Transitioning to Management.md

Transitioning to Management: Building Products and Startups, and Managing Managers

Building Products and Startups

As a leader of a product development team you might have a PM that you’re working with, but some of your role will involve deciding how/when product is built, who builds what, etc. So you’ll need to level up your product skills.

• Aligning Projects with Business Goals - by Anthony Eden. Provides a simple project management spreadsheet of six questions: 1) What is the problem we are trying to solve?; 2) What does success look like, and how does it fit in the big picture?; 3) What are the MUST DO and the MUST NOT DO items?; 4) What is the deadline?; 5) Who should I talk to for help and get feedback?; 6) Have we done this before? Something we already have to get started?

• Applying OKRs - by Dan North. Takeaway: Insights from Dan about working with companies applying Objectives and Key Results; do's and dont's.

• The Art of Project Management - notes by Joe Golberg about Scott Berkun's book.

• The Art of the Start: The Time-Tested, Battle-Hardened Guide for Anyone Starting Anything - by Joe Goldberg. Notes about the book by Guy Kawasaki.

• Blue Ocean Strategy - notes by Joe Goldberg about the book by W. Chan Kim and Renée Mauborgne.

• The Bootstrapper’s Bible - Joe Goldberg's notes about the book by Seth Godin.

• Do The Simple Thing First: The Engineering Behind Instagram - by Harry McCracken. Takeaway: Instagram founders made technical decisions using a principle which favored practicality over perfection. "If it solves a problem and gets us closer to launch, let’s do it."

• The Engineer/Manager Pendulum - by Charity Majors. Takeaway: "Fuck the whole idea that only managers get career progression. And fuckkkk the idea you have to choose a “lane” and grow old there. I completely reject this kind of slotting."

• Growth Hacking Notebook - notes by Joe Goldberg.

• Key Learnings in My First Year as a PM at Amazon - by Venkatraman Prabhu. Takeaway: Lessons learned after a year at the global retailer. Choose the right manager, always measure the product's impact, keep experimenting, have weekly 1:1's with key stakeholders, and get advice.

• Lean Startup - notes by Joe Goldberg about the book by Eric Ries.

• LeanStartup.com - based on the book. Offers an e-newsletter.

• Little Red Book Of Selling: 12.5 Principles of Sales Greatness - notes by Joe Goldberg about the book by Jeffrey Gitomer.

• The MVP is dead. Long live the RAT. - by Rik Higham. Takeaway: "There is a flaw at the heart of the term Minimum Viable Product: it’s not a product. It’s a way of testing whether you’ve found a problem worth solving. A way to reduce risk and quickly test your biggest assumption. Instead of building an MVP identify your Riskiest Assumption and Test it. Replacing your MVP with a RAT will save you a lot of pain."

• Paul Graham’s Startup Advice for the Lazy - by Stelios Constantinides. All of Paul Graham’s startup advice summarized in one article.

• The Product Dartboard - by Janet Brunckhorst at Carbon Five. Takeaway: offers a deep dive/description of a tool that assesses a team or individual against attributes associated with project success.

• Reminder: Your “Product” Company is Just an Implementation Detail - by Jeremy Baker. Takeaway: The progress our customer wants to make is the most important thing. We think about our features and what they can do, and present them that way. When we do this, we’re "forcing our customer to do the hard work. They have to map features to their process and figure out if it helps them make progress ... Instead, talk about the progress our customer wants to make, and build tools that enable that progress."

• Scaling Airbnb with Brian Chesky — Class 18 Notes of Stanford University’s CS183C - by Chris McCann. Takeaway: about Airbnb’s “10 star service” thought experiment, in which they transcended the usual five-star review by adding five more measurements for success.

• The Scrum Product Owner Theses - by Stefan Wolpers. Not necessarily tied to the Scrum agile framework, this list of 56 "theses" addresses the PO's role; examines product discovery and stakeholder management; roadmap planning, and more.

• To Grow Faster, Hit Pause — and Ask These Questions from Stripe’s COO - by First Round. Takeaway: "There’s a list of questions companies should ask themselves as they head into rapid growth — ideally in that relatively brief moment right after clinching product-market fit." The post provides these questions, to help you become less reactive and more proactive in managing your growth.

• The Ultimate Question - notes by Joe Goldberg about the book by Fred Reichheld, which focuses on measurements like the net promoter score (NPS).

• Why Software Sucks - by Scott Berkun. Good ways to think about why it happens and what you can do to make it happen less.

Leading Leaders

• Dealing with Team Rejection - by Ramez Hanna. Takeaway: "Team needs to establish healthy relationships between its members based on trust and communications." Provides useful context points and insight for when you have to tell your report that they need to improve.

• How Do You Know Someone Has True Leadership Skills? Look for These 5 Signs - by Marcel Schwantes. Takeaway: Leaders spread joy and drive fear away; provide employees with meaning, purpose anda sense of belonging; foster a learning spirit within the organization; build trust that leads to business outcomes; and are open and transparent in how they communicate.

• How to Ensure a New Manager Succeeds - by Lighthouse. Takeaway: Provide more support through 1:1's; give them good fundamentals to start; make some failure okay.

• The PM Mind Meld - by Ken Norton. Takeaway: what to do when your CEO and product manager aren't aligned, and tips on how to get them to align: 1:1's between them, keeping the conversation going both ways, talking about the future, and finding "third rails."

• The Sad Truth About Developing Executives - by Ben Horowitz. Takeaway: Instead of developing executives (which you can’t, and they should already be at the top of their game), give them information, expectations, and context to do their jobs.

• Transitioning to Meta-Management - by Lara Hogan. Covers measuring success, carving space to help others learn and grow, scratching the coding itch, and training your brain to focus on what's important.

• Who Do You Promote? 5 Qualities of a Good Leader - by Lighthouse. Takeaway: The aualities are 1) shows empathy for and consider motivations/needs of others; 2) is a good/active listener who builds rapport; 3) is consistent and accountable—you have to trust this person (sets a good example); 4) is interested in the life of a leader (show them what leadership really entails); 5) is committed to learning and growth mindset.

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.

• 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."

• 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."

• 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.

• 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.

• 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.

• 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 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.

• 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.

• 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.

• 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."

• 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’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 VP of Engineering Role

• 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.

• “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."