Dichotomy of What If versus Why Not

Product Management has many dichotomies.

Plan for the long-term, but prioritize diligently for the short-term. Listen to customers for product feedback, but form your own point of view. Lead your team, but don’t tell them what to do.

Another dichotomy is balancing optimism and pessimism when building your product.

What if captures the optimistic perspective. What if this works. What if this improves this problem. What if this exists.

Why not captures the pessimistic perspective. Why this shouldn’t exist. What could go wrong. Why we shouldn’t build this.

Depending on context, a Product Manager should be able to oscillate between both.

When pitching a new feature to stakeholders, embrace the optimistic what if vision. When planning a technical implementation, consider the pessimistic why not perspective to identify things that could go wrong.

I would guess that new (product management) hires veer towards the optimistic side, while seasoned (2+ years tenure) employees veer towards the pessimistic. The seasoned employee has lived through the organizational challenges of building products. These challenges can weigh on them, pushing them to default to why not versus what if. The new employee has an opportunity to inject a sense of optimism, an excitement for building, and a “pragmatic enthusiasm for what can be achieved“.

A Product Manager must be able to utilize both perspectives, in the right contexts. And if the Product Manager finds themselves relying too much on one perspective, they should deliberately practice the other perspective.