Learning Leadership

A presentation at Web Unleashed 2019 in September 2019 in Toronto, ON, Canada by Anne Thomas

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Anne Thomas @AlfalfaAnne LEARNING LEADERSHIP CONVERSATIONS AND QUESTIONS

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SYLLABUS THE OVERVIEW

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How often do you examine what leadership means to you? ● Read as many tech management books as possible before September ✅ ● Conduct a series of interviews with senior developers ranging from 1-15+ years of experience ✅ ● Learn that it’s not as simple as working your way up the ladder or reading a lot of books ✅

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LESSON 1 MANAGER VS SENIOR VS LEADER

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Senior. Could be an Individual Contributor, CTO, Lead developer, Senior Developer !5

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Leader. Able to guide and lead people. !6

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Manager. Job title assigned by a company and implies you are responsible for a team. !7

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“My leadership approach is relational leadership. So I believe that people are empowered and motivated and become followers. […] So I don’t look at it as positional. I see a difference in managing. And so I think that leadership has to be won or granted or grasped - maybe more than it has to be given by a company.” !8

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Quick stats ● 84% of organizations anticipate a shortfall of leaders ● Only 5% of companies have leadership development plans at all levels ● A mere 19% of organizations believe they are “very effective” at developing leaders ● [source]

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LESSON 2 NO PATH IS THE SAME

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Junior developer. Can you manage up? !11

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“Even if you’re in a junior position, you need to lead people, without authority.” !12

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Mid-range. Take on manager-esque tasks without the title. !13

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“I was a programmer, I became a better programmer. At some point they said you’re good at this, why don’t you do this thing that has no resemblance to it and go over and manage these other programmers.” !14

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Senior leadership. Brand new job. !15

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“Who am I if I can’t write code? […] Find the qualitative instead of the quantitative.” !16

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No two paths are the same. ● Just like any career path, it’s rare to find someone that has made the “right” choices every step of the way ● Some team leads had years of experience as senior developers under their belts, others at the director level had come from less technical background ● Consensus was that a need to “step up” separated them from coworkers

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LESSON 3 DEFINE YOUR SUCCESS

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Everyone has a different definition. What’s yours? ● Shipping a product on time, on budget, with appropriate resources ● Building a good team that functions, is efficient, knows what they are doing ● Giving people on team the capacity to “lead themselves” ● Fostering an environment of trust and openness

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“I think success can be mostly gauged by finding out if anyone is following.” !20

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LESSON 4 YOU’LL MAKE MISTAKES

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“I made the mistake of thinking I was just like the people on my team. […] I kind of felt awkward, felt like I was outside the circle so I did a lot of pretending that there was no difference.” !22

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“A mistake I made was thinking I could do it all.” !23

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“I was this dictator-style leader, cause I didn’t know any better.” !24

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Everyone makes mistakes. We just have to learn from them. !25

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LESSON 5 DO YOU REALLY WANT THIS?

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Ask yourself these questions. ● Are you comfortable giving your opinion feely but tactfully? ● Are you empathetic or can you learn to be? ● Do you want to solve large problems? ● Are you more interested in the why of something or the how?

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“If I had ever thought I would get into management? The answer was no. If you asked me today if I would get out of management? The answer is no. I love it. I just really like helping people.” !28

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LESSON 6 INVEST IN TRAINING

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Formal or informal management training ● What works best for you? Will you seek out books on your own? ● Does your organization have the budget for formal training? ● At the end of the day, nothing beats years of experience

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“Schools try to do their best traditional schools. There is no bootcamp for managers, but who knows? The best training for management is to be an empathy-building conversationalist.” !31

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LESSON 7 MENTORSHIP PAYS OFF

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Are you a mentor or a mentee? Or both? ● A mentor relationship should be scheduled, there is a danger of it being shuffled aside otherwise ● Mentors generally have knowledge in your space or industry, whereas coaches don’t need to

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“A mentor can be a bit more ‘when I was your age’ or ‘if I was in your shoes I would do this’ ” !34

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“A coach is someone that will not necessarily tell you what to do, but asks the questions to figure out what it is that you want to do and what’s best for you” !35

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“A sponsor or champion is usually within the same organization and will actually advocate for you and help you get the promotion” !36

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LESSON 8 HIRE FOR DIVERSITY AND INCLUSION

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Use your position of power for good. ● Confront your own biases ● Be intentional in your search for diverse team members ● Take a critical look at your own organization and leaders

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“Persistence. Especially for women it can be really hard to get into more senior positions. It can be difficult to talk highly of yourself and your achievements” !39

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LESSON 9 QUALITIES OF A LEADER

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Qualities that people deem important for management… are varied! ● Resilience, drive, ambition, excellence, fun ● Empathy and humility ● Ability to ship products and build a team ● Background in leadership from an early age (sports, community organizations, large family) ● Comfort with difficult conversations ● Being aware that the choices you make are amplified

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“Being able to make decisions in the face of uncertainty.” !42

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“Being pretty good at technology itself. […] I’ve known people who want to become managers because they just hate coding.” !43

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“When you are in a management role, you are looked to as having all the answers, but you need to be able to have that humility to say that even if you don’t know, that’s ok.” !44

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“I lead with empathy much more than before. I’ve learned to understand and appreciate the human aspect.” !45

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LESSON 10 RESOURCES ARE PLENTIFUL

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Most recommended resources ● The Making of a Manager - Julie Zhuo ● The Manager’s Path - Camille Fournier ● Radical Candor - Kim Scott ● How F*cked up is your Management? - Johnathan Nightingale and Melissa Martingale ● Resilient Management - Lara Hogan ● Crucial Conversations - Kerry Patterson, Joseph Grenny, and Ron McMillan and Al Switzler ● Dare to Lead - Brené Brown ● The Lead Developer conference

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Even more! ● Marcus Blankenship blog ● Becoming a Technical Leader - Gerald M. Weinberg ● Managing Humans - Michael Lopp ● Leaders Eat Last - Simon Sinek ● Managing Up podcast ● Clearbit Manager’s Handbook ● It Doesn’t Have to Be Crazy at Work - Jason Fried and David Heinemeier Hansson ● Leading Change - John P Kotter

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TAKEAWAYS AKA HOMEWORK

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How to learn more about leadership and management. ● Read or listen to resources on the topic (maybe start a bookclub?) ● Talk to people in your network in more senior roles ● Join a Slack group for development leads ● Check in regularly with yourself to self-reflect on what leadership means to you ● Always be on the lookout for opportunities for you to lead ● https://docs.google.com/forms/d/ 15mhUm5TSdPfRkWxzb6Ns1TorvtxIdGz5buFZ3p—5_k

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Thank you! @AlfalfaAnne