More Lessons Learned from Failure

My recent post, How I Failed, drew a huge amount of reader interest, and I wasn’t surprised. In fact, as we’ve been organizing the first Cultivate event—our new conference on how to build and sustain great companies by building a great culture—we’ve realized that people can learn more from  what leaders have done wrong, and learned from, than from their successes. (In fact, what inspired me to frame my talk around failure was the series of successful sessions on that subject that Joshua Schachter has led at Foo Camp over the past few years. They are always a great hit.)

We asked some of Cultivate’s speakers if they had their own failure stories they’d be willing to share. Not surprisingly, their answers were widely varied. It’s clear that even the people we see as most successful have lessons to learn. And these stories show that wisdom often comes from mistakes, not necessarily the vision that sets you on fire or the goals you’re aiming for.

Here are a few of their stories.

Yeah, I Had a Lot to Learn
Elaine Wherry, Meebo

At 24, I assumed I would be a good manager. I was smart, hard-working, creative, and had lots of leadership bullet points on my high school and college resume. But I quickly discovered that I had a ton to learn.

I had one direct report on my team. We’d worked together for a few weeks but because it was just the two of us, it was a little awkward. I felt like I was either too hands-on or too hands-off. I wanted to be her buddy but because I was her manager, there was a necessary professional distance. We hadn’t found a rhythm yet. My rude awakening came when she led a group meeting for the first time and I sat in as an observer. Afterwards, she asked me how it went and I said, “Oh, on a scale of 1-10, probably a 7.”

In my head, a 7 wasn’t bad. A 7 for your first attempt was pretty good. I thought I was being honest and supportive. But looking back, it was obviously the wrong thing to say.The tears welled immediately. I didn’t even have a chance to back pedal. She fled and locked herself in another conference room. I tried to awkwardly talk through the door a few times, hoping no one else picked up on the unfolding crisis, but I didn’t see her until the next day when we both pretended nothing happened. Obviously the group meeting and my analysis meant more to her than I’d realized. And in that context, I can’t imagine a more insensitive word of encouragement than “7.”

People Are an Important Part of the Equation
Hiten Shah, CrazyEgg / KISSmetrics

My co-founder and I spent two years and over $1,000,000 trying to start a web hosting company that never ended up launching. We communicated with our team poorly, managed our money irresponsibly and aimed for perfection before we were willing to release something to customers. Our partners were also not aligned with the values that we had both personally and professionally.

In the end, we learned that the people whom you partner with when starting a business is one of the critical factors to its success.

The “Win” That Was a Failure
Patty McCord, Patty McCord Consulting

Over the years, I’ve developed a fairly accurate intuition for reading people and situations. It’s not magic really, it’s a kind of pattern recognition that comes from closely observing people, teams, and situations. Much like the how the engineer or mathematician can see trends in data, I can often spot people issues in the making.

But, my skill isn’t obvious and it isn’t always measurable so with every leader I work with I must build credibility over time. I must be able to directly correlate what I see with what matters to the business or the team and be able to suggest improvements or solutions or alternatives.

When I first began to realize that it mattered that I thought the new VP was going to fail or that morale in a particular team was waning, I boldly (and often bravely) said so. Very often I was dismissed or ignored. Without concrete data, it was perceived to be only my opinion.

That is, until I was right. Oh, the joy and satisfaction getting that late night email that read, “I was wrong and you were right.” How I savored the thought that I had bested some of the smartest people I know!

Then, one day I got one of those messages and instead of making me feel smug and superior, I simply felt bad. Why hadn’t I been able to more effectively influence this person in the first place? How could I learn to articulate what I saw into consequences to the business or to the team in a way that made logical sense? How could I learn to teach this clueless person how to learn to read the behavioral clues in front of them?

I learned that “I told you so” isn’t nearly as satisfying as “let me tell you.”

To Criticize, and Criticize Well
Kate Matsudaira, popforms

My experience as a manager has changed my approach to feedback several times over the last few years. When I first became a manager, I was overseeing the work of my peers, so when I wanted something done differently (or more likely my manager wanted something done differently) I would hint at a change. Suggestions often formed statements like “Have you thought about trying it this way instead?” or “Maybe we could change the format so that section is at the top.” Sometimes they worked, and other times they had no effect. I was struggling at making change.

So after quite a while of “hinting” without success I moved into a more direct approach: “Please change the format to have a summary at the top.” You could not mistake what I was asking, and all of sudden changes started happening. People were listening and I was getting results. However, I was also coming off bossy, and well, who would want to receive feedback like that? I know I wouldn’t.

Therefore it was time to make a change again. Learning to give better feedback in a way that was helpful and direct, but also kind and thoughtful.

Here are some of the tips that helped me get there:
• Ask first. Before giving someone feedback on something they need to change ask them if they are open to feedback.
• Be timely. Feedback is most effective when it is delivered at the time of the event.
• Make it about the task, not the person.
• Give suggestions on how to improve.
• Provide a personal example.
• Identify the motive or reason for the changes.
• Allow the person to defend/vent/explain.
Of course critical feedback is still something I struggle with (and make mistakes in my delivery) but I honestly believe my quest to be better at it has made me a much stronger teammate and leader.

For more on the lessons of leadership, join us at Cultivate next Monday in New York City. We think that you’ll come away inspired to build companies that make a difference, and you’ll have the knowledge to make it happen.