Software Lead Weekly

Don’t Yolo Hard Conversations
3 minutes read.

"On the list of leadership merit badges, “Successfully deliver hard news” is one the hardest badges to acquire." -- Michael Lopp with a short and important post on how to deliver hard news or feedback. The first couple of tips on writing your feedback down and sharing it with a neutral person is something I saw (sadly) too few people do. You need to understand and answer these questions, and it's extremely hard to do it well without serious preparations: "What do you want the other person to take from it?", "Is it the most constructive way to phrase it?", "How would success look like if they will act now?", "Is there some time constraint that you think is important for them to know?".

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The Thinker vs. The Overthinker
1 minutes read.

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

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Your System Is Not a Sports Team
4 minutes read.

James Cowling from Dropbox shares the story of rebranding the team behind Magic Pocket (moving Dropbox data from AWS to an on-prem solution) and his motivation & takeaways from that transition. If you think about how to structure your team and how to guide managers in your organization to define their team's mission, this is a must-read post: "It’s the responsibility of an engineering team to do what’s right for the company, not to advocate for the system they own. Engineering teams need to be oriented around a mission not a system to avoid narrow-minded decision-making. [...] Orient your team around the problem you solve, not the tools you use to do it."

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Why I Changed My Mind on Team Stock Options
4 minutes read.

Nathan Barry, the founder of ConvertKit, is building one of the most interesting companies out there in my view. Other than being radically transparent about revenues (under the Open Startups), Nathan shared a lot of decisions that most founders don't do, or if they do, they keep it to themselves. Thinking about how to balance between equity and profit sharing is something that can benefit all employees, and open up opportunities to compete for talent in unique ways: "at our retreat last week we distributed a record $340,000 to the team (for the second half of 2018). That puts the total profit sharing at over $1,000,000 in just a couple years! [...] The point isn’t to increase one category at the expense of another, but instead to find a healthy balance between them. Healthy short-term compensation will allow a team member to hold onto equity for a long time to truly see the upsides."

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Tips From a Product Designer on Building Valuable Partnerships With Engineers
7 minutes read.

Jenny Wen wrote a post that I'd share with designers, product managers, and product engineers. Creating a delightful experience for our customers, while doing it in a way that is robust (not only "works on my machine", friendly to on-call support etc.) is something we should figure out together as a team. By looking at it as a team's goal (cross disciplines), you can align incentives so people will try to optimize for what is right on all various aspects, rather than a single dimension within their competence.

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5 Steps for Disagreeing Effectively
6 minutes read.

Julie Zhuo with a framework you can follow when disagreeing with others. I think it's helpful to understand which "hat" you want to put on when providing feedback: are you the (1) Owner of the task (the one who should get it done and care for it in the long run, the (2) Consultant (an expert with no direct ownership) or the (3) Preacher (you have some interest in the domain, but you neither the owner nor the expert). Understanding your role is where I'd start, as it will help to set the context in which you see the contradictions with the other person.

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Lessons From Keith Rabois Essay 2: How to Interview an Executive
6 minutes read.

Delian Asparouhov with his takeaways and summary of Keith Rabois's lessons for hiring an executive. The "Value creation vs Value protection" observation is an incredible way to phrase the mental model of the person you're looking for (and which questions you should ask to judge that). That advice by itself is worth probably reading this post a few times.

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When an Employee Is Underperforming, the First Question You Should Ask Yourself Is: "Do They Know, or Do They Not Know?" if They Know, the Problem Is Misalignment on Consequences of "Poor Work." if They Don't Know, the Problem Is Misalignment on Definition of "Good Work." (Thread)
2 minutes read.

Claire Lew with an important reminder to all of us: delaying feedback for underperforming employees hurt them and hurt people around them. Define (in writing) what good work means, and consult with peers who'd work with that person on the day to day, to see that they would define it the same.

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@Booligoosh: Habits are easy to keep up as soon as you stop treating them like chores to reach a distant goal and start treating them like little adventures every single day.

@captainsafia: My favorite thing to do in meetings with senior (like way senior) engineers is write down the questions that they ask. The engineers who get to that level are generally the best at their jobs and they always ask the best questions.