SWLW #560: Squeeze the system you have, Ask vs Guess culture, and more.

A weekly newsletter by Oren Ellenbogen with the best content I found around people, culture and leadership in tech. You can also read this issue online and recommend this newsletter to your teammates for a great discussion.

Heya,

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

This Week's Favorite


Squeeze the Hell Out of the System You Have
4 minutes read.

Dan Slimmon puts it so elegantly with a lesson that unfortunately takes years to deeply understand: "Sometimes, leaps in complexity must be made. It’s generally a good problem to have. If enough demand is being placed on your system to render obsolete your existing technology, then even more growth is probably on the horizon! [...] But don’t just consider the implementation cost. The real cost of increased complexity – often the much larger cost – is attention. [...] When complexity leaps are on the table, there’s usually also an opportunity to squeeze some extra juice out of the system you have. By tweaking the workload, tuning performance, or supplementing the system in some way, you may be able to add months or even years of runway. When viable, these options are always preferable to building out a next-gen system."

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Culture


Looks Like a Startup Trying to Find Product/Market Fit if Startups Were Lizards
1 minute read.

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

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The Rise of Engineering-Driven Development (EDD)
7 minutes read.

This post reminded me of an early interview I saw with Patrick Collison (Stripe's CEO), saying that they don't have Product Managers ("for now") as they expected their engineering team to figure out the product and not "only to write the code." Then I saw that mentioned in the post and felt Patrick was ahead of the curve again. EDD shouldn't be an all-or-nothing approach. In some areas of the company, having engineers officially responsible for the production definitions and measurements could be a tremendous benefit. Where might it work for you? An interesting discussion to have with your team.

Read it later via Pocket or Instapaper.
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Ask vs Guess Culture
5 minutes read.

Jean Hsu's framing of "guess culture" versus "ask culture" made me think where I am on the spectrum. To start with, I thought I was mainly on the "ask culture" side, but I do find myself on the Guess Culture both at home and at work in certain situations. I'm considering it from a place of avoiding burnout and creating more opportunities to make a positive impact with my skills and desires. It's not good or bad ("be less X and more Y") but rather something to notice and understand the tradeoffs.

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What Makes a Strategy Great
17 minutes read.

I've been thinking a lot about strategy in my personal life and at work. I see it as 70% art, given that many have different opinions on what a good strategy looks like. A bad strategy is easier to spot, but that doesn't help to write a good one. Looking at strategy from the lens of Simple, Candid, Decisive, Leveraged, Asymmetric, and Futuristic is a great way to measure the quality of your writing and apply judgment if it passes some imaginary threshold in terms of quality before you share it with others.

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Peopleware


49 Engineering Blogs Worth Reading to Improve Your System Design
9 minutes read.

John Crickett curated a list of engineering blogs worth skimming over and picking a few to follow. Information diet always starts with the type of content you consume, so consider following up on some of the blogs on the list that inspire you, e.g. check out the last 3-4 posts by each blog of similar size companies (to your company) and see if there are good ideas and takeaways to learn from them. You can skim over the post, given you'll quickly see if the content fits your current interests. You can always revisit the list in 6-12 months and pick other companies to follow.

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John Mayer Is a Master of His Craft. He’s Also One of the Best I’ve Come Across at Using Analogy and Demonstration to Articulate and Demystify the Creative Process.
4 minutes read.

John Mayer is a fascinating artist I highly respect (guitar skills, writing skills, what's not to like?). The takeaways captured by Billy Oppenheimer are powerful: "Writer’s block is when the two people inside of you—the writer and the reader—when the reader doesn’t love the writer. It is not a failure to write. It is a failure to catch the feedback loop of enjoying what you’re seeing and wanting to contribute more to it." and "Don't shoot ideas down before you have them. 'That won't work' is the worst thing you can ever say. 'That didn't work' is cool, but 'that won't work' is not a way to go through life."

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The Rise of the AI Engineer
9 minutes read.

Understanding how people will leverage LLM to build tools and products on top of it will be interesting to follow. There is no doubt that more "Full stack engineers" and "AI Engieners" will dominate the market in numbers of people working on it, now that more and more open source models and tools are available for everyone. As "All job titles are flawed, but some are useful," I wonder how engineers in your company will want to see their growth in the company to explore this field and maybe gain experience as "AI Engineers" to capitalize the next 10 years of their career.

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And finally, inspiring tweets...


@KunalBSarkar: Curiosity leads to questions. Questions lead to more curiosity. A curious person loves questions more than answers.

@mbrandolph: Don’t be concerned that “somebody is already doing it”. Even the largest companies have an under-defended niche. You just need to find it.



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.

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