The organisation accepts failure but takes no chances

Why is it that so many organisations say, “We’re ok with failure”, tout their literacy with psychological safety, and yet struggle with innovation?

Only 6% of CEOs are satisfied with their organisation’s innovation performance1.

Here’s a big part of the problem: most leaders focus on how they’ll react if something fails, but ignore whether it’s even possible to attempt something uncertain in the first place. It’s easy to promise acceptance of failure when no one can actually try something that might fail.

I’ve chatted with more than one CEO tearing their hair out, genuinely confused.

“We tell people it’s okay to fail. We back new ideas. We celebrate learning.”

And yet, when you look closely at how work actually gets funded, prioritised, and approved, almost every path available to people quietly steers them away from uncertainty.

I’m talking about everyday uncertainty, the critical majority of innovation that is often overshadowed by the Hail Mary bets. It’s the marketing manager who thinks an emerging channel might be amazing. The customer consultant with an idea for a more human approach to problem resolution. The lawyer with a vision for halving contract review time. All bring uncertainty.

Conventional practices make it near impossible to try these things because they often punish uncertainty. Annual budgeting pits departments against each other in a zero-sum fight for scarce resources: uncertain work is a red-rag to the bull and an easy cut. Backlog prioritisation pushes compliance first, then revenue, then customer experience. Anything experimental? Straight to backlog purgatory.

Compared to certain work, uncertain work looks bad on paper. If you have a dollar to spend, conventional practices give you every incentive to be certain of getting $1.10 back instead of taking a chance between a return of $0.50 and $2.00.

The issue often isn’t a lack of will from the boardroom, or a lack of psychological safety - it’s systemic impossibility.

Remember: your organisation is just a collection of practices. Most exist because we inherited them, built for industrial-age problems that no longer exist.

You can change them tomorrow.

So here’s one simple, better practice, and it’s super blunt: make it impossible to do a piece of work without a bet on something uncertain.

For each new piece of work, ask “What’s something we haven’t tried before that might just work?” Make it mandatory to try one or more (yep, it’s that simple). Your role as leader is to make no exceptions and to give people what they need to try.

This doesn’t rely on heroics, it builds doing uncertain things into your system of work. Now failure is genuinely possible, and so is wild success: now it will be time to accept some failure, but don’t worry too much, because you’ll also be soaking in the benefits of those wild successes.

As always, take what you learn, share it, and scale it. You might introduce the same question into project review gates and criteria for backlog prioritisation. These sorts of iterative steps are the quiet revolution that creates joyous and super productive work for more people, more often.

You can start tomorrow. Joyous work is within your reach.

At Joyous Work, we help organisations of all sizes configure their system of work so people spend more time using their skills on meaningful things. The result: organisations gain greater productivity in pursuit of their goals, and people experience more joy because their effort truly matters.

Visit joyouswork.com or reach out to john@joyouswork.com.