Harder Questions = Better Answers

Wanted to share something that I find myself struggling with quite often.

Asking harder questions.

Many of my friends, family, co-workers and peers are great at this.

My dad, for example, doesn’t skirt around even the most trivial of issues. He gets right to the heart of the matter, forcing me to think about and prepare for things that I never saw coming.

The creative director in my company asks the most and the toughest questions of anyone I know. Projects change — and are significantly improved — because he poses questions that make the team rethink the entire strategy.

I admire these folks and many like them in my life. They do not assume, guess, or settle. They avoid the known and dive into the unknown because that’s where nuggets of truth are buried.

Many times over the course of a day, I find myself in situations that require a deeper dive or an additional step. As a fellow human, I’m sure you’ve encountered this. Someone makes a request of you or your company. There are the simple questions you can ask for clarification. You know, the basic ones that will make this whole thing go smoothly (Who? What? Where? When? yadda, yadda). It’s easy to get the answers you need in order to complete something. It’s not wrong. It’s just less.

It’s the hard questions we’re afraid to ask — the “whys” — that make us uncomfortable. They cause more work and create stress. They might shut down an entire project or create an entirely new one. They upset the order of things because they’re ripping apart or reinventing an assumed way of doing things. Change is painful.

Hard questions make us squirm, but they force us to come up with better answers.

When you ask the hard questions, you tend to experience a lingering feeling of dread or uncertainty. This is because you already know the answer to your question. You know what’s coming. You just don’t want to ask, for fear of upsetting the calm or breaking the chain of routine.

Deep down, under all of our assumptions are the truly original ideas that help us shatter the status quo. If we don’t ask hard questions, we’ll have an easier time, but we’ll miss those important opportunities to create something new.

I’m making it a personal goal of mine to ask the hard questions. I’ll let you know where they lead me.

Toucan is a New Orleans-based advertising agency.

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