The Road Less Stupid

This is one of my favorite business books. I read this in 2023 as I was leading a team of 40 people during my time at Three Ships (Home Solutions).

My key takeaways

• Ask "what could go wrong" more than "what could go right"

This takeaway led me to start holding 'pre-mortems'. These are meetings where I would get the key stakeholders together before an important launch or key decision, and we'd fill out a sheet with two columns. One column is "what would cause this launch to fail", and the other is "how do we prevent this from happening".

• Set aside thinking time (2-3 hours per week) to think through tough questions.

I was already spending my Monday mornings thinking through tough problems. It was interesting to see how Keith approached this. I liked how he created more structure around this time. My approach was more haphazard thinking through these tough questions throughout the week.

• Culture isn't what you say, it's what you tolerate

I love this quote from the book. Many managers are willing to tolerate team members who are slow throughout or have poor work product, which inevitably lowers the bar for the whole team as other people see what's expected of them. Your A players will see this an never reach their full potential or potentially leave entirely. You should either be coaching up these under performers or actively managing them out to make space for someone who is going to raise the bar for the team.