30 October 2026
Stay Risky: Psychological Safety and Learning From Failure
40% Better - Engineering Leadership
About
Leaders say failure is a learning opportunity.
Their teams watch what they actually do when something breaks.
Rachel Franco, founder of Fail Smarter, spent years in innovation enablement at Optum and researched the barriers leaders face in learning from failure.
She explains what makes it truly safe to fail, how to measure psychological safety instead of guessing, and how to use innovation tools to turn failures into new solutions.
Bill shares how he got quiet engineers to speak up by asking the loudest voices to sit out for six months.
He also talks about a founder who shrugged off outages and fired abusive customers, and what he saw about playing it safe at Google.
Rachel closes with the numbers: why psychological safety isn’t fluff, and why it decides whether an AI transformation succeeds.
Connect with Rachel: https://www.fail-smarter.com/
Connect with Bill: https://40pb.com
Their teams watch what they actually do when something breaks.
Rachel Franco, founder of Fail Smarter, spent years in innovation enablement at Optum and researched the barriers leaders face in learning from failure.
She explains what makes it truly safe to fail, how to measure psychological safety instead of guessing, and how to use innovation tools to turn failures into new solutions.
Bill shares how he got quiet engineers to speak up by asking the loudest voices to sit out for six months.
He also talks about a founder who shrugged off outages and fired abusive customers, and what he saw about playing it safe at Google.
Rachel closes with the numbers: why psychological safety isn’t fluff, and why it decides whether an AI transformation succeeds.
Connect with Rachel: https://www.fail-smarter.com/
Connect with Bill: https://40pb.com