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Podcast Episode 098 : One move ahead, how to listen like a chess grandmaster – Scott Sandland

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One move ahead, how to listen like a chess grandmaster – Scott Sandland

Scott Sandlin is the CEO and founder of Cyrano –  a software company that helps corporations and people to listen better.

Scott is one of the youngest ever hypnotherapists. Now, he focuses his time and effort on building a company about empathy and strategic linguistics.

Previously, Scott was director and CEO of a mental health clinic supporting issues including teen-suicide.

He’s been published in Psychology Today and Forbes Entrepreneur magazine. He has presented at the United nations AI global conference for good.

Scott explains how single and multiple conversations are as strategic as a game of chess. Each word has a different value and a different way it can move during a conversation, with each of those moves providing you with more strategic options in your conversation.

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Podcast Episode 098: One move ahead, how to listen like a chess grandmaster – Scott Sandland

Scott Sandland (00:00):  What are the sentences our agents need to be saying to increase sales. What are the words that increase closings? You’re asking the complete wrong question. You need to be figuring out what to listen for not what to say.

Oscar Trimboli (00:28): Deep Listening: Impact Beyond Words. Hi. I’m Oscar Trimboli. And this is the Apple-award-winning podcast, Deep Listening, designed to move you for a distracted listener to a deep and impactful leader. Did you know you spend 55% of your day listening, yet only 2% of people have ever been taught how?

In each episode, we explore the five levels of listening. Communication is 50% speaking and 50% listening. Yet, as a leader, you are taught only the importance of communication from the perspective of how to speak. It’s critical you start to build some muscles for the next phase in how to listen. The cost of not listening, it’s confusion. It’s conflict. It’s projects running over schedule. It’s lost customers. It’s great employees that leave before they want to. When you implement the strategies, the tips and tactics that you’ll hear, you’ll get four hours a week back in your schedule. I wonder what you could do with an extra four hours a week.

Oscar Trimboli (01:37): Scott Sandland is the CEO and founder of Cyrano which is an AI software company that helps corporations and people to listen better. Scott is one of the youngest ever hypnotherapists. And later on, he focused his time and effort on building a company about empathy and strategic linguistics.

He used to be the director and CEO of a mental health clinic. He’s also a long-time technologist and spent a lot of time with purpose-led organizations. He’s been published in Psychology Today, Forbes, Entrepreneur Magazine. He’s presented his AI work at the United Nations AI Global Conference For Good. Today, we’re going to learn about how do you start to deconstruct what a conversation is using technology.

In doing so, so we’ll learn how to listen better as humans. Scott will take the time to explain how conversation and multiple conversations over time are as strategic as a game of chess. With each word having different values, each word having a different position, it can move to in a conversation. And each of those moves providing you with more strategic options in your conversation. We’ll learn about the transition from him listening to very complex issues in teen suicide and how he decided to reimagine the use of language in a commercial setting so that he can fund his quest, the quest to reduce US teen suicide.

Oscar Trimboli (03:26): A special thank you to Fallon who introduced us. Thank you very much, Fallon, for your timely and elegant introduction. I love the way you connect the dots in conversations. And I really value our very long-term relationship moving, I think, into our third decade now.

One of the things I would encourage you as a listener to the Deep Listening Podcast, if you think there’s somebody we should have on the show, please don’t hesitate to send me an email That’s And from there, sometimes, it takes a few weeks. And sometimes with our last episode with Commander Peter Scott, it could take up to six years to join the dots with the conversation.

Oscar Trimboli (04:19): Scott’s going to deconstruct a lot of mechanical elements of language. And one thing you may want to do is just take the time to think about not only how you listen in one conversation. How do you listen across the length of a relationship? That’s one of the distinguishing features of today’s conversation that I took a lot away from. It’s not only how you listen in the first conversation, but how you continue through the relationship.

Scott Sandland (04:52): The cost of not listening is humanity. Communicating is the thing that defines humans. Birds have feathers and different types of birds. A peacock has the big feathers. And deer have antlers. And camels have humps. And humans have complex communication. And that’s why we run the planet. It’s not thumbs. The reason we run the planet is because we can exchange complex ideas and transmit education. And half of that is listening. And so, the cost of not listening is evolution, global supremacy, the definition of our species. Listening is the most human thing there is.

Oscar Trimboli (05:37): Scott, when it comes to conversations you have had, what really frustrates you when other people don’t listen to you? What do you notice?

Scott Sandland (05:44): It’s the type where you have a natural pause in your conversation where there’s a moment of sort of like a comma in the sentence or a moment to kind of reflect and take your time to point towards where you want the next half of sentence ago. And the person jumps in there because they don’t realize you are not done with the thought. It sort of betrays this moment where they’re waiting to talk. And they’re not giving you time to fully develop your thought. That is the thing that frustrates me more than anything when someone’s not listening.

Oscar Trimboli (06:19): When it comes to your listening, Scott, what do you struggle with?

Scott Sandland (06:23): I’ve got a couple siblings. And so wanting to have everyone’s attention at dinner was definitely a thing growing up. And I’m fortunate that I’ve learned enough to appreciate not doing it. It’s sort of morphed in me that I get distracted by trying to come up with the best next question. And so, my intention is good. For me, my challenge is while you are talking, I’m almost racing ahead to think, “Where’s Oscar’s thought going? And what are the interesting things that I can do to add to the conversation and to build and grow?”

Oscar Trimboli (07:07): Tell me more about jumping ahead, thinking about the next most interesting question.

Scott Sandland (07:15): When I was seeing clients, I used questions and strategic questions and motivational interviewing, and that kind of work to really drive the process. I was very much leaning forward during sessions. And I think a lot of people in professional services have this. It can be a financial planner who’s thinking I have an agenda. And I know the outcome we want to get to that is best for this client and to my job to help us get there. And they’re going on a tangent.

And I’m not certain if that tangent is going to end up in a productive place or not. But I’m confident that where I want to go is. And so, I have to figure out what I want to do with my ego right there to either drive or facilitate. And then, all of a sudden, you have that as a process. And all of a sudden, now, you’ve got these layers of distractions in between you and being present, which should be the goal.

Oscar Trimboli (08:13): One of the things we talk about is a difference between holding the agenda and holding the process. In this example you’ve just mentioned, you talked about the financial planner, noticing that the client may be going off on a tangent. I think there’s quite a big difference between those who are fixated on their agenda and those who are fixated on the unifying process.

Scott Sandland (08:39): Yeah. There’s process versus outcome-oriented conversations. And the most enjoyable conversations are the ones where both are open. And it just naturally flows. And there are times in especially professional conversations or at least agenda-driven conversation where you have to make a decision whether you want to drive this thing or show enough respect for the process to be patient in it.

It’s more enjoyable when you are patient and it works out. And there are also times where you give the conversation and the other person the conversation space to do that. And one of you or both of you fall short of that miss. And so, it just kind of derails a little bit. And so, in the professional version of that, you start thinking to yourself, “Well, I’m the professional here. I’m the one who the onus is on me to make sure this conversation is productive because, ultimately, they’re paying for productive insights.”

Oscar Trimboli (09:46): Scott, Cyrano’s about coding, language, conversations, sales conversations, any workplace conversations, really into computer software. Where did it all start?

Scott Sandland (09:59): So the origin of that idea was teen suicide. I was the CEO and executive director of a mental health clinic. And we had a staff of about 10. And we had life coaches. We had psychotherapists. We had a broad range of professionals on the team. And we were working with a lot of at-risk teenagers and a lot of drug-addicted adolescents and young adults.

The clinic was absolutely working. And we were getting good results with the people we were working with. And we had a good caseload. And one day, I just walked in and I just said, “I feel like a garbage man.” There was a room. We had a group therapy room that had about 30 women at the time in the room doing group therapy sessions. We had one or two of the other treatment rooms that were full right then.

And I looked my clinical director in the face, and I was like, “Every one of these people didn’t get here early enough.” By the time all these people came to us, the problems gotten really big. And we need to get on the prevention side of things rather than the treatment side of things.

Scott Sandland (11:09): I looked at teen suicide as the second leading cause of death under 24 in America. And the numbers are terrifying that over the last 10 years, the average number of suicide attempts per day just for high school students, that’s just a four-year window, is 3000 attempts every single day. 80% of which had very clear predictors associated with them and cries for help in advance.

I watched teen suicide double while I was running my private practise. And in some demographics like 14-year-old girls, it tripled in that amount of time. It’s cross-cultural. It’s not connected to socioeconomics in America. We’re the richest nation on earth, and all the kids are killing themselves on purpose. And I just said, “I can’t think of a more important thing to invest everything into it. It’s everything.”

And I understand why some people would want to be talking about climate. To me, it’s very difficult for me to understand why anybody would want to tackle anything other than children are killing themselves at record paces. And so, I knew the only way to attack that problem at scale was with technology. We just need to build AI that approaches conversations strategically.

And they’ve built AI that can approach chess strategically and video games and poker. And they can bluff. And if they build a robot that can bluff and they build a robot that can beat me in chess, you’ve got to be to figure out how to build a robot that can listen and respond strategically and to look at all the words and phrases in a conversation the same way you can look at all the pieces on a chessboard.

Oscar Trimboli (13:08): What are we not listening to in that moment?

Scott Sandland (13:12): A lot. I’ve obviously had a lot of really hard conversations with people who are struggling with that, or the family members of people who have taken their life. And there’s an underlying theme in enough of them to be statistically significant that it’s about a belief that the future can’t be better than this, and that this is as good as it’s going to be, the idea that it can’t get better. It’s going to get worse. This will ultimately kill me or make my life so miserable it’s not worth living anyway, whatever it is, that it’s sort of a foregone conclusion that the suffering just won’t be worth it. And they’re not able.

There’s this term self-efficacy. So it’s just efficacy pointed towards self. Are you self-effective? Are you able to improve your situation? Are you able to conquer the obstacles in your life? And increasingly on this planet, children at a younger and younger age are exposed through social media to larger existential problems that they’re not ready for yet.

And whether that’s cyberbullying or climate change, 13-year-olds with a very underdeveloped brain, the brain’s not done until about 24. You get these kids that should be learning how to play the trumpet or learning how to dribble a basketball. And these kids are looking at massive existential problems and corruption and cyber-bullying. They just see, “Okay, well, it’s a rig system. And the world’s on fire. And what if I can never buy a house? And college is expensive. And a bunch of people are mean to me on the internet. And what’s the point?”

And if you’re a prisoner of that moment and you can’t zoom out and many of them can’t understandably, and if they can’t get to a perspective where they’re zoomed out enough to see hope, there’s a lot of evidence pointing to their belief system

Oscar Trimboli (15:32): As an adult in that situation, what should I be listening for?

Scott Sandland (15:37): There’s a lot of things to be listening for. And that’s the trick because I give talks, and I go to these places. And people ask me what should I say to them? The thing I say is “You shouldn’t say anything.” You need to listen to them. And, obviously, your question is more thoughtful than theirs and more productive than theirs, but equally well-intentioned.

And there’s a number of things to be listening for. One of them is incongruencies or fallacies in their beliefs that you can use to leverage and look for those sort of logical gaps or things where there’s an incongruence. And our brain is doing the same thing with confirmation bias. And so, if we can pull a little bit in the other direction, it’s much more like physical therapy. You’re trying to build some muscles with very targeted, lightweight, high repetitions, and getting them through your questions to start thinking about those things that flex those little muscles that becomes the game.

And so, it’s a lot of little lifts, not big ahas, because they don’t get there from one moment. That’s a big misunderstanding that there must be something traumatic. There must be something bad that happened. And overwhelmingly, that’s not the case. Overwhelmingly, it’s not one big, bad thing. It’s a hundred things that knock them 1% off target every time. And so, there isn’t a magic golden question that pulls them all the way back on track. You’ve got to do the similar kind of path.

Oscar Trimboli (17:21): Scott, what’s the origin of the name of the software.

Scott Sandland (17:25): We call it Cyrano. And that’s a play called Cyrano de Bergerac. And because I’m in tech now, a lot of the people who studied data science didn’t take a lot of classes in the humanities, Cyrano was the first play, the first story with the idea of one person who knows what to say whispering into the ear of the other person so that now this guy in that case can say what is being whispered into his ear to the girl so that the girl will fall in love with him.

And so that idea of just whispering, “Say this. Say this,” and the person doesn’t know why they’re saying it. They just trust the source. And they say it, and it works. It effectively makes the other person fall in love with the user rather than the source of the words.

The idea is I want to make your customers fall in love with you. I don’t want any credit. I don’t want anyone to learn our name. I want everyone to learn your company’s name. Our software can plug into other software so that, that software gets better.

I wanted to solve team crisis stuff with our technology. But there were two big problems that we were facing. One being funding for that, and the other being getting enough data to refine our models and our systems so that it would work highly effectively because, in AI and machine learning, your system obviously is learning. And that means it starts off at maybe okay, maybe a little bit worse than okay, and then gets better and better over time.

Scott Sandland (19:07): In the space that I’m talking about, mental health and in crisis, you don’t want to test your theories on that vulnerable population. Ethically, that’s a terrible idea. Getting from point A to point B has a lot more ethical guardrails in place when you’re looking at something so important. And also, the data is terrible because if I’m a clinician and I see a 15-year-old girl in my office, and I say, “How are you,” and she’s crying and says, “Everything’s horrible. I’m bad. I hate everyone,” then, I see her the next week, and she’s kind of bad, but maybe a little bit better.

And then, I see her on week number three, and she’s happy. Did she get happy over three sessions because I’m really good at my job or did she just get an A on her AP US history test? Did she just make the volleyball team or get asked to prong. That missing data from the dataset corrupts that outcome. And all of a sudden, you don’t have something that you can train on. The soft science’s clinical outcomes side of things is really bad training data for stuff like this.

But sales is not. You can compare apples to apples. It’s fairly binary on sale no sale. There’s a lot more of that data. And it’s a lot better organized. But I looked at this and I said, “If I can do a good enough job training this system on high ticket, high lifetime value, important conversations, and sales cycles, I can do a transfer learning system and see how much better that’s made all my base models for the social good side of things.”

Oscar Trimboli (20:48): Many people have concerns about the ethics of AI used in this context that a lot of people think about AI through the lens of how old it is, and how old it could process language at. Are those fees founded?

Scott Sandland (21:09): It’s easy to write an article saying AI is scary. And AI can be used in a scary way. But I’m not scared of AI for quite a few years. I am much more scared of people than I am of robots because people inherently have personal motives and self-interest. And an AI has outcomes that it’s optimizing for that are agreed upon. And they’re passive systems. They do what we want. And so, it’s the humans we should be paying attention to.

Thinking about these systems as it relates to age is useful. It’s a nice shorthand like sentiment analysis, I think of as an age level. Sentiment analysis is about a third or fourth-grade reading level. It’s not very advanced. And most linguistic systems today are talking and really pushing and promoting. We do good sentiment analysis. Our sentiment analysis is great. And you’re like, “Fantastic. We’re going to outsource our decision-making for our sales organization to a fourth-grader.” And if we want to automate fourth graders out of the sales jobs, that’s fine. But I don’t think that’s a real strong need.

Oscar Trimboli (22:25): Conversations are full of infinite choices. Cyrano needs to understand these infinite number of choices. It needs to listen and then whisper in somebody’s ear. Scott, what kind of classification, categorization do you use to divide a conversation up so it can be used by software? Do you think about adjectives or pronouns, positives, negatives? How do you start to structure something like a listening engine when all you have is a blank sheet of paper?

Scott Sandland (23:06): We really wanted to use the metaphor of chess as often as possible as we were thinking of it. And so, we look at different pieces of conversation, parts of speech like nouns and verbs or adjectives. And sometimes, it’s more about the strategic option value of those words in a given sentence. I want to buy a car. I can buy a car. I need to buy a car. I will buy a car. I did buy a car, right? Just changing that one word in the sentence changes a lot.

And so, if you think of that as a hierarchy of commitment, I want to buy a car, that’s what every car salesman thinks is the best sentence. Hey, I want to buy a car. Fantastic. This person’s going to buy a car. That’s just desire that’s missing a whole lot that allows you to convert. And so, we look at that. And we can say, “Okay, well this is sort of where they are in their commitment level.”

And so, real-time commitment to the thing being talked about is one of the first things we care about because that is the fuel. How committed they are gives us an idea of what friction they’re willing to overcome, likelihood that they’re going to actually convert when things get boring, and how much work you’re going to need to do to move them from where they are to where you want them to be.

So real-time commitment is one piece of that, and then also their priorities. Our system really cares about how you show up right now and what priorities you have. Are you prioritizing in this conversation for our relationship and feelings? Are you prioritizing for your ego? Are you prioritizing for process and structure so on and so forth?

And so as you start seeing the ranked order of how a person is prioritizing things, how committed they are, and also their communication and learning style like visual or auditory, you start putting these pieces together. And all of a sudden, that starts making the chessboard make sense. And you can say, “Well, with a person who is this committed and has this learning style and has this priority, well, that’s this type of chess piece.” And it can move like this, and it can attack like that. And these are the things it can and can’t do. And if you can label all the abilities of what each type of piece can and can’t do under certain circumstances, that allows you to build an AI system that can reverse engineer games to generate strategy.

Oscar Trimboli (25:50): Your story reminds me of when Jenny and I, my wife, are going car shopping. And the sales people, one, two, three, four, five, six, seven, eight took till the ninth salesperson to direct their questions to my wife rather than me. And that’s all we needed somebody to pay attention to my wife. Have you got some stories like that, that bring Cyrano to life?

Scott Sandland (26:21): Actually, our very first deployment was in car sales. We had a relationship with the general manager of this dealership. We showed up some stuff, and he said, “All right, we’ll try it.” We did a split test in the store for 120 days. We made a very simple app that half the dealership got and an easy thing. And we thought, “Okay, this is just a very lightweight web app proof of concept.”

And if we like this, then, we’ll start building something better. It was very hacked together. But after 120 days, we found that the people using our system sold 26% more cars. And more importantly, their time on the dealership lot was 44% less time because the car salespeople, they knew what to say. And maybe more importantly, they knew what not to say.

They were saving all the time of saying the things that were wrong and, therefore, hurting rapport that they would then have to overcome. So it wasn’t just time wasted. It was actually time saved doubly because there wasn’t also the backtracking that had to be done. And then, that same information could go to different departments in the sales cycle.

When you handed a person off from one department to the next department, that sort of archetype playbook went with them. And so every salesperson, every manager, every finance insurance guy, everybody through the chain all had this running start when they met the person. And so, they had rapport. And they knew where to go with it. And they loved using the tool, and they were incredibly sceptical at first. They were not open to it. But the results were sort of undeniable.

Oscar Trimboli (28:06): It proves the paradox that the deeper you listen, the shorter your conversations become because you’re talking about the things that matter. And the time spent in conversations is much more productive. Scott, I’m curious, what is this app helping the salespeople to listen for while the customers are looking for the cars?

Scott Sandland (28:33): We did this very easily. We said to the sales people, “There are 15 binary observations we want you to pay attention to about this person, lots of eye contact or little eye contact. They talk about their family or friends. They stay on task, things that are easy to notice that don’t take any training.” And like I said, there’s only 15 questions, and it’s the same 15 questions every time. And it’s yes, no every time.

And so, we just told the car sales people, “These are the 15 things you are going to be quizzed on in the middle of every single sale.” It’s a similar process everywhere when you’re buying a car. The idea is you show them a couple cars. You walk around a couple of cars. You look at some stuff. And then, it’s time for the test drive. When it’s time for the test drive, I take your driver’s licence. I go make a photocopy. And I get the key. And then, we go on drive. And right then, you walk away from your customer and you’re making a photocopy. And during that one minute, you answer your 15 questions, yes, no, yes, no.

And you know the questions because they’re in the order. You know what you were going to get quizzed on so you were paying attention to these. And it spits out, okay, here’s what you need to do on the test drive. Talk about this, and not that. And it’s very simple bullet points. Do this, not that. Do this, not that. Make sure they never feel like you’re surprising them. Make sure they never feel like you are wasting their time.

Talk to them about resale value. Do not worry about safety. Talk to them about prestige. Do not talk to them about maintenance. And we give them very simple bullet points for yes and no in a couple key categories. They can skim that very fast and then execute that on the test drive. It just tells them what to talk about while they’re driving the car around the block. And then, that same information goes to at that time all the other departments in the dealership. As you take that person from one desk to the other, everybody’s ready.

Oscar Trimboli (30:37): I think the backstory is really important to understand and where it started with Cyrano. Where’s Cyrano at now? What’s Cyrano listening for differently? I’m sure there’s many thousands of more users on the platform.

Scott Sandland (30:56): So we have almost 40,000 users on our Zoom tool right now. And all it does is just takes the transcript of a Zoom call. So it’s not listening to tonality, and it’s not looking at facial expressions. It’s just taking the words and phrases. And it does a report at the end of every call. You don’t have to press a button. There’s no interface. There is nothing to distract you. It just passively takes what was said by each person, and turns it into a report.

So you have a 20-minute or a one-hour Zoom call with two or 10 people. And at the end of that call, you get an email. And that email is about a one-page report on each person that was on the call. And it tells you, “Here’s a couple things you should know about them. Here’s your next steps. And here’s how to optimize for the lifetime value of this relationship.”

And the whole thing is really built around that, the idea of rapport, of connection. It’s not about how to close this person. It’s about how to make sure this relationship is the best it can possibly be. So we built it into Zoom. And now, we’re also in Gmail and Outlook so that you can take all the emails you’ve had with any individual and aggregate them together and say, “In your conversations, you’re showing up like this. They’re showing up like that. Here’s how aligned you to tend to be. And then, based on your context and your conversations, here’s advice we have.

Scott Sandland (32:27): So here’s how you should resolve conflict with Oscar because he’s probably mad at you right now. And here’s the ways to resolve that conflict that’s mutually respectful or here’s how to collaborate and brainstorm with him, or here’s how to negotiate against him without violating rapport so that you can still be productive on the other side of that negotiation.”

And so, we created all these different outputs that make it very simple, do this, not that. We want to whisper into your ear. And kind of going back to that metaphor of the play, Cyrano, there’s a comedy of errors that happens if you give the person too much whispering at any given time. It’s a wonderful cliché now in a lot of movies where the person puts the little earpiece in and then says the wrong things. And that’s been a real challenge for us from a user experience perspective that is not distracting and figuring out the time intervals on how frequently we should be giving you information and how long those bullet points should be so that it isn’t overwhelming.

Oscar Trimboli (33:33): Scott, let’s press end on this Zoom. And now transcript is going to come out. When you receive it, what is Cyrano saying about our conversation? And more importantly, what kind of report is it generating to help me understand how to connect the dots? I think it’d be great for those listening for you to join the dots in this conversation with what a report would look like when it comes out of Cyrano.

Scott Sandland (34:05): Oscar tends to care about things like relationships, the feelings of others. Oscar is interested in helping build up others. Oscar will be frustrated by people who appear to exploit or take advantage of. So you get a couple bullet points like that. Then, you’d say, “Next steps.” And it would measure our commitment in real time. And it would track how committed both of us were to the topics over time.

So it might notice we were trailing off or building up based on where you are. You should send a follow-up email of Oscar and include in it the people you’re going to send the link to, or the number and types of people you’re going to share this transcript with. And so you say, “Okay, now, it’s connecting to. It’s telling me what to do next steps with Oscar based on his priorities and his commitment level right now.”

And then, it’s going to say, “When working with Oscar, do your best to and give a couple pieces of advice there.” And right now, our system can generate about 28 billion different variations of these suggestions. I could have five conversations with you. And it would give me five similar reports because it would be about us every time. But they would be noticeably different.

So I would keep learning about you every time I had a conversation. And that also means that if I’m scaling out my sales organization and you’ve been an important customer of mine for the last five years, and now I’m moving into a different department or now I’m the manager and I have to bring in a person that’s going to now handle your relationship, that new hire can have the running start of understanding you without having to read all the emails you and I there exchanged or watch five videos of recordings of our call.

Scott Sandland (36:01): It can just get the synopsis, or before a very important conversation, I could take one of the recordings of your podcast or you on YouTube or excerpt from your book or your social media, and take you in your own words speaking about any topic. Throw it into Cyrano, and it’s going to say, “Here’s how to have the best first impression with Oscar.” Here’s how to make the most of this opportunity right now.

And rather than spending that first 15 minutes getting a feel for the person, which is a skill in and of itself that some people don’t have, many people don’t have, and it’s taken for granted by great sales people, it does that piece for you. So that first 15 minutes, you’re not feeling them out. You’re double checking to confirm it’s right. And then, you get to move with confidence with the advice it has suggested. So you get that first impression and nail it.

Oscar Trimboli (37:04): Scott, help us understand what Cyrano was actually listening for, for you to extract that Oscar values relationships?

Scott Sandland (37:15): In the last sentence, you said you used the word us and we. Instead of using the word I or me or you or I, you use the word us and we So you created a simple teaming. And that is an easy example of a choice you made because, ultimately, you’re talking about the same thing no matter what. So the way you talk about it is what matters. So it’s not necessarily about the nouns and the verbs. It’s more about the other words that are in the sentence. And we can see those words create themes.

And if you’re doing sentences that are us and we and family and my niece, my nephew, my daughter, my granddaughter, all of these words that are about the family, the unit and all that rather than just the topic at hand or just myself. It’s recognizing he’s thinking of others while talking about this which means that you are prioritizing things through those filters.

Oscar Trimboli (38:15): Scott, I always say one thing that people need to acknowledge that listening requires permission. And in your space, there are huge ethical and privacy dilemmas. How do you deal with that?

Scott Sandland (38:31): It’s critical. Number one, in Zoom, as an example, we won’t do anything unless the call is being recorded and everyone on the call is being notified that it’s being recorded. So number one, everyone knows they’re on the record. And then, the next thing we do is we anonymize everything. So we’re not looking at who said what? And then, the way we process and store the information is all done in aggregate and then very jumbled.

And that means that we can’t, we don’t have the ability as Cyrano to go back and audit or review any individual conversation after an hour or two. So we have the ability to like some quality control immediately. But that goes away. And then, everything gets aggregated and anonymized and really jumbled around and pulled out of context. And we built it this way on purpose. We can’t use it to create a long-form dragnet on a person.

Oscar Trimboli (39:36): Scott, the final question about where Cyrano is now in its life cycle, you’ve collected all this complex high-value, high-risk relationship conversations in a commercial context. How is that helping you to move forward the model that you are really most focused on, this is the model to reduce teen suicide?

Scott Sandland (40:05): There’s a few pieces. One is we get to refine our models. We get to prove efficacy in places where it’s easier to prove, obviously, generate funding. All those are great.

But from just a data science side of things, there’s a process called transfer learning. What it means is you can build the system to get very good at doing something in one domain. And by building up in one domain, it’s developing resources that can then be applied to domain number two. And so, we’re picking domains on purpose that lend itself actually to the pieces that we care about.

We are avoiding anything that is one-dimensional transactional processes. What we are not doing is going for high-volume sales. We want high-ticket sales, emotional sales. Residential real estate is the number one focus for us right now. And retail automotive is another good one, financial services and legal. And so, when we’re looking at legal depositions, these are emotional conversations.

When you’re taking the real estate conversations that are having, these are people in one of the largest financial investments of their life. And so, we are able to measure a person talking about things that are emotional and complicated over a multi-conversation span. And so, that life cycle of that conversation and seeing the patterns that emerge in that generate data for us that’s useful in that way.

Oscar Trimboli (41:49): What I took away from listening to Scott was how he was able to tune in to the way I use language and notice the value I place on relationships.

It’s an interesting inspection for me to have a mirror held up to me about the way I use my dialogue and what signal that is sending to the listener. I wonder what signals you’re all sending to the listener while you are speaking. I wonder how conscious you are of the patterns, the chess pieces that you’re using in a conversation. Are you adopting a mindset of advancing moving sideways?


Are you looking at the piece for the next move? Are you looking at the whole chessboard, or are you looking at the relationship across multiple games? I think Scott did a wonderful job of pulling apart what Cyrano is doing to listen to all of those things. All of this reminded me of the Deep Listening playing cards, especially listening for the context and card 38, which you can find

Oscar Trimboli (43:08): Card 38 is about the concept of patterns. It says everybody has a unique speaking signature based on their education, their experience and their cultures. Their speaking signature creates patterns through words, through sentences, and stories. The question the card poses is what patterns are you noticing while they’re speaking? I think this is a great question to hold as you know you’re going to be listening to somebody across multiple conversations, across a relationship. Notice their patterns. In selling enterprise software, I had to listen to a lot of patterns and working with one of the best salespeople.

Harry, he taught me many things about listening in these environments. Harry said to me, “It’s important that we show the software in its best light, Oscar. But we can only show it to them in a way that’s relevant to them.” He said, “Don’t turn up and throw up a whole bunch of features.” Listen carefully to what their business requirements are. And then, show them that you’ve listened by highlighting those business requirements.

Oscar Trimboli (44:29): In your software demonstrations, it’s no surprise to me that when I did, we were successful. And when I didn’t and when I didn’t listen carefully, the competition consistently won as well. I wonder where you haven’t applied strategic options in listening in your workplace conversations? I’ll be curious to know. Send me an email That’s, and share a time when you didn’t listen with a very strategic approach you just listened transactionally or maybe one move ahead.

I’m Oscar Trimboli, and I’m on a quest to create 100 million Deep Listeners in the world.

You’ve given me the greatest gift of all. You’ve listened to me.

Thanks for listening

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