2 min read

The brave questions

#256 - Jun.2025

"Why we should be doing [this] instead of [that]?"

Silence in the room.

It's hard to hear this type of question.

But it's needed.

Making good questions is likely to become one of the most important skills in an age of information abundance.

Good leaders make good questions. It signals curiosity to learn more and their ability to identify gaps or opportunities.

Questions can take different forms:

  • Evaluating risks
  • Confirming assumptions
  • Understanding backing evidence
  • Mapping dependencies and constraints

But I think one of the most important types of questions are those driving focus & clarity. Questions like: "Why now?" or "What is the most important problem we want to solve?"

These are the brave questions.

The questions that no one wants to ask since they create friction. These questions aren't comfortable to answer since they often reveal truth.

Over time, I have discovered that, while they might feel confrontational, these questions lead to strong trust bonds. They signal that you care about what you are building as a team.

In a world with so much noise and distraction, these are the questions that become indispensable.

¡Saludos!

César Rodríguez
César Rodríguez
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