SWLW #546: Technology decision making, 5 heuristics to measure managerial impact, and more.

Heya,

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

This Week's Favorite

​​Technology Decision Making (And Boring Technology)
5 minutes read.

This post by Andrea Corey should be part of your company's onboarding reading list (with the Choose Boring Technology deck) if you want to build a mature engineering organization, focusing on business outcomes while leveraging the right technologies.

Read it later via Pocket or Instapaper.
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Culture

Right When You Think You’ve Figured Out All the CEO Best Practices Now You Have to Learn Jiu Jitsu Also?
1 minute read.

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

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How Do You Handle Layoffs on a Large Scale?
11 minutes read.

Eyal Mrejen covers a painful topic many companies face these days. What are the factors you use to make such decisions? How do you present the tradeoffs? It's a worthy exercise to have (and produce possible recommendations) even if you aren't pressured to make the changes now. Be proactive about it. Given the market conditions, being ready to manage your burn-rate is part of our job so we can apply creativity and have some breathing room to make the right decisions.

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Another Common Question I’m Answering Working With Scaling Tech Companies Is… Q. What’s the Worst Leadership Advice You’ve Heard? A. By Far the Worst Is “Hire Great People and Get Out of Their Way”. Let Me Explain… (Thread)
6 minutes read.

Jean-Michel Lemieux with an eye-opener thread, one of my favorites ever in terms of the number of insights and helpful advice: "Why did I feel like success was maximizing autonomy and showing that I could take care of things without bugging my boss? I prioritized autonomy over alignment. It's a million times easier to measure and feel high autonomy than it is to measure high alignment."

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You Can't Hack Product Positioning
5 minutes read.

Viviana Faga's post is an essential read to understand better how to create a business and have a go-to-market strategy to execute: "The lesson is to be aggressive. Product positioning is a game of hardball—to win, you must be willing to directly counter-position against your competition."

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Peopleware

Evaluating Managers: 5 Heuristics to Measure Managerial Impact
8 minutes read.

AbdulFattah Popoola's questions and heuristics can serve you well to have a better sense of your performance as a manager. Which ones would you add? Worth discussing with your peers to ask them how they see their role and how they measure it.

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Recruiting Is Sales. Fundraising Is Sales. Marketing Is Sales at Scale. Sales Is the #1 Skill for Any Startup, VC, or Bootstrapped. What’s Your Go-to Source to Learn Sales? (Thread)
4 minutes read.

Learning how to sell and the psychology and process behind it is an important skill for every leader. Every time you try to push your ideas from the wishful thinking stage to providing real value is an opportunity to practice. Closing a candidate, selling an idea for a new tool or product, pushing for a big infrastructure change, etc. This thread has good resources (talks, posts, books) and tips.

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What Is Technical Debt?
7 minutes read.

Technical Debt is rarely only a technical problem. It's a sociotechnical problem, as different people will judge what is Technical Debt very differently. So approach it as a team but set up a way to discuss it based on some data and facts (not all), and anchor it around what the business needs and not what will be nice to have. It's worth discussing how you track and deal with it and aligning the team to have a framework around it, e.g. quarterly cadence to review as a team where the pain is, how much to invest in reducing it, celebrating progress, etc. Use this post by Laurat Tacho as a baseline for the discussion with the team.

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And finally, inspiring tweets...

@jjen_abel: From my startup experience, selling low-cost things is harder than selling high-cost things.

@reverentgeek: I just registered a domain. When will I ever learn?



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.