SWLW #580: The courage to imagine other failures, Dependencies in fast(er) growing companies, and more.

Happy holidays and happy new year! Like always, I share my best findings for the week.

 

This Week's Favorite

This Is the Person Selling Your Product: What I Wish Someone Had Told Me About Sales When I Was Starting My Career in Tech
5 minutes read.

"I had many negative misconceptions about sales teams before working in SaaS. After years as an engineer and product manager, high-skills sales reps are one of the groups whom I respect the most. [...] The person selling your product is a high-end matchmaker, not a used-car salesman. [...] So get closer to the person selling your product. Hop on a few sales calls – in aggregate, sales teams usually have a good sense for what it takes to win in your market. Help them sell your product better; let them help you build a better product. The person selling your product will make you both rich if you let them." -- A must-read post for non-sales reps trying to understand what sales is all about and the challenges around it. If you're a software engineer or a product manager, read it twice.

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Culture

Entering 2024 With This Energy
1 minute read.

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

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The Courage to Imagine Other Failures
4 minutes read.

This is a powerful mindset when thinking about risk management and how to prioritize it: "By prioritizing doing preventative work from recent incidents, we are implicitly assuming that a recent incident is the one most likely to bite us again in the future. It’s important to remember that this is an illusion: we feel like the follow-up work is the most important thing we can do for reliability because we have a visceral sense of the incident we just went through. It’s much more real to us than a hypothetical, never-happened-before future incident. Unfortunately, we only have a finite amount of resources to spend on reliability work, and our memory of the recent incident does not mean that the follow-up work is the reliability work which will provide the highest return on investment."

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Dependencies in Fast(er) Growing Companies
6 minutes read.

I highly recommend reading both parts of John Cutler's post and waiting for part 3 for some solutions. A good exercise is to think about these solutions while understanding that "There are managing dependencies and managing the context around dependencies" and "The challenge of managing dependencies is a) often about surrounding context, and b) efforts to manage dependencies can make things worse." So the challenge you deal with is how do you reduce friction and complexity effectively as it's so easy to make things worse.

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We Invested 10% to Pay Back Tech Debt; Here's What Happened
6 minutes read.

The practice of working on Tech Debt together (Friday every two weeks) as a team is a wonderful takeaway from this post by Alex Ewerlof: "Engineers looked forward to the Tech Debt Friday. The team would happily remind management that this day cannot (under any circumstances) be planned for regular feature/bugfix work. Although we fixed some bugs along the way, this was primarily an investment to make future feature development cheaper while improving the maintainability and reliability."

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Peopleware

How to Make Your Team Read Your Mind: Why Writing a Manager's ReadMe Is Not Weird
5 minutes read.

Anton Zaides shares his thought process for aligning his expectations with the team. A healthy process would drive people to write their expectations and foster a mutual discussion. These discussions should benefit everyone and help them understand how to perform well. After all, nothing is more frustrating than being misunderstood while making your best effort to produce high-quality work.

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What’s in My Bag, 2023
5 minutes read.

Matt Mullenweg (CEO of Automattic) has a unique taste in building companies. If you read about how Automattic operates (the company behind WordPress), you'll see what I mean. His "taste" in the equipment he has in his bag might reveal some lovely gifts for you to buy for yourself, your partner, or your teammates. I added a few items to my "wish list."

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What I Wish Someone Had Told Me
3 minutes read.

Sam Altman's insights are so good that each can be a wall poster. This one worth considering about your team: "It is easier for a team to do a hard thing that really matters than to do an easy thing that doesn’t really matter; audacious ideas motivate people."

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And finally, inspiring tweets...

@SahilBloom: One thing I've learned: A person is either holding you back or pushing you forward. There is no in between.

@JamesClear: New goals don't deliver new results. New lifestyles do. And a lifestyle is a process, not an outcome. For this reason, all of your energy should go into building better habits, not chasing better results.



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.