SWLW #555: Lessons from 5 bosses, On becoming a VP of Engineering, and more.

Heya,

As always, below you can read my best findings for the week.
 

This Week's Favorite

Lessons From 5 Bosses (Video)
33 minutes read.

Keith Rabois shared valuable lessons he has learned from five bosses: Peter Thiel, Reid Hoffman, Max Levchin, Jack Dorsey, and Vinod Khosla. Keith is known for saying exactly how he thinks about something without filters. It's often easier to ignore someone like that, but I feel there is plenty to learn from Keith's experience and insights.

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Culture

Every Startup Needs at Least One Founder Like This
1 minute read.

My humble effort to help you start the weekend with a smile on your face.

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Why Shopify Elevated the Non-Manager Career Path and Ditched Meetings
8 minutes read.

The interview with Kaz Nejatian (VP Product & COO of Shopify) is fascinating. Their focus on the branding and narrative (craftmanship at the center) is different: "Building great products is a matter of having taste and knowing when your product will resonate with customers. Unfortunately, this is why there are so few good product managers. I can't teach taste or the kind of extreme ownership over problems that we require, nor can I teach customer empathy. I can help fine-tune these skills, but my job is to select people who already possess these qualities." And yes, their internal tool Shopify Cost Calculator to show the cost of each meeting is something Google Calendar should have built-in.

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Alignment > Autonomy
5 minutes read.

This is one of my favorite posts and not the first time I have shared about the need for alignment over autonomy. There are so many nuggets in this post: "The biggest alignment problem is the gap between how much people think they have to align versus what they should align on. There are many strategic decisions in the “how”. eg, what technologies to use, new system vs integration, build in core or in an app." and "Tech companies worship autonomy to distance themselves from any inkling of command-and-control. If you get labelled as micro-managing you’re burnt at the stake. But the nuances or organizational problem solving has been lost. Without alignment, autonomy is squandered."

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If Times Are Tough — Don’t Hide. Be Present.
5 minutes read.

An important lesson by Jason Lemkin - if things are hard, strange, or scary - this is the time to show up. While this post mainly targets CEOs, it is relevant for all leaders. Remember that people are looking at you and how you behave.

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Peopleware

On Becoming a VP of Engineering, Part 1: The Path to VP
6 minutes read.

Emily Nakashima shares her growth journey in becoming the VP of Engineering at Honeycomb. Emily's take on "How to prepare" can serve you well in areas to invest in if you want to create a similar path. This is a critical takeaway: "An overgrown sense of responsibility. I have a bad habit of walking into a room with five problems and walking out owning six. This is helpful at a startup where lots of important work falls into gaps between functions. However, it needs to be counterbalanced with a constant effort to wrap up or hand off jobs to others to avoid getting bogged down or stifling the growth of the rest of the team."

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My DMs Are Filled With Variations of This Question: “Will You Be My Mentor?” I Say No to All of Them. Most of You Are Doing It Wrong. Here Is My Counterintuitive Advice for Finding Good Mentors/Advisors (Thread)
3 minutes read.

"STEP 3: Ask for specific advice. In step 1, you became someone doing cool shit. In step 2, you changed your attitude. Now look for mentors to help you when you get stuck. Go with a specific problem. Ask for help. This is the equivalent of a first date for mentoring." -- Michael Girdley's 3rd tip on asking for an explicit and specific problem makes it easier to help. Imagine you can have lunch with someone to get their thoughts about the problem. The context and dilemma must fit 30-45 minutes, including hearing their advice and suggestions. This is how you start building a relationship. Don't forget to summarize your takeaways from the conversation and follow up 2-3 weeks later to say how you used their feedback and advice.

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The Power of Strategic Narrative (Video)
62 minutes read.

After a colleague recommended it to me, I listened to this interview with Andy Raskin on my commute to work and found it inspirational and practical. I'll practice his framework in the next few decks I'll prepare on Engineering Strategy and investing in a few products we're taking to market. Where can you experiment with it?

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And finally, inspiring tweets...

@jackbutcher: to focus energy, design constraints

@fortelabs: Read to fill your mind, write to clear your mind



p.s. if you're interested in joining SWLW's Slack channel, simply reply to this email and let me know. If you're leading a team, consider writing your Manager README (it's free) or getting my e-book and interviews Leading Snowflakes: The New Engineering Manager's Handbook. You can also support me by becoming a SWLW Patron. Thank you ❤️




Keep reading, keep learning.
-- Oren Ellenbogen.