On Actually Embracing Actual Failure

Do not attempt to tackle complex, wicked problems without amply anticipating and preparing for the very real possibility of failure: On every attempt and at every stage. I’m talking about actual failure- not fun, exciting failure or even safe failure, because it might not ever be emotionally 100% safe. I’m talking about the real stuff. The painful, uncomfortable, embarrassing type of failure. The kind you look in the eye and learn from… that looks back and tells you things you didn’t know or care to admit.

It is only possible to anticipate all likely outcomes in a predictable system, and if the effects you are creating are predictable, you’re either inside an ordered system (which means you’re not facing a truly wicked problem and what you might actually need are simply the right experts) or you’re using the wrong tools for the task at hand. The right tools create effects that cannot be predicted. If you’re excessively protecting your efforts from failure, you might be preventing those efforts from having the characteristics they need to be effective. One of those characteristics is unpredictability. Unpredictability means we are opening ourselves up to failure; and we have to be prepared to greet and embrace it when it arrives.

Again, I go back to things I’ve learned from Cynefin:

Identifying the evolutionary potential of the present requires that you probe the system first to determine its current conditions and configurations. It is action that will give you the most decidable, orientating observations about the present context (AOOD loop, lol). Planning that action is important, to make sure it produces the right kind and quantity of information, but more important is what you do with the unpredictable outputs of that action.

Those outputs can come from both successful actions and from failures, and you better be prepared for both.

This week I ran a workshop attempting to tackle some very complex issues. One part of the plan failed. I felt a very strong urge to try and pretend it hadn’t — to lie to myself and those I was working for and say that we had achieved the desired outcomes. I’m serious. I almost did it, because I was confused and stressed and it was a lot to process. Instead, I saw the failure. I poked and prodded it for a few minutes to make sure it was failure… very uncomfortably… with a room full of people who were waiting for me to tell them what happens next… I decided it was definitely a failure, and then I stepped into it and looked around. I’m still in it, and it’s still telling me new things.

You might have seen my post Thursday night as I was processing that failure the night before the last day of our workshop. It was very stressful and I am extremely glad it happened, because, in my opinion, that failure actually told us a great deal more about the problem we were tackling than if everything had gone according to plan. I have already written a short novel about the possible implications of that failure.

The second part of this little rant about failure goes like this:

Call failure what it is. Please, I implore you, do not call it success. Is your innovation cell failing? Say it. Is your workshop failing? Say it. Did an exercise or activity fail? Say it out loud and celebrate it for what it is: It is new information that you need for the next go. If you refuse to see and say that information, to say “We failed. Here’s what that means. Therefore, here’s what’s next,” what you are doing is refusing to adapt. Your effort is a soon-to-be extinct species because you are blocking what ought to be a feedback loop connecting environmental interaction to genetic adaptation. You probed. Now sense. Then respond.

But there’s this other thing that’s gonna make all of this really difficult. Seeing failure is hard, because we are primed, programmed, and pressured to push through it and call it success. It can also be hard to see, which is one reason anticipating and preparing for it is so important. If we had pressed in that exercise that failed, which part of me really wanted to do because I didn’t realize it at first, we might have even been able to convince ourselves that the outputs were meaningful and thus we had succeeded. We might have been able to effectively shield ourselves from new and necessary information on behalf of our feelings. In the context of this workshop, I was able to recognize failure because I had thought through what the outputs of the action were supposed to look and feel like, and that enabled me to test them against my criteria. On the spot, I thought of a few additional tests to try and salvage the sequence and we simply didn’t have time.

For the record, in the end, our workshop this week was a fantastic success. There was some failure involved, and we managed to face it, name it, process it, and move to the next task, which didn’t fail (phew). For my own mental health, I am so very glad we ended with a mix of success and failure, because failure is difficult. Probably good to throw some easy tasks in there to make sure you’re diversifying your portfolio of failures and successes. Failure is stressful, and you can’t expect people to stick around if they’re not getting enough time above water.

I don’t see enough stories of failure in innovation in the Air Force, DoD, or government, and I think I know why. Part of it is that we fear the shame that comes from failure, because we automatically attribute it to not being or doing enough, which as I stated in my post on Thursday is a bunch of misleading and demotivating bullshit and not helpful.

Part of it is also that our organizations still punish failure, at basically every level. If you want your innovation cell to survive and keep getting more chances to try again, you might actually feel the legitimate need to hide failure, or to pretend that it is success. I don’t think I can or even should try and convince organizations whose survival is on the line to become as capable of failure as they need to be to take on the really wicked problems, because if all they can do is fix small problems while hiding their failures, that might be better than if they were to go away entirely. Telling stories of impact is important. You might even feel the need to contradict what I’m saying here, because you also see success in Air Force innovation and you don’t want the narrative of failure to suppress what you think should be a celebration. In a system as large and complex as this, we often fail and succeed all at once.

There’s a tension there that I recognize. We should face that and figure out how to navigate it.

The shame that we collectively feel when confronted with our failures is one of the most innovation-inspiring things I can think of. Think of the incredible transformations we accomplish in the wake of great disasters, in which we feel ashamed as a country or community, that we allowed something to happen. If all we are telling are stories of success, what motivation is there to change then? If every experiment is deemed a success, what information is there to move forward with? If your innovation cell or effort is limping along, buoyed by good intentions and positive attitudes, your failure to call its failing aspects out might be the greatest barrier to achieving your true potential.

So in the recognition and processing of failure, I see two things that are critical for the long-term success of our efforts:

  • The information about what failed, how it failed, and what that means about the evolutionary potential of the present
  • The impact that failure and stories of failure have on us emotionally, which can be an instrument for progress if properly employed

I don’t have a good answer for this problem of the need for more failure and more stories of failure in the face of a culture that still selects for (perceived) success alone, in which past success is deemed a predictor of future success, when it might actually just be a predictor of sticking to non-wicked problems or lying to ourselves to maintain a brand and reputation that is keeping us well-funded and in the good graces of our leadership.

I just think we should fail more, and talk more about actual failure. Not theoretical failure, which we do like to bring up a lot. Let’s talk about what actually happened, and what we can all learn from it. At the end of this week’s workshop, as is my standard practice, I included a retrospective exercise to give space to all the participants to share their thoughts about what happened. In every retrospective, we make room specifically for people to say what failed. I genuinely believe that retrospective activities, if properly employed, might be the most impactful facilitated practice you can introduce to a team, organization, or culture. Make space, create safety, and normalize the uncomfortable experience of facing, naming, and stepping into your failures.

I’ve been talking about my workshop failure in the Agitare community. There’s more insight in there than I’ve had time to process still.

I’d be interested to hear your experiences and thoughts.

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