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Can You Ask Good Questions – Part 4

Mike Kelly  |  August 3, 2021
  1. Can You Ask Good Questions? (Hint: that’s not one.)
  2. Can You Ask Good Questions – Part 2
  3. Can You Ask Good Questions – Part 3
  4. Can You Ask Good Questions – Part 4
  5. Can You Ask Good Questions – Part 5

How to Ask When You Already Know

You should know more than the people you mentor and shepherd. It’s your job, after all, to share wisdom, impart content, and open new perspectives. There are a number of methods to that end, but none get as much attention in ministry as telling, which has the advantage of being the fastest and easiest way to transfer knowledge. It’s also central to the life of the Church. We call it preaching. Telling is a good thing, but it can be overused because asking is almost always slower and harder. What’s more, ministry training focuses on telling. For those reasons, the mentor needs to learn how to ask instead of tell, which means they need to learn to ask when they already know. That takes self-control, patience, and practice.  So, I’ll now tell you how to ask instead of tell through the art of mental reverse engineering. Mental reverse engineering is the act of reflecting on how you came to a conclusion so that you can help someone discover it for themselves by asking them questions. Here’s some help doing that.

Think (Backwards) Before You Speak

Established practitioners eventually compress their experience and training into service without processing things “discursively” that is, without thinking consciously through an A + B = C equation.  After years on the job, C often just “appears” intuitively. This dynamic is exaggerated when we observe less experienced people operate in our area of expertise. That’s why elite athletes don’t always make good coaches. Batting champions sometimes feel like they just stand at the plate and swing. That “advice” doesn’t help a AAA prospect. So, before you blurt your C to the struggling learner, you need to pause and reflect on what observations led you to your answers. Thinking backwards requires the mentor to ask herself questions like,

  • What did I see or hear that led me to my view?
  • How does that observation lead me to my inference?
  • What experiences do I have that help me see that?
  • How likely is my learner to share that experience?
  • What might block them from seeing the steps that led me to my conclusion?

That’s a lot to process during a real-time conversation. It takes practice, but keep in mind that you are not starting from scratch. Questions like those all have answers or you wouldn’t have an idea of where to guide the learner. Practice will lead proficiency.

For those reasons, the mentor needs to learn how to ask instead of tell, which means they need to learn to ask when they already know.

Link What You Think

After you’ve thought backwards and identified how you got C, the next step is to reflect on the sequence of the observations that lead you to your insight: the A + B that gave you C.  The order is important for two reasons. First, they usually build on one another so helping your mentee discover them in order is akin to leading a hiker to a vista that reveals the next leg of the journey. Secondly, by thinking about how one link connects to the other, good questions often present themselves. For example, after asking a simple question like, “Where did the plan first start falling apart?”, you can ask a deeper question like, “How could you have responded better to that moment?” “Thinking Backwards” and “Linking What You Think” will help the mentor break the learner’s situation into its component parts, so that they can examine smaller pieces instead of trying to figure out a complex circumstance as a whole.

How do you know what to ask them about? First, assume they don’t see any of the particular As or Bs that led to the C. Then start asking them about each of those components you’ve identified through mental reverse engineering. If they already see what you see, good. Move on. If not, ask questions that reveal it to them. As they identify the parts they often begin to see how they fit together like parts of the puzzle.

If through practice you learn to think about how you think, you’ll be able to create questions that help the other see what you see. Once they do, their intuition often kicks in and the discussion creates its own learning energy. Don’t fret too much about where those questions go at first. Instead just start asking the learner about the first link and use their answers to ask more questions. You’ll be surprised at how often the discussion flows along as if guided.

Keep in mind that you can’t become proficient without practice, so this road will be bumpy and occasionally reach dead ends. When your questions don’t seem to be working, acknowledge it. Then ask the learner how you can be more helpful. Remember too, that the point is to help, not be a great asker of great questions.  Sometimes, you just need to blurt it out. Telling is not bad, as long as it’s not your only tool. Plus, once the telling is done, you can ask the learner what she thinks of that perspective, how you came to it, what implications it has for her next steps and many more. As Chesterton said, “Anything that’s worth doing is worth doing poorly.”

Example: Helping the Overwhelmed Leader

You’re mentoring a gifted, energetic young leader in your organization whose responsibilities have grown substantially over the last year. They have the potential to steward their new opportunity, but right now they are overwhelmed and have begun to wonder if they can handle the job. After watching them work in previous roles and in this new expanded position, it’s obvious to you that whatever else is blocking their progress, this manager hides from stress and vulnerability by leaning into work functions that they’re naturally good at and avoiding “left hand” work, that is duties that require them to use their non-dominant giftings. It won’t help to just tell them they need to embrace-the-suck and start climbing the steep learning curve like an adult. You need to help them see that for themselves, so you think backwards and then link what you think.

Backwards Thinking. By listening to him, watching him work and noticing what he stresses about and what he celebrates, you’ve noticed that his schedule doesn’t always reflect the urgency or relative importance of his responsibilities. That’s the A in the equation. As you reflect on that you note that strategic planning and networking, which are strong suits, eat up a lot of his time. That’s the B in the equation. 

Linking Thinking: Now that you have A and B to support your C, you’ll begin by asking questions that help him see what you see about how he fills his schedule. Your aim is to help him begin to see what his days and weeks look like relative to his responsibilities and deadlines. So you ask,

  • What fills his days? 
  • How does he decide? 
  • What duties take most of his time? 
  • How well does that rhythm fit with his stronger gifts? 
  • His weaker gifts? 
  • How does he prioritize?
  • What kind of work does he do at different parts of the day? 
  • What’s the flow of a given day, week, or month?
  • How often does a day’s schedule unexpectedly change?
  • What does it change?

Once he’s had the chance to examine and reflect on his workflow and focus, you can change the aim of your questions. Now you want him to self-discover why his schedule is the way it is. Your hope is that he’ll come to your C through a process of questions and answers. If so, he’ll realize that he’s making choices that keep him in his comfort zones and, ironically, make his work more difficult, hence more uncomfortable. To do that, you ask him things like,

  • What patterns do you notice about what you focus on?
  • What things force you to change your plans? Why those things?
  • What kinds of things do you see need more attention?
  • How proficient and confident are you at those things?
  • What functions do you like most about your job?
  • How much time do you spend on those?

These kinds of questions often lead to “Ah ha” moments and self-diagnosis when the mentee puts the pieces together, but not always. If the eureka moment isn’t forthcoming, you can ask directly leading questions like “Why do you think you spend so much time on the things you’re good at?” or “What do the things that get the least amount of your time have in common?” Of course, you can also just blurt out C and ask him what he thinks of that but remember; you might be wrong so be ready to learn from the learner.

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Mike Kelly
Mike founded the Northwest Church Planting Network in 2001. Through his leadership the Network has been involved in the planting of 19 churches in Washington, Oregon, and Alaska. Mike also planted a church in Indiana and revitalized a church in Seattle that he pastored for 20 years. He offers decades of pastoral and leadership experience for young emerging ministers.
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