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  • Writer's pictureCaleb Kaltenbach

Asking Questions Makes You Better

In my opinion, Dallas Seminary professor Howard Hendricks was a legend. He mentored numerous students that went on to become tremendous leaders in their field. He’s probably most well known for his dynamic teaching style and understanding of how to study the Bible. With his son William Hendricks, Howard Hendricks outlined his Bible study methodology in his book, Living By the Book. To date, I believe it’s the best book on Bible study methods and if you were to read it, you’d find its pages are filled with questions. In the beginning of the book he’s actually very upfront with his fondness when he says, “If you want to understand a biblical text, you’ve got to bombard it with questions.” I’d like to borrow his phrase and adjust it a bit: If you want to understand how to move forward in a difficult circumstance, you’ve got to bombard it with questions.

Lest you think I’m an expert on questions, I'm not. For most of my life, I haven’t been a good “question asker.” Thinking through and developing helpful questions hasn’t been my forte. Truthfully, I’m the polar opposite—I want to know the answer right now and charge the hill without much discussion. Unfortunately, I’ve found that when I’ve made the decision to charge the hill with unchecked answers, I trip and fall down the hill before reaching the top! Really good questions stop us from tripping and...

-Allow processing

-Create discussion

-Build a well-rounded perspective

-Reveal assumptions, motives, reasoning, etc.

-Lead to intentional responses instead of impulsive reactions

-Set boundaries

-Bring down everyone’s guard

-Help develop empathy

-Move towards resolution

So, how do you ask really good questions? Well, I'm still researching that myself, but here are some brief tips I've found.

Listen to how others ask questions

If you want to ask good questions, listen to podcast interviews, watch interviews, etc. You'll get better when you surround yourself with good questioners. Podcasts I listen to that have insightful questions are HBR IdeaCast, Parent Cue Live, Carey Nieuwhof Leadership Podcast, The Productivity Show, The Table Podcast, unSeminary Podcast, and more.

Study the person and the circumstance

It might be that you want to ask someone a good question or a series of questions, My advice-- think through the individual and circumstance you are dealing with. Are you tackling a subject that is personal for them? Is the issue personal for you and do they know it? What are the emotions surrounding the context of the circumstance? How does the other person normally respond to questions? Are you asking in a physical environment that allows for concentration? These are just a few examples of questions that you should ask of the person or circumstance that can help you develop better questions.

Plan for potential answers

Too often, it's not enough to just think of one response a person might have. Depending on the seriousness of the situation or the question, we might need to think about different ways they might respond to the question. After thinking through possible answers they might give you, how might you respond to each that would drive the conversation towards resolution?

Be intentional with your words

Words like "might" open up possibilities. Words like "why" take us backwards into the past and are FAR TOO ambiguous, Our intentionality in choosing words for our questions will move the conversation forward to stall it! Notice the difference between the following 3 questions:

Why did you make the same mistake again?

How might you better prepare in the future to avoid the same outcome?

How might I help you better prepare in the future to avoid the same outcome?

The 2nd and 3rd questions aren't perfect, but they are moving towards a solution rather than merely focusing on the past. Our words matter.

Practice makes perfect

Prepare for the conversation by writing down your possible questions. Look at them, let them sit, and re word them. Say them out loud and notice how they sound. Ask them of someone else and get their feedback. Have spare questions at the ready.

When we get better at asking questions, we'll get better resolutions.


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