Important Questions


I’m a big fan of questions.

I started my career as a classroom teacher believing good teachers knew all the answers. Experience taught me that questions mattered more than answers. It’s a principle that extends beyond the classroom. We do better when we resist the temptation to provide (easy, quick) answers and focus on asking better questions.

We just completed our One-Day Prologue and Front Range Tour. In a couple of weeks we’ll tour the Colorado mountains. As FREEDOM TOUR ’18 winds down, I’m wondering about questions. We’ll have lots of discussions about how things went, what needs to improve, what went great. In those conversations I don’t need answers, I need better questions.

A while back I listened to a commencement address by Dean James Ryan at Harvard Graduate School of Education. In his address there’s a short segment in which he lists 5 Essential Questions. I’m thinking this list might help me, and maybe you, as we seek to learn.

Some thoughts on Ryan’s questions:

Wait, what? Essentially, this says I’d like to stop and clarify. Rather than jumping to conclusions, this question says it’s worth taking the time to fully understand. It’s the way we expose and overcome our inevitable bias.

I wonder, why/if…? I’m conflicted about this one. Honestly, “why” questions often seem like a stall technique. When we’re spinning about “why,” we get to avoid actually solving the problem. However, in some situations great insight can be gained from exploring “why.”

“I wonder, if…” opens doors, encourages dreams. I hope everyone who’s invested in a big idea takes some time to discuss this question.

Couldn’t we at least? This accomplishes two key purposes.

First, it gets us to common ground. “We don’t all ride bikes, but couldn’t we at least find a way to work together to support kids rescued from human trafficking?”

Second, it gets us unstuck when a problem seems too big. “We can’t help all victims, but couldn’t we at least help kids at one safe house?”

How can I help? This, for me, is at the heart of how we work together. Simply offering to lend a hand wherever it’s needed is perhaps the simplest, most basic way to encourage someone. It’s a sign of humility and a willingness to serve.

What really matters? It’s awfully easy to get sidetracked and lose sight of the core mission. It’s important, I think, to stop once in a while and make sure everyone agrees on and understands what really matters.

I need to ask better questions. Maybe you do, too.

These are a good place to begin.

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