Setting Yourself Up for Failure

Part 2: Culture

March 26, 2021

In part 1, we looked through some examples of how failure is a part of life and some of my own epic failures. Here, we’ll look at how to cultivate a culture where failure can be celebrated.


These stories, my experiences, they wouldn’t have been possible had I not been given the space to try new things and the support to learn from my failures. I have been fortunate enough to be a part of and to help build a culture where failure is celebrated.

Another quick definition so we’re all on the same page:

A company’s culture is the set of shared values, goals, attitudes, and practices that characterizes a group.

Culture is not what’s written down, but what is lived. Your culture sets the context for everything a company does. Values, beliefs, behaviors are shared by all levels of the group.

The thing is though, failure is emotionally charged. And because of that, a culture that allows and even encourages failure is necessary. A strong culture, with shared values, goals, and behaviors creates trust, ownership, enables better and quicker decision making, collaboration, and it drives every activity. It encourages learning from predictable failures, failures in complex systems that are unavoidable, and it encourages experimentation through learning.

Amazon Culture

Our culture at Amazon is driven by Leadership Principles. They are the DNA of the company. We live and breathe these 14 Leadership Principles. And this is what really drove me to the role at AWS, these Leadership Principles. I’d already been living them. They are what allowed me to fail spectacularly and still be successful in my previous work.

The Amazon Leadership Principles aren’t just inspirational posters hanging on the wall in the lunch room. They are guiding our every interaction with customers, when we discuss new ideas, make decisions, and when hiring.

When I first started, I was a little skeptical that all 14 of these would be values that we all live and breathe. 14 is a lot. I’m used to seeing 5 or 6 on a poster on a wall in a break room. Or on an About page on a company website. But we’re a peculiar bunch. And I have confirmed that it’s possible to work all 14 of these leadership principles into one sentence. Just kidding! But they are used all the time. And they apply to everyone, from the CEO to the intern and everyone in between.

These Leadership Principles work both with each other and against each other. There’s intentionally supposed to be some tension between them.

I want to touch on a few that really work together when it comes to failure and success, and innovation.

Customer Obsession

Leaders start with the customer and work backwards. They work vigorously to earn and keep customer trust. Although leaders pay attention to competitors, they obsess over customers.

In his 2016 letter to shareholders, Jeff Bezos wrote: “Customers are always beautifully, wonderfully dissatisfied, even when they report being happy and business is great. Even when they don’t yet know it, customers want something better, and your desire to delight customers will drive you to invent on their behalf.”

90% of what we build at Amazon is what our customers have asked for. The other 10% is us “looking around corners” to figure out what they need but don’t know they need. So, this is more than “the customer is always right” and customer satisfaction. It’s about doing what is right for the customer and then working backward from that. Because if you’re building the wrong thing for your customers, it’s going to be difficult to innovate on their behalf.

Invent and Simplify

Leaders expect and require innovation and invention from their teams and always find ways to simplify. They are externally aware, look for new ideas from everywhere, and are not limited by “not invented here.” As we do new things, we accept that we may be misunderstood for long periods of time.

Remember that intense fear I felt leading up to our first Hack the Gap hackathon? It was so uncomfortable. Not everyone understood what we were doing, but we did it anyway and it paid off.

Learn and Be Curious

Leaders are never done learning and always seek to improve themselves. They are curious about new possibilities and act to explore them.

This feels like a common sense value because if we’re in tech, we’re constantly curious and constantly learning. We have to be. Because tech is constantly changing. But this isn’t just learning about the next javascript framework; it’s also about learning what’s working and not working in your current tech, for your customers, in your team, and in your career. And continuing to experiment with it and learn from it. Without learning, innovation won’t occur, so it’s important to build learning into the system from the start.

Have Backbone; Disagree and Commit

Leaders are obligated to respectfully challenge decisions when they disagree, even when doing so is uncomfortable or exhausting. Leaders have conviction and are tenacious. They do not compromise for the sake of social cohesion. Once a decision is determined, they commit wholly.

This is probably my favorite Leadership Principle. I think we all can fall into the trap of just going with the status quo and succumbing to social pressures of wanting to fit in or even just wanting to get through that Zoom meeting so you can go back to homeschooling your 5 and 7-year-old kids. But when we don’t challenge the ideas and decisions around us, we don’t move forward. You were hired into this position for a reason. We expect you to stand up for your ideas. Because they are good ideas. This Leadership Principle means that everyone’s ideas are heard AND a decision is made.

The last part here, means that when a decision is made, you will commit to it whether it was yours or not. Because you still need to move forward.

Bias for Action

Speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk taking.

Remember my last story about leaving my business behind and joining AWS? That decision I had to make was reversible. I calculated the risks, made the decision, and moved on, knowing I could change my mind later.

At Amazon, we look at these decisions as 1-way vs 2-way doors. A 1-way door decision is one that is not reversible or very difficult to reverse and consideration should be taken to mitigate the risks. A 2-way door decision is reversible. If it doesn’t work out, you can go back to the original state. Because 2-way doors decisions are reversible, employees are encouraged to take them.

This is the culture. As I said, these are all very interrelated and they have some tension between them. For instance, thinking big isn’t always the most frugal choice. Even a bias for action needs to be balanced with diving deep.

You definitely don’t need to have these leadership principles or even these exact values. You probably already have some, whether they are documented somewhere or not. I’d encourage you to talk about them as a team, figure out which ones are most important for your team and maybe even what’s missing or what you’d change.

Psychological Safety

The other thing I’ve had in all of my failures has been psychological safety.

Imagine being in a large team meeting, where the director (a few levels above you) is discussing a problem with one of the new widgets. You have no idea what they are talking about. You could go on, nodding your head as if you understand, and hopefully, no one will ask you about it or ask you to take action on it later. Or you could speak up, and ask for clarification. And Lisa and Mark sitting next to you, nod along because they needed the clarification too. Are you comfortable speaking up like that at your company? On your team? In big groups?

How about if a customer found a hairy bug in production and as you’re debugging through it, you find out it’s caused by your code? Code you spent a lot of time on last week. You even created a couple of tests, but you were under a deadline and missed part of a conditional statement. You know that the git commit history is there for everyone to see, so they’ll know it’s your code. Are you comfortable speaking up and telling your team it was your code? Can you ask for their help in fixing it and getting it reviewed without feeling like crap? Will they be willing to help you figure out how it slipped through and improve the processes for next time? What will you tell the customer?

Psychological safety is when a team feels safe to engage in learning behaviors like asking for help, admitting errors, disagreeing, and trying something new without fear of negative consequences like embarrassment or punishment. You are given permission to challenge the status quo, to not know something. To fail. Psychologically safe teams are free to come as their full selves, contributing their creativity and talents in a way that enhances the entire team. In a way that allows success and innovation to happen.

Celebrating Failure

Back in 2016, Ryn Daniels accidentally upgraded Apache on every single server at Etsy. Apache for some reason didn’t start up properly and left and their other sites in a bad state. It only lasted for 20-30 minutes, but it earned them Etsy’s Three-Armed Sweater award.

This award is given to the engineer who inadvertently causes the most interesting or most learning-filled incident. Ryn was rewarded publicly for failing and for learning from it.

And if you’re wondering about an organization that doesn’t have a lot of room for error, NASA has the Lean Forward; Fail Smart Award.

This award encourages, recognizes, and celebrates the spirit that propels individuals to take the risk to innovate, unfortunately failing to reach the desired outcome; but learning from the attempt.

Psychological safety impacts your culture. And your values should support it. It’s something you work on together to define what safe means to each of you because it could look different for different teams, different people.

Looking to build psychological safety in your virtual team? Here is some info on doing that.

What’s Next

We’ve looked at what some epic failures can look like, what we need to feel ok about failing spectacularly, but how do we fail better? We’ll take a look at three ways we learn from failure and some ideas you can implement in part 3.