Category: Investments
Air Date: 05.26.2021

How To Become A Trusted Advisor

Today’s guest, Brian Caffarelli, is a partner at STS Consulting. He shares tips and insight into how to become a trusted advisor. Don’t miss this episode!

Brian Caffarelli helps his clients grow their revenues and margins through a broad spectrum of sales effectiveness and relationship management strategies. Using a unique combination of his prior sales expertise and the organizational psychology insights he has gained through working at STS Consulting, Brian assists organizations in selling better and more effectively by helping them see the value of putting trust before the sale. In today’s episode, he explains that what makes selling so difficult is the fact that buying is equally difficult, and it’s important to put yourself in the position of the buyer in order to meet them where they are on the buyer journey and best serve their needs. Tuning in, you’ll learn more about the buyer journey, from problem to deal, and come to better understand the trust equation, a concept borrowed from The Trusted Advisor by David Maister, Charles Green, and Robert Galford. Ultimately, what has served Brian in his career was taking the ‘trust before sale’ concept to heart and realizing that it wasn’t about helping the buyer understand him, but rather about helping the buyer understand themselves. This is an insightful conversation full of practical advice and wisdom, so make sure not to miss it!


Key Points From This Episode:

  • An introduction to Brian Caffarelli and his career trajectory.
  • Brian explains that what makes selling difficult is the fact that buying is equally difficult.
  • The value of the ability to guide someone in making an informed and competent decision.
  • Hear about the buyer journey and why it is so important to meet them where they are at.
  • How conflict can arise when the seller doesn’t take the time to understand the buyer’s problem, which is step one on their journey.
  • Understanding the partner before the deal and putting trust before the sale.
  • The trust equation: earn credibility, demonstrate reliability, create an environment of professional intimacy, and manage out your self-orientation.
  • The emotional, affective, or heart-oriented elements of the equation that are most powerful.
  • Find out what intimacy means in this context and how to create it.
  • Creating intimacy at scale with many different personality types, starting with listening.
  • Why part of listening is asking really good, thought-provoking questions.
  • Why Brian believes it’s all about helping the buyer understand themselves.
  • The important role that showing vulnerability plays in earning the trust of others.
  • Learn more about self-orientation and how to go about minimizing it.
  • Some practical advice for listeners: think like a buyer, earn their trust, and be their guide.
  • One question the buyer should ask the seller: what would you do in my shoes and why?
  • Brian describes his proudest career moments; helping sellers realize selling isn’t so bad.
  • Hear his number one key to success, which is understanding trust comes before the sale.



“The buyer’s decision is bound up in their personal identity very often. There’s usually a lot of risk, either personal risk or organizational risk associated with the decision. The reason selling is hard is because buying is really hard.” — Brian Caffarelli [0:05:06]

“A really effective seller reflexively and instinctively thinks like the buyer and safely guides the buyer through the journey – problem, urgency, solution, partner, deal – to an informed and confident decision.” — Brian Caffarelli [0:10:01]

“Earn credibility, demonstrate reliability, create an environment of professional intimacy, and manage out your self-orientation. If you can focus on that, you can earn and inspire the trust of others.” — Brian Caffarelli [0:20:31]

“We ended up winning not because we helped the buyer understand us, but because we helped the buyer understand themselves.” — Brian Caffarelli [0:32:07]

“Early on in my career, a wise person told me, trust comes before the sale. Trust comes before the sale. When I was successful as a seller, it’s because I took that to heart and focused my efforts on earnestly inspiring buyers’ trust.” — Brian Caffarelli [0:48:07]


Links Mentioned in Today’s Episode:

Brian Caffarelli on LinkedIn

Strategic Talent Solutions

The Trusted Advisor

Kent Ritter

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Thanks for listening!

—Full Transcript Below—

“BC: There’s a client I work with and she really said something that resonated with me about a particular deal, an important deal for her term that they won. She said, “We ended up winning not because we helped the buyer understand us, but because we helped the buyer understand themselves.” 


[00:00:24] KR: Welcome to Ritter on Real Estate, the show about how to passively invest like a pro. On each episode, I interview real estate experts who give their top investing advice, strategies, and tools that break down the insights into practical steps to avoid the pitfalls and make better investments. I want to help you passively invest like a pro. This is Ritter on Real Estate, and I’m your host, Kent Ritter. 


[00:00:47] KR: Hello, fellow investors. Welcome to Ritter on Real Estate, where we teach you how to passively invest like a pro. Today, I’ve got a very special guest. He’s a blast from my past and I’m really blessed to have him on the show today. His name is Brian Caffarelli. Brian is a partner at STS Consulting. Brian and I met each other 8, 10 years ago at this point, back when I was a management consultant, and Brian taught a course on sales, and just effective selling. The principles have stuck with me through my entire career and as I’ve transferred into being a multifamily investor and into raising capital, and really those same principles ring true if you are really in anything in life, but if you are out there trying to raise capital, if you’re seeking partners, if you’re trying to build interest in your deal, I think all of those things have overlay back to what Brian is going to talk to us about today. Just so excited to have him on. Thanks, Brian, for coming on the show.

[00:01:55] BC: Kent, thank you. It’s an honor. I was delighted to be asked.

[00:01:59] KR: Yeah, well, thank you. So, Brian, tell the audience a little bit about yourself and your background and help them understand how you’ve become such a master salesman?

[00:02:08] BC: I’m hardly a master. So, let me just start there. Just from a background perspective, I spent the majority of my career, 25 years, at a firm called Hewitt Associates in a sales role or in a sales leadership role. I kind got the opportunity of a lifetime in 2007, to work on Chicago’s bid to bring the Olympic Games, the 2016 Olympic Games to Chicago. If you’re a fan of the Olympics, you know those games took place in Rio, so that didn’t quite turn out the way that I hoped.

After that, I was looking for a way to actually apply what I learned, the lessons I learned at Hewitt, which was largely how to win, and the lessons I’ve learned from the Olympic Games, which unfortunately was largely how to lose, in a more professional setting. I joined a firm called Strategic Talent Solutions, STS Consulting, and they’re primarily a firm of organizational psychologists that study human behavior and organizational behavior. I thought it would be interesting to be able to marry their insights as PhDs in psychology, with what I might have known or experienced in terms of how to sell and see if we could help organizations, small stuff and professional services organizations, sell better and more effectively. So, that’s what I do.

[00:03:21] KR: Just a proof point, I could tell you that that the lessons definitely helped us and my old firm sell more successfully and be more successful. So, it does work. I think that that’s an interesting mix, right? Because you’re kind of the blue collar, boots on the ground guy. You were doing it, you’re in the trenches, and you’re marrying that up with the academics and coming together and kind of saying, “Okay, what works?” and things that maybe worked for you. Maybe you didn’t know necessarily why they worked, and so they’re able to add that context. That’s really cool.

[00:03:51] BC: Kent, that’s exactly right. I didn’t know, if it worked. I didn’t know why it worked. And more often than not, if it didn’t work, I actually didn’t know why it didn’t work either. So, this has been very helpful for me.

[00:04:02] KR: So, selling is something that I think a lot of people struggle with, for many different reasons. Maybe it’s just getting over the mindset of not wanting to sell and the used car salesman, right image, or there’s a lot of different things. But why is selling so hard?

[00:04:21] BC: Well, Kent, I agree with those. A lot of different things that maybe make selling hard, but I think one thing that people – that makes selling hard and people don’t think about enough is that buying is hard. Buying is really hard. If you think about things from the buyer’s perspective, a lot of times there has to make a choice in an unfamiliar area for them. The choices that they might make are complex. There’s an overwhelming abundance of information out there right now. Some of it is conflicting, so it’s hard to make sense of all the information that’s out there. There are always a variety of alternatives. Each alternative is sort of saying it’s the best alternative to a particular situation. The buyer’s decision is sort of bound up in their personal identity very often. There’s usually a lot of risk, either personal risk or organizational risk associated with the decision. The reason selling is hard is because buying is really hard. I think buying is really hard and that’s what makes selling difficult.

[00:05:26] KR: I can relate to that just from a buyer side going through this recently. So, within our firm, we’ve been really focused on implementing new technologies. There are so many new technologies related to multifamily and we know that they’re going to be game changers, and we need to stay ahead of the curve, so we have to, but the problem is exactly what you said. There’s been such an explosion of prop tech, of property technology, that there’s so many players, so many different options. They’re all just a little bit different than the other, right? But largely, maybe may compare. There are big players, small players, and buying was hard, because it was difficult to know and be confident we were making the right decision, because there’s so many options, right?

When you get me thinking about that, I think that, why did we choose who we chose? I think there is something to the fact that, like, I think in some instances maybe the product just blew the others out of the water, but I think, at most, it was the people that I really resonated with because I think they made it easier. I think they made the decision easier. I think they provided the right level of information. They didn’t overcomplicate. They helped us understand how it was a win for us. As I’m thinking about the process that we went through, which was like a six-month intensive process to choose these technologies, I felt a lot of those things that you’re talking about on the buyer’s side. So, it’s interesting,

[00:06:53] BC: I think the way that you describe it, Kent, and sometimes the way that I think about it is that the buyer maybe would value or appreciate the services of a guide, somebody to guide them through their journey – guide them through their journey – so, just to go right to the words that you said, “help them make an informed and competent decision.” Because the journey is tenuous, it’s complicated, it’s complex, it loops back on itself, and so if somebody can guide them and help them make an informed, competent decision, that in and of itself might be the differentiating factor, not the product services or features so much, but the ability to guide might be the differentiating factor.

[00:07:34] KR: Right, so the concept of not focusing so much as the seller on the what, of the widget, the bells and whistles, but focusing even on kind of why they’re buying it and aligning with that purpose, and become a trusted advisor, if you will. It’s showing that you’re aligned to help them on their mission, whatever that is, help them accomplish their goal, build that trust, and then, as long as the the widget is fairly similar and working, there’s a likelihood that they will pick you.

Something that has stuck with me for let’s just call it 10 years, since you did the first training that I attended, has been this idea of the buyer journey and this idea of meeting the buyer where they’re at on that journey. Can you expand on that for us and explain the journey?

[00:08:33] BC: Sure. Kent, when we worked together, I think we talked about the buyer’s journey and in a relatively simple form, in that the buyer probably has to make five decisions. Five decisions. They might not be linear, they might not be sequential. But ultimately, the buyer probably has to come to the realization that, “I have a problem.” That’s the first step in the journey. A problem could be too much of a bad thing or not enough of a good thing, but one step in the journey is, “I have a problem.”

Another step in the journey is that the problem is so serious, I must solve it now. We all have more problems than we’ll ever choose to solve. So, another step in the journey is one of urgency, “The problem is so serious, I need to solve it now.” Another step in the journey is, “I see a solution that works for me.” There’s always more than one solution to any one problem. So, at some point in time, the buyer has to see the right solution, solution that worked for them. If there’s more than one solution for any one problem, there’s probably more than one partner or provider for any one solution. So, then there’s the selection of the partner. Finally, “I see a deal that works for me.”

If we think about the buyer’s journey, it probably has five steps, not necessarily linear, not necessarily sequential, but ultimately the buyer has to make five steps. Problem, urgency, solution, partner, and deal. Because you talked about the concept of a guide, a really effective seller reflexively and instinctively thinks like the buyer and safely guides the buyer through the journey, problem, urgency, solution, partner, deal to an informed and confident decision.

[00:10:19] KR: So, if I relate this to my world now, and in the world of a lot of my listeners, say, folks are trying to raise capital for the real estate deals that we’re doing. We’re seeking to attract investors, where our interests are aligned, and they want to invest. So, if I think about that, and said, “Okay, well, they have a problem.” There are multiple reasons of why people invest in the type of deals that we offer. If you don’t understand at the beginning, the reason that they’re doing it, it’s really difficult to help them along that path.

I love the idea of starting with the problem, because it may be that they’re in a job that they don’t like, and they’re seeking other sources of income to be able to leave their W2 job and be able to have that kind of “financial freedom.” It could be that maybe they like their job, but they want to find alternate investments, and they want to diversify, and they want to build wealth. So, they’re not as concerned about cash flow, like the first person. They’re concerned about building overall wealth, like generational wealth, right? Or it could be that they have the wealth, and they’ve got a tax problem. They’ve done really well so they’ve got a lot of taxes that they’re facing, and real estate is a way for them to offset some of those taxes.

There are different reasons why people come to the investment, so I think understanding the problem makes so much sense, because if you’re talking to somebody about building generational wealth and an estate for their grandkids, and they’re worried about cash flow now, so they can leave their job, like those things just – it’s just a nonstarter.

[00:12:04] BC: Kent, that’s exactly right. I want to go back to something that you said earlier about the importance of meeting the buyer where they are. I do think a good guide, an effective seller, understands where the buyer is in their journey and chooses to meet them there. I wouldn’t be surprised if you might say, sometimes, when I speak to investors, they aren’t quite clear on what their problem is yet. I wouldn’t be surprised if some of the greatest value you provide to those individuals is help them think through all of the things swirling around in their head as to what could be their problem and help them begin to crystallize what their priorities and objectives are.

[00:12:45] KR: What I found to be most effective is not getting on the phone with someone and saying, “Hey, I got this great deal. Let me tell you about it. Let me tell you about all these returns, and everything that’s going to happen.” The most effective approach has been just opening up the conversation to understand what their goals are, just asking their goals, because I think sometimes, you’re right, it can help them clarify if they don’t have them, but if they do have an understanding of where they’re coming from. What that’s doing, I think, is helping me understand the problem through their goals that they’re trying to solve. If you were to approach it from just, “Hey, I’ve got this great deal.” Well, the deal is step five on the journey. So, it just makes sense to me why that doesn’t work.

[00:13:26] BC: That effectively is the definition of that pushy or obnoxious salesperson that everybody fears they may be where the seller is at the end. I’m the guy, here’s the deal. I’m the guy, here’s the deal. The seller’s at the end, the buyer may very well be at the beginning of their journey, which is, “I’m not sure what my goals are. I have multiple goals. I’m not sure how to prioritize them. I’m not sure what they are. I’ve actually had these goals for a while. I don’t know whether I should act on them right now.” They may be a problem, urgency, solution.

The buyer is early in the journey and the seller who’s successful probably meets the buyer there, in their early stages, and joins them there. The seller that’s unsuccessful, puts their stake in the ground at the end of the journey. I’m the person, here’s the deal, and tries to just yank the buyer forward. That’s where that conflict happens and that’s, more often than not, a bad outcome for everybody.

[00:14:31] KR: I like what you said going back to like the pushy salesman. That’s what creates that feeling that we’ve all had of like, I feel like I need a shower. I just got sold to, I feel kind of gross. That feeling that we’ve all had. It’s that conflict of being at different parts in the journey. Wow, I think that that’s really insightful. So, you pick your partner, again, before you choose the deal. On my show here, on Ritter on Real Estate, we’ve spent a lot of time talking about how do you select the right deal sponsor. How do you pick the right partner? And how that has to come first in the process.

I use a term where a good sponsor can save a bad deal and a bad sponsor can kill a good deal. So, it starts with that partner and understand – so, it’s step four, really, but understanding the partner, again, before the deal.

[00:15:29] BC: Yeah. Two things on that, Kent. I think, which is understanding the partner before the deal, and you would have to help me with this. But I wouldn’t be surprised if sometimes the buyers or your investors make the partner decision even before they make the urgency decision, meaning that, Kent, at some point in time, we are going to work together. I am going to invest with you. But I’m not sure if it’s now. I’ve made the partner decision, even before I’ve made the urgency decision. That’s why it’s not always necessarily sequential, but things can happen in different orders.

[00:16:09] KR: Well, I think that’s a great point and I think that’s where patience really comes in. You have to have a long view of this. I view this as a 30 – I mean, heck, maybe even more year career. I’m building relationships with that mindset, that we’re all going to be working together for a long time. But I think you’re right, it will come because we’re putting out thought leadership, I’m putting myself out there, I will have conversations with people where they’re trying to find and vet and understand the sponsor, and they’re not quite sure if they want to invest yet. But they’re kind of interested.

I think that, again, is where you’ve got to focus on providing information and, like you said, helping them make an informed decision, and not pushing that deal. Again, it’s like not pushing the deal, but helping them. So, you mentioned the trusted advisor, right? It’s being that advisor to them and that’s really kind of how I view myself. I think folks that will be successful in this have to be themselves that way is you’re like a financial advisor. I mean, you really are acting in that way, as an advisor for these people that try to help them make good investment decisions.

You may have to do the work on the front end to get there. It’s not that everybody’s going to want to invest in that deal. But I’ve had plenty of people who maybe didn’t invest in my first deal, but have invested in my third or fourth.

[00:17:34] BC: Yeah. Kent, I think you hit on a really important term, when you and I are talking and we’re talking about the seller essentially being the guide, guiding the buyer through their journey. You might ask, “Well, why would a buyer let a seller guide them?” I do think in the end, the buyer will let sellers guide them if they trust the buyer. Trust really comes before the sale. If the seller is able to inspire and earn the trust of the buyer, then the buyer feels comfortable letting the seller guide them, guide them through their journey, because they know the seller’s guiding them to an informed and competent decision. It’s not manipulative. It’s not based on a specified seller outcome. I’m guiding you to help you make an informed and competent decision.

[00:18:30] KR: That makes a ton of sense. Even when I just think about what you said, I have no anxiety thinking about that. That sounds like such a smooth process. If you can build trust, and then bring them through in this kind of collaborative, trusting relationship. That seems like a very easy, smooth process. If you can build that trust on the front end. People won’t buy from you unless they know I can trust you. I hear that all the time. How do you build that trust?

[00:18:58] BC: That’s part of the reason I joined STS Consulting was because I wanted to learn from people that study human behavior. Psychologists help people grant trust, and inversely, how people can inspire and earn trust. When I think about how to describe it most simply, I actually really do like the framework that was laid out way back when, in the year 2000 actually, in the book, The Trusted Advisor by David Maister and Charles Green. Back then, the term trusted advisor wasn’t necessarily in vogue, it wasn’t a cliché, yet. It became a term because of the success of this book that Maister and Green wrote. When they wrote about trust, they structured their book in such a way that it was around an equation, a metaphorical equation about how to earn trust, and it’s a question actually.

Basically, what they said is, “You will inspire so much trust if you can earn credibility, demonstrate reliability, and create an environment of professional intimacy.” So, think about that as the numerator, credibility, reliability, and intimacy, and then divide it by your self-orientation. Since it’s a quotient, we want a really low denominator. So, if you can just drive yourself orientation as low as possible, we’re all oriented to self a little bit. But if you can manage out your self-orientation, make it all about the client, now, that’ll supercharge the quotient and inspire trust. So, earn credibility, demonstrate reliability, create an environment of professional intimacy, and manage out your self-orientation. If you can focus on that, you can earn and inspire for the trust of others.

[00:20:44] KR: Interesting. So, there are four components then to this equation. Can you walk us through kind of – well, I guess, first of all question is, do all of these things, all four of these components, have to be happening simultaneously? Or do you start with one and then work toward others? What’s the best way to approach it?

[00:21:05] BC: That’s a fascinating question. Folks that trust an advisor actually have a really interesting diagnostic, and some really interesting research around this. Basically, their diagnostic says that, often, we believe that the first steps in building trust might be focused on earning credibility or demonstrating reliability. We might just default there. Those are the aspects or elements of the trust equation that are more head-oriented, rational, cognitive, logical, head-oriented. But their research shows and, you can probably anticipate where this is going. But the research shows that it’s actually more of the emotional, affective, or heart-oriented elements of the equation that are more powerful.

Part of that is because I think what you said a little bit earlier, which is, at some level, all of the good people I speak with, I’m going to find credible and reliable. The competitive firms, I’m sure that you respect, they don’t really have people that aren’t credible and aren’t reliable. So, for buyers, they experience a lot of credible people and a lot of reliable people. It’s those individuals that create an environment of professional intimacy. Those individuals who sincerely manage out their self-orientation that then begin to differentiate themselves, rise to that higher level of impact, and inspire trust at a deeper level.

[00:22:46] KR: So, we’re narrowing in on, it seems like what the game changers are, where – sounds like what I heard you say was that the credibility and reliability, that’s kind of like table stakes. That’s like the baseline. If you want to be successful, you have to be credible, you have to be reliable. But like you said, any firm that’s successful is going to have credibility and reliability. So, then why choose firm A over firm B, right? And then you get into, okay, this idea of intimacy. So, what does intimacy mean in this context?

[00:23:22] BC: Kent, there, I think maybe what it means first, and then a little bit about how you get there.

[00:23:26] KR: Yeah. Yes.

[00:23:27] BC: One of my favorite assignments that I often get as a consultant is to interview the customers with my clients. Early on in my career, I would interview the customers and my clients, “Why have you hired Kent? Why do you like to work with Kent?” Et cetera or, “Why don’t you work with Kent? Why haven’t you hired him in the past?” And the phrase I heard over and over again is, “I like to work with this firm because they just get it. They just get it.”

What I found is when I tried to dig into, when I really tried to dig into what does “they just get it” means? What it meant was, “he just gets me.” Not “they get it.” It’s “he gets me” or “she gets me.” I think that’s what professional intimacy is all about. When I feel that you get me, you understand me deeply. You can think the way I think and feel the way I feel. That doesn’t mean that you agree with me, but that you can understand and think the way I think, feel the way I feel, so that when we communicate, we communicate perfectly. We’re in perfect sync in our communication and that’s pretty hard to achieve.

[00:24:48] KR: So, is that really the same idea of empathy?

[00:24:52] BC: I think empathy is another great word for it. Authors of the book use the concept of intimacy, but I think empathy is another great word for it, that I know that you think the way I think, and you feel the way I feel. But I think where Maister and Green took it to the next level, is that not only do I know that you think the way I think and feel the way I feel, but I can begin to also think the way you think, and feel the way you feel. So, there’s a symbiotic nature to the relationship that goes beyond just one person being empathetic to the other. There’s a connection between the two individuals that’s deeper. It’s rooted in empathy, but it’s not one sided. It becomes deeper.

[00:25:37] KR: Well, it seems difficult to do. I can see why that, really, that can be this differentiator, this kind of game changer in the process of what sets others apart. One reason why it seems difficult is I mean, everybody’s different. So, how do you create intimacy at a larger scale with many different personality types?

[00:26:01] BC: I’ll share some thoughts on that, Kent, but I bet as I do share those thoughts, you can come back where it’s actually specific examples about how you’ve done that with different personality types. I think there are four things that are often associated with creating an environment of professional intimacy. The first and the foremost is your listening skills, and not just your listening skills, but your willingness to just give yourself fully to the individual and listen without an agenda, without objectives, or without distractions. But just to fully listen, and not listen passively, I think, ask the type of questions that help me hear myself think. So, listening is one. I think the second thing that’s interesting is finding affinities. There is some research that says, they are more likely to trust somebody like us than we are to trust somebody we like. There’s that nature of like [inaudible 00:27:07].

[00:27:07] KR: So, finding a similarity?

[00:27:09] BC: Yeah, something deeper. I was just working with working with a client and they talked about the key to unlocking a particular relationship was my client was the mother of a triplets and her client was a triplet. Now, that’s a tribe. That’s a unique tribe. And finding that affinity begins to unlock the ability to create professional intimacy.

[00:27:37] KR: So, it’s like a shared value, or maybe even not as kind of ephemeral as a value. But even, like you said, you got the same amount of kids, you’re both into dogs, you like fishing. I can tell you like one thing, when I was a consultant, what I used to do on these lines was when I first meet someone, we’d always meet in their office. I go to meet someone, we meet in their office. As soon as they got in their office, I’m just scanning around looking at all the pictures, everything on their desk, what’s on their walls, what is something that I can relate to that they have. Okay, they’re into dogs, they’re into fishing, they’re into baseball, whatever it is, to try to create that, the similarity, right?

[00:28:22] BC: Right. So, if we can find with affinities. So, listen, one, find affinities, two. The third is kind of simple, but that can be ignored sometimes is just be familiar, be present. It’s easier for me to trust you if I see or experience you often. It’s harder for me to trust you, create that professional intimacy if I see or experience you rarely. I hate to just use this example, but sometimes there’s that quote, I think it’s attributed to Woody Allen, that “half of life is just showing up.” Well, a little bit of professional intimacy is just showing up.

I think the last thing, and this too, Kent, gets to your point about everybody being different, is to be able to understand and appreciate each individual’s natural and preferred communication style and then be willing to adapt your communication styles to match theirs. That creates the level of comfort and ease in the relationship and it accelerates the sort of perfect communication that we’re after. So, listen, first and foremost, find affinities, be familiar, be present, and match on our communication style.

[00:29:47] KR: Yeah, and I think that listening goes back to what we were talking about, again, with like the buyer journey, of starting with understanding the problem, and yet, the only way you can do that is by listening. Again, in the first meetings, maybe the first meetings with a new investor. It’s not pitching the deal and even your track record and all these things. It’s about them. It’s about their story, understand their story, their goals.

It should be such an easy thing. Listening, I mean, you’re just sitting there. It should be such an easy thing to do, but it’s not. I mean, we, as people like to hear ourselves talk. If we’re the expert, we want to share it. We want to tell everybody about it, but it’s just so counterintuitive to what is successful, which is really just – passive is not the right word, because it’s active listening, but just making it about them, I guess, and just understanding their story first.

[00:30:41] BC: Yeah. Kent, you hit on it. I think a big part of listening is asking really good and thought-provoking questions. Sometimes, it’s hard to ask good questions. Sometimes those questions get a little bit personal, or there’s always a “why” to those questions. Whatever question we ask, there’s always a why-based question that follows on to that, and you got to be willing to ask those types of questions.

[00:30:41] KR: Well, I think, one, asking good questions is more difficult than just giving the answers and just just telling what they should be thinking. But it’s so much more powerful, because you’re letting people come to the conclusion on their own. You’re helping them clarify. It goes back to the trusted advisor. You’re helping them clarify their decision making, maybe clarify their goals, understand what they really want, and then you can help them get what they really want. But if they’re not clear on that, I think it’s one of the most important skills in life is the ability to ask good questions.

[00:31:53] BC: There’s a client I work with and she really said something that resonated with me about a particular deal, an important deal for her term that they won. She said, “We ended up winning not because we helped the buyer understand us, but because we helped the buyer understand themselves. He hired us not because he understood us, but because we were the ones who helped him understand himself. We did that by really asking good, challenging, thought-provoking questions and not stopping at the first answer.” I thought that was really interesting when she described it.

[00:32:36] KR: That’s great. I think that’s a great perspective, and I’m sure that’s right on. I’m thinking about how, as folks who are out raising capital, in turn, generate interest in deals kind of ways ways that we can do that. When I think about putting out a lot of thought leadership, right, whether it’s this podcast, whether it’s my blog and other things, I think those are all great avenues to start asking some of those questions and helping people try to figure those answers out. I’m trying to think about how I can kind of build that into what we’re doing, to create situations that are thought provoking for people.

[00:33:22] BC: The word thought provoking, Kent, I think is so right on. In preparing for this conversation, I’ve just listened to a number of your podcasts, and I left each of them smarter, in some cases, and actually, even more aware of what I didn’t know. Each one of those podcasts, and the people that you had on them made me think, and made me think a little bit differently and a little better. People appreciate that. If you can make me think differently, or better. I actually want more of you. I want more of you because you’re making me think differently or better. I certainly personally experienced that through your guests and your interviewing style.

[00:34:12] KR: I appreciate that and I’m glad that that that’s coming through. I think, for me, it’s now how to do that much more intentionally. The other thing, we talked about the affinities a little bit and the just showing up. I mean, it is so important. I mean, I think in the world that we’re in today with social media, where people are just inundated constantly with so much information, I think consistency is key. That’s the showing up, it’s the consistency, it’s making sure that you’re ever present.

For me, it’s goals about posting on social media every day, and I’ve had to get over things of my own limiting beliefs of making sure every post has to be perfect. We’ve got to get it right. I mean, really, it is about showing up to a certain extent and just getting it out there, and people appreciate the authenticity of it not always being 100% perfect. But I think that’s been a big thing, for me personally.

[00:35:11] BC: Kent, since we’re on this topic, and since we talked a little bit about the concept of professional intimacy and you mentioned not having to be perfect, for me to trust you, I have to be somewhat vulnerable. I mean, I am being vulnerable when I choose to trust you. You posting every day and I know it’s not going to be perfect, but I’m just going to get it out there, that’s actually you exhibiting or showing your vulnerability. It might not be perfect, but I just want to get it out there to help people. And when you’re vulnerable first, then it makes it easier for me to be vulnerable and trust you. There’s an aspect or element of vulnerability implicit in trust. If you can be vulnerable first, it makes it easier for me to let my guard down and be vulnerable with you.

[00:36:06] KR: Brian, I think that’s such a good perspective to take for people that are stuck at that hump of knowing they need to get out there, they need to be doing more networking, they need active on social media, they need to be putting thought leadership out, but just kind of can’t get over that fear. I think what you just outlined is such a good perspective to take that, well, one, it’s okay not to be perfect. It’s actually better not to be perfect, because you’re able to show that vulnerability.

I tell people this all the time when they ask for my advice, it’s “just get started and improve through iteration,” and that’s exactly what you’re talking about. Just get started and and it’ll get better over time. But those little things that you may say, “Oh, man that didn’t turn out that well.” Somebody else may see that and appreciate that vulnerability, that you’re just being real.

[00:37:00] BC: Yeah. I want to give credit to the authors here. The other thing, sometimes when you’re so obsessed with the perfect, sometimes it’s “I’m obsessed with the perfect because I’m obsessed just about me and how it looks on me.” Then the question is, where’s your self-orientation there?

[00:37:19] KR: I love it. You took it right there. Yeah, that’s a perfect segue. For me, self-orientation is probably the least familiar. So, help us understand what do you mean by self-orientation and by minimizing it?

[00:37:36] BC: Self-orientation, I think, is about what’s in it for me? How does it look for me? How does it reflect on me? I’m thinking about me. Sometimes, entertainers lose themselves on the stage, because they’re completely invested in their audience’s reaction. They’re not thinking about how do I look? They’re thinking about how does my audience feel? So, how do I look, that’s all about me, that’s high self-orientation. Divesting myself from that concern and investing myself completely into how am I entertaining my audience, that’s low self-orientation, high audience or client orientation. I think about this as sort of the difference between your perspective, Kent, on the smartest person you know versus the wisest person you know.

If you were to think about, if there was an issue that was important to you, personally important to you, and you wanted to explore it, talk it through with somebody, just sit down and think out loud with somebody, would you go after the smartest person you know? Or would you turn to the wisest person you know? Most of the people I ask, don’t ask that question. They say, “I’d probably turn to the wisest person I know.” And then when I asked them to describe the characteristics of the wisest person you know, those often the characteristics associated with low self-orientation.

[00:39:17] KR: When you said that, two people immediately popped in my head, smart and wise, and I started thinking about that wise person. You’re absolutely right. I see the low self-orientation. I see that the conversation is always about how to help others, what’s going on with me, they hardly talk about them. I see that. That’s really interesting and I think that’s this idea of the self-orientation. I think again, that is maybe like this kind of like a service mentality, if you will.

I’m thinking about it again from my own experience of – so, I went through some of this starting the podcast, because starting the podcast, I had ideas like, “Well, who am I to start a podcast?” So, there’s some of that, but also, “Who’s going to want to listen to me?” and all these. When I really dug into it, it was, a lot of those things are coming from my own insecurities. They’re not the reality of things. It’s not what other people were telling me. It was all about me, all about me, and my own issues. What really helped me, I had a mentor really help me get over that and it was similar. The advice is, there’s a lot of people out there that need to hear this, and maybe other people are sharing similar information, but they’re not going to do it in the same way that you do. Certain people are going to resonate with you and because you’re putting that information out there, they’re going to make better decisions, they’re going to make better investments. They’re not going to fall into the same pitfalls that you fell into, because you didn’t have a go-to resource like that.

Really being able to think about it from a service mentality and serving others was really what helped me kind of get over some of my insecurities to launch the podcast.

[00:41:11] BC: Yeah, I mean, your self-orientation went way down, your others, your service orientation, your other orientation went way up.

[00:41:18] KR: Yeah. So, I can see that. It makes sense. So, your credibility, your reliability, your intimacy, on the top line, those are all things that you want to seek to improve. At the same time, you’re limiting your self-orientation, you’re making it about others, not about yourself. That’s just amplifying those other three. Amplifying everything that you do. Man, that’s a good formula to follow. I can see why there’s a great book about it.

[00:41:48] BC: Right.

[00:41:47] KR: Yeah. Well, very good. As people are taking away things from this episode. I mean, how do you kind of summarize the topics that we’ve discussed for people? Are there – maybe asking it this way, are there some tangible things that folks can go out and start doing that will help them change their position on the trust quotient, and improve those areas or be more effective sellers? What are some tips that you can give the audience?

[00:42:17] BC: Well, maybe a couple things, Kent, that come to mind for me right off the bat, which is, one, is buying is hard, and so the challenges facing our buyers are difficult ones. The more that we can train ourselves to instinctively or ultimately, reflexively think like a buyer, the better we can. The more successful we can be as sellers. So, buying is hard. That’s number one.

Number two is, I hope this metaphor works. But if you’ve ever gone maybe on vacation to an unfamiliar place, maybe they don’t speak the same language, you’ve never been there before, there are certain things you want to experience, you’re spending a lot of money to go on this vacation, maybe it’s physically demanding. For me, it was climbing Mount Kilimanjaro. You need and want and appreciate the services of a guide. Buyers are sort of doing the same thing. They are going into an unfamiliar place, they might not speak the language. They’re probably investing a lot in this journey. They want the guide. They might not say they want a salesperson, but they do want a guide.

If you can earn their trust, first and foremost, you can be their guide. Credibility, make them think differently or better. That’s what you’re doing in the podcast. Reliability, set expectations, and meet them, set, met, set, met, the repeated experience of expectations set and met. Professional intimacy, we talked about that, listening being key. And then as you prepare for each meeting, I think sometimes, especially, perhaps younger consultants, they prepare for each meeting, and they prepare as hard as they can to be as smart as they can. That’s good, we should always prepare to be smart. But think about the characteristics of the wise person. Take a deep breath, think about the characteristics of your wise person, and prepare just the same sort of discipline to be wise, be wise in them. But I think if you can do that, good things will happen.

[00:44:27] KR: Yeah, I think those are great tips, Brian. I appreciate you simplifying it for the audience and bring it back home. Before I let you go, I want to ask you the same questions that we ask every person that’s on the show. This is our keys to success round and it’s four questions. The first one is, what is one question, if you only got one question, that the buyer should ask the seller?

[00:44:51] BC: What would you do if you were in my situation and why? Because I do think if the buyer says “what would you do if you were in my situation and why?” that says one of two things. It forces the seller to think hard about what the buyer situation is, and/or it makes the seller describe what they think the buyer’s situation is. If there’s a complete mismatch there, or the seller is tone deaf, you don’t understand my situation. If you don’t understand my situation, I can’t begin to respect your solution.

I think “what would you do in my situation and why?” is a great question for the buyer to ask the seller because it helps us get on common ground. To help to see if we are on common ground, or if we’re not.

[00:45:44] KR: What’s the first question every seller should ask the buyer?

[00:45:47] BC: I don’t know how to ask this question. But what I do try to discern is, where is the buyer in their journey right now?

[00:45:55] KR: That makes total sense. So, do they know what the problem is they’re trying to solve? Step one, if they don’t, then you need to have prepared the thoughtful questions to help them frame that up and understand that. If they know that, do they have urgency? So, well, if they don’t have urgency, should they have urgency? Can you help them understand why there should be urgency? So, you create that urgency for them and kind of continue through the different steps. I think, as I’m thinking about what I’m going to take away from this, I think that’s something I’m going to take away is to outline the buyer journey and have some things prepared based on where someone is in the journey. What are those thoughtful questions I can be asking them to help clarify or get them to think differently? That’s my takeaway. The next question is, what are you most proud of in your career?

[00:46:54] BC: I’m most proud of those moments when somebody who thinks selling is bad, or they can’t do it, realizes that selling isn’t really so bad. It’s just about helping people make good decisions. And you know what, I actually can do that. But it doesn’t happen every day. But those times when it does happen, that’s when I’m most proud.

Well, you might think I’ve got a financial interest in these folks. I don’t. But just because we’ve talked about it so much. I might say if you haven’t read it, I think the book, The Trusted Advisor, by David Maister, and Charles Green, and Daniel Gafford, is a really great book to read. I think they just released their 20th anniversary version of it. Much of what we talked about only much more eloquently and powerfully stated, you’ll find in that book.

[00:47:50] KR: I’ve read the book. I read it a number of years ago. I probably want to need to pick up again and reread through because I think there are so many relevant things to what I’m doing right now. And lastly, what is your number one key to success?

[00:48:07] BC: Early on in my career, a wise person told me, trust comes before the sale. Trust comes before the sale. When I was successful as a seller, it’s because I took that to heart and focused my efforts on earnestly inspiring buyers’ trust. When I failed, it’s because I got the – I turn the sentence around. For some reason, I thought the sale came before trust. So, I think trust comes from being diligent about an earnest, and believing that trust comes before the sale and acting that way. I think it’s been key.

[00:48:45] KR: It should be an easy lesson to follow. It should be easy. But I think it’s not because some of it goes back to that self-orientation, because there are a lot of pressures driving us to sell, right? Whether it’s to hit quotas, or in my world, it’s because there’s a deal, and the deal is likely closing in 60 days, and that’s all the time that we have to raise this money. So, there’s urgency around needing to bring the capital to this deal that could cause us to try to like you said, flip the cycle, try to sell before there’s real trust there and not take the right approach. 

In that way, I think those external pressures and the thought of me and I have to get this done for me and what’s going to happen if I don’t do it, are the things that seem could get in our way of doing that the right way.

[00:49:39] BC: Kent, if you don’t mind me sort of ending with a compliment on this. I feel what I’ve experienced with you is, since you know that, at some point in time, there’s deals with 60-day windows to them and we have to close them early on, you’ve been diligent about building trust well in advance of the deal actually ever been created. I mean, things like this podcast, and I’m sure that interpersonal things that you do outside this podcast are all efforts to build trust with investors that don’t even know their investors yet. Create a preference, make it a partner sale, before the deal has even been constructed. So, if you do believe trust comes before the sale, that means you got to start early, early on trust.

[00:50:30] KR: Well, 100%. I mean, building trust never stops. I think this is actually a great, final thought for the show is that, that is why I do this, because you never want to have the deal and not know where the money is coming from. The way that you do that is by always building relationships, and always building trust. It’s actually so much easier, when you don’t have that pressure of a deal breathing down your neck. It’s so much more of a natural process. I think it’s easier to then just focus on trust, because you don’t even have to worry about that deal part. There isn’t one so. So, it is something that you always have to be doing if you want to be successful, because building trust takes time. Most of the time, building trust takes more than than 60 days.

Yeah, I think that’s a great tip for folks and a great place to kind of wrap this up. Brian, thank you so much for coming on the show and sharing your your expertise. I think it’s so applicable to what a lot of folks that are listening are doing and the challenges that they’re facing. So, if folks want to get in touch with you or want to learn more about what you’re doing, how can folks get a hold of you?

[00:51:43] BC: Yeah, the best way, Kent, is really through our website. So, it’s STS Consulting all one word. You can email me, it’s

[00:51:56] KR: Great. Awesome. Well, thanks again, Brian, and have a great rest of the day.

[00:52:01] BC: Thanks. My pleasure. Thank you very much.

[00:52:03] KR: Absolutely.


[00:52:04] KR: Thanks for listening to another great episode of Ritter on Real Estate. Hit the subscribe button and make sure you don’t miss out on the content that will make you a better investor. Also, visit for articles, videos, and tools curated just for passive investors. Until next time, this is Kent Ritter with Ritter on Real Estate. Now, go out and invest like a pro.