overlooked, it’s important for X, Y, Z reasons,” then I think it becomes real to people. A lot of the things that I’m really interested in content strategy and information, science and all of that stuff are still not things that are super mainstream for a lot of folks in the developer community. There are definitely companies and organizations, I mean, the government has legions of content strategies and people like that that do all of this stuff. But it’s not something that we’ve seen a lot in the dev community and at startups. Startup might not really need that, so as a result, people might not see it as a real discipline with real implications for the work that we do and also, what the end user sees.

JAMEY:  It’s frustrating to me that programmers are so quick to devalue what other people do sometimes because I find that as a programmer, I experienced people devaluing what I do, not from other highly technical people usually, if I’m doing something highly technical but for instance, the sales team at my company. Sometimes, there’s fiction there because they’re like, “Well, can’t you just do this?” and I’m like, “It’s not that easy as you’re acting like it is.”

I have that emotional response to be like, “Please don’t devalue what I’m doing here and act like it’s not hard as it is,” and that a lot of programmers turn around and do that to other people and it’s frustrating to see.

STEPHANIE:  We could all benefit more from empathy but actually, approaching things with an open mind and actually trying to have conversations with people. I don’t know obviously, what situations the folks on your sales team are going through but when people actually sit down to try to say, “What’s the deal? What’s going on? Help me understand what it is that you’re working on. What are the pain points and the pressure points?” we start to see a lot of things and all of the different conflicting priorities and messages and things that we’re hearing.

The sales team might be getting hounded to meet certain numbers and customers are probably yelling at them because this one thing isn’t working, whereas you see things from the backend and you know that there’s certain functionality can’t be created or whatever, that there’s a process or priorities and all of these other things. You can’t just anytime a customer complaints, your job as the programmer, isn’t to just build something out to make them happy and there’s reasons why you’re not able to do that.

It’s frustrating because yes, there are people who straight up devalue that and then I think there are people who just don’t have enough information or understanding really about what someone does or had expressed any kind of interest in knowing more, which keep some tension in their working relationship and stuff.

JOHN:  Yeah. This discussion is sort of bringing up an idea like you were saying Coraline that everyone is saying, “The developers should just get better at writing. We need to level this up there,” but I would imagine that behind that was not, “And by the way will send you to a week-long writing course so that you can actually level up at this.” It’s sort of, “Oh, just go do it.”

I think that also sort of devalues what the skills are and I’m wondering if there was actually a writing course that you could send developers to, not only would they get better at writing but they would also get a good sense of how hard that writing is because they would have to be doing it and be graded on it and actually work at it and that might actually start to bring some of that empathy in.

STEPHANIE:  I’m actually given a talk in a few weeks that all things open about content strategy and documentation and one of the things that I recommend in that talk is for developers to start going into spaces where writers are. At developer conferences, I have not seen many technical writers and at technical writing conferences, not very many developers with the exception of developers who are tasked with doing the writing. As a result, there’s like a huge silo between communities of people that should be working much closer and should develop an understanding of what it is that they do.

One of my suggestions is if you can’t go to a conference, Write the Docs for example has meetups all over the world and they have a Slack group if you prefer something a little bit more asynchronous. But if we continue to do things as they are and if we don’t actually start going to where the people who are doing the thing that we need to know more of are, it makes it difficult to develop that empathy.

In my talk, I recognized technical writing is really hard and people have written books on it. There are a lot of blog posts out there and it can be very intimidating especially for people who don’t feel comfortable writing but the first step definitely is to just develop enough curiosity to try to see what that entails and also, try to learn from the people who are actually doing this day-in/day-out.

CORALINE:  Are you saying that we would better at our jobs if we became better communicators? Is that your premise? I don’t know about all that.

STEPHANIE:  If you happen to be kind of prolific, you write a lot, you have a book coming out, aha, yes exactly.

JOHN:  It actually reminds me of what Steven Shorrock was talking about on an earlier episode of Safety-II culture, which is part of the increasing the safety of a system is making sure the teams trust each other and understand what the other team is doing so that when information comes from that other team, you trust it and act on it, rather than saying, “Those folks don’t know what’s going on over there, so we’re just going to ignore the information.”

It’s sounds like it got some of that same concept of let’s trust the writers, let’s trust what they’re telling us about, what needs to be written, let’s trust the UX people, let’s trust the designers, let’s bring everybody together so that we’re all working on the same stuff.

STEPHANIE:  And to also feel that, as part of developing that relationship, that you can ask for why. Someone would tell you, the UX person will say, “Oh, we need to do this because of this.” Well, let’s backtrack a little bit. Explain to me what the reasoning is behind it, just so we can start to see things a little bit from their point of view and understand what the challenges are and what the things they’re coming up against or even, assumptions that other people have, in general. That’s also really good to know. We want to know what kind of assumptions or expectations people have going into their work and in their approach with working in partnership to other people. That’s really important and that’s something, I think that unfortunately took me up until recently in my career to actually start doing and to see that really as part of the process of developing a great working partnership with people.

Individuals are individuals, right? So your mileage may vary but by and large, I find that when I have done that and really try to understand why people do certain things, the process has always been a little bit illuminating. I think this really helps me to remind myself that we’re all on the same team, especially if you’re coworkers but you’re not on the same actual team within the organization. For the most part, we’re all driving towards similar goals. I think it’s always good to remind oneself of that but also remind other people that there might be tension and there might be conflicting priorities and conflicting goals and objectives and all of that stuff but ultimately, we are here to work together on this thing and try to make this thing as good as it can.

I don’t want to sound too optimistic. I’m not trying to give anybody any Kool-Aid but I’m just saying, that approach has really helped me develop a better working relationship with people, instead of just giving into my initial reaction to any particular thing or interaction or direction or task that I’ve been given. That’s what’s helping me.

CORALINE:  I like the idea of asking why too because being on the receiving end of a why question makes me question some of my own knee jerk reactions to things or habits that I’ve internalized that maybe aren’t the best answers or the best solutions to problems anymore. That’s something I experience quite a bit when I do my mentoring. I encourage the people that I work with to ask me why because it challenges me. I can learn a lot about my own habits and my own sort of patterns by having to explain them. It happens quite often that it’s like I don’t know why I do that. That’s just the way I’ve always done it. Maybe there is a better way.

JOHN:  Yeah. I think it is a bit of a challenge to develop that self-awareness though, that ability to say, “This question makes me uncomfortable,” but to be able to not just react with, “Yeah, well no, it’s just that way. Just go do it,” then sort of dig in to your position because you’re getting a threatened response.

STEPHANIE:  Agreed, agreed.

JOHN:  Stephanie, a couple of days ago you tweeted some things that were really interesting to me and sort of brought up things that I’ve been thinking about myself. You said, “One of the best and worst things about working in tech is how easy it is to get excited about something and wanting to learn it, right up until your brain tells you that you’re not doing enough, not working hard enough, leading you to get overwhelmed with just how much there is to learn. It’s much too easy to compare what one knows with what one needs to work on with the staggering amounts of content being produced and thought leadered out there, so be kind to yourselves and don’t minimize your current efforts and the knowledge you possess.”

It’s simply a pattern I’ve noticed in tech where you’re always moving forward, you’re always moving up against things either you don’t know or that are broken in the code that you’re looking at or in the things that haven’t been written yet and it’s very easy to lose track of your progress.

STEPHANIE:  Yeah. I’ve been feeling that acutely lately and not because of anything that I’m forced to learn from my job but because I hold myself to a standard of wanting to develop enough of an understanding of what it is that people are talking about and the products that we create to be able to speak on them. I feel that that’s really important just from a user-empathy standpoint. It’s trying to understand things from the point of view of our users as best as possible.

Lately, I’ve been tasking myself with learning Azure and then I’ve been subscribing to a bunch of newsletters that are cloud developer advocates because I want to get an understanding of what it is that they’re seeing and all of it is really exciting and it’s also a lot. I tend to get a little bit overzealous sometimes, with the amount that I think I need to be doing, then I develop this thing that I need to get better at this, I need to know as much about it as possible so that I can confidently speak to it but then I forget.

I’m actually in grad school. I am learning outside of work. This part time open source gig, it’s not like I’m not doing anything but because we’re in an environment where people are sharing the things that they’ve learned, sharing the things that they do a lot, it’s very easy sometimes, to feel like I’m not doing enough compared to that person. It’s always that trap, I think. It’s the trap of wanting to learn a lot which is great but then that could easily snowball into something else.

I had a conversation with my husband this weekend. We were just hanging out he was telling me, “You know, you tend to minimize the stuff that you do.” He tells me all time. He’s like, “You know when I told you that you’re amazing, you really are and look at all the stuff that you’ve done. You’re a Dominican woman from the Bronx, then where you’re at now and they’re not a lot of people like you,” and just six years ago, I was homeless and unemployed and coming off of a really bad breakup and that’s really where Ruby came into my life. Since that point, my upward trajectory, it’s been impressive, so I had to really take a step back and really just kind of marvel at all the stuff that I’ve done and allow myself to say, “Wow, that’s actually really cool that you’ve done all of this stuff,” and really basically, allow myself to be impressed with my own efforts and not in an arrogant way but in a, ‘wow, look at how far we’ve come, Stephanie’ kind of way and really being my own hype person, you know?

You know, like in rap music, you always have that person in the stage. There’s a rapper and then you have a person the stage who’s trying to hype the crowd up. That’s what they call the ‘hype man.’ I have to be my own hype woman. I have to be a rapper and I have to be the hype woman for myself and my efforts and I think that’s really important because we’re in an industry that really forces people to have to learn because everything is changing so much at such a quick pace.

It’s really impressive just how different the landscape looks now than it did when I first got into it about five or six years ago. There’s definitely this pressure, I think for a lot of people, a lot of technologists to constantly be ahead of the eight ball but then, we have to be careful to not fall into that trap of comparing what we’ve done to what we think other people are doing or where they’re at and really, just take a moment to try to put this into perspective from how far we’ve come and then of course, making sure that we enjoy it because if it becomes a chore, we could easily burn ourselves out and not give ourselves the credit that’s due.

CORALINE:  That really resonates with me. I created a to-do system because I’ve struggled with staying organized my entire life. It’s called LFTM. It’s on my GitHub, low-friction task management and basically, it’s like work journals and personal journals where I record what I do every day. I record the things that I need to do in the future, so I have less things to carry around in my head. I recently added something called ‘achievements.’ It’s a simple document where I will write down, “Oh, on this date, this thing happened and I’m very proud of it,” or, “On this date, I learned about X and was able to successfully implement it in a project that I was working on.”

I think it’s great to actually have a physical record of your accomplishments because so often with what we do and what you’re talking about with being overwhelmed by the sheer volume of things that remain to be learned, it’s really important to have a roadmap of just how far we have come and of the good things that we have done. For nothing else as a reminder, when you do hit those low points, when you do find yourself played yourself out, you can look back on it and say, “I’m actually doing things and I’m actually learning and I’m actually growing as a person.”

STEPHANIE:  I actually love that idea and that’s something I’m going to do. I think that’s great. Like you said, having a physical record is important because the record ain’t lying. You wrote that you did this thing, you know, on August 18th, it happened and you learned it and I think it’s even more wonderful to see how a document like that grows over months and years. I think that’s really awesome and I like to journal, so I think that’s a great thing to add to my journaling.

JOHN:  Yeah. I wrote a talk about this earlier in the year that I need to sort of reformat and bring up. It’s called ‘Everything Is Broken, and It’s OK.’ The metaphor I used to talk about this is like if you’re climbing a pyramid, it’s really steep walls of stone and you’re just going up and everything you look at in front of you is just more steep walls of stone. Until you get to the top, it’s what you’re always looking at. It always looks like you’re dealing with the same difficult problem. But if you pause and turnaround, all of a sudden you look behind you and see how far up you are and what the amazing plateau behind you looks like and if you can schedule rests like that where you stop and look at your progress and have recordings of your achievements you made along the way, then you can really keep yourself motivated in your journey.

CORALINE:  That’s really an interesting metaphor, John and it reminds me of an opposite but complimentary metaphor. When I first started planning my gender transition, it felt like things were snowballing. I remember talking to my therapist and saying, “I feel like I’m falling down a mountain and the further I get along, the more speed I’m picking up. I know it’s at the bottom and it’s kind of terrifying,” and she said, “Why don’t you take a break and enjoy the view.”


JAMEY:  That’s really beautiful.

STEPHANIE:  Yeah, that is.

JAMEY:  I saw a post online once that was like whenever someone talks about like, “My therapist said…” my ears perk up because I’m like, “Free therapy!” and I also want to tell a story about something my therapist said, which was — spoiler alert — the moral of my story is that it’s very important to surround yourself with people who have perspective on you, which has a lot of us is thinking about when you were talking, Stephanie. I was talking to my therapist once and I was sitting there and [inaudible] and I was like, “You know, I feel like a failure. I feel like I’m doing such a bad job at things. I feel like I’m annoying to people in my life and all of these negative things.”

My therapist was like, “What do other people in your life have to say about this?” I’m like, “Well, they’re trying to tell me that it’s not true but I don’t know.” They were like, “Why don’t you think what your friends are telling you it’s true,” and I was like, “Well, maybe they’re just saying that,” and he was like, “Well, why would they be just saying that?” I’m like, “I don’t know because they want me to feel better,” and he was like, “Well, why do they want you to feel better?” I’m like, “I don’t know. I guess because they care about me,” and then I had to say it and I was like, “Oh, I guess it’s because they care about me and why would they lie about this.” I think about that a lot because I felt like I was led into saying this very true thing that I was having trouble coming to grips with.

JOHN:  That’s fantastic. Normally, at this point of the show, we move into what we call reflections, where each one of us talks about something that really struck us from the conversation that we’re going to takeaway from it. My thought here is Stephanie, you were talking about like doing your work to understand the teams that you’re working with better so that you can better coordinate and sort of lead us into a larger conversation about teams working together and trusting each other. It’s something that was actually a topic of discussion as I was at Devopsdays Boston all this week.

I think it’s something that’s really important and even as a manager within a team, it’s not something you’re necessarily thinking about like coordinating the work with the other team and then managing the perception of the other teams within your team or vice versa but I think it’s really important to think about at a company systems level like if you’ve got one team that everyone sort of craps on and just like, “Oh, yeah. They’re just bozos over there,” that’s a really problematic part of the culture and it’s going to lead to lots of problems in your company and so, trying to spot those around you and try and do work to counteract that, I think is going to be really valuable. It’s something that I’m going to keep thinking about.

CORALINE:  John, I was going to talk about trust as well but since you covered that one so well, I want to touch on another thing that Stephanie made me think about and that is the power of dreams and the dreams that we had for who we would become when we were children and how our past might diverge from that but we find ways to fulfill those childhood dreams in surprising ways.

I think there’s a lot of value in connecting to those childish ideals of who we might be and finding ways to bring them to life, maybe not exactly in the way that we have anticipated them but the value of fulfilling them in some way and creating a sense of continuity of self between the things that were so interesting to us and so fastened into us and so core to our beings at one point in our lives and how we can maintain a connection to that sort of innocent view and bring that sort of joy and wonder into our lives and not get lost in the day-to-day details and actually, to sort of assess. Yes, I am doing something amazing. Yes, this is something that is related to something that I saw myself becoming earlier in my life and yes, that means I am a successful human being.

JAMEY:  I guess in a way, I also want to talk about trust but I think I want to get it from a subtly different angle. There was something that Stephanie said when we’re talking about feedback that I thought was really great advice, which was when you get feedback, you have to try and filter it for if it’s coming… I forgot exactly how you word it and I’m sorry but essentially like, is this coming from a source that’s essentially in good faith. I think that in a way, that’s also related to this conversation we had right at the end about surrounding yourself with people who have perspective on you and the value of being able to know when people in your life are interacting with you in good faith because they care about you and because they see something in yourself or in a situation that you don’t necessarily see versus people that are interacting in bad faith, which is something I think about a lot when dealing with people in tech and on the internet and deciding if I’m going to invest any emotional energy into a conversation or an argument.

I think it’s a difficult road to walk between deciding, like someone I respect said something nice to me and I really want to internalize that versus someone that I don’t necessarily respect said something that wasn’t so nice to me and I pointedly don’t want to internalize that. I think thinking consciously about that is really important and I try to do it but I think now, I have another tool to do it better.

CORALINE:  Just to build on that, that’s something I need to internalize too, with the position I’m in and my visibility and how many people seem to think that I am an evil scorch on the open source world, so thanks for that perspective too, Jamey.

JAMEY:  I think you’re great and I hope that you respect me enough to internalize it.

CORALINE:  Thank you. Stephanie, what are your thoughts?

STEPHANIE:  I really appreciated both the story Coraline that you gave and Jamey gave about what your therapist said. I think one important thing about that is that therapists are wonderful. They’re just so great at helping you suss out your emotions but also things that we might have trouble articulating and Jamey, I really like, in your particular story, how your therapist helped to get there by asking a bunch of why questions and that brought me back to the conversation we were having earlier about talking to other teams and trying to figure out why they do things or why they said something.

It’s funny because that is a tool that therapist has using very thoughtfully and while I’m not suggesting that we can all develop the same communication style, there’s definitely something to be learned probably taking things from an approach we’re being inquisitive but genuinely from because we’re taking the approach of caring enough about the other person. We want them to help understand some of their motivations and we also want to be able to clarify that for ourselves. I really love just how communication and differing perspectives and offering a different perspective was reflective both of your stories.

JOHN:  Another thing I thought that just sort of related to what we’re talking about earlier is when you get that positive praise, you can put that in your achievement journal as well and it’s a good way of filtering out the bad stuff because you can write that down and then you keep this rolling log of the good stuff.

CORALINE:  I actually have a folder that I keep on Dropbox that I can access it from any device, called ‘kindnesses,’ so anytime someone says something nice about me on Twitter or a nice email or something like that, I take a screenshot of it and I drop it into my kindnesses folder and when I’m feeling really low, I look through my kindnesses folder and it reminds me that some people think I’m a worthwhile human being and just maybe, they’re right.

STEPHANIE:  They are right.

JOHN:  Yes.

STEPHANIE:  You can put that in your kindnesses folder with lots of hearts and by the way, I do want to say before we leave that I’m really happy about the work that you did for Ruby Me and bringing that to life and for folks who don’t know what Ruby Me is, Ruby Me is a paid mentorship program, which pairs early career developers with seasoned Rubyist to work together on open source projects and this is an idea that Coraline came up with and which is now a thing that is going to happen. I think that in the world of open source in the work that you have done, it’s definitely undeniable, the impact that you would have had and I’m just really excited to see that people, that more early career developers, especially people from marginalized backgrounds are going to have hopefully the same kind of experience I did in terms of my entry into open source. Meaning, being in an environment with people who care about you as a person and who care about your learning and your growth and that’s definitely something we need more of. Thank you.

CORALINE:  Thank you, Stephanie. That about wraps up Episode 99. Stephanie, you’ve been a delightful guest and I am so glad that we were able to spend this hour with you.

JAMEY:  This was wonderful.

STEPHANIE:  Thank you. Same to you.

JOHN:  Yeah.

CORALINE:  And we will talk to you all later with Episode 100, believe it or not.

JAMEY:  Wohoo, 100!

JOHN:  Greater Than Code is a listener supported podcast and if you want to support us, head on over to Patreon.com/GreaterThanCode and sign up. If you give any amount on a regular basis, we will give you access to our private Slack community where you get to hang out with all the wonderful people that you get to listen to every day and fascinating conversations all the time.

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