Hey product folks!
Today we will continue talking about Untrustworthiness as one of the Five Deadly Sins of Strategy. In the previous newsletter, we explored why this sin is so detrimental and learned how to spot it in your organization.
In this newsletter, I'm going to share a personal story from early in my career that taught me a valuable lesson about trust.

The Illusion of Perfection: When Hiding Failures Backfires
Early in my career as a product leader, I was always proud of my team's accomplishments. I'd showcase our wins like trophies, polishing them until they gleamed. But when it came to failures? I swept those under the rug faster than you could say "strategic pivot."
For months, I thought I was crushing it. My team was working hard, and I was sure our highlight reel of successes was impressing everyone. But then came the wake-up call.
A whisper from sales hit me like a ton of bricks: "We don't know what doesn't work in your product. We don't see the whole picture. It feels like we're only getting part of the story."
When Striving for Perfection Breaks Trust
My world tilted on its axis. I'd been so focused on projecting an image of perfection that I'd created a wall of distrust around my team. The final blow came when a critical project stalled because another department refused to share vital data, citing trust issues.
Naked Truth: Embracing Vulnerability in Post-Mortems
I realized something had to change. I started by making post-mortems public, sharing both triumphs and face-plants with all departmental leaders. It felt like standing naked in front of my colleagues, but to my surprise, they appreciated the honesty.
I didn't stop there. I encouraged my team to embrace failure as a learning opportunity, creating protocols for when things went sideways.
Radical Honesty: How Sharing Stumbles Strengthens Teams"
The results were astounding. By sharing our vulnerabilities, the team became tighter and more supportive. We started growing faster than before, each failure becoming a stepping stone to success.
The Transparency Transformation: When Honesty Becomes Strategy
As I reflected on my journey, I realized that true leadership wasn't about projecting perfection—it was about fostering trust through radical transparency. "In the game of product strategy," I now say, "honesty isn't just the best policy—it's the winning move."
This Week’s Challenge
Choose one recent project or initiative and conduct a transparent post-mortem. Share both the successes and the setbacks with your team and relevant stakeholders. Ask for feedback on this new approach and note how it impacts trust and collaboration.
Share your experience with me in the comments - I'd love to hear how it goes!
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Ready to unwrap a strategy that doesn't gather dust faster than your holiday decorations? I offer a free workshop as a Holiday special to help product leaders craft their strategy for the next year.

Here is the link for the workshop description
Don't let another year go by with a strategy that's as stale as last year's gingerbread house. Join me for a session that's more fun than untangling holiday lights.
