🔤 argue well


This week is an alphabetical experiment from a long piece of content.

No one knows everything but we don't know what specifically we are wrong about. Sometimes we guess right. Sometimes we don't. Sometimes the HiPPO chooses. Sometimes the Highest Paid Person's Opinion is right. Sometimes it's not.

The solution to all the 'sometimes' is a debate. Good arguments are central to that.

Devil's advocate, red teams, debate are all synonyms for this idea - and it doesn't matter what we call it so much as how we do it. John McCain said that arguing well was one of Ted Kennedy's biggest strengths. Ted argued well because, McCain explained, "he divorced personal relationships and personality from the issues." Arguing well is about ideas, not individuals.

Kim Malone Scott calls this approach "radical candor" and saw it during her work within Google on AdSense, YouTube, and Doubleclick Online Sales. She recalled one meeting where Matt Cutts was yelling at Larry Page. She told Kara Swisher:

"I started to worry that Matt was going to get fired. Then I looked at Larry and he's got this big grin, his whole face was lit up. It was such a productive way to have arguments… being willing to challenge authority and the authority welcoming it."

Good arguments require the boss to be focused more on the truth than their ego.

Technology companies seem to do this well. As a venture capital company, a16z seeks investments with large possible payouts. Scott Kupor was one of the early hires and said that a cardinal mistake of the venture capital industry "is investing in something that turns out to be a good business in a small market." Avoiding this mistake, Kupor explained, was the reason a16z failed to initially invest in Airbnb.

The ‘A' in a16z is for (Marc) Andreessen and the ‘Z' is for (Ben) Horowitz. The mistake they try to avoid the most is missing something, like Airbnb. To do this, the bosses model good arguments.

Marc told Tim Ferriss that when Ben brings an idea he will pounce all over it. Andreessen sounds like a natural contrarian and he's supernaturally inclined to being right. With a boss on both sides of the issue, it's easier for employees to avoid career risk and say what they believe rather than what they believe will get them promoted.

Like all the tools that follow, this one is quite situational. Sometimes a business must focus on making the trains run on time and sometimes a business is laying new track. Once a good argument is over everyone should still be able to break bread or go get beers but then focus on the collective choice.