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Asking Powerful Questions

January 18

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About This Episode

(Season 5, Episode 3)

Community engagement, co-creation and collaboration depend on meaningful conversations. Asking the right question is the most effective way of expanding a conversation, keeping it engaging and making it meaningful.

In this Practicing Connection practicast, Jessica Beckendorf shares a practice to help us engage people in the meaningful conversations we need to have in order to plan and do our work together.

“Practicasts” are shorter episodes of the podcast highlighting a specific practice to help empower us to work together to improve our resilience and readiness.



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Bob Bertsch: Community engagement, co-creation, and collaboration depend on meaningful conversations. Asking the right question is the most effective way of expanding a conversation, keeping it engaging, and making it meaningful. Hi, I’m Bob Bertsch and welcome to this week’s Practicing Connection Practicast, where we highlight a specific practice you can use in your life and work. This week’s practice is focused on asking powerful questions.

This practice can help us engage people in the meaningful conversations we need to have in order to build relationships and to plan and do our work together. My Practicing Connection co-host, Jessica Beckendorf, will be guiding us through a practice to help us build rapport and ask powerful questions in a few minutes. First, let’s learn more about it. Jessica, what is a powerful question? What makes it powerful?

Jessica Beckendorf: Bob, I’m sure there’s a lot of definitions out there on powerful questions. My own very simple definition is that powerful questions are open-ended questions that touch on a person’s motivations, hopes, and stories. They’re powerful in part because they recognize the person answering the question is the expert of their own experiences. They’re also powerful because they connect people through storytelling and authentic curiosity. They’re also powerful because the sharing that occurs when a powerful question has been asked opens up possibilities for more questions, more conversation, and more connection.

Lastly, I would say that they are most powerful when the person’s intent for asking the question comes from authentic curiosity rather than a desire to lead or control the conversation or to try to make a point or because maybe they’re making an assumption about the other person they’re trying to talk to or about the group that they’re trying to talk with.

Bob Bertsch: Yes, that’s really helpful. I’m curious about how powerful questions might have helped you in your work, especially your work with groups.

Jessica Beckendorf: I didn’t start out by intentionally asking powerful questions. I didn’t think, I do group process work. I’m going to ask them powerful questions all the time and it’s going to be amazing and everything’s going to work all the time. We all have natural patterns of interaction, the things that we do automatically when we have conversations. We already know how to communicate is what I’m trying to say based on what we’ve observed or what we’ve already been taught, either through others or through trial and error our whole lives.

I was pretty good at small talk, and I really enjoyed it and I know that’s going to make a lot of people cringe, but I did, I was able to build rapport quickly and get from small talk to deeper connections, but I didn’t know how I did it for a long time. Once I started to understand more about connection and collaborative relationships and how powerful the right questions can be, I began to use them with intention. For someone who already feels like, “Ah, I’m good at that,” I’m telling you, it can help you out a lot if you do it with intention.

Then for someone who feels like, “Ooh, I’m not very good at that,” and she was already natural at it, so there’s no way that it’s going to work for me, no, that’s not true. I know people who it doesn’t come supernaturally to them and they worked at it and it works for them as well. Once I understood this, I began to use these questions with intention. When I noticed that a group I was working with was struggling, I would work on finding the right powerful question for the moment.

If I was able to, I would plan several questions ahead of time before going into the situation, or if I was in the moment, which happens, I would pull out a broader question and just trust the group to share. I think that’s so important is when we ask questions, we have to trust the person to answer from their own experience or trust the people to answer. Sometimes a really well-placed what’s essential right now asked to a whole group or a question like what matters to you in this moment can do wonders for a group that’s stuck, especially if everyone gets a chance to respond to the question.

We know people who are very excited and we also know people who will dominate a conversation. If you can give everyone a chance to answer those questions and respond on their own, that’s even more powerful. Another way that I’ve used these questions in my group process work has been to infuse connection where it’s been brushed aside. I’ve seen it brushed aside lots and lots of times.

I think what’s essential here is that without real social connections in the groups that we work with, we’re just creating more meetings and tasks and obligations for ourselves and meetings and tasks and obligations are all working toward a goal. There’s some meeting there, but it’s not the same as when there’s also some real social connections being built.

Bob Bertsch: You’re going to guide us through the practice a little bit in just a moment, but I’m just trying to get sort of a context of how these work, how powerful questions work in practice. For example, like how many do we need for our conversation and when should we use them? Do I need, plan out all my conversations in advance so I’m ready with my powerful questions?

Jessica Beckendorf: I’d say that in practice, to me, asking powerful questions begins with noticing what we’re curious about and asking questions about it. It sounds really, really simple, but we need to recognize that curiosity and how we engage with it presents itself differently for each person. Some people are wildly curious about people and some aren’t. Some are more curious about ideas or about other things, about nature. That’s perfectly okay. I’d say that developing your curiosity will help you ask powerful questions more intuitively. That’s why I like to start with curiosity.

Essentially, this is about being present to and noticing what your heart and mind are drawing you toward during your interactions with others. Notice it and engage with it by asking open-ended questions. Of course, while you’re working on your curiosity, I do also recommend starting out by having a couple of powerful questions that you enjoy hearing the answers to and that you’re willing to answer yourself. Never ask a question that you aren’t willing to answer yourself.

Connecting involves at least some mutual vulnerability. We’re not asking you to, I certainly wouldn’t start with a question like, “What’s the most embarrassing thing that has ever happened to you?” Don’t ask that question, especially if you’re not willing to answer it. I also wouldn’t start with that question or a question like it. As far as when powerful questions should be used, the answer is going to depend on the situation. I think as a general guideline, if you’re just meeting someone or you’re just getting together for the first time as a group, you could start by just practicing your noticing and asking skills that I just mentioned a minute ago, just to build some rapport.

What you’re noticing about the person or the group that’s making you curious is what I’m talking about when I say noticing and asking. Maybe it’s even something that seems simple, like something they’re wearing or something that they’ve said about their favorite sport, right? Those aren’t powerful questions, but they are questions to ease into the deeper questions that we’re trying to get at. Then, to me, once there’s a little bit of rapport built, and this is something that I learned from Chad Littlefield and Will Wise’s work, they have a book called Ask Powerful Questions.

Once there’s a little bit of rapport between people, that’s when you can get into some more of the powerful questions. I wouldn’t use them before you’ve established just a little bit of rapport in an interaction.

Bob Bertsch: Awesome. Thanks. That was really helpful just to get us grounded in sort of what this looks like. You mentioned you had some steps to walk us through, so we’d love to hear them.

Jessica Beckendorf: All right. The first step is to have a couple of questions that you’ll always remember and have with you in the back of your mind. These should be questions, like I said before, that you love to hear the answers to and that you’re willing to share your own answer to. For example, a question that we often use on this podcast with guests is a question that I really love is, how did you get into your field or how did it find you? You can change up the word field with anything you want. How did you get into that hobby or how did it find you or anything you want that you could fill in there.

How did you get into blank or how did it find you? It’s also good to have a follow-up question, something like, “Tell me more about blank. I find it fascinating,” or, “That sounds really cool. My grandfather used to do that, but I never understood how he did X,” or whatever is leading you to ask about it. “Tell me more about blank,” is another good one to have in the background. Now, if those don’t feel natural to you, I would recommend making up your own, try to make up questions that sound natural to you that start with the words how or what, and then have a follow-up question like, “Tell me more about–” whatever language you need to use to make it sound like you is what I recommend.

Have a couple of questions as step one. Second, as you’re interacting with someone or with a group, as you’re building that rapport with them, you’re having sort of the shorter, smaller talk, whatever you want to call it. You’re meeting with them. You’re just in a meeting with them. Maybe any kind of discussion that you’re having, I want you to find your natural authentic curiosity, whatever your heart and mind is drawing you toward. You might notice this through a gut reaction and I would say, probably a positive gut reaction, like, “Ooh, that’s cool.” “Oh, I’ve always wanted to learn that. Now I know someone who does it.”

Maybe through sort of a lightness, like, “Oh my goodness, so many possibilities. My mind is firing. I’ve got lots of ideas for this person. I’d love to share with them,” or something that even just makes you go, “Huh, interesting.” You find that thing. Then step three is asking an open-ended question about it, starting with how or what. “How did you get into X?” Or, “Wow, what was your process? What were you thinking about as this was happening?”

Those are the two questions that it’s so easy to keep a how or what in your mind, just those two words in your mind as you’re in conversation with someone and you want to get to know them better. You use those two beginnings of questions to try to propel you to asking a more powerful question than something that might get you a one or two word answer. Quick recap, number one, have a couple of questions to get started. Number two, when you’re in an interaction with someone, find that natural, authentic curiosity through your internal reactions to what they’re saying. Then ask an open-ended question about something that made you curious, starting with how or what.

My advice would be to allow the conversation go where it goes and enjoy the journey. That’s it, three steps. Now you’re experts.

Bob Bertsch: There you go. Thanks. We’re all experts now. Thanks for getting us to do that, Jessica. We really appreciate it.

Jessica Beckendorf: Ah, you’re so welcome.

Bob Bertsch: That’s it for this episode. Thanks so much for joining us. We hope you’ll give this practice a try and share your experience in the Practicing Connection LinkedIn group where people supporting military families practice the skills that empower us to work together so that we can positively impact our communities and help families thrive. You’ll find the link to the group on our website at We’ll be back next week with a practice for learning from each other. Until then, keep practicing.

Kalin Goble: The Practicing Connection Podcast is a production of OneOp and is supported by the National Institute of Food and Agriculture, US Department of Agriculture, and the Office of Military Family Readiness Policy, US Department of Defense under Award Numbers 2019-48770-30366 and 2023-48770-41333.


[00:13:42] [END OF AUDIO]


January 18
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