De-Risk Riskiest Ideas First

"Taking the things in the top, the biggest swing and actually prioritizing those first in terms of product discovery and figuring out what can you do to start de-risking because if you constantly put those off in favor of the lower risk or more predictable smaller swings, how are you ever going to truly innovate and get to the next level." - Camille Hearst

What It Is

This is a prioritization principle for product discovery: when looking at your opportunity space on an impact/effort or risk/reward matrix, deliberately prioritize the high-risk, high-reward ideas for discovery work first - not last.

Most teams naturally gravitate toward safer bets because they're easier to execute and more likely to succeed. But this creates a pattern where the biggest opportunities - the ones that could truly differentiate your product - never get explored because they're perpetually deprioritized in favor of incremental wins.

The insight is that risky ideas don't stay risky forever. Through deliberate discovery work (experiments, prototypes, user research), you can systematically de-risk them until they become predictable enough to execute. But this only happens if you allocate discovery resources to them.

How It Works

The Traditional (Problematic) Approach:

Map opportunities on impact/effort or risk/reward matrix
Pick the "safe" high-impact, low-risk quadrant first
Never get to the high-impact, high-risk ideas because safer options always exist

The De-Risk First Approach:

Map opportunities the same way
Allocate discovery resources to high-risk, high-reward ideas first
Run experiments to validate or invalidate key assumptions
Either: Convert risky ideas into de-risked deliverables, or learn they won't work and move on
Execute on de-risked opportunities in delivery track

How to Apply It

Identify your biggest swings - Which ideas could be transformative if they worked?
List the key risks - What assumptions need to be true for this to succeed?
Design cheap validation experiments - How can you test assumptions quickly?
Prioritize discovery resources - Allocate research, prototyping, and experimentation time to risky ideas
Accept leadership accountability - As a leader, own the outcomes so your team has permission to fail
Convert or kill - Either de-risk ideas until they're ready for delivery, or learn they won't work and stop investing

When to Use It

When your team keeps working on incremental improvements but never tackles big opportunities
When you have high-potential ideas that keep getting deprioritized as "too risky"
When you want to create space for genuine innovation, not just optimization
When you're willing to accept that some experiments will fail

Source

Guest: Camille Hearst
Episode: "Monetizing passions, scaling marketplaces, and stories from a creator economy vet"
Key Discussion: (00:54:16) - Camille explains the importance of prioritizing risky ideas in discovery
YouTube: Watch on YouTube

Related Frameworks

Dual Track Agile - The operating model where this prioritization applies
Biggest Problem First - Related prioritization principle
Thinking in Bets - Framework for making decisions under uncertainty