What if hell is your organization?

"Midway through life, I found myself in a dark forest."
Dante Alighieri - The Divine Comedy

Dante Alighieri is not describing the wanderings of a lonely man. He is describing an experience we can all identify with. The moment when the direction is no longer clear. What was once obvious becomes unclear. Where, despite one's experience and position, one finds that one does not quite know how to proceed.

Now we like to call it something other than a dark forest: uncertainty, pressure, lack of direction. But the experience is the same.

And perhaps the most important point is precisely this: we are not alone in this. We often need help to move forward. That is why Dante gets a guide: the Roman poet Virgil. They begin to walk. Down into hell.

Going through hell isn't exactly the metaphor we usually use when talking about leadership development. But maybe we should do it more often?

What if hell is your organization?
Not because there is anything wrong with people. But because something happens to us when it is not safe to say what we see. Amy Edmondson at Harvard Business School has spent much of her research career trying to understand something seemingly simple: why do some teams do so much better than others? The answer she found was not technology, not processes, and not smarter people. The answer was psychological safety; the collective experience that it is safe to take interpersonal risks. That you can say what you think, ask the stupid question, admit the mistake.

When it's not safe to say what we see.
Edmondson also found something that surprised many: those teams with the highest psychological safety reported more mistakes, not fewer. It's tempting to interpret that as a sign of poorer performance. There are mistakes. They saw the mistakes, they talked about them, and they learned from them. Mistakes became information. Information became development. The question is not whether mistakes are being made in your organization. The question is whether they are visible.
Psychological safety provides space to speak. It is necessary. But it is not enough. Saying something is one thing.
Because the real question is not whether people dare to say something in the meeting room. It's whether they dare to stand in what they don't fully understand themselves. Show the unfinished, what they don't understand yet.

It requires something else. It requires vulnerability trust.

Vulnerability trust is the willingness and courage to show uncertainty, mistakes, and one's own vulnerability in relationships with other people, even if it involves interpersonal risk.
It is built on a trust that the relationship is strong enough to carry it and turn it into learning.

Psychological safety makes it safe to say something. Vulnerability trust makes it possible to stay standing, even when you don't know the way forward. That's why Dante keeps walking.

Vulnerability trust
The first and perhaps most underrated point in Dante's journey is that he can't do it alone. He needs Virgil. He needs a guide who knows the darkness, who doesn't judge him for getting lost, and who is willing to walk beside him through the worst.

This is what vulnerability trust is.
To stay in what you don't understand yet, because the relationship can handle it.

In practice, this is what happens when an adept says to his mentor: I'm unsure if I'm the right person for this role. Or: I don't know how to handle this. It's about showing the other person your vulnerability. And trusting that it won't be used against you. But it's also something more than that.

The difference is important: Psychological safety allows you to dare to speak up in the meeting room. Vulnerability trust does not replace psychological safety. It elevates it. Where safety gives you room to speak, vulnerability trust gives you the courage to act.

Dante shows Vergil that he is afraid. More than once. Dante trembles. He faints. He cries. And Vergil never judges him. It is as if he is saying, “You are here to learn. Let us continue.”

It is guidance in its purest form.

In the Norwegian Armed Forces mentoring program, I encounter this at every single gathering. Colonels and lieutenant colonels – experienced, competent, selected leaders – who allow themselves to be vulnerable. They ask questions they wouldn't ask at work. They share doubts they wouldn't show in the department. That's not weakness. That's courage. And that's where learning begins.

What makes it possible? That we do not use what we hear to assess, rank or report. The relationship is protected. And in that protection, learning grows. This also happens in the conversation with the mentor.

In the program, we call this “the learning alliance.” That’s exactly what Dante and Virgil represent. Not a master teaching a student, but two who go into the darkness together, with different experiences and a shared will to understand.
Perhaps that is why Dante's journey is still relevant.
It's not just about hell. It's about what it takes to get through it.

The leader who never makes mistakes

In the third circle of hell, Dante meets the greedy. They lie on cold, dirty earth in a perpetual downpour. Their faces are pressed to the ground. They do not see each other. They do not speak to each other. Each is locked in his own pain, unable to receive or give anything.

It's a strong picture Dante paints. Not because the suffering is most dramatic, but because the isolation is so total. They learn nothing. They are frozen in what they have always been.

I think of leaders I've met who never allow themselves to be wrong. Who never ask for help. Behind the armor of competence and authority sits something that no longer teaches.

Shame is the currency of hell. It makes us mute.

And then the question is: As a leader, do you create a space where your closest employees dare to show you their vulnerability? Or have you, without thinking about it, built a climate where everyone presents the polished, the secure, the finished?

Psychological safety can reduce shame in a group. But it is the trust in vulnerability that gives the individual leader the courage to say: I don't know. I was wrong. Help me.

That's where the learning actually begins.

Where everything freezes
Dante's Hell is not arbitrarily structured. The deeper he and Virgil go, the more serious the sin, and the more isolated and hardened the sinners are. In the very deepest, ninth circle, he finds Lucifer.

Frozen to the waist in ice. Not even able to communicate. That's the picture of an organization where all trust has been broken. Where everyone is silent. Where no one learns from each other anymore.

But something important happens there. Dante and Vergil turn. They climb down along Lucifer's body and discover that down is actually up. They break through the Earth's core and begin their climb towards the light. They rise again and see the stars again.

The journey through the darkness was necessary. It was not a punishment. It was formation.

What does this mean for you as a leader?
Edmondson's findings point to something important: learning requires that it is safe to make mistakes. But safety is not created by structures alone. It is created by people. By leaders who lead the way and show that it is possible.

Vulnerability based trust is not something you introduce. It develops in the relationship between people. Because we dare to show something of ourselves.

In every conversation where someone dares to say "I don't know," and the other chooses to face it without using it against them.

It requires relationships where what is shown is met, and not used against anyone.

You don't have to have all the answers. But you must be willing to walk into the dark forest with those you lead. Not in front. Together.

Dante did not find the light despite going through hell.

He found it. Because he went through it.

And he had a guide who followed him all the way through the darkness. At the entrance to Paradiso, Virgil stops. Not because he fails. But because reason has its limits. He has followed Dante through hell and purgatory, through all the darkness that reason can navigate. But the last steps into the light it cannot take. There Beatrice (the love Dante never had) takes over and leads him on. To heaven.

That is perhaps the deepest insight from this poem: reason is necessary, but not sufficient. What ultimately lifts us up is something more. The willingness to care about the other. The willingness to take care of the other even in their vulnerability.

That's what you will be remembered for..

References

Dante Alighieri. (ca. 1308–1320). The Divine Comedy.

Amy Edmondson. (2019). The Fearless Organization.