Mistakes I Have Made
No Mud, No Lotus
Hiring several dozen people in five years at Volpe was exhilarating. Building my own team and getting the right people on the bus, as Jim Collins puts it, was deeply fulfilling. Few things validate your career choices like hundreds of smart applicants vying for a spot on your team. When hiring, I trusted my gut, prized unconventional résumés, and prided myself on my eye for intangibles.
Now the boot is on the other foot. I’m a candidate again, trying to make my intangibles tangible and re-living the flaws in the system I once ran. Long timelines. Canned questions. Minimal feedback. At times, we treated applicants like a sea turtle treats her eggs: deposited and left to fend for themselves in a Darwinian dash to the shoals.
What Mistakes Have You Made?
Whether by design or default, our interviews often included trap questions. Chief among them: “Tell us about a mistake you made and what you learned.” The actual mistake rarely mattered. We were screening for humility, reflection, and a growth mindset.
Now I’m thinking about how I might have answered that question, and this one sticks with me. The easiest errors to recall are the humiliating ones: labeling units in a graph axis as millions instead of billions, or arguing with a client in front of my boss. These mistakes are branded onto memory by embarrassment.
As I became a manager, the stakes rose and the feedback grew subtler. After a tough year, I gave two top performers tough love reviews on principle. Even star employees can have off years, I reasoned. They both quit within months. I still wonder if the message was worth the cost. I vowed to be more strategic in the future.
Shuhari
For me, being more strategic meant taking each case as it comes, not clinging to imagined rules or principles. I learned to weigh benefits, risks, and costs, and to examine my own motivations before acting. Aikido offers a useful model for this evolution: Shu-Ha-Ri.
Shu: Follow the teaching of the master precisely.
Ha: Break from tradition, experiment, question, and explore.
Ri: Transcend the forms and move intuitively, no longer constrained by technique.
Even as I learned from my mistakes and gained confidence in my intuition, I remained wary of the mistakes I wasn’t seeing. In martial arts, when you make a mistake, you might get thrown to the mat or hit in the face. But it depends on the quality of your opponent. In organizations, as your power rises, feedback narrows. People start telling you what they think you want to hear. Like driving a big truck, your blind spots grow. And the bigger your blind spots, the harder it becomes to learn.
Success breeds confidence, and confidence is what allows us to transcend. Yet successful leaders must always walk in fear of the gods, as the Greeks might say. Often, when leaders make strategic errors, it’s because the strategies that once made them successful no longer fit the situation. Strategy, as Mintzberg reminds us, is “a pattern in a stream of decisions.” If the pattern shifts and we fail to see it, our strength becomes our downfall.
The Zen monk Thích Nhất Hạnh taught, “No mud, no lotus.” As leaders, we need to understand our mistakes as the mud from which learning grows. Even when the water clears, there is always mud. Learning to discern it requires cultivating greater sensitivity.
Elite athletes do this. They play at what sports psychologists call Next-Play Speed. They may miss more shots than they make, but they are trained to register the miss, reset, and move on. They can study the film later.
Feedback by Any Means: From Surveys to Gossip
Managers rarely get film. That’s why feedback and self-reflection are essential.
It begins with simply asking. Ask clients. Ask staff. They might be too polite or deferential to be completely honest, but ask anyway. Anonymous pulse surveys help too. Survey your team every six months: How are we doing? What should we change? What can I do better? The act of inviting feedback sends a signal—you are listening, you are learning, and their voices matter.
Still, I found formal feedback incomplete. Informal, indirect feedback was often more honest. The best source of indirect feedback? Gossip.
Gossip isn’t necessarily malicious. Even healthy organizational cultures have their share, and I think it’s an essential form of cultural sensing. Gossip catches patterns of behavior and enforces norms. As a leader, I found it a valuable early warning system. I’d hear things about behaviors, reputations, and social dynamics that formal feedback channels never surfaced.
When you’re building a high-trust team, gossip can function as adaptive intelligence. It helps identify unspoken concerns and steer around dysfunction. Of course, you can’t believe everything you hear. It’s important to triangulate indirect feedback with more observable evidence.
All of this comes back to understanding the context in which you’re operating, discerning the changing patterns, so you can learn and adapt your strategy. It doesn’t matter how much feedback you collect if you don’t use it.
Sensitivity vs. Connectivity
In How to Do Nothing, Jenny Odell contrasts connectivity with sensitivity. Connectivity is about volume and visibility: conference chatter, hot takes, secondhand insights. Sensitivity, by contrast, is slow, attentive, and quiet. It’s not just listening. It’s attunement.
Too often I watched program managers return from conferences and pivot their programs based on a few hallway conversations. This is flimsy decision-making at best, based on a form of untriangulated gossip, and it often leads to groupthink. Many managers think their job is to figure out where the crowd is going and follow – the opposite of leading.
The best leaders do something else. They are sensitive. They listen for what isn’t being said. They create time and space to hear themselves think. They learn to detect subtle signals in the noise and translate them into insight.
Sensitivity corresponds to what the Buddhist tradition calls spaciousness. By cultivating awareness and resisting urgency, aversion, and attachment, we create space between stimulus and response. That space allows room for the unknown, for becoming.
Sensitivity helps us notice what we didn’t know to look for. It reveals cultural drift, employee dissatisfaction, early risk indicators, or hidden talent before it shows up in lagging indicators. It helps us see substance beneath performance, allowing quieter wisdom to surface. Most importantly, sensitivity helps us see potential. What might this person or this idea become?
The most amazing thing is this. The more you tune into subtle signals, the more the noise around you settles. As your team sees that you value substance over flash, they adjust. As you model calm and patience, honesty grows. You become the eye of the storm: a center of clarity where inclusion, insight, and innovation emerges.
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