The Gentle Failure
Early in my career I discovered something that felt radical at the time: saying “I don’t know” out loud to a client. It didn’t get me fired, and it didn’t even end the conversation. What it did was buy me something more valuable than a quick answer I wasn’t sure about. It bought me trust.
Genuine transparency was the foundation. What I’ve built on top of it over thirty years is something a little different.
Here’s the scenario. A faculty member contacts me with a Canvas issue. I prepare ahead of time, think through the likely cause, queue up the solution, and schedule a live consult. I’m ready. They arrive into the Zoom meeting, I have already shared my browser window while masquerading as their account, I navigate to the problem area in their course, and execute the fix I’ve been carrying in my head since I read their email.
It doesn’t work.
What I’ve overlooked, not for the first time and probably not for the last, is that I’m navigating around their course with their teacher-level rights, but I’m still carrying administrator-level permissions they don’t have. The fix works for me. It won’t work for them. The demo has failed in the specific way that only becomes obvious when you’re already in the middle of it with someone watching.
The easier response in that moment is deflection. Blame the web browser. Blame the client’s network. Blame a recent system update nobody asked for. Blame it on the rain, anything but pointing the blame on themself. Most clients won’t push back, and the tech walks away with their composure and dignity intact while the client remains confused about what actually went wrong. I understand that choice of response. The profession produces it. But deflection is a slow leak in the trust balloon that takes years to fill, and I’ve spent thirty years breathing into mine carefully without getting light-headed.
In that moment when I see things aren’t working, something happens in my head that most clients would never fully understand. I flash to a memory of Bill Gates introducing Windows 98 at COMDEX, standing in front of a massive audience, and watching his demo machine produce a Blue Screen of Death on a projection screen visible to everyone in the room. The CEO of Microsoft. Global stage. Complete system failure. His response was a slight smile and a dry acknowledgment that this was why they hadn’t shipped the product yet.
Most of my clients aren’t familiar with that reference. But I am.
So instead of the internal spiral, I look up from the screen, and I say: “Well. That was a C-minus for a demo.”
They chuckle. Most of them have genuine grace for me in that moment. And here’s why: they’ve stood at the front of a lecture hall with a hundred students watching and felt technology fail underneath them in real time, with nowhere to go and no way to pretend it isn’t happening. They know exactly what this feels like. When I acknowledge the demo failure with a teacher’s grading scale, I’m not just defusing the moment with humor. I’m speaking their language. I’m meeting them where they live.
As I am recalibrating my path toward issue resolution using their teacher rights I will say to them as I’m clicking around the screen at 80 mph, “I appreciate your patience while I do all these nerdy things to get to the solution. Once I get to where we need to be, I’ll walk through the steps again in a more deliberate way so you aren’t getting dizzy from the quick scrolling and all the clicky-clicky I’m doing now.” That’s the other phrase that comes out in those moments. It’s an invitation rather than an apology. Come with me while I figure this out. You’re not waiting for me to perform competence. You’re watching competence actually work, which sometimes includes hitting a wall and finding a way around it.
The best baseball players don’t get to first base six out of ten times. A .400 batting average is one of the rarest achievements in the history of the sport. Michael Jordan missed game-winning shots. He talked about it openly, not as confession but as context. The misses were part of the methodology. You can’t take the shots that matter without accepting that some of them won’t go in.
I think about that when the demo doesn’t work. Not as consolation, but as permission given to myself to mess up.
What’s changed over thirty years is the internal experience of the moment. There was a version of me, younger and less certain, who would smile at the client and say something graceful and laugh nervously while running a Chris Farley internal monologue disparaging himself in a Saturday Night Live skit from the ‘90s where he asked lame interview questions. Stupid. Stupid. Stupid. Admonishing myself in real time for the error while projecting something that looked like professional composure. The gap between the external grace and the internal spiral was exhausting to maintain.
That gap has closed. Not because I’ve stopped caring about doing good work, but because I’ve done enough good work to trust the aggregate. The C-minus demo is one data point. The career is the dataset. I know what the dataset shows.
The “darn it” feeling that arrives now when the demo goes sideways isn’t indifference. It’s proportion. Something didn’t work. I’ll find what did. I know what I am capable of. My client is still in the video meeting, still patient, still rooting for the solution to arrive. Rarely will any of them kick me when I’m down for acknowledging an error. They’re too busy recognizing something they’ve felt themselves.
The gentle failure isn’t a lesser version of competence. It’s what competence actually looks like when it’s honest about being human.
More later...