Keynote: Leading From Where You Are

by Rose Wiegley

The keynote titled "Leading From Where You Are" delivered by Rose Wiegley at RubyConf Mini 2022 explores the importance of leadership in the tech industry, particularly in the context of diversity and inclusion. Rose, a seasoned developer at Shopify, shares her journey and challenges as a woman in tech, urging attendees to embrace their leadership potential regardless of their position or title.

Key Points Discussed:
- Finding Your Voice: Rose initially planned a technical presentation but opted instead to focus on leadership, highlighting the pressure many women feel to establish technical credibility.

Understanding Context: She emphasizes the decline of women in tech from the 1950s to the present day, tracing significant historical milestones, such as the creation of COBOL and the introduction of Ruby, while linking these to broader societal issues affecting LGBTQ+ and marginalized communities.
The Urgency for Leaders: Rose argues that there is an immediate need for leadership in tech due to the increasing comfort with sharing harmful ideologies. She cites the statistic that only 30% of programmers are women, underscoring the gap in representation and the importance of diverse voices.
What Constitutes Leadership: Leadership is portrayed not just as a title but as a set of behaviors, including initiating solutions to problems, mentoring peers, and advocating for team members. It involves enabling others and sharing responsibilities rather than merely holding a senior position.
Practical Tips to Lead:
- Distributing responsibilities to prevent burnout from "glue work," which often falls disproportionately on women.
- Recognizing and praising leadership behaviors in others, particularly in team settings.
- Facilitating the voices of quieter team members and encouraging discussion during meetings.
- Identifying and addressing issues proactively, using structured proposals when permissions are needed for initiatives.
Visibility Matters: Rose stresses the importance of maintaining visibility in one's work to facilitate promotions and mentorship, especially for those from underrepresented groups in technology.

Conclusions and Takeaways:
- Each individual holds the potential to lead from their current position.
- Emphasizing the necessity of empowering others is crucial for fostering an inclusive tech environment.
- The call to action for all attendees to reflect on their own positions and contributions within their teams and the wider tech landscape.

00:00:00.299 Welcome to RubyConf Mini 2022!

00:00:10.920 It has been an awesome three days.

00:00:13.000 We are going to end it with one of the best sessions of all, because I have the distinct privilege of introducing our final keynote speaker.

00:00:28.859 Rose Wigley is a senior staff developer at Shopify. She has been a developer for over 25 years and has worked on a wide range of software, from printer firmware to Ruby on Rails applications.

00:00:41.460 She wanted me to mention that she is a mom to teenagers, which is particularly important because for those who don't know Rose, she's very active in both the wnb.rb communities and on Twitter. As a highly visible parent and distinguished engineer within the community, she paves the way for others who might not see women with children continuing to be engineers and leveling up in their careers.

00:01:07.320 Rose can often be found giving great advice on WNB Slack or on Twitter, public speaking at events like this, or organizing panels for WNB. I truly could not think of anyone better to conclude the RubyConf Mini program with her very first keynote.

00:01:45.840 As you heard, my name is Rose Wigley, and my pronouns are she/her. I work at Shopify, and I want to let everybody know that even with the current tech slowdowns, we are still hiring for some mission-critical roles. So please check our website if you're interested.

00:02:22.980 This is not the talk I originally planned on giving. My original talk involved some very complex code I once wrote and the importance of simplicity in code. However, as I thought more about it, the original plan fell flat.

00:03:02.280 I realized I was writing a technical keynote because I am a woman giving a talk at a programming conference, and I felt the need to maintain my credibility. I have been programming for over 25 years, and I hold a master's degree in electrical and computer engineering. I have written code ranging from C and assembly to Ruby on Rails web apps.

00:03:26.239 Yet, I was worried you wouldn't think I was technical enough to be standing here right now.

00:03:33.620 Then I asked myself, if I wanted everyone here to walk away with a message, what would it be? This led to the talk titled, 'Leading from Where You Are'.

00:03:40.099 For this, we are going to discuss four different questions: Where are you? Why should you lead? What is leadership? And then, some very practical advice on how to lead.

00:03:51.299 First, where are you? In the most literal sense, we're all at RubyConf Mini in Providence, Rhode Island. We are here to learn about programming and connect with our fellow Ruby enthusiasts.

00:04:07.620 However, the literal sense does not tell the entire picture. To give you perspective, let's take a little trip back in time to 1959. This was 15 years before I was born.

00:04:21.180 I know at least half of you are busy doing some math in your head, and because programmers hate date math, I'll save you some trouble: I'm 48 years old. 1959 was a pivotal year in computer programming.

00:04:41.579 It was the year COBOL was created, largely thanks to the work of Dr. Grace Murray Hopper, later known as Rear Admiral Grace Hopper. COBOL was built on the radical concept that computer languages should be close to human languages and should run on various types of computers.

00:04:53.759 It is not surprising that the driving force behind one of our first major programming languages was a woman. At that time, it was estimated that between 30% to 50% of all programmers were women, though this number had already declined from earlier days when programming was considered clerical work mostly done by women.

00:05:11.639 Before continuing, I want to acknowledge that while women are a minority in tech, I speak from a place of immense privilege as an upper-middle-class, straight, cisgender white woman. A lot of the history I'll share with you today, I had to learn for this talk.

00:05:30.360 I wish I had taken the time to learn this sooner. When discussing history, it's essential to view it in the full context of its times. 1959 was not a good year for all Americans; it was the year of the Cooper Donuts riots.

00:05:58.699 Before researching this talk, I knew about the more famous Stonewall riots in New York City, but I didn't know that ten years earlier, anti-cross-dressing laws were commonly used by police to harass and arrest LGBTQ+ people.

00:06:17.280 The Cooper Donuts riots occurred in downtown L.A. when police arrested five LGBT patrons at Cooper Donuts and attempted to cram them into a single police car. Some historians view this as the first LGBTQ+ uprising against police harassment in the United States.

00:06:35.460 At the same time, while we were busy developing languages like COBOL, the state of social issues was hectic.

00:06:47.460 Now let's jump ahead to 1972. By this time, we are one year before my parents got married and two years before I was born.

00:07:02.460 1972 was another significant milestone in programming history with the first high-level programming language, C, created by Dennis Ritchie. C has a special place in my heart because in 24 more years, it will be the first programming language I use professionally.

00:07:22.860 However, even as programming advances quickly, other things are falling behind. Remember in the late 50s when 30% to 50% of programmers were women? This number dropped significantly by 1971, one year before I was born, when only 14% of computer science degree graduates were women.

00:07:39.300 The world was changing in other ways. In 1973, the American Psychiatric Association issued a statement declaring that homosexuality was not a mental illness, a significant change in understanding.

00:07:56.460 By 1975, Minneapolis became the first city in the United States to pass transgender-inclusive civil rights legislation. Interestingly, this pass came with barely a murmur, as the controversy had already occurred a year earlier with the passage of gay rights legislation.

00:08:12.960 Before we look at another programming milestone, let’s briefly stop in 1986. In that year, 36% of computer science degree recipients were women. This was a significant moment as it was the only time since the 50s that women had such a large presence in computer science.

00:08:30.600 However, from this point forward, the trend would decline. In 1986, I was 12 years old, and by this time, my parents had divorced, and my mom had started medical school as a single mom with two kids.

00:08:49.260 While 36% of computer science graduates were women and a woman could get into medical school, it didn't mean it was easy. I remember my mom recounting an interview where she was told, 'How can you possibly expect to be a doctor? Doctors can't just run home at 5 PM to cook dinner for their kids.'

00:09:06.720 1986 was also notable for the Bowers v. Hardwick case, where the Supreme Court ruled that anti-homosexual legislation was constitutional in America. It would be another 17 years before this decision was overturned.

00:09:26.520 At 12 years old, I had no idea about this ruling, but I knew my parents divorced because my dad realized he was gay. To survive public school, I had to refer to my dad's boyfriend as 'his friend'; I don’t think a single friend of mine knew my dad’s truth until I reached college.

00:09:49.620 Jump ahead to 1995, and I find it hard to believe that it was just 27 years ago. In 1995, I was one year from graduating with my master's in electrical and computer engineering.

00:10:06.000 The year 1995 is crucial for all of us; it's the reason we're all here together. On December 21st, 1995, Mats announced the first public release of Ruby in Japanese news groups.

00:10:35.520 I also want to share that during this exciting time, women’s presence in computer science was again dropping. In my graduating year, only 28% of computer science majors in the U.S. were women. For those of us who studied electrical and computer engineering, it was even worse; under 10% of the 150 students accepted into the program were women.

00:10:53.520 I recall being in a software engineering class of 40 students. Every morning, the professor would greet us with, 'Good morning, gentlemen and lady.'

00:11:12.000 Now, I want to discuss a serious topic. For the next few minutes, I will talk about anti-trans violence. For many members of our audience, this is not just a history lesson; it is a very real and present danger in their lives. If anyone feels the need to excuse themselves, please feel free.

00:11:30.540 Our last historical stop will be 1999, just four years after Ruby's first release, right before the start of the 21st century.

00:11:47.760 November 20th, 1999, marks the first transgender day of remembrance, established a year after Rita Hester, a transgendered Black woman, was murdered. Her death led to the establishment of the day to remember transgender individuals who have lost their lives.

00:12:05.220 22 years later, in 2021, the toll was high: 57 lives lost in a single year to transgender violence—49 of whom were trans women, and 39 were Black trans women.

00:12:22.980 So, why are we here? Yes, in the literal sense, we are at RubyConf Mini in Providence, Rhode Island.

00:12:40.560 However, the deeper answer is complex. We are not at RubyConf in Houston, Texas because many of our peers have safety concerns that others may not think twice about.

00:12:56.640 These concerns become exponentially greater based on government actions that make someone's existence illegal.

00:13:15.240 So why should you lead? Because of where we are, we need leaders right now. We have reached a point in our society where certain subsets of people are becoming very comfortable sharing the quiet parts out loud, sometimes through words, sometimes through actions, and sometimes with life-altering consequences.

00:13:30.180 I emphasize this need for leadership because significant incidents have occurred in the single small city where I live over the last few years, and what I’ve shared isn't even everything.

00:13:47.820 Additionally, my city is not unique. We need you all to be comfortable leading because right now, only 30% of programmers are women and only 20% of computer science graduates.

00:14:05.640 Moreover, only 8.1% of programmers identify as Hispanic, while 4.6% are Black, and only 0.3% are from Indigenous communities, the original inhabitants of these lands.

00:14:20.640 Furthermore, only 6.6% of programmers identify as LGBTQ+. As Barbara Tannenbaum eloquently expressed in her keynote, we need your voices, especially those representing these statistics.

00:14:31.500 We need to make sure that all of our voices are louder than those who want to drown them out.

00:14:51.960 I am asking you to lead. But what does leadership truly mean?

00:15:05.220 Is it just a fancy title, like senior staff software engineer?

00:15:10.799 The part of me taught never to brag or push myself forward cringes at writing this.

00:15:20.580 But I want to highlight an important question: What comes first, the title or the behavior? One of the unspoken rules of tech promotions is that you don't get promoted just for being very good at your current responsibilities.

00:15:40.440 You also don't get promoted simply for being in your role for a certain number of years. You get promoted because you are already doing the work at the next level, and you are doing it in a way that is noticeable.

00:15:56.880 For instance, I joined a nine-person startup four years ago as a staff software engineer. When I arrived, I noticed the documentation was completely outdated and required updates.

00:16:15.180 After realizing the CEO was also working off an outdated schedule, I initiated discussions with other developers, figured out what they were doing, and created an up-to-date schedule.

00:16:37.200 I also guided our interns, given that we had two interns in a nine-person company.

00:16:48.300 Then one day, the CEO approached me and asked, 'We're fundraising, and we need a VP of Engineering. Would you like the role?' He added, 'You don’t even have to change what you’re doing now.'

00:17:06.360 This story raises two questions: First, was I lucky? I don't mean lucky in the sense of being in the right place at the right time. I mean, a lot of the work I was doing leaned towards the non-technical.

00:17:25.440 It required a broad understanding of building software products but wasn’t technical like the engineer optimized for encrypted video streaming.

00:17:46.680 If you have never seen Tanya Riley's excellent talk on being glue, I highly recommend it. Glue work is the work that keeps your software team functioning but does not directly contribute to the product.

00:18:10.560 Examples of glue work include documentation, developing developer tools, organizing team activities, and taking notes. Glue work is often disproportionately picked up by women.

00:18:29.640 It's one of the reasons women can be overlooked for promotions; their efforts may be regarded as excellent but not technical enough.

00:18:39.480 So yes, I was lucky. I was fortunate to be in an environment that recognized the value of the work I did. I managed to straddle the line between leadership and glue work.

00:18:56.640 The second question is, if you need to do the work before you can earn the title, and if titles vary so widely from company to company, should we even care about them? My answer is an unequivocal yes.

00:19:13.920 Titles matter. If someone tells you they don't matter, it's likely they speak from a place of privilege where titles are meaningless.

00:19:38.220 Worse, they could be attempting to undermine the title you have earned. Titles serve as shortcuts that eliminate the need to establish your credentials every time you enter a room.

00:19:48.540 I didn't have to elaborate on my entire resume when I started this speech because my title 'Senior Staff Software Engineer at Shopify' succinctly encapsulated who I am.

00:19:59.789 I am a soft-spoken, older blonde mother in tech. I definitely utilize my title when needed.

00:20:12.139 To quote my children's favorite musical, 'I want to be in the room where it happens.' Being invited into such rooms is crucial. At a different level, it allows you to participate in high-level planning and cross-team discussions.

00:20:30.879 Your title provides access to places where you can share insights and have your voice heard.

00:20:54.719 Titles also help pave the way for fairer compensation. While there is still a problem with fair pay in tech, especially for women and minority roles, it becomes significantly easier to assess if your salary aligns with industry standards when your title reflects your level of work.

00:21:11.640 I typically do not flaunt my title unless there's a necessity. If I introduced myself to individuals at this conference, I would simply say I'm Rose, and mention I work at Shopify.

00:21:31.080 However, in some situations, I might specify, 'As a Senior Staff Software Engineer at Shopify, with over 25 years of experience...'

00:21:53.160 And that serves as my polite way of implying, 'Hey, you might want to reconsider burning bridges right now.'

00:22:14.040 Now, let's touch on titles that are not useful. Contrary to certain social media narratives, a title does not guarantee you will always get your way.

00:22:30.420 This holds especially true on the tech track, where your role often involves advising instead of commanding. The strength of your ideas is what matters.

00:22:45.420 While my title can grant me entry into discussions and provide space for my voice to be heard, if I utter complete nonsense, I hope nobody blindly follows my lead.

00:23:05.280 In a healthy organization, there should be room for everyone to advocate for good ideas.

00:23:25.080 There are also specific things that titles don't facilitate. They don't guarantee that others will feel comfortable speaking freely.

00:23:38.760 There's a real reason why I don't introduce myself with my complete title; as a woman, it may seem pushy, and it can create an imbalance of power.

00:23:58.560 Remember a time when the VP of Engineering ended a Q&A and asked for Slack feedback? I spent a significant amount of time crafting the right message with my feedback, grappling with the fear of potential career consequences.

00:24:18.135 The reply I received the next day was positive, thanking me for my willingness to share my thoughts. This illustrates how important feedback can be, yet past experiences led me to worry.

00:24:35.640 I keep in mind that if a new developer or intern needs to disagree with me, they may feel the same way about addressing me as I did when reaching out to the VP.

00:24:51.840 This is why this talk on leadership is directed at everyone in this room, regardless of your current level. Even if you have only written a single line of code, your insights can help with aspects that someone at a higher level might never be aware of.

00:25:10.320 Additionally, as we discussed yesterday, titles do not mean someone has all the answers; experience may teach us how to find those answers quickly and what questions to ask.

00:25:31.860 However, it will also continuously remind us of the multitude of things we still don't know.

00:25:53.340 A good leader is willing to say, 'I don't know; let's figure it out together.'

00:26:04.800 Let's go back to our original question: What is leadership? It can't simply be a title since you need to show leadership before you earn one.

00:26:20.940 I believe the best way to articulate this is through examples.

00:26:37.680 Leadership is stepping up and creating a solution when you see a problem.

00:26:45.960 While we're on this slide, let’s take a moment to recognize our exceptional conference organizers with a round of applause.

00:27:10.260 Leadership is about teaching your peers something that will help you all work better together.

00:27:20.880 Leadership involves discussing difficult topics so that others may learn and feel supported.

00:27:30.180 What I really want to emphasize is that leadership is not just about those grand gestures.

00:27:42.180 I am not expecting this entire room to become the next RubyConf Mini organizers.

00:27:53.520 Leadership can be as simple as having a single conversation with another developer.

00:28:10.980 Luckily for me, I happen to have another developer in my house. Early in our careers, during the dot-com boom, my husband Doug and I worked together at a small email startup.

00:28:27.720 One evening, after work, I was venting about my frustration with not yet receiving a raise. After listening for a while, Doug asked me a simple question: 'Have you asked for a raise?' At that moment, I looked horrified.

00:28:50.420 I replied, 'Of course not! I've been putting in extra hours, so they should recognize my work.' He then said, 'Okay, take a seat; we need to talk.'

00:29:12.999 It was then that I learned how naive my views on raises and promotions truly were. You don't need to be someone's spouse to give career advice like that, but I recommend kittens as a comforting presence.

00:29:41.480 For me, leadership distills down to a core principle. As developers, we assess ourselves based on our individual contributions—features delivered, lines of code added, and ideally, lines of code removed.

00:29:58.740 As leaders, we need to reverse that metric. We should judge ourselves on what we enable others to accomplish.

00:30:20.020 So far, we've covered where you are, why you should lead, and what leadership entails.

00:30:32.940 In this last part of my talk, I want to get down to practicalities: How do you lead? What skills can you take away today that will bolster your leadership capabilities?

00:30:47.040 If leadership is about enabling others, the biggest and easiest thing you can start with is to help lift others up.

00:31:01.560 For starters, friends shouldn't let friends bear all the glue work. Here are a few simple phrases that can help distribute glue responsibilities across the team.

00:31:14.880 One of my favorites is, 'Let's rotate who takes the notes.' Or, 'Let's rotate who organizes the social events.' I also like to suggest, 'Can one of the managers please take care of this task?'

00:31:31.680 Often, what may feel like glue work for you might actually fall under your manager's duties. Managers are not just there to instruct you; they're there to buffer your team against external challenges.

00:31:52.680 Furthermore, it is essential to highlight leadership when you observe it. Frequently, the distinction between glue work and leadership work is simply whether or not someone is recognized for it.

00:32:04.410 Feel free to reach out to someone’s manager and say, 'Hey, I noticed that so-and-so displayed exceptional leadership skills when they reorganized our docs' or 'I really appreciate when this person explained this complex concept to me.'

00:32:19.620 Actively advocate for each other; managers often lack awareness of the remarkable contributions happening around them.

00:32:33.300 In safe environments, don't hesitate to point out observable inequalities, such as, 'I’ve noticed that all the women on our team have been organizing all the social events. Let's make a change.'

00:32:45.180 Another practical action is being mindful of when others struggle to speak up during meetings.

00:32:55.740 If you notice an intern trying to voice an idea and getting cut off, pause the conversation and ask, 'John, were you about to say something?'

00:33:06.840 By allowing space for others, especially as leaders, you empower everyone at all levels to express their thoughts.

00:33:18.120 Finally, remember that as you advance in leadership, it's often beneficial to talk less. Allow others a chance to propose solutions in team meetings.

00:33:31.560 Encourage them to come up with solutions instead of always providing the answers yourself. Instead, ask probing questions to inspire their thinking.

00:33:44.520 There’s so much more you can do to support your peers. Consider mentoring opportunities or being that sympathetic ear for colleagues sharing their frustrations.

00:34:03.480 You can also embrace your role by sharing your learnings. For instance, I'm currently at RubyConf, which means I must bring knowledge back to my team.

00:34:20.520 I've started a thread for my day one insights, and although I'm falling behind on my day two thread, I can still share nuggets of wisdom.

00:34:36.680 Share what you've learned from conferences; recommend watching specific presentations or highlight resources that could be beneficial.

00:34:53.160 Even more critical, talk openly about your mistakes. It’s vital for everyone to know that nobody in tech is perfect.

00:35:07.560 Indeed, if you're comfortable raising your hand if you've ever introduced an error into production, let’s acknowledge we’ve all faced mishaps.

00:35:23.640 And as a significant reminder, don't forget to compliment your peers when they excel. Approach a presenter after a session and express that you appreciated their insights or thank a colleague for their help.

00:35:38.040 Additionally, identify problems. I earlier presented a talk at Shopify on the essence of being a staff software engineer.

00:35:52.920 A senior engineer is typically a problem-solver while a staff engineer focuses on finding problems and presenting those for the team to consider.

00:36:09.900 We often hear the phrase 'think outside the box'; however, I encourage you to first look inside the box for problems you know about that frustrate you.

00:36:27.540 If you can improve something in the tooling that saves your entire team valuable hours of work, you will make a substantial impact.

00:36:44.520 Next, think outside the box—consider the product as a whole and what challenges may exist in the teams you interact with.

00:37:04.740 Lastly, zoom out to the warehouse; take time to contemplate ideas that may seem too absurd to realistically consider.

00:37:23.520 While I don't expect you to act on every outlandish thought, stretching your thinking may lead to discover significant improvements.

00:37:38.640 Now, if you’ve identified a problem, do you need permission to address it? The answer varies. I will share a story; Shopify hosts hack days.

00:37:53.520 During my first hack days, I was introduced to a data scientist who needed assistance with a JavaScript issue. I helped him, and through this experience, I recognized a common concern during hack days.

00:38:14.520 Anyone at Shopify can participate in hack days, but there's a challenge of information availability depending on team composition.

00:38:35.520 So, during my next hack days, I initiated a project called Hack Day Helpers. It was designed to assist others in getting unstuck and didn't require any formal permission.

00:38:54.720 Eventually, Hack Day Helpers became an official part of Shopify's hack days, all because I had the opportunity to implement it without needing permission.

00:39:14.880 However, other initiatives may require permission. In cases when you need a nod to pursue an idea, I recommend utilizing a five-step mini-proposal approach.

00:39:33.840 This approach involves stating the issue with supporting data, proposing a solution, estimating the necessary time and number of engineers, discussing trade-offs, and finally requesting permission.

00:39:50.640 For example, we might consider the issue: 'Every week, hours are wasted finding error data in the logs.' My solution would be, 'I would like to add a page to our internal diagnostics tool that makes those errors visible.'

00:40:09.540 'This effort should take one to two days to complete and will push back the design document slightly. Do you foresee any issues with me prioritizing this work?'

00:40:27.240 It's most effective to communicate this in a message, especially if discussing it in person feels intimidating.

00:40:46.440 As we round this discussion off, I must touch on an essential point about visibility. I had the opportunity to run an earlier talk organized by Eileen, and one suggestion she made was to emphasize visibility.

00:41:03.720 It is significantly harder to lead if people don't recognize your work. Tanya Riley remarked, 'Getting promoted is diversity work.'

00:41:22.920 If you are underrepresented in tech and attain a promotion, you now serve as a role model and mentor, impacting others climbing the ladder behind you.

00:41:39.720 Visibility is not self-serving, especially for those of us conditioned to remain quiet, blend in, and take up no space.

00:41:56.400 We must overcome that conditioning and allow ourselves to be seen.

00:42:14.640 So, how do you achieve visibility? Julia Evans has written extensively on this topic, particularly in her blog post about creating a 'brag document.'

00:42:31.440 Essentially, if you do wonderful work and expect acknowledgment or rewards automatically from management, you will be sorely disappointed.

00:42:53.040 You must keep track of your accomplishments so you can share them with your manager, making their job easier.

00:43:12.240 This lesson comes full circle. Leading from where you are is about empowerment. Every single person in this room holds a unique position.

00:43:29.640 As tech increasingly influences society, we are the ones driving it forward. In closing, what was the core message I wanted you to take away?

00:43:47.280 Leading from where you are is essential. We can simplify the challenges that individuals face, such as updating their name in an app.

00:44:02.640 We are the individuals who can drive that change. I urge you all to reflect: Where are you, and how can you contribute towards leading?

00:44:16.560 Finally, I want to express my gratitude to all of you for this incredible conference. Thank you to the organizers for trusting me with this closing talk.