Decisions, Decisions: Why Business Choices Are Harder Than They Look In this episode of the Process Debt Podcast, Toby and Chris wrestle with one of the toughest challenges in business: decision making. From the small “what’s for dinner?” fatigue to high-stakes strategic moves that can make or break a company, they explore why decisions are so hard to evaluate—especially after the fact.

The conversation unpacks:

• Why great leaders like Steve Jobs and Obama simplified everyday choices.
• How businesses often miss the mark by failing to track the effectiveness of their decisions.
• The tension between purchasing vs. finance, short-term results vs. long-term strategy.
• Why not making a decision is still a decision—and sometimes the right one.
• How bias, politics, and poor prediction skills quietly build process debt.

With humor, hard truths, and real-world stories—from e-commerce purchasing metrics to massive enterprise launches—this episode challenges you to rethink how you (and your teams) make and measure decisions.

If you’ve ever wondered, “How do I know if that was the right call?”—this one’s for you.