SWLW #599: Surfing through trade-offs, How to do hard things, and more.

Like always, sharing my best findings for the week. 

 

This Week's Favorite

Surfing Through Trade-Offs
7 minutes read.

"Note that different people tend to be drawn to different ends of these trade-offs. For example, TPMs typically are drawn to the “control” side and prototyping engineers are typically drawn to the “autonomy” end. This means that people will have their ego attached to one end of the trade-off, making the debate — especially if it frames the question as a binary and not a trade-off — somewhat emotionally charged." -- This may be the most challenging problem when leading a team, dealing with strong opinions often aiming for the end of the spectrum. Small(er) iterations, review, and aim to create value for your users/customers rather than win arguments.

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Culture

Entrepreneurs Trying to Have Fun on Vacation
1 minute read.

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

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Why Coaching (Really) Matters for Engineering Leadership
5 minutes read.

"But isn’t it a little strange that despite so much information, teams and companies continue to be so challenging for most leaders? (1) Teams and companies are notoriously complex and difficult. (2) Reading and listening to content provides an illusion of learning. (3) Most leaders are on their own and don’t have good role models." -- learning to become a better coach for your teammates is important as you need to, as Paulo frames it: "Coaching is all about helping other people change (in some way). And we have an innate tendency to resist change. A good coach learns how to spend time in the other person’s mind, curious about their belief systems and mental models until it becomes second nature to do so." Having a coach (or a mentor) to work with can often provide you with new tools, frameworks, and observations of blind spots you're missing. The same goes for an external support group you can consult with.

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How We Do Architecture at Okta (Video)
17 minutes read.

Figuring out the Software Architect's role in a company and whether or not to make it a title has always fascinated me. Okta shares their structure, what architects are responsible for, and how they lead. They also provide some case studies and prioritization functions they aim for, e.g. "Prioritize the areas where scale, resilience, and cost most: one goal, not three."

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Peopleware

Avoid Blundering: 80% of a Winning Strategy
15 minutes read.

Jason Cohen shares a great analysis of why companies (really) fail. Understanding failure scenarios can help (not always, but often) build expectations and set the best environment to increase one's chance to live and fight another day.

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How to Do Hard Things: A Therapy Practice Helped Me Face My Struggles as a Founder
9 minutes read.

Peer pressure that is both fun and effective is a wonderful leverage to create and make progress: "Then, toward the end of last year, I was talking with Dan Shipper, and it turned out that we both wanted to bring more consistency to our writing process. We decided to start meeting daily in the mornings for two-to-three hours of writing, and it turned out to be a game changer for both of us. Even when we’d miss a day, since we enjoy hanging out, we’d show up the next day and push through the resistance to starting again. Now, several months later, writing has become intrinsically rewarding: I enjoy it enough that I'll write even if we don't have a session on the calendar. Over time, committed action is about creating larger and larger patterns of behavior in the service of our values. What starts out one day as putting on running shoes and going for a walk could eventually turn into training for a half marathon. [...] When working with committed action, there are no 'right' or 'wrong' behaviors, and no step is too small—anything done in service of your values is a step toward building a life that matters to you. Living fully is the ultimate goal, and looks different for each and every person."

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How to Talk to Users (Video)
17 minutes read.

Asking the right questions can help you build products people love using even if they wouldn't imagine the solution that way. This is true for taking products to market and when building internal tools and products. Make sure to watch the part on "Follow ups" and which questions to avoid. I've seen it happen so many times when building internal tools with zero adoption and numerous execuses of why nobody is using it even though everyone asked for it.

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And finally, inspiring tweets...

@eastdakota: The theme of the age of AI: The demo is extremely impressive and relatively easy. The product is really, really, really hard. It is, perhaps, the perfect VC trap.

@naval: You don’t want fame, you want respect. Respect comes from living up to their standards. You don’t want respect, you want self-respect. Self-respect comes from living up to your own standards. The same standards that you apply to other people.
 


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.