Software Lead Weekly

Strategy Letter I: Ben and Jerry’s vs. Amazon
7 minutes read.

This post from 24 years ago shows you a couple of beautiful things: How insightful of a writer Joel Spolsky is (I miss following his Joel On Software RSS feed) and how the business landscape didn't change much other than the names of (some of) the companies. Which company style better match your preferences?

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Taking Off Your VR Headset and AirPods Because the Flight Attendant Asked You if You Want a Drink
1 minutes read.

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

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What Really Motivates You at Work?
5 minutes read.

"You may be engaged in your work, stimulated by your team, and motivated by your employer’s mission. But their rewards and recognition strategy may need improving. To keep a good thing going, reflect on and talk about what you want and need to feel appreciated and validated." -- Carrie Ott-Holland covers an important topic I didn't pay much attention to. How much do we match our teammates' preference for recognition with what we do? Did you ever set expectations with your direct manager?

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$3M to $40M: 11 Years of Unfiltered Business Advice (Video)
97 minutes read.

Nathan Barry and CovnertKit (now known as Kit) were always a bit different. This interview reveals how hard it is to build and lead a company. Nathan and Barrett Brooks (ConvertKit's ex-COO) cover many challenges, debates, and leadership learnings they had while working together and taking ConvertKit from zero to over $40M ARR. I highly recommend listening to it on your next commute as very few people are as open, honest and transparent about how it really is building a company.

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The Confrontation Obligation
3 minutes read.

"Of course you need to hire great people. But you can’t get out of their way. The best leaders set the standard and relentlessly reinforce it. Greatness is forged through high expectations and difficult conversations. [...] No one likes confrontation. But mediocrity creeps in when conflict ends. And if you want to be a great leader, that is not your fault…but it is your problem." -- Ravi Gupta captures it so well. Conflict and friction are part of every successful and meaningful journey.

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Feedback Loops
3 minutes read.

"You are already in a feedback loop whether you are aware of it or not. Better off being in a feedback loop that helps you grow. One of your own making." -- Understanding how to build feedback loops (habits) for yourself that can help you build patience for long-term results is challenging. It's worth sharing this post with your team and discussing over lunch how each one of you constructs their feedback loops to drive motivation and inspiration.

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How to Get to Coaching Mastery — A 16 Minute Masterclass With Principles & Examples (Video)
16 minutes read.

When you're in "Coaching mode," the goal is to help others understand themselves. This is an incredibly difficult skill to learn because it forces you to feel comfortable within your skin first and avoid pitfalls that don't come naturally to us. Shreyas Doshi shares a few practical tips to help you improve your coaching skills.

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Dream in Decades
3 minutes read.

Thinking in decades often frees you from real constraints, but more often, from made-up constraints that you can easily break. What becomes possible if you give it a try? What is exciting? What can you do tomorrow to start moving in that direction?

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@ShaanVP: when it comes to advice, here's who to listen to: 1st - ignore everyone who's never actually done it. 2nd - ignore everyone who's selling you their service . Even though that eliminates almost everyone, there will be a few people left. Then ignore them too.

@dharmesh: People don't like to be micro-managed. But they also don't like to to be macro-neglected. One of the most powerful things leaders can do is to help people master their craft and raise their currency. The best want to get better.