How do you communicate the importance of embracing failure?

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Senior Executive Advisor in Software, 10,001+ employees
As I went up through the ranks, I found the inability to tolerate failure so interesting. We all fail every day, at every single step. We wouldn't be where we are now if we had not failed almost every day. Rather than embracing that failure, you suddenly have this artificial, stoic personality at higher levels. People start to think, "Failure is not an option, you have to be 100% up all the time," which are limiting beliefs. You should embrace failure because that's the only way you learn and grow. I talk about it in depth in my book, Leading with Empathy.
VP - Head of Information Technology in Software, 1,001 - 5,000 employees
Failure is how we learn. I had this eager employee who wanted to learn networking, and I'm an expert in that, so I was happy to teach them. But I said, “We only have production in this environment. There is no dev. So at some point, you're going to make a mistake in production." They kept insisting they wouldn’t, but of course they did later on. I said, "You're developing a little Iago that will sit on your shoulder and say, ‘Are you sure you're ready to hit enter?’ If you don't ever screw up, you'll never develop that little voice, so it's okay. I'm not mad at all."

There's an interesting psychological/neurobiological element of failure, which is that some research shows you're practicing failure when you fail. It allows you to detect that failure is about to happen, and that’s the actual skill you're trying to get from failing. I took piano lessons as a kid and hated it; even though I loved the piano, I hated the lessons. When I got a keyboard years later, I could play with headphones and I loved it because nobody could hear me practice. I could experiment and I was able to pick up three other instruments after that.
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Global CIO & CISO in Manufacturing, 201 - 500 employees

I read Blink many years ago and the concepts are interesting. There’s what your brain says, what your heart says and what your gut says, and the gut is something you develop. When you can get all three aligned, or you know which one's the strongest and you know how to move forward, it's a very empowering way to look at everything: "What is my heart telling me? What is my gut telling me about the risk, and what does my brain say to do logistically?"

Global CIO & CISO in Manufacturing, 201 - 500 employees
I've been coaching a colleague to help them understand how to level up. They’re making one third of what they could be making. They’ll tell me what they do and I’ll say, "So effectively, you run enterprise program management for IT." For each thing that they come up with as a failure, I'm able to show it in a different light.

I apply the same mentality that I use when I’m helping folks work on their resume, because it’s all about how to pitch themselves, and how to look at what they’ve done. Then they'll realize, "I guess that wasn't a failure. It was a success because we were able to reduce something after the fact." Your mindset is really important. You have to find a way to ensure the team has the comfort zone to say, "I can do this and here's why. And here are two or three contingency components." Building a mindset to handle risk is critical. 

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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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