Failure has been written about, talked about, and reframed a thousand times. “Fail fast.” “Embrace failure.” “There’s no innovation without risk.” We’ve heard the slogans. And many leaders I work with would nod along—intellectually, they understand that failure is part of the process. Necessary, even.
But in practice? It still carries weight.
In company after company, I see how failure—even small, recoverable failure—still comes with shame, hesitation, and a tendency to minimize. Teams try to solve problems quietly, before anyone notices. Leaders soften the language to avoid sounding alarmist. People delay raising concerns until the issue is big enough to require attention. And all of this happens not because people are careless or manipulative—but because they care deeply, and they know that failure, despite all the talk, still feels like something to avoid.
That’s the paradox. We say failure is acceptable, but culturally we’re still wired to fear it. And that fear makes us hide it, delay it, or dress it up. I’ve seen this pattern everywhere—from early-stage founders to mature executive teams. The reflex is the same: protect others, protect ourselves, avoid judgment.
But the result is lost time, missed learning, and worse—issues that compound and become part of how things are done.
Failure Is Not a Red Light
So I’m not going to argue that failure is good. I’m not going to pretend this is new thinking. What I will say, from experience, is this: the real danger isn’t failure—it’s invisibility.
Failure is not a red light. It’s a green one.
It tells us where to look. What to learn. Where to grow. It shows us that we are paying attention and that we care. But only if we see it—and only if we allow others to speak about it without fear.
In companies that grow well, I’ve noticed a different relationship to failure. People speak up sooner. Not dramatically, not self-righteously—but early. “Something feels off.” “This isn’t behaving the way we expected.” “We’ve tried to patch it, but the root issue keeps showing up.”
These are not admissions of guilt. They are acts of leadership.
And they’re only possible when the organization is intentionally designed to absorb them—not reactively, but purposefully.
That’s the shift we need: from tolerating failure to embracing it as part of the learning infrastructure. Not romanticizing it, not putting it on T-shirts—but building systems that actually allow it to serve us.
How to Build a System That Can Handle Failure
We don’t need more slogans. We need more intentional design. And from what I’ve seen, there are four areas where organizations can do much more to create the conditions for failure to be surfaced, shared, and used.
- Mindset: Redefining What It Means to Raise a Flag
This begins with a subtle but powerful shift: seeing the person who raises an issue not as the source of the problem, but as someone protecting the integrity of the system. That means rewriting the mental model. A red flag is not a disruption—it’s a contribution. Surfacing failure is not disloyal—it’s how we move forward.
And to get there, we have to examine the language we’ve normalized in business. Phrases like “Don’t bring me problems, bring me solutions” may sound efficient, but they shut down early detection. They teach people that they must figure everything out alone before they’re allowed to speak. That sharing a concern without a fix is a burden. But it’s not. Sharing the thinking—sharing the weight of the problem—is how we learn.
Mindset has to be communicated, modeled, and reinforced constantly. If your teams believe that naming failure is risky, no mechanism will save you.
- Mechanisms: Create Safe, Visible Spaces to Talk About What’s Not Working
But mindset alone is not enough. We need mechanisms—concrete, repeatable forums where failure is expected, invited, and unpacked. That might look like regular post-mortems after projects, where the focus is not just on what succeeded but on what surprised us, what didn’t go as planned, and what we’d do differently next time. It might look like Red Flag rituals in leadership meetings, where anyone can bring up a concern before it snowballs. It might mean creating internal “failure libraries”—documented case studies where teams share what went wrong and what was learned.
These mechanisms work best when they are not just tolerated but built into the rhythm of the organization. Because in many teams, there’s still an unspoken belief that “no news is good news.” That mindset allows slow-building issues to hide in plain sight. A healthy system shouldn’t rely on silence as a proxy for progress—it should actively seek out early signals and have built-in pathways for people to say, “something feels off.”
When failure has a place in the structure, it becomes less threatening—and more useful.
- Capability: Teach People How to Detect and Investigate
It also requires capability. Many people don’t speak up simply because they haven’t been taught how to spot the early signals of a problem, much less how to articulate them clearly. Others hesitate because they worry they’ll sound vague, overly critical, or alarmist. That’s where training becomes essential—not just training in communication, but in structured observation and analysis.
Teams need to develop the ability to detect subtle anomalies, inconsistencies, or signs of friction in how things work. They need frameworks that help them examine what’s not working without turning every issue into a blame game. And just as importantly, they need the confidence to name what feels off—even if they can’t yet explain it fully, even if the failure hasn’t yet “broken” anything.
Because too often, we default to the saying, “If it ain’t broke, don’t fix it.” But in high-complexity, high-velocity environments, that mentality is risky. The goal is not to wait for collapse—it’s to build the muscle that sees what’s starting to crack, so we can intervene early. When people know how to spot problems, name them, and explore them without fear, failure stops being a threat—and becomes a source of progress.
- Leadership: Model It. Visibly. Repeatedly.
Of all the factors that influence how failure is treated inside a company, none is more powerful than leadership behavior. Because nothing sends a clearer message than watching someone at the top speak openly about what didn’t work. The most impactful leaders I’ve worked with don’t just allow failure—they model their own. Not performatively, and not with forced vulnerability, but with honesty, clarity, and perspective. They create a culture where failure doesn’t need to be dressed up. Where it’s not the quiet shame behind closed doors, but a living part of how the organization gets better.
I’ve seen leaders begin a strategy session by naming a decision they would take differently today. I’ve heard executives walk into a boardroom and say, “We missed the mark here, and we need to understand why.” I’ve watched founders stand in front of their teams and acknowledge what they didn’t see coming—and what they learned from it. These moments don’t weaken trust. They build it. They invite others to participate in the work of learning, not just the celebration of success.
This is what sets the tone. Not slogans or values painted on the wall—but real moments where people in power say, “We don’t hide what went wrong—we use it to get stronger.”
Because if failure is going to speak, someone has to go first.
No company can design failure out of its story.
But every company can choose what to do with it once it arrives.
And if we make that choice deliberately—through mindset, mechanisms, skill-building, and leadership—we don’t just get better at handling failure.
We get better at growing.
