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Leading while human: A seven-part approach to failing forward

Updated: Mar 19, 2021

There’s a lot of hype about failing fast and how companies and people who do are inevitably better at innovation. I’d like to offer another way to fail: forward. Which, I’m sorry to have to tell you, cannot happen unless you also fail deeply.

I recently failed in front of my team where I work. I had co-led them through a virtual meeting experience and the outcome was not at all what I had planned for, hoped for, or predicted. It fell flat, and I lost their engagement around a topic of incredible strategic importance. It happened on a Friday and for the rest of the day my gut, heart, and head were all talking to me: That wasn’t quite right, Amanda. I felt like I had let my team down, but I couldn’t put my finger on it. Even though no one was hurt and likely most of the participants wouldn’t describe it as a failure at all, I was disappointed in myself and eager to sort through what to me was a series of missteps, even if I couldn’t nail down exactly where I or others had missed the mark.

One of my favorite poems is by ee cummings: “since feeling is first…” I say to him, YES. My feelings came first as soon as I clicked the red button to end the meeting: Disappointment, confusion, shame, regret. I called a friend that afternoon and we talked through it. I grossly overexaggerated every single part of it. She was there for all of it, believing the hype, believing me, and at times ranting right along with me. She met me squarely in the mess of my feelings, which worked wonders at neutralizing them so that I could move on. I ate pasta for dinner, carb-loading for the next day when I would do the bulk of my thinking and writing, putting myself in rational space.

Monday, I called my coach to talk through the facts of it. That was when I came to see the lessons. The AHA moments began piling up around me as insights got clearer. By the time we were done with our 90-minute session, I had developed two new ‘rules’ to use when working with a team around big, ambiguous, strategic material. One relates to ensuring the agenda serves the people and not the other way around and the other relates to a filter I can use on the content I provide to ensure dignity and respect to those receiving it.

These are important lessons that I would have missed if I had a.) ignored the feelings that told me I had screwed up or b.) stayed in my feelings and drowned in a sea of regret without processing.

Throughout this process, I circled back to one team member in particular, one who had reached out to say the experience was difficult for them, who had disengaged because of it. I was grateful they trusted me with their truth which wasn’t a five-star rating, and grateful they received my apology, my summary of learning, and my commitment to do better. In these exchanges, we were able to repair the tiny snag of damage that had been done because my apology wasn't empty baggage, or a race to 'move past it', or a request for absolution. And: I was able to share my learning with them, which means the lessons will integrate more deeply into our team and organization.

The good news is that every time the sun comes up we have a new chance to integrate our learning, and I was glad for another team meeting just a few days later. I built the agenda differently, even cutting an item so that we’d have plenty of time for another, more critical one. I paid attention differently during the time, and I was careful with the content I shared, remembering to use the filters I had developed from the retreat mess-up. It went well. For them and for me. First we know better, then we do better.

Based on my experiences and those of people in my world who have leaned on me as coach or boss or friend to process their own mess-ups, I’ve developed a seven-part process for failing forward. It begins and ends and is held by freedom. There’s a really inconvenient element to failure, one that my coach told me as we were processing: The only way to never misstep is to never step - and that means we go nowhere. This isn't an option for anyone who dreams of a better tomorrow.



FREEDOM: Stepping means risking a misstep.

FAILURE: The outcome did not match the intention. You knew better but didn’t do better. Or, you just didn’t know. You failed to prepare or you failed to execute or you failed to connect. There are a thousand million ways to fail. It will happen.

FEELING: The emotions come quickly: shame, frustration, disappointment, anger, fear. Mostly they are not pleasant emotions. They will not kill you. It's OK to feel them.

FOCUS: Zoom in on the experience. What happened? Move the lens around. Who else owns a piece of the mess? (Reminder: it isn’t always all about you.) Where do you see opportunity for taking a different path? Where was what you did out of integrity with a value you hold? This is where you get rational and clear and thoughtful like a detective. Your job here is to learn without the interference of your precious and fragile ego.

'FESSING UP: If you have apologies to make, do it now, after you’ve moved beyond all the feelings that can cause you to do additional damage, and after you’ve learned some lessons. As my mother taught me: Don’t say you’re sorry until you can also say how you will not do that thing again. Otherwise, our apologies become emotional baggage for another person to carry around, an unfair request to a person we’ve already potentially harmed.

FORGIVENESS: I know. It's a strange word to throw into workplace relations. But it is a necessary part of the work of failing. Forgive yourself for not knowing better, not doing better, being human. And allow others to forgive you. This means that you officially quit allowing the shame of the failure dictate your path forward.

FORWARD: Take your learning and your redeemed relationship forward and put their power to use in your next try. As Maggie Smith says, “keep moving.”

For a free printable resource outlining the seven parts of failing forward, subscribe to my mailing list.


The beauty of this approach (other than the fact that it uses alliteration, one of my most favorite tools of language) is that it integrates the emotional, rational, relational, and cultural elements of failing. It's human and complex, like us. Failing in front of people, showing your very work-in-progress self, or as the saying goes, those awkward moments between birth and death: this is not my favorite thing. I do not know a person for whom this is fun. If it were a deal-breaker for leaders to be free from error, to be inhumanly perfect, then we would not have WD-40 or pacemakers, or many of my favorite go-to recipes. And I don't want to live in a world without those.

Here's to slower, deeper failing - failing that moves us forward. And here's to you, leader, in all your humanity. Keep up the good work.

Photo credit: the blowup on Unsplash

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