Valley of Death

Note to the reader: This is a repost from LinkedIn

The valley of death between idea and impact.

Lately I’ve been reflecting on the challenge of fostering genuine innovation in Big Tech. It might not be intuitively obvious but I highly recommend Scott Belsky’s “The Messy Middle”. It hit home why so many potentially great ideas die in this valley.

Two brutal truths I’ve learned:

1. We say “fail fast,” but in reality, most Big Tech products die slow, painful deaths. It’s more like “too big to fail”. They become zombies - not successful enough to celebrate, not failing badly enough to kill. I’ve seen teams spend years maintaining, or worse, building a product we all knew wasn’t working, because no one wanted to be the first to say it.
2. The deadliest enemy isn’t failure - it’s comfortable mediocrity. I’ve watched teams (including my own) unconsciously retreat to small changes when we should be tackling core product-market fit issues. Why? Because showing “progress” feels better than admitting fundamental problems.

Three counterintuitive practices I am thinking about and going to try:

1. Normalize the “pivot or persevere” conversation. Regular meetings where we explicitly discuss killing features or changing direction. Sounds harsh, but it gives teams permission to take bigger risks.
2. Some discomfort is okay. If your team feels completely comfortable with what they’re building, you’re probably not pushing hard enough. Real innovation lives at the edge of your comfort zone.
3. Track “learning velocity” over vanity metrics.We should celebrate shipping features, but for zero-to-one we need to celebrate validated learnings about user behavior - even (especially!) when they prove our assumptions wrong.

The messy middle in Big Tech isn’t just about persistence. It’s about having the courage to face uncomfortable truths, and the wisdom to know when to push through versus when to pivot.

What’s your experience navigating this “valley of death” in large organizations? Would love to hear your stories.