Hello everyone and welcome to episode 123, “Ask Thoughtful Questions and See What Happens”

In last week’s episode, no. 122, “The Questions We Ask … and Fail to Ask,” I suggested that to deepen our relationships with people try asking the two questions asked of me recently. Namely, what are you looking forward to? And, what are you dreading?

Since I suggested that you give this a try, I thought I should do the same thing. I was curious to see how this would work, to ask thoughtful questions like these. Plus I wanted to brush up on my listening skills. Like any skill, good listening takes practice and I need all the practice I can get.

So in today’s episode, you’ll hear phone calls I made to several people, asking them the two questions I mentioned. At the end of each call, I comment on how the call went and what I learned from it. Keep listening to see how this
could work for you in moving you from the shallow end of your relational swimming pool to the deep end where all the good stuff happens.

The first phone call

My first call is to Maureen, who was my guest on episode 66 “A Solution Better Than Suicide,” and then episode 67, “Self-monitoring How We Listen.”

Those two episodes were some of my favorites as Maureen talked quite openly about her struggle with depression to the point she seriously considered taking her own life several years ago. She’s in a much better place now. These episodes are two of my favorites because they speak to the power of caring relationships to help us through dark days. They’re very encouraging. You’ll find links to them at the bottom of the show notes.

Fast forward to a few weeks ago when I called Maureen. By the way, I did not give her or any of the other guests I called a “heads up” that I would be contacting them. My calls came completely out of the blue for all of them. So her goes with my call to Maureen:

[I’m sorry there is no transcript of the phone call. Please listen to the audio of this episode]

What I learned from the call
  • I start with, “Do you have a minute to talk?” Good to ask. But when I say “no” people will often talk anyway
  • I love the excitement in Maureen’s voice, more surprise than anything. Happy for the kids to be now in school. “It’s been a long summer.”
  • “You sound elated,” act like a mirror listening principle, just reflect back what you observe.”
  • Her extroversion drew me out of my introversion. The laughing, the louder voice.
  • I asked my first thoughtful question, What are you looking forward to? Looking forward to routine, which leads to “space for better self-care.”
  • “Wow, those are deep questions?” Hmm. Reminds me of the deep end of the relational swimming pool.
  • Dreading? “Oooh. Such a strong word. We’ve already had Covid.” Humor.
  • Like everyone else, as you’ll see. She had to think longer about this thoughtful question
  • I stumbled trying to tone this question down. I couldn't think of a synonym for “dreading.” Apprehensive, anxious about, or simply, not looking forward to would have worked better.
  • She dreaded all the driving and time in the car with the kids taking them to activities in the fall
  • “Yeah, I can understand that” to what she was dreading. Good response, I think. Reminds me of the book I reviewed in Episode 105, I Hear You, where the author’s main point of the book is that affirming people and identifying with their feelings and experiences goes a long way to deepening relationships.
What I wish I would have done differently
  • I missed an opportunity to ask a follow-up thoughtful question. From what you heard, what follow-up question would you have asked?
  • When Maureen said she looked forward to the routine of fall because “It will give me space for better self-care” I could have asked this: “What would better self-care look like for you this fall?”
  • I didn’t have the time to talk because of the others I needed to contact.
The temptation I avoided
  • When Maureen talked about dreading all the driving of the kids, I thought of ways to fix her problem. I could have asked, “Are there podcasts you could be listening to during your time in the car, such as You Were Made… or,  you get the idea. Could your husband Mike do some of the driving? Would your parents or in-laws be willing to help
  • Thankfully, I didn’t ask those questions because they were born out of my knee-jerk reaction to want to fix things. I’m a guy. And it’s a curse we carry.
  • Besides, I’m positive Maureen thought of the same solutions herself, and several others I’m sure.
  • So I was glad I put into practice that quote from W.C. Fields a few episodes back, “Never miss a good chance to shut up.”
The second call to a former podcast guest

The second phone call I made was to Gail Rohde, someone I interviewed in episodes 29 and 30, two years ago in 2019. These were also two of my favorite shows. They are the stories of Gail’s search for her birth-mother, and eventually finding her, and all the relational issues related to an adult adoptee wanting to know more of where they came from. Her story so resonated with me because I also was born to an unwed mother and searched for my birth father, as Gail did for her birth mother. Again, there will be links to these episodes at the end of the show notes.

Well, my call to Gail started off with a technical glitch that turned out to be a blessing. Listen in

[I’m sorry there is no transcript of the phone call. Please listen to the audio of this episode]

Wrong numbers aren’t always wrong
  • When my call to Gail went to her husband Mike by mistake I learned the surprising news of Gail tracking down her birth-father. The last time I talked to her she had given up hope in ever finding him.
  • I was excited to learn this because I remember it being important to Gail
  • At the end of my call with Mike, I asked him about his new job. I turned off the recording at this point and Mike and I got caught up on each other’s life. It was an extra blessing to connect with him.
Another technical glitch
  • Mike gave me Gail’s new cell phone number which I called and then asked her the same two thoughtful questions I asked Maureen
  • However, I discovered I forgot to press the “record” button, so I had to call her back. Here is what she had to say:

[I’m sorry there is no transcript of the phone call. Please listen to the audio of this episode]

What I learned from my call to Gail
  • It’s great having people in your life you can admit your mistakes to, knowing that it's not going to change how they feel about you
  • There are times when our greatest blessings are also our greatest challenges, as Gail mentioned in finding her birth father
  • Because I had limited time I could talk with Gail, I didn’t ask any follow-up questions. And I have a lot of them. If you are rushed for time, it’s better NOT to engage with additional questions, because if you do you can easily come across as someone who doesn’t care and who just wants to cross something off their to-do list.
  • I learned it’s better to hold off further engagement until you do have time, as I did when I told Gail I’d like to do another episode. Save your questions for another time. Timing is everything.
  • My interaction with Gail demonstrates the ORA principle of deepening relationships. ObserveRememberAct. It started with Observing, in its listening form, to what her husband Mike said about Gail finding her birth-father.
  • There is a heavy dose of Remembering that’s apparent here. Remembering what Gail shared several years ago in those episodes about searching for her birth mother. And then Acting. Talking to Gail about doing another episode about the process of searching for her birth father.
The third call – to Carol Steward, my executive director boss

Like Gail, Carol was also the subject of two episodes of You Were Made for This, number 100, our first triple-digit episode, “Start Conversations With Remembering.” Followed by episode 101, “Life-Giving Relationships”

These episodes answer the question listeners had been asking me, “Who is this Carol we hear at the very beginning of each episode?” I explain the long history Janet and I have with Carol and her husband Terry. It was a heavy dose of the importance of remembering in relationships.

And then in episode 101 I share the story of how Carol introduces Janet and me to a personal relationship with Jesus Christ, and how that has changed our entire life.

The day I called Carol for this episode she was working out of her home. Have a listen to what she has to say:

[I’m sorry there is no transcript of the phone call. Please listen to the audio of this episode]

What I learned from my call to Carol
  • Sometimes thoughtful questions require time to think about before answering, as Carol answered about looking forward to spending school days with her grandkids. That’s because one of her daughters is a teacher and she provides childcare for them, as well as watching older grandkids after school while her other daughter is at work
  • That what are you not looking forward to questioning can reveal a bit about a person’s state of stress and contentment with life at the moment. It took Carol longer to answer this second question than it did the first, more positive question. This tells me something I’ve known for years, that Carol has a very positive outlook on life.
  • With some other people, they’ll have a much easier time talking about what they’re dreading than what they’re looking forward to. Not so with Carol.
  • Similar to Gail’s answers, the thing Carol was looking forward to also had a negative element to it.
  • One follow-up question I wish I would have asked is “Why do you look forward to babysitting your grandkids? What do you like about it?” That would have been a thoughtful question worth sking.
  • After I turned off the record button Carol and I continued to talk. She and her husband Terry, and Janet and I, have been friends for decades.
My fourth and final call – to another previous podcast guest

Hannah Barbeau and her sister Abbey were featured in a two-part interview in episodes 17 and 18. They are sisters living in Chicago. Hannah is a millennial and Abbey is from Gen Z. I interviewed them to talk about their relationship with each other, both growing up as kids and now as young adults. From there, we talked about what it was like for them to relate to older generations, roommates, their relationship with the church, and what young women their age need from their parents now. That was all in episodes 17 and 18.

Then in episode 19, I share 5 ways I was encouraged by my conversation with Hannah & Abby who are so different from me: different generation (I’m a boomer), a different stage in life, different gender, different marital status. I had a great time listening and learning from them.

But the other day, I just spoke to Hannah on the phone to ask her the same two questions I asked the other podcast guests I mentioned. We had played phone tag for a while, but we eventually connected with each other. So let’s see now how a millennial answers the two thoughtful questions I’ve been asking.

[I’m sorry there is no transcript of the phone call. Please listen to the audio of this episode]

What I learned from my call to Hannah
  • Some people are very reflective and deliberate in how they answer questions. Like Hannah, they may need more time than others to respond. So I need to give people the silence-filled space they need.
  • I happened to catch Hannah at the start of a whole new exciting chapter in her life. 3 new things coming up for her. What a privilege to hear about it!
  • I was glad I asked the follow-up questions about the classes she was taking and her new job. It gave me a better picture of what her life is going to be like for the next few months.
  • Somehow the end of the conversation got cut off, but we were almost at the end anyway.

The next day I got an email from Hannah about something else. She closed with referencing the conversation we had the day before with this:

“Also, thanks so much for taking the time to catch up yesterday! It was just nice. Made me wonder why I don't call others more often for a short, simple conversation! Take care!”

What a sweet and encouraging thing for her to tell me

So what does all this mean for YOU

You can also ask thoughtful questions of people, like the two I asked,  and see the good that can happen: what are you looking forward to? And, what are you dreading (or some version of it.)

Here’s the main point I hope you remember from today’s episode

When you ask thoughtful questions of the important people in your life you’ll be surprised at the good that can come from it. The joy they experience can overflow into your life, and you can share in it.

I’d love to hear any thoughts you have about today’s episode. Just send them to me in an email to john [at] caringforothers [dot] org. Or you can share your thoughts in the “Leave a Reply” box at the bottom of the show notes.


In closing, if you found this podcast helpful, please subscribe wherever you get your podcasts if you haven’t already done so.

I hope your thinking was stimulated by today’s show, to both reflect and to act. Especially to ask thoughtful questions of the important people in your life. All so that you will find the joy God intends for you through your relationships. Because after all, You Were Made for This.

Well, that’s all for today. I look forward to connecting with you again next week. Goodbye for now.

Related episodes you may want to listen to:

O17:  Two Sisters – Part 1

018:  Two Sisters – Part 2

029: An Adoption Relationship Story – Part 1

030: An Adoption Relationship Story – Part 2

066: A Solution Better Than Suicide

067: Self-monitoring How We Listen

100: Start Conversations with Remembering

101: Life-Giving Relationships

105: How to Listen Better

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