You can’t process shame alone. Compete to be the biggest failure instead.
Last week I ran a session on failure at ‘s Con Con – a conference of 50 solo consultants and entrepreneurs. A room of people who position themselves daily as expert problem solvers and wise partners – they’d never share, would they? They will if it’s a competition to find the best (worst!) failure.
Here’s how it worked:
Intro: I briefed the room on the ground rules and shared my own biggest failure
Table shares: 1 minute each, share your biggest failure, then send one winner up to the front
Stage shares: 1 minute each, tell the whole room
Vote: Get up and stand with the biggest failure
Cheer the winner
50 people, done in 30 minutes. You can do this with many more people; just introduce multiple rounds and a bit more time.
Why it works as an activity
Admitting failure means losing status – an existential threat we work hard to avoid – but competing to ‘win’ offers a route to higher social status. The social incentive is inverted. And also, i went first with my embarrassing, shameful and relatable failure. I’ve put the bar so low it’s in the basement. I won’t share that failure here – being in the room is the point.
Why it works to heal
Of course, it is fun and it builds trust. It’s a great conference activity (not one for co-workers!). But it works at a deeper level than you might expect.
The underlying issue is the unhealthily instrumental approach to failure in our culture. We strip-mine mistakes for learning opportunities and then pretend it’s done with. ‘Fail fast, build back better’ turns a failure into something solely rational. But debriefs don’t heal guilt and shame.
Guilt says ‘I did bad’. We can work through guilt alone through acceptance, confession or restitution. Self-forgiveness ameliorates it completely. Many people in the session had done this work alone already.
But shame hooks deeper; it says ‘I am bad’. This cannot be resolved alone. Shame is interpersonal; it only gets worse in isolation. The only cure for shame is through human relationships: for shame to be heard, experienced, felt.
Conventional failure-sharing (‘what did you learn?’) creates a evaluative frame. It implies the failure needs to be justified by its utility, which reintroduces shame: what if I didn’t learn the right thing, or anything at all? The format closes off emotional recovery.
In this format, a prize –a reaction in others, the social prize of winning, or an actual physical prize – acts to restore status. The thought ‘I risk losing status by being a failure’ becomes ‘I am a winner!’
Participants said
One person said the session had ‘connected the dots of my last twenty years, why I do what I do now’. Others told me they felt ‘a weight come off their shoulders’, ‘like I’m with people who get it’, and ‘I’m not alone anymore’.
Wider lessons
Leaders need safer places to deal with shame and guilt. Showing up to an Exec or Board meeting while carrying guilt and shame will lead to protective behaviours in the group – over-indexing on risk avoidance. It will also lead to choosing apparently-safe options. But a Board / Exec workshop on guilt and shame won’t work – Board colleagues are the wrong peers for this sharing. Industry conferences are much better places.
A great facilitator, advisor or coach can hold the room’s feelings of guilt and shame, and the anxieties around risking those in future. They hold the space without forcing exposure. When hiring, it’s helpful to ask, do I feel this person might judge me? If the answer is yes, don’t hire them.
Shame doesn’t stay inside – it travels into the next meeting and degrades presence and decisions. Unprocessed, it distorts the everything a leadership group produces. The conditions that allow it to be processed – safety, the right peers, no evaluative frame – don’t happen by accident. Someone has to create them.
First published in Strategy, Applied.
