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Avoiding failure vs pursuing success

Coming from the startup world, I used to think this advice was unambiguously Good Advice not just for hiring, but for How to Be Good. "I don't care how smart someone is—if they are unable to work hard and crank out a large amount of high quality work, they will weigh down your startup." I was used to a world where speed of execution was critical, and I was proud of my bias for action and tolerance of uncertainty.

After all, in startups, speed is an advantage. You can't sit there and think your way to product-market fit. You just have to put something out there quickly and then iterate, and do it faster than may feel reasonable. If you don't, your company will definitely die.

One of the symptoms of "inability to get things done" that Elad lists is:

Arguing incessantly about how to do something rather then just doing it.

This resonated with me. I've worked with a few people on various projects where I felt this way. It was frustrating. I am just trying to get this done...why are they making this so complicated? We'll never get it done if we go this slow. Let's just get it out the door and go from there.

But sometimes being forced to slow down was useful. I learned some things I'd glossed over, or planned for a possible failure mode I hadn't previously considered. Moving slowly was supposed to be a Bad Thing, so why was it sometimes Pretty Good? I didn't have a structured way to think about it.

So this article was remarkably useful: Do You Play to Win—or to Not Lose? It divides people into two types. The first is what the article (unfortunately) dubs "promotion-focused":

They are eager and they play to win. You’ll recognize promotion-focused people as those who are comfortable taking chances, who like to work quickly, who dream big and think creatively.

You will not be surprised to hear that I fall into this bucket. The flip side of this coin:

Prevention-focused people, in contrast, see their goals as responsibilities, and they concentrate on staying safe. They worry about what might go wrong if they don’t work hard enough or aren’t careful enough. They are vigilant and play to not lose, to hang on to what they have, to maintain the status quo. They are often more risk-averse, but their work is also more thorough, accurate, and carefully considered. To succeed, they work slowly and meticulously. They aren’t usually the most creative thinkers, but they may have excellent analytical and problem-solving skills.

The article is worth a read, particularly if you are a manager or want to understand the other side. It helped me see the value of the prevention mindset, and it helped me see that my mindset has its own weaknesses. I love that the article is immediately actionable, as it breaks down to manage, motivate, and work with people of each type. Even if you are not a manager, it can shed some light on how you can ask your manager to manage you.

Now I have a name for this, I see it in more places, like this advice from Warren Buffet and Charlie Munger (italics mine):

  1. We’ve done a lot of stupid things but we’ve avoided a small subset of stupidity and that subset is important. It’s about avoiding the dumb things [Charlie]. They hammer this every year. Their success does not come from doing so many things right. It comes from avoiding the things that are terribly wrong. Some say this is two sides of the same coin. But it’s not. It requires a fundamental shift in psychology. The stories are endless of people who did a few things right and were massively successful, but then did something stupid that took them back to zero. Before Charlie and Warren do anything, they “invert, always invert” as Charlie says. They list every way imaginable in which they could fail at a particular task and then take massive effort to avoid those failures. Do that and the success will come automatically.

I've come to see this as a useful push and pull in my daily work and collaborations. My default urge to push things forward as quickly as possible is nicely balanced by collaborators raising important questions to think through. And those colleagues who love to spit and polish get a little kick from me to ship before it's 100% perfect.

Starting a non-startup business has been incredible for showing me the value set I had absorbed unconsciously via osmosis. After all, context is everything: if your greatest risk is growing too slowly then you have to run like hell to get off the ground before your big competitor squashes you. But if you have a lot to lose, moving cautiously makes sense. Where your company falls on this spectrum shapes the values you prize. "Moving quickly" is a value, and values are not universal.

Our business is not a startup, and we need a balance of both mindsets. I'm learning to choose prevention or promotion modes when appropriate. The task at hand matters too. For instance, I have always moved carefully in parts of my work that involve managing or mentoring humans, where a little recklessness can kill a lot of trust.

Where do you fall?



I was on the Building AI Products podcast

"Technical" skills