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Comment by epolanski | Hacker News Reader

One of the most brilliant pieces of wisdom I got from Munger comes from his early years when he was a flight operator at some navy or air force base.

At the beginning he felt the job to be difficult and stressful, he had to know how to assist planes fly safely and it wasn't always clear what had the highest priority.

So he inversed the problem: what could he do to make the planes crash?

It was easier to do his job by focusing on the things he could do wrong and just avoid those.

It's a powerful framework I use consistently in my life.

I really like Munger. I also love how unfiltered he is.

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Yeah, I like this and I think the same way. Except it's not popular at work, where everything has to be polite and pleasant and delivered gently. I'm constantly thinking about what could go wrong, poking holes in plans, trying to minimize bad outcomes. People don't like this.

But in general this is how I've always learned. And some of my best teachers and mentors over the years have been laser focused on what not to do. This really resonates with me, though I find most people aren't built this way. It comes across as a "negative" mindset.

A better way to frame this for colleagues might be: if we want this project to fail, what would we do?

This kind of adversarial design work is great if you can get the right people involved. The problems I’ve seen when you get the wrong people, though, are:

1) Often it’s much easier to point out potential issues than it is to properly address them. It can end up as a Gish gallop of low effort criticisms which must be countered on the spot or the initial idea is deemed entirely wrong.

2) If roles aren’t rotated regularly, some people settle into the “problem finder” role and start to prioritise finding problems over the success of the overall project, and now you have a saboteur on the team.

Obviously, I don't know the specifics about you. However, one thing I have witnessed many times is the following.

Just about every decision a team considers involves tradeoffs; if not, then it would be a no-brainer and there would be no need to convene a team to discuss it. Getting to the point now, some people will, no matter which alternative is under consideration, do nothing but point out the downside of choosing every option, even if that downside is obvious and known to everyone. Such people aren't insightful contrarians, they are a drag on problem solving. It is also politically safe: no matter which decision is arrived at, if things go wrong they can tsk tsk and say I told you so.

Usually the quickest way to shut them up it to ask them: OK what is your suggestion for what we should do?

When in doubt, always invert.

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