There are as many questions as there are colors on a color palette, but like the artist’s medium, every question shares common shades, hues, and primary color variations. By necessity every painter uses colors, but with those givens, they create a palette that serves their eye’s style and their subject’s presentation. The accomplished questioner can do the same by building a palette of queries that rest, as it were, at the ready to be used, and mixed like colors, in a given conversation. You can build your palette by composing generic questions like the examples below. Consider them the basic colors that you’ll mix and accent as you use them. Belabored metaphors aside, practice makes proficiency. Or put another way, what do you have to lose by learning to ask better questions?
What are you excited about? Why does that excite you?
What are you discouraged about? Why does that discourage you?
What is your biggest challenge right now?
What would change in your work, family, friendship, etc. if you overcame it?
What is at the root of that challenge?
What are you better at than you thought you were?
What are you not as good at as you had hoped?
Who are the most involved and helpful folks around you? What do they have in common?
Who is around but not involved or even obstructive? What do they have in common?
What area in your life has the most potential right now?
What kinds of things do you just not know how to approach?
What do you find yourself dealing with reactively most often?
What areas of life/work do you most often get to last minute? Or simply ignore?
What parts of your dreams are in the best shape? Which are in the worst shape?
What commitments or opportunities might need to be cut or added?
What is more difficult than you thought it would be?
What does success look like in 7 years? How would you feel if that happened? Didn’t?
What areas do you want to process first? Why?
What is your most common emotion?
How often do you pray with your spouse, friends, or roommate?
Can we look at your schedule for the last month?
Where can we get some beer? (If they have no answer you may leave.)
Thank you for trekking through this journey into asking well. Please allow me to end by asking how the Title Question for this series could be improved? I’m asking for a friend.
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.
Didactic Questions are questions that help lead a learner to discovery through dialog rather than simple information transfer. For example, if you see that a friend could reach their goals more quickly if they managed their time better, you could ask:
What do your work days look like?
How satisfied are you with your work flow?
What gets in your way?
These are Didactic Questions because they are intended to help the mentee see what you see so that they can confirm, clarify, and ultimately own it. Of course, the questions can be manipulative if asked condescendingly. They can also come from your own wrong answers so be willing to be corrected.
All good askers ask questions with ears wide open to learn, especially when they know the answer.
Discovery Questions are intended to open up situations and feelings without a clear understanding of where the answers will lead the discussion. For example:
What do your work days look like?
How satisfied are you with your work flow?
What gets in your way?
Observant readers will notice that those are the same questions! As Discovery Questions, however, they lead you both toward an unknown insight. In this case you don’t have a sense of what’s blocking their progress.
As you can see, the two types of questions overlap. Sometimes didactic inquiries surprise us with new discoveries. All good askers ask questions with ears wide open to learn, especially when they know the answer.
Whether Didactic or Discovery, good questions are generated by asking yourself questions first. In the case of Didactic Questions, ask how you came to your conclusion or observation and then turn your answers into questions. In the case of Discovery Questions, reflect on what information remains out of reach for you and what appears to be blocking it.
Stay tuned for Part 4 where we’ll discuss how to ask when you already know.
We run out of questions when we are finished listening. Deep hearing is the art of generating deeper curiosity from a person’s answers by carefully observing their words, tone, and body language. Deep hearing is a kind of prayer that involves conscious reliance on the Holy Spirit, intense focus on the speaker, and real-time, internal processing of both. It creates questions through a “What / Why” axis. The listener focuses to understand what is being said (words, tone, body language) and prayerfully asks himself why it is being said.
Deep hearing is the art of generating deeper curiosity from a person’s answers by carefully observing their words, tone, and body language.
The “What” can be easy to discern. The “Why” can be more difficult to perceive. A person’s “Why” can be good or bad, right or wrong, complete or partial, obvious or obscure, or some mix. But it always operates out of their presuppositions and deeper motivations. By working on a clear understanding of “What” and prayerfully exploring your best perception of “Why” good questions will begin to emerge. However, remember that you are exploring with them, not for them. Hold your perceptions and ask your questions humbly.
Stay tuned for Part 3 where we’ll discuss Two Kinds of Questions: Didactic and Discovery.
Can You Ask Good Questions? (Hint: that’s not one.)
Can You Ask Good Questions? (Hint: that’s not one.)
A long while ago when I began my journey to help rising leaders I discovered the world of coaching literature (of which there is plenty). During that season I met an older minister from a different denomination and learned he was friends with two of the authors I was reading. I was excited to hear that because after a few books, I had a big question:
“Randy, why do all these books go on and on about asking questions as if the coach shouldn’t give advice? I mean, people want their coach to have answers, right? Paul’s letters to Timothy and Titus don’t have many (actually, any) questions. He just tells them what they need to do.”
“Yes,” answered the sage, “he does tell them what to do and people need that. But let’s be honest about guys like us. We don’t need to be taught how to tell people what to do. We need to learn to listen and among other things, that means we need to learn to ask questions.”
It’s worth noting that Randy’s answer about why questions are critical was not a question. Coaches and pastors, like parents and peers, should be ready to offer wise counsel when it’s helpful. But it won’t be as helpful as they hope if they haven’t listened deeply. To do that we need to become as familiar with the Asker’s Path as we are with the Teller’s Path.
The Asker’s Helping Path
The Teller’s Helping Path
This series is offered as a prompt to learn how to help by asking questions that make a difference for the asker and the answerer. We’ll explore:
Where Questions Come From and How to Listen to Answers
Deep Hearing
Two Kinds of Questions
How to Ask When You Already Know
Create Your Question Palette
Where Questions Come from and How to Listen to Answers
The first question to ask yourself about your question is why you’re asking it. Of course, the most important part of the answer has to do with your heart’s motive and your goodwill toward the other. But it’s also important to have a plan for every question you ask. In other words, good askers know what they are “asking” their question to do. Here are six basic purposes for good questions.
Ignorance: Sometimes you just don’t know and even if you think you do, it’s best to incline away from the first diagnosis. Questions born of ignorance can help you find a better explanation or a better reason for your first observations.
Certainty: Asking questions does not mean you don’t know the answer. Lawyers famously (and sometimes questionably!) only ask questions they know the answers to. That’s not a bad thing, unless it’s adversarial. So ask questions that help the other person discover what you already perceive about the situation.
Clarity: Questions for clarity can help you, or more importantly your mentee, understand the issue more deeply or broadly. “Why, How, What if” questions can sharpen diagnosis and solution.
Boldness: Good relationships have room for disruption. You may ask questions that challenge his assumptions, behavior, diagnosis, strategy, feelings, etc.
Patience: The urge to tell is strong but asking gives space for listening. Patience questions provide room to wait for a clearer sense of what to ask. They can tend to be one-dimensional, but they force you to be patient with the process. Remember too, that silence isn’t necessarily bad.
Guessing: Asking questions is like fishing. You cast a lot of line before you reel in a keeper. It is ok to not be sure where you are going and to come up empty. At the very least you’ve eliminated one possible avenue.
Stay tuned for Part 2 where we’ll discuss Deep Hearing.
