305 Questions and 4 Extraordinary Truths

A couple of years ago, my extended family voted on who the worst listener in our family was. Somehow, I won the crown… When they told me this, I jokingly said, “What did you say? I wasn’t really listening.” And while it was done in a casual, funny way, I haven’t forgotten that moment. And, even if it’s just a little bit true (which I’m sure it is), I don’t like that about me.

Since that day, I have been on a journey to see if I can become a better listener. It’s not the easiest goal to measure, but one thing I’ve learned on this journey is that a good listener asks good questions. So, if I want to be a better listener, I need to learn to ask better questions.

How do we grow in the art of asking better questions?

There is no one I try to pattern after more than Jesus. So, I did what I knew was best: I literally found and recorded all the questions Jesus ever asked. There were 305 of them and, for the sake of your time, you can find them all listed at the bottom of this blog. The important thing is what I discovered in reviewing all 305 of Jesus’s questions.

As you read through my quick insights, feel free to comment below on what you would add about Jesus’s questions — after all, I’m listening, and your insight might just help me on my journey, which I’m sure my family would love!

Truth 1: Jesus asked curiosity questions.

Carey Nieuwhof has interviewed more than 500 people on his podcast. From my estimation, he has crafted the art behind asking great questions. He says, “Curiosity is your best friend as a leader. So when you’re interviewing, act more like a 6-year-old than a 36-year-old.”

The two best questions to ask if you are curious:

  • “How…?”
  • “Why…?”

Altogether, about 80 of the questions that Jesus asked are “how” and “why” questions. He asked questions like “Why do you doubt?” and “Why are you thinking these things?”

Great leaders remain curious. They want to know how and why things work, understand how and why people are the way they are, etc.

What stands out to me even more, though, is that Jesus was not only fully man, but also fully God. Jesus was omniscient and all-knowing. So, in one sense, Jesus didn’t have to ask curiosity questions. He already knew everything… and yet, He still did!

Why did He do this? To help us grow in our faith.

Some would argue that questions are opposed to faith, but I think it’s fairer to say that our faith and questions form a powerful pair. Our faith grows more in uncertainty, doubt, and trying times than it does when everything is in perfect order. Jesus asking questions of curiosity allowed His listeners to wrestle with their faith.

Truth 2: Jesus asked open-ended questions.

As you scroll through the questions that Jesus asked, there aren’t many that could have a “yes” or “no” answer. They go beyond the superficial “How are you doing?” and “What do you do?” questions that we typically start with.

On numerous occasions, Jesus would ask questions like “What do you want?” and “Why do you call me good?” These are questions that require the person to honestly think before responding. They likely can’t be answered quickly.

One of the things that prevents so many of us from asking good questions is that it feels like we are too hurried. If we ask open-ended questions and are genuinely interested in their answers, this means we need to have time for people.

Jesus, who had the most critical responsibility and task of anyone to ever walk this planet, was able to spend time going deep with family, friends, and sometimes even strangers. Do you have the time to do this?

Truth 3: Jesus asked challenging questions.

The heart of the Gospel is an invitation to be in a life-giving, real relationship with God. This relationship includes the opportunity to follow Him daily, right here and now. As Jesus was announcing the Good News through preaching, teaching, and healing, He was unafraid to issue challenging questions to His followers and those listening.

Questions like “Will you really lay down your life for me?” and “What good is it for a man to gain the whole world but forfeit his soul?”

The invitation to follow after Jesus is the most incredible opportunity any of us will ever have. It is a life filled with significance, meaning, and purpose. However, to truly live out the faith that Jesus is inviting us into will require a substantial cost. To do anything of significance comes with significant challenges, and following Jesus is no exception.

As a pastor, I often wonder how much growth the church loses out on simply because we don’t ask or challenge our people enough. I think most pastors are skilled at proclaiming the justification of Jesus, but far fewer are skilled at challenging their people towards a life of holiness. It’s good to ask someone to believe in Jesus, but it’s deeper and more challenging to ask someone to follow Jesus.

Amazingly, only once in Matthew, Mark, and Luke does Jesus ask a question with the word “believe” in it. Of course, we should never abandon the invitation to believe in Jesus, but we certainly should frequently be challenging our people to truly follow Jesus.

Truth 4: Jesus didn’t ask “when” questions…ever.

We ask a lot of “when” questions.

  • “When will I find a spouse?”
  • “When will we have a child?”
  • “When will I get my dream job?”
  • “When will the Cleveland Browns win a Super Bowl?”
  • “When will Jesus come back?”

I think that Jesus will be back before the Browns ever win!

Amazingly, not once in all the 305 questions that Jesus asked, does Jesus ask a “when” question.

While you will find the word “when” in 11 of His questions, never was “when” the question’s emphasis. For instance, Mark 22:35 says, “When I sent you without purse, bag or sandals, did you lack anything?” Though the word “when” is in the question, the question’s emphasis is “did you lack anything?”

What could all of this mean?

Maybe “when” you live with an eternal framework as Jesus did, the “when” questions just aren’t as important. The more you have certainty and confidence in who Jesus is and the promises He declared, the less critical our “when” questions are. All of the “when” questions we ask may feel important at the time, and I don’t mean to trivialize what we go through in this life, but “when” you already know the outcome, you don’t need to live with worry. God is in control.

More important to Jesus is who we are following and how we are growing.

I hope that helps. Without further ado, here are the 305 questions that Jesus asks. Which one sticks out to you, and why?