The following is a transcription of Voice of Bold Business Radio Program 61: THE Best Question

Program Notes Can be Found Here.

Transcript of Program 61 – THE Best Question

Jessica: This is The Voice of Bold Business Radio and I am your host Jessica Dewell of Red Direction. You are listening to ‘THE Best Question’. I have to tell you that I love THE best question. In fact, if you listen to my shows enough, you know that I like questions, you know I like to create questions on the fly. There’s a reason for that, and I think some of that comes through in the dialogue that Jeff Sherman and Scott Scowcroft have with me today in this panel discussion.

Whether we’re thinking about what do we learn about, whether we’re thinking about we have a intention, without motives, and where are we trying to go, how do we find common ground… I mean that’s just the tip of the iceberg here ladies and gentlemen. I want you to stay tuned, because right after this you are going to hear a fantastic conversation.

Before we get there, I want to introduce you to Scott Scowcroft. He happens to be our technical producer for The Voice of Bold Business, and he’s joining in on this conversation because he enjoys this type of conversation and thought-provoking process just as much as myself and Jeff, and I have to admit, what he does with the ‘Scott treatment’ reflects that. He takes something that you give him in video and he figures out what it is supposed to actually become, and edits it that way. I speak from experience. You guys listen to all these shows. You know it too now.

Jeff Sherman of ‘Sherman Speaks’ is the developer of core theory. It’s the quadrants of accountability, character, opportunity, relationships, and education. We’ll see you right after this.

Announcer (amid background music): Welcome to The Voice of Bold Business, the show that provides everything smart leaders need to evaluate situations, build relationships, and create solutions. Jessica Dewell candidly talks about the skills necessary to build tenacity, and do more with less. And now, here’s Jessica:

Jessica: The idea, what we want to explore is; How do we ask THE Best Question?

Jeff: It takes focus. Asking the best question actually takes gathering some information. But you can’t ask random questions to get specific answers. So you do have to be trained a little bit in information gathering. Cues and things like that. We’ve talked about some of that on previous shows that I recommend they look up. Asking the right question dials it in and that is something that they’re going to have to think about. So if we’re asking them commonplace questions, common consulting questions or common interview questions, we’re going to get their prepared answers. What we want when we ask a question is we want original thought. In other words, they have to compile the answer, and then you get such a better response.

If I said to you “Do you recall who gave you your favorite set of earrings?”

Jessica: I do.

Jeff: Do you remember when you got them?

Jessica: I do.

Jeff: Would you explain why they gave them to you?

Jessica: I gave them to myself. It was the first nice jewelry that I ever bought.

They all laugh

Jeff: Nice. But I said that someone gave to you! You cheated!

Jessica: People don’t buy me jewelry because I’m hard to shop for that way.

Jeff: Okay, but do you see what I’m saying about my question?

Jessica: Yes.

Jeff: Then you went to an answer that was more safe, because it’s going to take some initial thought, original thought I call it, to where you’re going to have to formulate the answer. But we are in a rush society, so we give out so many answers that are pre-programmed, and then we will follow them up with statements to make them fit. Does that make sense? Rather than actually answering the question at hand. So how do we help people answer better? We ask questions that cannot be answered in yes or no, and we ask questions that are going to open up something they like about their views.

We’re not going to open up people to talk about things they don’t like to talk about. So how do we open up a business to talk about their pain? They don’t like to talk about their pains. They want to talk about what they’re doing right. So we can say ‘Looking at your focus going forward, what are some of the opportunities for change that will amplify your success?’

Now I’m in the affirmative, and I’m not asking them to talk to me about what’s wrong. I’m asking them to talk to me about their opportunities that are going to advance them.

Jessica: Yeah, right.

Jeff: Wording. Wording and then just being honest with what information we’re trying to get. Remember I said we’re going to look at things that are going to take your company further, and issues you’ve been dealing with. Before we do that… and then you can go right in to your question about what will promote your company best going forward. They’re going to be talking about opportunities to change, but they just don’t see it that way. Now they’re going to come up with original thought and they’re going to not guard it.

The interview process is more about what do we do that helps them not guard their answer and not go to automatic answers.

Jessica: Yeah, breaks the norm. I like it. Do you have a hashtag around that? What are your hashtags Jeff?

Jeff: My hashtags are #BraveLeadership, #BraveLeaders. If you go to #BraveLeadership, you’re going to see all these posts that I love to make that are like spontaneous words of encouragement, or little things that help you remember how awesome life is. I put my little S in the corner, but I don’t really try to advertise with them.

Jessica: Okay, awesome.  Scott, how would you answer that question? How do we ask THE best question?

Scott: One of my favorite sayings ever is “A question well asked is an answer half given.” That’s actually a deeper statement than what it appears to be on the surface. Because you can ask, and a lot of people ask a question not because they want to elicit an answer from you, but that you have something in mind that you want to manipulate them into answering in a particular way. So that’s not a question well asked. A question well asked is one as Jeff had inferred that elicits perhaps, or either, an original thinking so you’re thinking out of the box or you’re learning something brand new, or it uncovers something that is otherwise hidden. If for example a person has a pain point, or there’s something that they really should address… if you ask the question in just the right way, then you’ll be able to bring that out so that you can, the two of you, look at the answer and then maybe come to some sort of a resolution. But in order for that to happen, there’s something deeper that has to be established first, and that is trust. If you don’t have trust between the two of you, then that’s a barrier to the answer being given. That’s how I would begin to answer your question Jess.

Jeff: You’re saying in the preparation of a communication where you’re going to ask someone to dig a little deeper Scott… you’re saying before you do that, even the most prepared questions will have less efficacy if they are not built upon a trust. So maybe the best thing to do is to ask questions that open up vulnerabilities a little bit, we get more comfortable with the person, and they don’t feel they are being interrogated, they feel like they’re communicating openly about common issues or common causes, right, and that trust builds. You know, we say to people, ‘build trust’, I wonder if they know how you actually do that?

Jessica: Right. That’s very good. How do you do that?

Jeff: Well I like to get them talking about themselves. If they talk about themselves, then generally they’ll share cues that I can use for comfort zones. Then I talk a little bit about myself, so they can now relate. They can now build common ground, and that’s where I think that trust starts.

I remember coming in to a meeting, and I don’t recall, but it was like my shirt was spilled on, or something was wrong. You know, maybe I had two different shoes on… And it just put everybody at ‘okay, we’re human, right’? It was a laugh and we all laughed and then we started talking and the meeting was amazing. It lowers tension. So I think getting them to talk about themselves, to recap, sharing something about ourselves, build upon common ground is probably a great start.

Scott: You ask a person a question about themselves and what happens to their body language? They kind of tense up.

Jeff: Yes. Get those shoulders up.

Scott: I can only imagine you get past the introductory questions, and then you can start digging in to some more of the more interesting components. That only really happens if there’s also a little bit of a sincerity there. If I’m asking questions, Jeff, and you kind of, you know, people can smell a rat a mile away, and if you’re seeing that I’m asking these questions and I’m really not interested in you, then what type of answer is that going to elicit?

Jeff: It elicits the answer of ‘What is your point? What are you getting at? Why are you here?’ If you’re insincere, or you’ve got a little too close to the pain too soon, they’re going to say, ‘Is there a point to this?’

That would be a great topic; how to ask the uncommon question.

Jessica: Let’s do that. What’s the process? I mean if we’re looking for uncommon questions, what’s the process to find them?

Jeff: Who are you asking questions to? A total stranger? A spouse that you love dearly? A neighbor whose dog got in your yard? We’ve got to know the relevancy. We have to know the parameters of the conversation. Then we need to look clear ahead at where we want the conversation to go, because if we don’t have an end result, then you and I and Scott… well we’re just talking. Neither party knows the end result. But if you’re upfront with your question, ‘today I’d like to get to the deeper end of your fiscal year compared to last year and I want to do that by looking at opportunities’, now they’re putting it in to a mindset, they’re comfortable, and they’re not going to ask the question where is this headed. They already know. So we put them at ease on the end, we put them at ease at the start, and we know each other’s communication and the purpose for it, now that’s going to help a lot, just right there.

Jessica: Do you want to add anything Scott?

Scott: The opposite of questioning is listening, I guess. How can you listen if the other person is not talking? I guess maybe that’s the juxtaposition. If you can elicit the response from the, in this case the employee, that’s half the battle. The other half of the battle is the topic. It’s up to you to decide the purpose for the meeting and what the end goal is and then to guide the conversation so that it will be in that arena. It can be… (overlapping voices) when you’re talking about supervisor, you’re always thinking disciplinary or there’s something wrong. It could be that there are things that are right. Employees have so many great things to contribute, and you can set the tone and the atmosphere to elicit their great ideas by listening to them through asking the right questions.

Jeff: That was so well said. I’m glad you captivated that. Let me ask a follow-up question. (Scott makes a face and straightens shoulders) See how that worked?

Jessica: Like it. Yes.

Jeff: Let me ask a follow-up question Scott. And it just totally put you at a position to be ready.

Scott: Did you notice my body language?

Jeff: Yeah, you were like ‘oh cool. I’m ready’.

Scott: So how did you know how to do that?

Jeff: Gosh, I guess it’s just years of actually trying to think what am I going to do to enter this conversation fairly and draw out what it is we’re both aiming to do from this conversation.

Jessica: So I think it’s my responsibility to show up and interact with you guys, and be ready to answer your questions, because I understand why I’m here as much as you understand why you are here. Because then we get this idea of a place of, okay, we’re going to know pretty quickly if we’re not on the same page, if we have two different intentions, and then we can figure out how to close that and find some common ground. Or, I mean, what’s the worst that could happen? You reschedule the meeting, or you find out you didn’t need it in the first place and you’ve got an extra 30 minutes somewhere in your day. Right?

Jeff: You said we begin to work together to take it where it needs to go. I think that is the mutual respect. You came prepared, we came prepared, now, here’s where we’re headed with the conversation. Oh, we needed redirect. Let’s redirect our thoughts. To be vocal about expectation throughout the conversation, and if it goes a different route, we should be able to clearly state… this is really important information, it is different from where I was heading on my initial goal of this conversation, and we need to be able to pull it back in. But what if you came to a meeting and you didn’t know what you were going to ask?

Jessica: This happened to me recently. Showed up in a situation and what you expected to be happening was not what was happening, yet there was not enough knowledge of each other for me to actually speak up and say ‘what is going on here?’ It continued to spiral out of control, and I was like, okay, I guess I’m going to go with the flow here and we’re going to just get done, because this person had an intention so different than mine that once I realized what was going on, it was easier to just get through than it was to try and redirect at that point.

Jeff: Think about your conflicting conversations, like when you had a disagreement. Let’s say it probably escalated more than that. It’s when you go in without a common ground, you state what you’re going to state without letting the person know the end result. They have no idea the perspective you’ve taken prior to the meeting, and you jump in. We do it because it’s been on our mind… we’re going in to something someone else was thinking about what fertilizers they are going to use on their grapes tonight when they get home.

All laugh

Jessica: Okay, that’s funny because I don’t live around where you grow grapes, so I’m like, why would I fertilize the grapes I’m going to eat at the dinner table?

Jeff: I said grape-vines didn’t I? I hope so!

Jessica: If you did I missed the vine part! Laughs Hilarious!

Jeff: That’s a perfect example!

Jessica: Perfect example, yeah. I like the humor here though.

Jeff: Scott do you think selfishness played a part perhaps? I want my communication to be what I want it to be about, and I’m going to leave it out, you know, or something like that. Selfishness I think has to do with communication.

Scott: One of Jess’s other guests on The Voice of Bold Business I heard was Tom Rhodes, and you reminded me that he once said that he goes in to meetings without any questions in mind at all. What he wants to do is have the people go around the table and for them to contribute whatever it is that they want to contribute, or they have to contribute. He doesn’t go in with any questions ahead of time. He lets what they have become the agenda for the meeting. That’s his management style. Does that mean that selfishness is bad? Well I don’t know. Maybe it’s like technology. Technology is neutral. You can use it for the forces of good or the forces of evil, or whatever. Maybe that’s not a very skillful question that I would be asking if I were to be asked is selfishness good or bad. Somewhere along the line, what’s popped in to my mind is that there’s another realm of asking questions as well… and that’s a prosecutor in a court of law. So you’re up on the witness stand, and you’ve got a lawyer decide it doesn’t matter… they’re asking questions not to elicit information from you but to… well I mean that’s the case, to elicit information, but they’ve got an agenda. They’ll ask a question and then a second and a third, and by the time they get to the fourth or fifth question it’s like a chess game, isn’t it? You’re checkmate, because you said this that and the other thing, the only conclusion that we can have is that my defendant is not guilty!

Jessica: How do you know if somebody has motives when they go in to a meeting like that?

Scott: Well, transparency.

Jessica: How many people do you know that are actually transparent?

Scott: A lot.

Jessica: We talk about it a lot, but that’s a skill that a lot of people still have a long way to go.

Scott: I want you to chime in on this Jeff, because I think you’ll have some really valuable things to say. If you’re in a well…

Jeff: I’m glad you think that.

Scott: I do. Sincerely. If you’re in a well-organized working unit, doesn’t the leader of that want to set a tone that is transparent so that people won’t have to try and read between the lines? That you can quickly get right to the point and you don’t have to try and expend extra energy to figure out what’s really going on, because it’s there. Everyone is transparent

Jeff: This goes right back to where we started a little bit ago of… what are the parameters of the meeting? What is the end goal? Why are we together? Those things have to be understood or else we go in to some form of assumptions that we almost base assumptions on former schemata of this setting, or ‘last time I was here in this room this what happened’. We have to state up front what we’re doing. I think it’s true with any meeting. You know, Mr. Rhodes says that he opens it up to thought. I love that. That’s a great approach. ‘Ladies and gentlemen, in this meeting today, we’re going to open it up to thoughts that you’ve been having. We are going to go around the room and then we’re going to share things that are on our minds.’ Doesn’t that put an understood parameter and an understood reason of the meeting? But if I did that six meetings in a row, and then I came I and I started talking straight out and started asking questions and wasn’t allowing anybody to talk, they’re going to feel like somethings wrong, and it might just be that the last six times I did that, I didn’t take a turn, and I want to do it now.

They all laugh

Jeff: Right? But they will not see it that way because they don’t understand the norm is shifting. I think, there’s so many meetings… it takes a really good meeting to get anything done. It’s almost better to have no meeting and just talk to people one-on-one. If you’re going to pull that many people together, you ought to know what the focus is. They ought to know what the focus is. They should have time to have thought about some things. Then when you come in, ask questions that are refreshingly new about those topics that will create initial thought. You will get better answers, you will get more resolved, and they will have buy-in because they’re not pre-programming the solutions for the meeting of the day. If they go in without any thought at all towards it, then their thoughts are going to be sincere, but they’re going to be so random because they haven’t placed them in context.

Contextual meeting, with an agenda, clearly stated questions, respect for the answers, and don’t you love it when someone acknowledges you for having contributed to the meeting with at least, ‘Jessica, thank you for that, that was well said.” Or, do we like ‘Okay Scott, what are your thoughts?’. You know what I mean? A little recognition, a little humanity…

Jessica: Is a big deal. Now, what about people who have their paradigms set? They have their life experiences, they have their conditioning… and all of us do. We all have some kind of conditioning that we’re working with. So thinking about conditioning, I would be curious, when that becomes known or felt or experienced in some way, what are the steps to start building that bridge?

Jeff: Not only should we speak to be understood, but we have to actionably make sure that we’re not misunderstood. There’s a big difference.

Jessica: Say it again.

Jeff: We should speak to be understood, yes. But we should also speak to never be misunderstood. One may very well understand what it is we said, but without proper inference, wouldn’t it be a total misunderstanding?

We tell a child do this and they go do something that’s perfectly in harmony with what we said, but it was out of context. So they understood what the words could have meant, but they misunderstood the meaning.

Jessica: It’s the perfect example because we do that at work too, don’t we? Leaders that are around doing what they do… they say to go do something, and if there is not that shared meaning, that common ground, that place that everybody’s working from, the result is going to be in line with the words that were said or with the understanding of the individual, yet it was out of line with what the actual initiative or the goal or the milestone might have been. You make a really good point there, and it’s an extra responsibility as somebody who leads people, for telling them to go so something, or asking them to show up and contribute in some way, and if there’s no understanding, there’s just unnecessary dissonance there.

Jeff: It’s not like we’re going to sit down and think about every meeting we’re going to go in today.

Jessica: Right.

Jeff: Somebody stops in my office and says, ‘Hey can you shoot in to my office for a minute?’, I don’t have a context. But wouldn’t it be better just to say instead of saying ‘Hey jump in my office’, wouldn’t it be better if we actually got good at this and we came in and said, ‘I’d like to speak with you about AT&T and that concept we were putting together for them. Will you have a few minutes shortly?’ Oh, absolutely. Now, not only am I finishing up whatever I was doing, I’m anticipating what the meetings about. Am I not that much more prepared when I walk in that room, and is that not going to lower the dissonance as you said, or create more clarity? No, we shortcut… because we really haven’t gotten in the habit of seeking clarity on what comes out of our mouth.

Jessica: mmmmm   shoot. I am guilty of that all day long because I have so much fun in life, I just assume everybody’s in my head, like, ‘yeah, come join my party’.

They laugh

Jeff: That is right! We should live with spontaneity though!

Jessica: I know. So when somebody says, “What did you just say?” or, “Can you reframe that another way?”, I’m like yeah, absolutely, and then I realize no, this person is sitting next to me, they’re not a part of me, got it… and we can keep going. I’m glad I can laugh about it, because I know some people would never admit this, let alone acknowledge that that could even be a possibility. It’s just good to know about ourselves. If I were to pick a skill on how to ask the best question, that’s probably the skill I would pick. Just understanding what you were just talking about… the words I use. Communication is a skill, but I don’t mean it in here’s how we have a conversation and get to a common goal. It’s am I saying what I actually mean to say?

Scott: From the context within which you’ve asked your question… it occurred to me that the most valuable skill is to have your act together in the first place. In other words, if you’ve got your act together on the inside, and then you’re able to bring it together into a well-formed question, then you’ll be able to do that. If you’ve got confusion within yourself, or confusion within your organization, then you cannot possibly manifest something that’s “together” in the form of a question or statement. I’m thinking back on the handful of people who’ve really impressed me in terms of meetings and so forth, and they’re the ones who are able to just not say much during the meeting, but when they have a sentence… it’s a simple declarative sentence or a great question… and it’s obvious to everyone in the room that they’re right, or that that’s the direction that we should be going or that they have hit the nail on the head. They haven’t hit the tomato on the head, they’ve hit the nail on the head.

Jeff: Or the grapes.

They all laugh

Jeff: Spot on. How can we be something more to our guests if we can’t provide it within ourselves? I must listen without bias when I ask a question… or I’m going to hear the answer I was wanting. I have to ask a question that is thought out and spoken with clarity, but even more importantly, without bias. I have to seek for an answer. And I need to listen without bias. Now that’s a work of art. That’s a lifetime pursuit. Wouldn’t it be nice if each other on the sides of the table was listening to one another without bias?

Jessica takes a deep breath

Jeff: Breath that in.

Jessica: I know, I’ve got to breath it in. You heard my brain explode.

Scott: And you heard mine calm down.


Jessica: You will find all of the notes at You can also search for “THE Best Question”.

From building trust, from slowing down, from understanding what the process is, from recognizing your motives… all of these things come in to play when we’re talking about the best question. We ended with three skills that if you choose one to practice, you will practice in to better questions.

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Being a leader, and what it means today really starts with us and our experiences and what we’re learning along the way. We want you to share your story, your experience, to develop what a leader means and how that impacts our businesses every day. We want to know from you how do you ask the best question?

Announcer – Subscribe at and get more information, program notes, and past episodes. Bold leaders approach each situation and focus on action to achieve a higher level of leadership. Jessica Dewell, your business advocate is the host of The Voice of Bold Business Radio. Thank you for joining us.