Transitioning to Management.md

Transitioning to Management

Transitioning from Individual Contributor to Manager

• The 'Aha' Behind Leading Aha Moments - by George Bradt. Takeaway: Aha moments are pleasurable, because the experience makes us feel smarter. Making others feel smart, not making others see how smart you are, is the goal.

• Assessing Technical Risks for Startups - by kate{mats}. Takeaway: "As a new technology executive it is imperative that you take the time to understand the technology strategy and risk and communicate that to senior management." Comes with a great checklist for doing just that.

• Becoming Your Future Self - by Leo Polovets. Takeaway: Bottlenecks that prevent leaders from adapting to the role and scaling up include being good but not great; being unwilling to delegate, and not becoming well-rounded skills-wise. Listen to your gut, do 360-degree reviews, talk to great leadership peers and explore executive coaching to level up and overcome these hurdles.

• Chaotic Beautiful Snowflakes - by Rands in Repose. Takeaway: Think about the new work you’re creating with your words and actions. "The hard work of great leadership isn’t just managing the expected tasks that we can predict, it’s the art of successfully traversing the unexpected."

• Communicate Like a Boss - by Kathryn Koehler. Takeaway: well-rounded, pragmatic communication overview for new and first-line managers delivered in a well organized as well as entertaining manner.

• Conversations with Your Team, Peers and Boss - by kate{mats}. Takeaway: "Whenever you first join a new team the most important thing you can do is listen and observe. Get to know the players and the company culture."

• The Curious Transition to Becoming an Engineering Manager - by GitPrime. Takeaway: A conversation with Engineering Leadership coach Jean Hsu about knowing one's impact, handling self-doubt, and growing into the role. “'Actually, we don’t really dock people for those lacks, as an industry,' she says. 'People get rewarded for their technical focus. We put them in management positions, or just keep promoting them, and people can get pretty high up without really thinking too much about people’s intrinsic motivations.'”

• Don’t Leave Developers in the Dark - by Joe Stump. Takeaway: Help developers understand the full scope of their work so they can make sound decisions. Includes questions to ask developers to make this possible.

• The Five Flavors of Being a CTO - by Koan CEO Matt Tucker. Takeaway: The five types include "(External) Evangelist," a visionary/spokesperson for the technology; "(External) Super Sales Engineer," a charismatic, customer-focused spokesperson; "(Internal) Super Engineer," a coding virtuoso; "(Internal) People Leader," who manages and recruits like a VP Engineering (this is antipattern); and "(Internal) Innovator/Disruptor," who's "next big thing”-oriented.

• Four of My Biggest Mistakes as a New CEO and the Single Reason I Made Them - by Carrie Kerpen, CEO of Likeable Media. Takeaway: Kerpen identifies "not wanting to rock the boat," "not setting boundaries," "not giving direct feedback," and "not firing fast enough" as her four mistakes, and explains why.

• The 4-Letter-Word That Makes My Blood Boil - by Marcus Blankenship. Takeaway: Avoid words like “just”, “simply”, and “trivial." They could lead you to overlook or forget how detail-oriented technical work can be.

• From Coding To Management to Leadership - by Lorenzo Pasqualis. Takeaway: an examination of why developers are asked to manage, and why some developers go into management.

• Google’s New Manager Training - by Google. Takeaway: Training materials that Google uses to help transition an individual contributor to a manager, including a manager facilitation training guide and exercises for students.

• How to Fail as a New Engineering Manager - by Brad Armstrong. Takeaway: You can fail by continuing to code; focusing only on work, not people; measuring your value by your output; expecting without expressing; leaving the team out of commitments; mistaking directing for leading; avoiding hard conversations; not learning your craft anymore.

• How to Make the Leap from Engineer to Manager - by Kirby Frugia at New Relic. Takeaway: "The key to making processes work is to make incremental changes, measure them, and then improve them." Also, managerial success and developer success differ in that the former is often achieved through others, more about strategic impact, and happen less frequently.

• How to Win Friends and Influence People - by Dale Carnegie; summary by Joe Goldberg. Notes on the legendary book, whose mention might make you wince but we suggest getting past that. :)

• The Leadership Paradox: Why Managers Must Be Consistently Inconsistent - by Lighthouse. Takeaway: "Balancing when to be rigid and when to be flexible is one of the hardest things to learn as a manager." Provides guidance on how to manage this.

• The Manager's Path [$] - by Camille Fournier. A collection of advice for leaders at all levels of the career ladder. Valuable whether you are just starting out in management, a veteran, or just curious about common problems and challenges that managers face on a daily basis.

• Manager Tools Podcast - by Manager Tools. Takeaway: Informative podcasts that focus on key opportunities that a manager can leverage to step up their game.

• Managing More Experienced People - by Julie Zhuo. Takeaway: "For me, despite knowing I’m not as strong of a designer as my senior reports, I understood how to approach design at Facebook and could support my team members in setting ambitious goals and working effectively with their partners."

• The Missing Piece of a Manager’s Responsibilities - by Cynthia Maxwell. Takeaway: "[it's] 'digging deep': owning your successes and knowing that you can overcome whatever challenges come your way."

• The More Senior Your Job Title, the More You Need to Keep a Journal - by Dan Ciampa. Takeaway: "The French philosopher Blaise Pascal pointed out that 'All of humanity’s problems come from man’s inability to sit quietly in a room alone.' He didn’t mean sitting quietly in front of a laptop responding to emails. The best thinking comes from structured reflection — and the best way to do that is keeping a personal journal."

• The Most Important Management Concept You’re Missing - by Lighthouse. The article advocates Task Relevant Maturity, described like so: “How often you monitor should not be based on what you believe your subordinate can do in general, but on [their] experience with a specific task and [their] prior performance with it – [their] task relevant maturity…as the subordinate’s work improves over time, you should respond with a corresponding reduction in the intensity of the monitoring.”

• The Most Important, Yet Overlooked Management Skill - by Lighthouse. Takeaway: Curiosity is the most important trait of a leader. Ask questions.

• New Leader's 100-Day Action Plan & First 90 Days - by Joe Goldberg (summary). Highly detailed document with TOC. Covers topics ranging from due diligence (before you accept a job) to choosing the right approach for the culture and context.

• The New Manager Death Spiral - by Michael Lopp. Takeaway: management isn't a promotion. Thinking, "I can do it all. I’m The Boss," will lead you to take on too much responsibility and set yourself up for failure. Avoid this outcome by delegating, hiring a diverse team, and listening.

• Not Everyone Is a Manager - by Shem Magnezi. Takeaway: "[D]iscovering that I don’t have to be a manager to get promoted in a tech company was a huge relief. A lot of companies (and individuals) understand now that there is a place for engineers to grow as individuals outside of the management track, and every one of us should know about this alternative. For me—if I had had the opportunity to read this kind of post, I would have been thinking about my career development differently."

• On Managing Your Friends - by Jennifer Dary. Takeaway: "At the end of the day, you cannot control the emotional growth or maturity of anyone but yourself. So if your friend is going to hold it against you, if they’re going to be resentful and stick their tongue out when you’re not looking, then you keep on keeping on."

• Only 10% of CEOs Have This Critical Skill - by Ryan Holmes. Takeaway: Social media skills are increasingly worthwhile for leaders to develop, for reasons ranging from recruitment outreach to promoting products.

• Popforms New Manager Guide - by the Popforms team. A four-step how-to for new managers to own their new role. Long but actionable.

• Progressing from Tech to Leadership - by Icamtuf. Takeaway: "[P]eople in leadership roles have their allegiance divided between the company and the people who depend on them. The obligation to the company is more formal, but the impact you have on your team is longer-lasting and more intimate. When the obligations to the employer and to your team collide in some way, make sure you can make the right call; it might be one of the the most consequential decisions you'll ever make."

• The Secret Ingredient Behind a Successful Tech Lead - by Guido de Caso. Takeaway: One thing all great tech leads have is a great second-in-command engineer.

• Secure Early Wins in the First Three Months - by kate{mats}. Takeaway: "In order to the set the right tone and get started on the best path, it is key to secure early wins." Includes helpful strategies.

• The 7 Habits of Highly Effective People - notes by Joe Goldberg of the popular book by Steven Covey. The seven habits: Be proactive; begin with the end in mind; put first things first; think win/win; seek first to understand, then to be understood; cooperate creatively, and balance self-renewal

• So You Think You Want to Manage? - by Julie Zhuo. Takeaway: Make sure your transition to management is an intentional and well informed decision by answering a bunch of questions.

• Speed Matters: Why Working Quickly Is More Important than It Seems - by James Somers. Takeaway: "The obvious benefit to working quickly is that you’ll finish more stuff per unit time. But there’s more to it than that. If you work quickly, the cost of doing something new will seem lower in your mind. So you’ll be inclined to do more."

• Speeding up Your Engineering Org, Part I: Beyond the Cost Center Mentality - by Edmund Jorgensen. Takeaway: "[I]t isn’t actually a law of nature that engineering orgs have to slow down as they mature and grow. With active, contravening investment, it’s possible to maintain and even gain speed."

• Team Lead — Here Is What Your Boss Isn’t Telling You, Yet Still Expects of You - by Oren Ellenbogen. Takeaway: as a team lead, it is your job to enable your company’s scalability. You do this by removing blockers, making your people happy, planning for growth, and delegating.

• Tech Lead Skills for Developers (video) - by Patrick Lua. Takeaway: To lead you need to have respect, and for developers that means spending time in the code and empathizing with the problems they're having.

• Ten Principles for Growth as an Engineer - by Dan Heller. Takeaway: Reason about business value; unblock yourself; take initiative; improve your writing; own your project management; own your education; master your tools; communicate proactively; find opportunities to collaborate; and be professional and reliable.

• 10 Hard Truths About Management No One Tells You - by Emma Brudner. Takeaway: Management can be lonely; you stop practicing your craft; GSD turns into GTD; you don’t get as much feedback; you have to do hard things (and you still have the same feelings); management is emotional; self-regulation, all day, every day; you spend less time in the spotlight; you’re the “shit umbrella"; your relationships change.

• Things I've Learned Transitioning from Engineer to Engineering Manager - by Gergely Orosz. Takeaway: Mentors matter, especially within the company; understand the most important priorities of your new role; decide on a time and task management strategy; set short-term goals; and take time to read, experiment, learn and reflect.

• This Is What Impactful Engineering Leadership Looks Like - by First Round Capital. An inspiring article about the amazing Jessica McKellar (Dropbox, Python Software Foundation) and how she manages people/teams. Takeaway: "When engineering management is done right, you're focusing on three big things ... You're directly supporting the people on your team; you're managing execution and coordination across teams; and you're stepping back to observe and evolve the broader organization and its processes as it grows."

• The Right Way to Ship Software - by Jocelyn Goldfein, angel investor and former engineering executive at Facebook and VMware. Takeaway: There’s no one-size-fits-all for SDLC. "Please stop asking, 'Is this process good or bad?' and start asking, 'Is it well-suited to my situation?'”

• Thrown Into Management: Lessons Learned Leading Thumbtack’s Design Team - by Audrey Liu. Takeaway: "I learned many lessons, but two stand out as the most important ones that helped me and the team get unstuck and get moving: build trust (quickly) and keep the team engaged once that trust is in place." Includes a cheatsheet with additional context on these two tips.

• The Top 10 Reasons Companies Fail at Promoting from Within - by Lighthouse. Takeaway: "Done well, promoting from within rewards and retains your best people for the long term. It also helps strengthen your culture. However, if you don’t put the effort and attention into making those promoted successful, it can backfire massively. No one likes working for a leader that doesn’t know what they’re doing, and those failing in a new role will feel terrible."

• The Top 10 Reasons Why You Should Become a Manager - by Tom Bartels. Takeaway: If you care about your coworkers, have good listening and communications skills, trust your colleagues, have an eye for talent, and demonstrate a few other abilities—and you haven't thought of managing people yet—maybe you should, because otherwise someone without those skills might do it instead.

• This 90 Day Plan Turns Engineers Into Remarkable Managers - by David Loftesness. Takeaway: "A newly-minted technical leader typically has no idea how to manage people". This provides a time-bound plan with checkpoints for opting out and leveling up. If you've already transitioned from IC to manager, you might read this and think, "this is the article I wish I'd had before transitioning."

• Understanding Company Strategy: New Tech Leader Series - by kate{mats}. Takeaway: "The very first thing you need to do in a leadership role is understand the goals of the company and the way your organization fits into that strategy." Provides the steps to make that happen.

• What Are Common Mistakes That New or Inexperienced Managers Make? - by Ian McAllister. Takeaway: Some of them include being slow to deal with performance issues, not investing in recruiting or team development, taking credit for others' work and blaming, and simply not leading.

• What Stops Us from Transitioning Into a Leadership Role - by Femgineer. Takeaway: A chat with leadership coach Jean Hsu about why our perception of who or what we think it takes to be in a role is often wrong, and why we are more capable of learning and growing in a new role than we realize.

• What’s Your Learning Stack? - by Mattan Griffel and Álvaro Sanmartín. Takeaway: Analogous to a tech stack, a learning stack codifies how learning is done in an org.

The CTO Role

• Chief Technology Officer Job Description: What Does a CTO Do? - by Roger Jin. Takeaway: how to put the "chief" in CTO. "A great CTO should be ready to delegate, while also being comfortable enough to work on the frontline, coding alongside their fellow developers. Furthermore, they will be required to be even more flexible if they’re working in a startup."

• How to Identify and Address CTO Smells: Process - by Andy Skipper. Takeaway: "Smells" include poor hiring, the inability to frame technology challenges against business challenges, a lack of succession planning and/or technical vision and/or belief, insufficient focus on quality, and an inability to manage upwards or sideways.

• Mastering Sales as a CTO - by Joseph Jude. Takeaway: Most careers turn into sales jobs when you get senior enough. For an IT services company, there is none better suited to build trust in the minds of prospects than a chief technology officer. A CTO can follow a structured approach to handle sales calls. The structure could be: Pre-call preparation, on-call performance, and retro (post-call and post-closure).

The VP of Engineering Role

• The CTO to VP Engineering Fork - by Julia Austin. Takeaway: "When you’ve decided it’s time to fork that technology leadership role and have both a CTO and a VPE, look for someone eager to create a partnership. Someone who prefers to lean into GSD and growing teams and who values the technology leadership, vision and evangelism of your CTO. Be leery of career CTOs who seek a role as VPE at your company — they may say they’re willing to be in charge of GSD, but could easily step on your CTOs toes."

• Hire a VP of Engineering - by Martin Casado. Takeaway: A VPE is responsible for product planning, building the engineering team and culture, ensuring execution, maintaining morale, delivering quality releases on time.

• The Role of a VP of Engineering - by Bruno Miranda. Takeaway: VPEs are measured by the success of their team; set process in terms of "why we do what we do"; keep coding; manage up and down.

• What Does a VP of Engineering Do? - by Dan DeMeyere. Takeaway: "VP’s of Engineering are essential to making sure the trains run on time and identifying the best way to lay down tracks. If the CTO knows the destination, the VPE is identifying the route to get there."

• “What Does a VP of Engineering Do, Again?” - by Raffi Krikorian & Dave Loftesness. Takeaway: a VP Engineering's primary duties involve "establishing focus; leading and designing the engineering org; and representing engineering at the leadership level."