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Hello everyone! I hope you're having a fantastic RailsConf. Welcome to day four. My name is Jessie Link, and today I'll be talking to you about how to be a boss without the BS. When you take the BS out of boss, you're left with 'OS', which I like to think stands for 'Outstanding Sauce', which this talk is clearly full of—and hopefully, you will be too.
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Let's get right into it. Today, we are going to cover the 5 W's: why you should consider management and moving into that track, who makes a good boss, the skills needed to be an effective manager and leader, when and how to make the jump into management, and finally, where you can find some resources.
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Now, when I do a talk like this, I also like to cover the things that this talk is explicitly not about. The abstract only allowed for a very short amount of characters, so I want to make sure this is the talk you actually want to be in. This is explicitly not about how to found a startup or how to get VC financing; there are other folks here who can help you with that, and I'm sure they'll be happy to talk to you. I won't really be covering that topic. This is also not about how to make your employees obey you. We will only be covering light-side Jedi mind tricks. There are no shortcuts or tricks that I can tell you to make your employees obey you. You can only work on the skills that we will discuss today and try to cultivate your leadership abilities.
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First, a little bit about me: why am I qualified to talk to you about being a boss? My company made me get a headshot for our corporate website, and this is it. My mother loves this picture because she thinks I look like a fancy professional lady. I like this headshot because she doesn’t know I’m wearing shorts and flip-flops—so take that, Mom! Business up top, party on the bottom. Don't worry.
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I've actually served in a variety of leadership roles. I served in the U.S. Air Force for six years as a captain, which is an O-3 rank for those of you who know that military structure. When I transitioned into the civilian software development world, I've been doing that since about the year 2000. I also have a computer science background and have been in civilian leadership since around 2010. Over that time, I've studied leadership principles for over 18 years now. The military is very focused on training you in these areas, so I've tried to keep up that practice. Currently, I am the Director of Engineering at a company called Lookingglass Cyber Solutions, a cybersecurity firm based out of Baltimore. Look us up—we're pretty great! I also have certifications as a Scrum Master and in Project Management Professional, which sounds more impressive than it really is.
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So why make the leap? Why become a boss? Don't worry; it's not all TPS reports! Many people have a misconception about what it means to move into a formal management role. They think it’s all paperwork, drudgery, and about being the enemy. I want to clarify that management is about much more than that. Let’s talk about why you might want to make that leap because, make no mistake, this is not just a job change; it’s a career change.
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Let's say you’re a founder and you’ve started a business—fantastic! So we know you can start a business; it's right in the title. But can you grow your business? Can you finish? Can you exit startup mode? To start, all you need is a great idea and some coding ability, but to sustain a business, you need management skills. You need to know how to sustain your business, lead your people, and take your company to the next level of great success.
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Even if you haven’t started a startup, you may have just hit your ceiling in the technical track. You may not be interested in moving into a chief architect role; you may be feeling bored, frankly, because the challenges you’re taking on aren’t that exciting anymore. That’s okay! Moving into the management track means taking on new and exciting challenges. However, being a boss is very, very challenging. Now, I know what you might be thinking: how hard can it be? My boss is an idiot; they don't know what they're talking about, and I don't really know what she does all day.
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Let me amend my statement: being a bad boss is very, very easy, but being a good boss is very hard. Most importantly, when you move into the management track, you get to be in the driver's seat. If you’re a founder, that’s your baby, and you have a vision you want to drive towards with that company. If you don’t want to take on management responsibility, that’s okay, but it means you’re seeding control to someone else who will run your business for you, and you might not like the direction they take you in. If you want to maintain control over that thing you started and take it to the finish line, you need to cultivate those management skills.
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If you're a senior developer, you might say, 'I don't really care for the decisions they're making; I think I can do better.' Then go do better! Prove it! The most important aspect of this transition is that you get to have an impact on the careers of your employees. You get to help mold and develop them into the people they will become, and that is tremendously rewarding. There is nothing better than watching a junior developer blossom into a big, beautiful senior engineer—a butterfly they were always meant to be, and you play a significant role in taking them on that journey.
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Lastly, as a boss, you gain a new perspective on the business. Part of your boredom may stem from staying in a narrow engineering track. However, as you move into a management role, you get a chance to touch other parts of the business. You can see how marketing works, how sales operate, how financing is managed, and how you deal with customers. You gain insights into what happens at the C-suite level, and understanding these dynamics can be tremendously rewarding.
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As a manager, you take on responsibilities beyond just writing code and developing systems. You are now responsible for people, schedules, budgets, and scope. So who makes a good boss? What are the characteristics of a person who can move into this track and experience success? First and foremost, you should like people. You will have to deal with people in your job, which doesn’t mean you need to be an extrovert; you can be an introvert and still succeed at being a boss. However, it does mean you can't be anti-social. If you despise people, that’s fine, but perhaps management isn’t for you.
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You should care about the people you lead, as well as your customers. This is a key component. You also can't fear conflict. Some individuals are conflict-averse, and that’s okay, but if you’re not willing to confront conflict head-on, it will overwhelm you and your team. You need to be ready to get a little spicy sometimes and get a bit scrappy. Adaptability is probably one of the most important traits as well. I don’t think I’ve ever had a project go smoothly and according to plan. Many of you have probably experienced this too. If you can’t be adaptable when things go wrong, you are really going to struggle, and you’ll drag your team down.
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Confidence is essential; confidence is contagious, just as lack of confidence is. If you don’t believe in what you’re doing or in the game plan you’ve set, your team will sense that and lose faith in their efforts. You must also have the confidence to move forward with that game plan. However, you need to remain humble. There’s nothing worse than a boss who knows it all—maybe some of you have worked for that kind of person. You need to recognize that you’re not a perfect person, that you may make mistakes, and you must have the humility to listen to your team and accept feedback when you’re wrong.
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You have to be empathetic. If you can't understand people, you can't lead them. Leadership is about understanding people's motivations, desires, and drives, and then allowing them to move forward and embrace these things in a productive way. Lastly, you must have integrity. Moving into the management track imbues you with certain responsibilities, and with great power comes great responsibility. You must be trustworthy in doing the right thing. You will be responsible for budget, hiring, firing, and promotion decisions. If you are not an honest person, your team will suffer, and so will your business.
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Up until now, you’ve been cultivating your technical skills. You're at RailsConf probably to continue to grow those technical skills, which is fantastic. But again, this is a career change and requires a whole new set of skills that you need to cultivate alongside those technical skills. First and foremost is communication. Communication encompasses a lot: it’s verbal, it’s how you speak to people, and it’s also non-verbal. Seventy percent of the communication we have with each other is actually non-verbal. Understanding how non-verbal communication works, especially when dealing with someone remote over a webcam, is very important.
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You also must understand how to articulate your thoughts in writing. We’re currently in an industry where a lot of communication happens asynchronously: pull requests, formal emails, memos. This is the most critical ability you must develop. You cannot execute other skills effectively without this one, and you’ll see the theme of communication echo throughout my following points.
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Communication means knowing how to tailor your message to your audience. It’s not just what you say; it’s how you say it. Understand how to tune your message when communicating downward to your employees, laterally with peers, and upwards with C-suite executives. Do you know how to manage upwards? How do you communicate with customers? How do you deal with other business units? These are all things you need to grasp.
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As participants of something like RailsConf, we pride ourselves on being polyglots—we speak many programming languages. It’s important to apply the same principle to management-level communication. As you shift into management, consider domain-specific languages—terms that may differ between a salesman and an engineer, for example. Understanding how to communicate using these different languages, tailoring your message so that it resonates with whom you’re speaking, is a vital skill to cultivate.
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Now, communication is too broad for me to cover in just one slide; I could probably give a talk solely on this topic. I will start with a few key skills that I believe form the foundation for effective communication. The first principle is that communication is a two-way street. When you start learning how to communicate and analyze your own style, ask yourself: am I an active listener? Have you ever had a conversation with someone and could tell they weren’t really listening? They’re just waiting for their turn to speak? Don’t be that person.
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Part of being an active listener is respecting the other person's opinion. You don’t have to agree, but it’s about understanding where they’re coming from. Hear what they’re saying, and only then do you respond. That’s the difference between reactive listening and active listening.
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When you start to grow your team, the skill of delegation becomes critical. Your job is to ensure the team gets the work done, not to do the work yourself anymore. You may have several people working for you, and you cannot outpace their output. Learning to delegate means you must set clear direction and communicate what needs to be done clearly. Are your objectives clear? Does the person understand what they need to get done? This can be challenging because it requires trust.
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A misconception some people have is that gaining the title of manager means they have unlimited power—like the emperor. The most important thing to understand is that you do not have control. You are responsible for the project's ultimate success, but you can’t do the work on your own anymore. You can only establish the conditions to allow success to happen, and that’s what delegation is about. Managers who can’t let go are often referred to as micromanagers. You have probably worked with some of them; don’t be one of them. Micromanagement is incredibly disruptive to the team and will lead to a lack of productivity.
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Also, you have to let your employees fail on their own. I've learned more from the one time I misplaced a semicolon than from countless times I got it right. Failure can be a tremendously valuable learning experience for your people, so you cannot be afraid to let them occasionally work through challenges on their own. Balancing this can be difficult; if they’re crashing in a fiery mess, then yes, step in and rescue them when needed. But let them navigate difficult spots themselves, something many struggle with.
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Another essential skill when stepping into management is coaching. Vince Lombardi, a legendary figure in American football, is famous not just for his strategies, but also for his ability to lead and inspire the team. Coaching is about ensuring your people continue to grow. This ties back to the previous slide defining why we delegate: it's our responsibility to cultivate the leaders of tomorrow.
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I once interviewed a technical team lead and asked how he managed his team. He said he gave them the grunt work and then did the fun stuff himself. Do you think his team ever grew out of their junior roles? No! As a coach, you must inspire and motivate your team to be their best. Lombardi said, 'Practice doesn’t make perfect; only perfect practice makes perfect.' Your team will make mistakes; your job is to correct those and help them develop better habits. There's an art in communicating and coaching effectively so they can receive constructive criticism in a way that builds them up, not tears them down.
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Coaching is also about empowering the team to execute the game plan. Vince Lombardi was brilliant, but he didn’t run onto the field himself—he empowered his players to execute. Learning to trust your team can be difficult, but it becomes much easier when you believe in the game plan and if you have a good structure in place for your people to do things right.
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Another important skill is understanding how to lead with soft power rather than hard power. General Dwight Eisenhower once said that leadership is the art of getting someone else to do something you want done because they want to do it. As you move into management, you’ll find yourself imbued with formal responsibilities—what I like to call hard power: 'Do it because I say so; I can fire you if I want.' However, it’s not about wielding hard power, even if you have it.
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Lazy or bad bosses revert to hard power because they lack other tools. Understanding how to apply soft power to communicate effectively and foster a sense of ownership over other people's ideas is critical. There’s nothing more powerful than an idea that someone feels is their own.
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Another essential skill is courage—not just in decision-making but also in owning failures. As a manager, the buck stops with you. A bad boss blames others when things don’t go right, but having the courage to accept responsibility and own your mistakes is vital.
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Being able to say 'no' can also be difficult. Just because you have power doesn't mean you're the only one who wields it. Sometimes you will encounter other managers or stakeholders who request things you’re not comfortable with. It’s your responsibility to understand how to say no. This requires courage and can be tricky.
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As you establish direction, not everyone may buy into it right away. Sometimes people fear not being liked, and that’s understandable. You will encounter challenges that require you to trust in your vision and conviction. A boss lacking courage or vision may change course at every challenge. However, leaders need to understand the difference between a bump in the road and a chasm ahead, and be willing to embrace change when necessary.
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Finally, always embrace the truth, even when it's unpleasant. People will often tell their bosses what they think they want to hear. As a manager, create an environment where honesty is rewarded—even when the truth is uncomfortable. It's also your job to communicate this truth to your own management.
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Let’s discuss project management skills now. Moving into project management means tracking work, measuring it, managing risk, and knowing how to report status. Understanding the art of risk management is crucial. You will often need to make decisions with uncertain outcomes. Your role is to ensure informed choices are available based on the facts at hand.
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To successfully manage projects, you must understand various project management frameworks (like Waterfall, Spiral, Kanban, XP, and Agile). You must be a student of process. Being dogmatic about any single framework can lead to issues. Even if you don’t often use frameworks like Waterfall, it’s wise to understand them and recognize when they might apply.
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Administrative and financial aspects also impact your management approach. In particular, if you’re working at a startup, understanding budgeting is key. Knowing the concept of 'colors of money', which refers to money earmarked for specific purposes, is critical. For example, if you have allocated funds for servers, you can't repurpose that money for bonuses. It's also essential to project a budget, understand salary impacts, and how financial flows affect your organization.
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Understanding the hiring, retention, and firing processes is also crucial. It's costly to hire employees, which is why retaining talent is key. However, sometimes it becomes necessary to let someone go. Each state has different employment laws that must be understood to navigate these processes successfully.
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Though I said it isn’t all TPS reports, there will be times when you need to be compliant with various regulations and documentation. Privacy laws are critical in industries like cybersecurity, and it's important to understand and comply with them. This administrative aspect of management gives insight into how businesses operate.
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Hopefully you are now intrigued by the idea of management. You might think it doesn’t sound so terrible. To successfully transition into management, you’ll want to find a mentor. Finding a safe person who can guide you, like a Jedi Master, and who you can turn to for advice is invaluable.
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If you’re already in leadership roles, even without formal authority, seek opportunities to lead projects or mentor others. This is a good way to gauge if management is a fit for you. Be open to trying various tasks across your company: go on a sales call, help out with marketing, or get involved in customer support to understand what others do.
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Finally, think about what kind of leadership style resonates with you; there isn’t a one-size-fits-all approach. Understanding your unique style and practicing those skills is key. There will be some big questions that arise as you consider moving on: if it's a career change and I leave the technical track—will I still get to write code? The answer is yes, sort of!
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I’ve heard many folks say they balance coding and management roles with varying degrees of success. It’s crucial to stay technical while supervising technical people to know what they're discussing. However, your primary responsibility will shift away from writing code to other managerial tasks.
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Can you still be friends with your employees? Yes, somewhat. If you’re promoted among your peers, you’ll need to carefully navigate those relationships. Having open communication and a clear understanding of boundaries will be necessary to avoid conflicts of interest.
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Do you need a PMP certification? No, it’s not mandatory; however, it can help in large organizations or the government setting. In these contexts, having certain certifications might be a prerequisite. Do your research and find out what works best for your career and aspirations.
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As we get ready to wrap up, I encourage you to constantly reflect on your leadership style and the impact you want to have. Here are some key leadership principles that guide my own journey. First, 'leaders eat last.' This reflects the idea of putting your team's needs before your own.
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Second, lead from the front. Don’t ask your team to do something you aren’t willing to do yourself. Finally, remember: your team’s job is not to bear your burdens. It’s your responsibility to ensure they can be successful.
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A high-performing team can often exceed the sum of its parts, so focus on cultivating that environment. Always be open to learning—Vince Lombardi said it well: 'Leaders are not born; they are made through hard work and dedication.' Keep striving to educate yourself and improve.
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Finally, I want to leave you with a quote from Admiral Grace Hopper, a pioneer in computer science: 'You manage things; you lead people.' Understanding this concept is the essence of effective leadership. I will share resources on my slides in the link provided.
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Thank you very much for your time and attention! If you have any questions, I’d be happy to answer them now or connect with you afterwards.