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Technical Leadership Through the Underground Railroad



Technical leaders are often tasked with guiding teams through difficult times. The Underground Railroad provides insights into how to navigate challenging conditions and find success. The principles that Conductors on the Underground Railroad followed can be directly applied to technical leadership.


Anjuan Simmons is a Technologist & Technical Program Manager at Questback. He is an energetic and informative speaker who presents at conferences, seminars, schools, and community centers around the world on topics including Agile software development, inclusion, and leadership.

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Simmons: This is a talk about technical leadership, and whether you're currently in a leadership role or you aspire to be in one, I think that there are lessons that are really applicable for that work in this talk. I've been a technical leader for over 20 years at companies as big as Accenture and Deloitte, and as small as several startups that you may have never heard of. It's a tough job being a technical leader. You're always managing complexity, there are often changing requirements. You often have to communicate over and over again to make sure that everyone is on the same page.

One of the biggest challenges of being a leader is that you often have to solve problems that other people have failed to solve. I'm fairly good at what I do, but I'm always looking for ways to get better. I've read a lot of leadership books to try to understand what I can do to become a better technical leader, and if you come to my AMA, I'm happy to share that list.

Leadership and History

One underutilized tool to become a better leader is history. I know that technical books on leadership often give you a lot of the theory about what it takes to be a good leader but history lets you know what people who actually had to solve hard problems did to be successful. I really am a big fan of going to history to better understand leadership. Many of you probably took history classes in high school or in college, and you may not have been a big fan of history. After all, why should you be a fan of real history with this fake history like Game of Thrones, which is so exciting and awesome. I really do believe that there are great lessons to be learned from history and understand the conditions under which real leaders have to operate.

I'm going to talk about a technical leader from history who had a very tough project, and we're going to learn lessons that I believe that everyone can apply to your technical teams, either now or in the future. This technical leader was named John P. Parker. We're going to talk a lot about John P. Parker during this talk. He had a development team that was in trouble. He was the lead developer for Project Phoenix and he had a team that was very low on morale. The person who was initially assigned to lead the team left not long after the project started, and the team had just seen a team member recently depart. Even though there was a recent reduction in scope, his team was racing to get everything finished on time. Does this sound familiar to anyone? You've been in this situation? While the finish line was literally in sight, Project Phoenix was in great danger of failing to release into production.

The Underground Railroad Network

John P. Parker was not a leader of a team similar to maybe yours where you're developing web applications delivered on a network. No, he was the leader on a network called the Underground Railroad. The Underground Railroad was in operation in the 19th century in the United States, and this was a time when slavery, where you can own people, was legal. Not only was it legal, but there were immense protections legally in the United States, from the Constitution itself, to local laws that protected this system of oppression. John P. Parker was a conductor on the Underground Railroad, whose mission was to help people escape slavery, and then to get to freedom.

The Underground Railroad, if you really want to understand it, we have to go back to that period of history. I know that this is hard history. This is a history or a time in history that people often don't want to talk about. I know in my country, in the United States, we don't talk about this really much at all. It's really important that we learn to lean into hard history. Part of being an adult and being a professional is leaning into some of the hard things, leaning into some of the dark areas of history. It's really important that we develop the ability to do this.

Code Bases

I'm sure that you work at companies that have code bases. If you're like the code base at Help Scout, our code base is immense. It's almost a decade old. There are parts of the code base that we don't like looking at because it's just old code back there. It's really hard to understand, there's some Marionette Backbone stuff in there that we try to forget about because we're trying to go into React. We found and my developers have found that reading those lines of old code, you get patterns and you get understanding that helps you write better new code. I think that reading through the lines of history, even though it's challenging, even though it's painful, has the same effect. If we can read through those lines of history, I think we'll be better positioned to write a new future for ourselves.

Again, I know that this can be a very difficult endeavor to do that, but if you can learn from hard history, if you can parse hard history, then you'll get familiar with being uncomfortable. You'll get familiar with doing the hard work of looking at hard times, and trying to find things that you can apply to today. I think that that's a skill that is often not very well understood in today's time. We live in this world where there's so many things that we can use with technology, and we can press a button on our phones and a car appears, or we can book a flight to anywhere in the world simply with what we carry in our pockets or in our purses. I really think that hard history is something that we should all be invested and learning from.

One important thing about hard history is that history doesn't really repeat itself, but as Mark Twain said, it often rhymes with itself. If we're going to avoid repeating this harmony in the past and bring ourselves into a more harmonious future, then it's really important that we understand hard history.

Understanding the Underground Railroad

To understand John P. Parker, it's really important that we understand the Underground Railroad. First, it was not an actual railroad. I know that when you hear Underground Railroad you think subway or a system of rails. It was not that. The Underground Railroad was a codename for the operation. For those of you who read comic books, you may have heard the X-Men, the mutant team called the X-Men. They're not x men, though that would be a cool superhero team. The Underground Railroad was a codename for the network. It was a collection of people and pathways and processes that was used during the 19th century to help enslaved people escape to freedom.

It was underground in the sense that it operated in secret. That secrecy was really important because you were trying to dismantle a legal system and help people escape that legal system into freedom. It's really interesting to me that this was a collection of mostly either black people like myself, many of them were former slaves, but they borrowed from the leading ride sharing service of the 19th century, and that was the railroad and the locomotive engine. They borrowed high tech terminology to explain how they operated. I think that that's so cool that these people who lived 200 years ago, were using technical terms to understand how this system worked. I really think that that's a very key point.

That way of borrowing from outside technology to apply to what we do today should not really be that surprising, we do this today. You all may have practiced Scrum. That agile technique is actually from a sport called rugby. A Scrum is a play in rugby. We borrow from the world of sports a term that we use to describe our work today. Sprints, that comes from track and field. I'm not sure if any of these runners ever wrote JavaScript or PHP, but web developers every day use Sprints as a way to describe the work that they do every day. We have in our world today of technology, the pattern of going outside of our field to understand how to build new technology. In a similar fashion, the operatives on the Underground Railroad, borrowed terms from the rail system to really describe their network.

To understand some of the geography, again, the Underground Railroad was a system and they helped slaves leave the slave states in the south and escape to the free states in the northern part of the United States. This operated in 19th century. This picture is from roughly 1860. You see that there was a lot of ground to cover right from Texas where I'm from, all the way to Delaware on the East Coast. This was slave territory where people literally toiled for free, almost always for the entire lives. To be a slave meant that you knew that not only would you live your entire life in slavery, in bondage, but any children that you had, would also live their entire lives in bondage and their children will live their entire lives in bondage. It's a very oppressive system. The Underground Railroad was a secret network of self-organizing teams that almost always operated in a period of immense uncertainty, and their job was to ship the most important product of all, and that's freedom.

3.2 Million Enslaved People (1850 U.S. Census)

The 1860 census, taken at the height of the operation of the Underground Railroad, found this number of slaves in the United States, 3.2 million people. Can you believe that, 3.2 million people, mostly black people were enslaved in the United States? That just shows you how immense this franchise was in my country. By the way, do you know how many people were enslaved in Britain in 1860? Zero, because Britain abolished slavery 17 years earlier in 1833. You know what they say about the United States, you can always trust us to do the right thing, after we've tried everything else. We eventually got there, but Britain got there earlier. That's important to note because a lot of slaves, they fled to the northern states to find freedom but the laws changed surely after 1860, where people who owned slaves could go into the northern states and capture people and take them back into slavery. In fact, there was a phenomenon called the reverse Underground Railroad, where free blacks in the north were captured and taken to slavery in the south. This system was immensely strong and immensely oppressive. The mission of the Underground Railroad was to dismantle this system and to help as many people escape from slavery and find freedom.

By the way, a lot of people when they realized that, even though they were living in the free north, and that they could be recaptured, they fled to other countries like Canada and even to the United Kingdom. The Underground Railroad also came through London. This was where a lot of black Americans found ultimate freedom here in the UK. The mission of the Underground Railroad was again to help as many people as possible escape to freedom.

Software Development Today

It's really interesting that the Underground Railroad was structured with a system that was surprisingly close to how we build software today. Let me explain. Remember, the Underground Railroad used terminology from their day from the railroad system to explain how their system operated. You had stations, and stations were places where there were supplies and food because when you were trying to escape, you could only go so far in a day. There was always a station a day's journey or so away that you can go to and then you can get fresh clothing and get supplies, water, food. That was where you had a structure in place to support the people who were using the Underground Railroad. Today, we call this the office.

Station masters were people who were tasked with making sure that the people who were coming to the stations had support. This was often property that the station masters owned or it could be even some types of natural structures like caves. Station masters also helped the other people that were going through the network to get news, to understand what was happening around the network around the country, but also on the Underground Railroad. Today, we call these people the executive team.

The stockholders were people who donated food, and clothing, and supplies, and even money that helped people who were traveling on the Underground Railroad get to where they needed to be. Today, we might call these people venture capitalists.

Travelers were the people who were using the Underground Railroad to get to freedom. They often had to brave enormous risk to take the Underground Railroad and get to freedom in the north or in other countries. Today, we call these people the development team.

Then, you know this person. This is the person who was a conductor. We're going to talk about John P. Parker, a conductor, today. Conductors were people who often had escaped from slavery themselves. They were risking not only their freedom but their lives to help other people find freedom as well. There were some conductors who operated in the Underground Railroad network but there were also those who were freelancers. Today, we call these people managers.

Do you see yourself in this picture? Do you see your role in the Underground Railroad? I really want to emphasize that this was a network that was operated by many people where it was illegal to teach them how to read, but they were able to form this really sophisticated way of navigating life and navigating the physical world in order to get people to freedom.

Leadership Lessons from John P. Parker

Now that we understand the Underground Railroad, let's go back to John P. Parker. I think that there were a lot of direct leadership lessons that we can apply from what John P. Parker did to what we're doing today. I learned most of what I know about John P. Parker in this book called, "His Promised Land," which is a memoir of sorts of John P. Parker. It's a really great book. You can find it easily on Amazon, or wherever you read books.

John P. Parker was born into slavery. It did not take you long to realize that he hated the institution. At the age of 8 years old, he was chained to an older slave and forced to walk roughly 100 miles from Norfolk to Mobile. I know that most of you may not be from the United States, but that was a long way through really hard territory. He was doing this at 8 years old. Although it was illegal to teach people how to read, he worked for a local doctor because slaves would often hire themselves out in order to try to make money, and so he hired himself out to a doctor who had sons who taught John P. Parker how to read and write.

Parker spent most of his teen years trying to unsuccessfully escape slavery. If you read in the book, you find that he just found himself in these really just hilarious situations where he was trying to get away, he would almost get there, but then he will be recaptured. This happened over and over again. While he was doing this, he also hired himself out to people who were metal workers. He learned the trade of working metal, and this became a way that he could make money. Then John Parker eventually hired himself out to a patient of the doctor, and they came up with this payment plan, where he could learn how to save money, and eventually get enough money to save so that by 18 he paid off his debt. He became a free man. John P. Parker went from being born into slavery to becoming a free man.

Parker eventually settled in Ripley, Ohio, and we're going to learn more about Ripley, Ohio in a little bit, but he actually started up his own foundry. He owned his own business. He had a startup of making metal in Ripley, Ohio, and over time, his foundry became so successful that he was one of the wealthiest men in Ohio, which was a remarkable feat for his time. Parker found a career in Ripley, but he also found a cause. There was a very strong antislavery movement in Ripley and Parker, almost by accident, became an agent on the Underground Railroad.

This isn't a drawing of Parker because even though photography had been invented, John P. Parker was very careful to never have his likeness captured or a picture of him taken, because if you're a rich person who in his part time helps people find freedom, you don't want any pictures of yourself around. There aren't any pictures of John P. Parker even to this day. Parker eventually changed from a wealthy industrialist to someone who lived a double life. He would run his successful business by day, and almost every night, he would take his boat across the Ohio River to help people find freedom on the Underground Railroad.

I know that this is a difficult concept. You have a wealthy person who at nighttime, goes out and helps people, but that was John P. Parker. It's really difficult that this brilliant inventor who worked in iron would risk his life for the benefit of other people. That's who John P. Parker was. He was really a hero of his time, and I just love so much how he really lived his life. I really think that it was his early childhood as a slave that motivated Parker to risk his life again and again, as a conductor on the Underground Railroad. Over the time he was active, he started helping dozens of people, and eventually, he helped hundreds of people escape from the south and find freedom in the north and in other countries. John P. Parker was a very skilled operative or conductor on the Underground Railroad. The Phoenix project was one of his toughest missions, and we're going to learn a lot of leadership lessons from what he learned with this release.

The Borderlands

I don't want to assume that everyone knows the geography of the United States. I don't know the geography of Europe very well. I really don't know the difference between Belgium and Budapest. I'm joking, I've been to both cities. I don't want to assume that you know the geography. I have a map and I want to make sure that we're all on the same page. Our story begins in Central Kentucky. This is a map you see most of Texas all the way over to the coast, Kentucky is in the central-east part of the country. This is where our story starts. This is where Project Phoenix starts out. This was a group of 10 individuals that were fleeing slavery. They're trying to find freedom in the north.

I want to make sure that we all understand that there was this real barrier, that you could be in a slave territory for most of your life, and then you could flee across the border, and then you would suddenly become free. It's easy for me to walk across the stage and show that, but there were often forests and rivers that were the boundary of the states. They were hoping to cross over from where they started in Kentucky to go to Ohio, which was a free state. Right after they started out their leader was captured. You can probably imagine that their velocity went down to almost zero. Not only did their velocity go down but they stopped making progress. They found themselves stuck in a part of the country called the Borderlands.

Let's zoom in a little bit to get context and understand what the Borderlands were. The Borderlands were almost like a DMZ between the slaveholding southern states and the free states in the north. You had the Ohio River which was a physical border between Ohio and Kentucky, and so these slaves were trying to make their way through the Borderlands. The danger was extremely real because the Borderlands were constantly patrolled by people who were looking for escaping slaves. If you were captured, then you would be taken back to where you came from, and often you will be beaten or punished in horrible ways for trying to escape to freedom. Not only that, but these patrollers had dogs, if you could find a boat to cross some of the either rivers or lakes, they will often be tied up with the oars removed to keep people from using them. It was the case that almost every night, you had a person who would cross the Borderlands to find freedom, but without the Underground Railroad, it would have been almost impossible to do this. The risk was very real and Parker himself would go on to have a $1,000 bounty on his head if captured. That might not be a lot of money in our days, but back in the 19th century, this was an enormous sum. This was a reward that was given whether you found Parker dead or alive.

Let's zoom into Ripley, Ohio, where John P. Parker lived. These slaves were stuck in the Borderland trying to get to the Ohio River, and you see Ripley on the top part of the screen. Their job or their mission was to try to cross through the Borderlands to get to the river so they could find freedom in Ohio. That's what they were trying to do. The story of these slaves who were now stuck in the Borderlands, eventually got to Ripley where Parker lived. They began to try to plan, what are we going to do to help these people get to freedom? Parker eventually found a way to get to the Borderlands and begin to cross over. Parker, when he did this, he took two pistols and he put them in his belt, and he said that he did that for emergency purposes.

I'm not saying that you should arm yourself when dealing with your engineering teams, but I think that Parker learned something from Harriet Tubman. Harriet Tubman is probably the most famous conductor on the Underground Railroad. While they probably never met, she was really famous and she was very well known for carrying a pistol because often when people were on the Underground Railroad, they got scared. Harry would incentivize them to keep going by pulling out her pistol and saying, "You can either continue with me, you can die here."

Leadership Lesson 1: Prepare Your Incentives Before You Need Them

I think Parker was really finding a way to incentivize his people, which is, really, the first leadership lesson, prepare your incentives before you need them. There are a lot of ways to motivate engineering teams. Some people use spot bonuses, which is usually a nice gift card, maybe $50 bucks to $100 bucks, but I like to use incentives that are really giving people back the one nonrenewable resource and that's time. I find creative ways to help my teams use time to however they want. This may be time to work on a project that they choose. We work in Sprint at Help Scout and we work in dev cycles, which were a collection of four Sprints. On that four Sprints, I really try to give my team time to work on whatever they want. Maybe they want to go on and refactor something that they've been trying to clean up or maybe it's just some pet project. I really love to give my team time back. Or, we can provide external funding for books or conferences like QCon, or to get certified.

The one key thing is to be very intentional in how you design your incentives. You can only do this if you prepare them in advance. You may like to take your team out to get drinks at a local pub. That's great, but what if you have someone who may have a family, and they may not drink alcohol? You may for them, get them the day off and give them a gift card to buy something nice for their kids. By thinking about the incentives in advance, you'll be better able to tailor them to what your team needs. You really can't do this, if you don't plan them in advance.

Let's go back to Parker. There was a guy who lived in Ripley, who took Parker across the river, and they began to go toward the area where the Project Phoenix team was stuck. It's really important to understand that this area, again, was constantly patrolled and Parker could have been killed on site. Parker and this guy go to the cabin of a slave who was an operative on the Underground Railroad and he knew where the Phoenix team was, but it was almost day time, and so Parker hid in the woods until nightfall. You have to understand that the Underground Railroad often, people moved around at night, because you could be easily detected during the day. The sun went down, and Parker and the guy eventually found the location of the Phoenix team.

The Phoenix team, through friends and other operatives had been given food, so they really weren't hungry but because their previous leader had been lost, they were demoralized. They were even filled with fear. They were very afraid. In fact, many of them wanted to just quit and give up and say, "We're just going to give ourselves up. We know people are looking for us. Let's just quit." Parker knew that it took decisive action, that decisive action was needed at this time. In fact, one of the men in the group began to complain because Parker said, "We have to move. We can't just stay here." What did Parker do? He used one of his incentives. He pulled out his pistol and said, "You can come with me, or I'll shoot you where you stand," and the man quieted down. Eventually, the team accepted Parker's leadership. They began to move. To translate this rough way from the past, let's use some of the more elegant weapons we have in today's civilized age.

Leadership Lesson 2: Bold Actions Set the Tone

Leadership lesson number two is bold actions set the tone. This is especially important when you start leading a new team. I've had a career for over 20 years, again, for huge corporations like Accenture and smaller companies. I've done a lot of new team introductions, when I was, 10 years ago, the new Scrum Master or the new engineering manager, and it's really important that in those first few days or couple weeks, what you do speaks volumes. The tone that you set and the practices that you begin to implement are so crucial for how the team will perceive you as you lead them. It's very important that you understand how to take bold actions when necessary.

I remember one team, I was the new Scrum Master and I went to my first stand-up with the team and everyone was sitting down at a table, and the meeting lasted for over an hour. I was like, "This is not a stand-up. This is a Shakespearean play." I knew that I needed to get this meeting under control. The next day, I got to the conference room early, and I took all the chairs out of the conference room and put them into the hallway. Then when the first person came in, he just looked and said, "What's going on?" I'm like, "Stand with me." The next person came in, and she said the same thing. Eventually, we were standing around the table. Then we began to have an actual stand-up, we went over, "What have you done since the last stand-up? What do you plan to do today? What are your blockers?" I began to help them understand that there are principles that we were trying to apply to our meeting. That bold action set the tone and that meeting began to be less than five minutes. We had true stand-ups and we were able to create a daily lightweight plan for what we were going to do and that lightweight plan would eventually become what we would do every Sprint and every dev cycle and our velocity began to go up. That bold action helped me get that stand-up meeting into a pattern that would work.

Parker didn't have time to explain the theory but his actions were effective. Parker knew that the Phoenix team couldn't use the roads because those were heavily patrolled in the Borderlands. He began to lead them through the thick woods. This was really hard and exhausting work. There were lots of trees. Remember, they could only travel mostly at night, but during the daytime when they had tree cover, they were able to travel during the day. They began to make a lot of progress but there was a problem. While Parker was an experienced conductor, the people that he was leading weren't. These were people who were unused to traveling long distances through rough terrain, and so they lacked Parker's experience, and they were constantly breaking through bushes and twigs, and there were snaps and crackles and pops and loud noises, which isn't really good for a group that's trying to move in secret. The team, as they heard the noise of their movement echoing through the woods, they began to get scared that someone would discover them. Some of you have been there. You've been leading a team through thick woods. That's basically the 19th century version of JavaScript. They were really trying to get through this rough time.

Leadership Lesson 3: Don't Let Your Experience Bias You

That leads to lesson number three, which is, don't let your experience bias you. Parker was used to going through the woods, but his team was not. Often, as leaders, we have a lot of influence. We have a lot of power. We have a lot of control. We often want to let that power drive the team toward decisions. Maybe you have a lot of experience in AWS but Google Cloud Platform is really better for what the team is doing, or maybe you've used Angular but you know React will be better for what the team is doing. We have to be able to step aside and let our teams do what's best for what they're doing and tailor their tools and their practices to what is at hand at the project. It's really important that we don't let our experience bias what our teams do. It's hard to do, because honestly, as a leader, you can get a big ego. It's really important that we put our ego aside and learn what's best for our team.

That's what he did. He found out that going through the woods is problematic. He found that when they went through ravines that it was a soft, carpeted area, basically, so they could move in silence. He basically converted the team from JavaScript to TypeScript. The team began to get happy because they realized that they could move throughout this Borderland area, and they could go in a more stealthy way.

Then there was another problem. Again, the Phoenix team were 10 people and there was a single man in the team who got thirsty and he decided that he was going to go find some water. Parker objected, but the man was insistent. Many of you have dealt with thirsty single men, but this single man went out and so they saw him wander off to find water. Eventually, a few minutes later, they heard him cry out, and then they saw him racing through the woods. Then they saw that he was being chased by two Slave Hunters. Parker had the team lay down and hide. This thirsty man must have forgotten where the team was because he ran right past them, and then soon they saw the pursuers chasing him, and they disappeared through the brush. Then they heard the sound of a gunshot.

Parker looked at his team, and he saw that they were beginning to stress. Some of them looked like they might cry out, or they may go running after this person, but Parker knew that if they did that, then that would jeopardize the entire team. Parker turned back to his incentives, he pulled out his pistol and he basically quietly said that if anyone says a sound, he will shoot them, which calmed the team down surprisingly. You may say, "This Parker person was really quick with the pistols." Then you may remember that this is the second time that he used that incentive to deal with the drop in morale. It was a similar problem and a similar solution.

Leadership Lesson 4: Embrace Continuous Solving

That's the next leadership lesson, which is, embrace continuous solving. Most leaders that I work with and coach, they get a little bit depressed when they see the same problems happen over and over again. That's part of being a leader. People are almost like code bases. They're constantly evolving, constantly changing. There's often breaking changes introduced to the team. That's why we do regression testing. You're going to find that the same problems crop up over and over again. In many ways, problems never die, only people do. Be good to your people and work with them to solve your problems. As I worked with that team that I got their stand-up squared away, but I just found that other meetings where there was Sprint planning or the Sprint, even the Sprint Retrospective was just in shambles, that I had to constantly work against what was really a very poor meeting culture. I had to continuously use the same principles to solve many of the same problems. As leaders, we have to be comfortable engaging in continuous solving. That's really something that you only get after you've led several teams and then you just get comfortable, repeating yourself over and over again in different ways, is part of leadership. The good news is that your portfolio of incentives that I mentioned before, if you have to prepare it in advance then you can deploy them as needed to solve those problems. Just make sure you keep that portfolio very well stocked.

Soon, they heard rustling in the bush and they saw the thirsty man being led by two men. He had a rope around his neck and his arms were tied behind the back so he had been captured. Parker realized that his team had just narrowly escaped being captured and returned to slavery. He realized that this person who just got captured may tell the people who caught him that he wasn't traveling alone and that he may alert them to the presence of the Phoenix team. Parker knew that he needed to get the team as far away from the spot as possible. They came to a road but they realized that it's during the day, and so it was too well traveled to risk trying to cross it, so that he had his team hide in the woods until nightfall. After dark, they crossed the road and started the last lap of their journey toward freedom. They finally got to the Ohio River, which was now in sight.

Let's zoom in. You see, they were on the south bank of the Ohio River and across the river was Ripley which represented freedom. They began to slowly move toward the riverbank, but then suddenly, as they were moving toward the riverbank they, by surprise, came across a patrol person, and so they froze in place. This patrol person seeing that he was outnumbered, ran away, and so they began to continue moving toward the riverbank. There was a problem, because since the team had moved during the day, because they were able to move through the ravines, they had made a lot of time and they were basically 24 hours early. They were a day in advance that maybe you never had a project in before the due date, but they actually got there. There was no boat, because the people in Ripley were planning them to get there a day later so they weren't there. It's almost like if you're working on the weekend, you try to check in your code, but the build server is down.

Now we're back where we started this story. The team was scared. The first leader was long gone. They just had seen a team member depart. They began to figure out that if they didn't move quick, then failure was imminent. Someone in the team found a boat next to the riverbank but there were no oars to power it, and so, Parker had the team fan out and begin trying to find oars, at least one oar so they could go across the Ohio River, but they soon heard the barking of hounds. That patrolman must have been a C++ developer because he'd run really fast.

What do you do when you're running behind? You cut scope. John hopped into the boat to try to look for oars, or to try to actually tear a seat out to use that as a makeshift oar, but there was an oar actually inside the boat. John got everyone into the boat, but he heard the sounds of the pursuers coming because they were getting closer and closer. There was a problem, because the boat could only carry eight members of the nine people who were left on the Phoenix project team. One man was left standing on the riverbank while everyone else was in a boat. John couldn't wait, so he began to push the boat into the river, but then one of the women on the boat cried out that the man standing there was her husband and she wasn't going to leave without him.

Leadership Lesson 5: You're a Leader of Leaders

This leads us to our final leadership lesson, and that is, you're a leader of leaders. I know often we have the title of engineering manager, or a lead developer, or a technical lead and we think that every problem has to be solved by us, that we have to come up with every single solution to the problem. That's not realistic. We don't invent every solution. Did you invent Kubernetes? Did you invent Angular? Maybe someone in here did, I don't know. We use tools every day to solve problems that we did not invent. We have to be comfortable letting our team invent their own solutions. You're working with very smart people who are very capable, very driven, or they probably would not be working for your companies. There are times where you have to trust that they're going to be able to solve some of the problems that you're struggling with. Over and over again, I've been very honored and privileged to lead teams just with great leaders. I may have the title, but I find that when I empower my teams, and let them walk in their leadership, we get so much more done, than if I try to hoard power for myself, and think that only I can fix it, only I can solve it. By having the mentality where my team is smart and capable, and that they're leaders, then we get so much better outcomes than if I try to do it myself.

This happened during this incident with John P. Parker. He redeemed a single men, got out, and quietly walked to the riverbank and let the husband get into the boat, and so John P. Parker began rolling away. He looked behind where the man was standing and then he was suddenly surrounded by lights, and John Parker knew that he had been recaptured.

They're able to go over to Ripley, and they go to the house where the Underground Railroad operators were. They were surprised to see him because he was early. He transitioned the team to another leader there, and then he would take them over from there. Parker has successfully completed this part of the release. He never saw the Phoenix team again. One part of leadership that sometimes when your time's over, you move on, and that team finds success with other leaders. Parker was one of many former slaves who risked his life again and again on the Underground Railroad. I hope you've learned a lot of leadership lessons from him. Then they go over to Ripley.

The Underground Mindset

I want to talk about the underground mindset because I think it's so crucial to building strong leadership. Part of this mindset is fearlessness, and that's not fearing failure. If you were someone like John P. Parker, who was a former slave going in the state territory over and over again, there was always the possibility that you could be captured. He had to deal with that but he could not let that fear get to him. He could not let that fear keep him from doing the right thing. He could have given in to the, "What if I do something wrong?" Or, "What if my teams don't like me, who cares I have guns." Or, "What if I do something wrong?" You can't be afraid to make mistakes. Mistakes are part of building software. We have to be willing to get it wrong 1000 times in order to get it right once. Don't fear mistakes, learn from them.

The other aspect of the underground mindset is courage. You can't fight an oppressive system if you don't have the courage to do so. The Underground Railroad operated in a time of extreme oppression. You had a system of slavery that was federally protected by the constitution itself. It was extremely dangerous to do what they were doing. They realized that "You know what? Even though I'm breaking the law, I'm going to a higher principle." Often, the unjust laws that people write have to be overwritten by the laws of humanity. The people in the Underground Railroad had the courage to help enslaved people get to freedom, because it was right.

Like Parker, I'm sure that many of the Underground Railroad operatives had regular jobs, and helping people escape slavery wasn't part of their job description, but they realized that it's the right thing to do. Many of you have jobs that you have to do every day and you have requirements, and doing things like helping fix the toxic culture that often is part of tech isn't part of your job description. I really hope that you do that, because it's the right thing to do.

The underground mindset also required empathy. Many people thought slavery was evil, but it was too risky to do anything about it. They were held back by the question, "If I help people escape from slavery, what will happen to me?" Empathy reverses that question and asks, "If I don't help free slaves, what will happen to them?" Many of us have to do that same reversal. There may be people who are marginalized groups in tech because of their sexuality or their gender or their race. You may think, "If I help them, what's going to happen to me?" We have to be willing to say, "If I don't help them, what will happen to them?"

Past Experience

I've been working in tech for a long time, and the people who I worked with 20 years ago, the software that we wrote back then, it's not in production anymore. Some of it didn't even last one year, but the impact that they had on my life, in my compensation, in my career path, has lasted up to the present day, and will last for generations. I hope that people feel when you leave them, that you made a lifelong change in their lives, that the way that you cared about them, the way that you had empathy for them was life changing, and that it will power them through their career.

I've sat in multi-million dollar meetings and helped people solve hard problems, and when I've sat there, a part of the Underground Railroad was sitting in that meeting, because I'm the descendant of slaves, my ancestors were slaves. That mindset empowers my decisions. It empowers the empathy that I use for leading my teams. It's part of who I am. There are those of you who may not come from illustrious backgrounds, you may not have gone to Harvard or Oxford, or you may not have worked for Google or Facebook or Amazon, but there are things in your past, things in how you were raised that I hope you bring to your teams, that you walk in your humanity, and be willing to be vulnerable with your teams. I hope that you take from your past and you apply that. I never thought that slavery would be a technical topic at a conference like this, but it's such a powerful way of thinking about how to be a leader. I hope that you go through your history and find aspects of what you can learn from that past and apply it to the teams you're leading now or in the future. I think that the Underground Railroad is a great place to start.


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Recorded at:

Apr 15, 2020