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Quotable Podcast Episode #86: Great Conversations Are the Key to Great Sales, with Howard Brown

Hosts: Kevin Micalizzi, Justin Royal
Great salespeople can build strong relationships with their customers and prospects because they’re skilled at having great conversations. Join Howard Brown, Founder and CEO of RingDNA, as he shares insights on how the best reps build rapport and grow long-term relationships. Many reps are tempted to ask questions of their prospects with an outcome already in mind. But truly successful conversations require genuine curiosity about the customer’s goals and pain. Asking open-ended questions, listening more, confirming the customer has been heard, and seeking out feedback and coaching will help you bring your sales to the next level by consistently delivering value.

If you're just trying to prove you're right, you're really missing the point.”

Howard Brown | Founder and CEO of RingDNA

Episode Transcript

Kevin Micalizzi: Welcome to the Quotable Podcast. Today we have Howard Brown, the CEO and Founder of RingDNA, joining us here in the studio. We’re going to talk about the psychology of selling and the importance of making sure that you’re not only doing the right actions, but you’re taking the right approach and the right perspective in all the work you’re doing.

I’m Kevin Micalizzi. Let’s jump into it.

Howard, thank you so much for joining us in the studio today.

Howard Brown: Thank you for having me. It’s phenomenal to be here.

Micalizzi: And I’m excited. We have Justin Royal, who is on the Sales Cloud product marketing team with me, joining us as the co-host.

Justin Royal: Yeah. Thanks for joining, Howard.

Brown: Nice to meet you, Justin.

Royal: Nice to meet you.

Micalizzi: Howard, as we were prepping for this and discussing it, talking about conversation and how people engage my degree is actually in interpersonal communication.

Brown: Oh, nice.

Micalizzi: So it’s near and dear to my heart. What brought you down this path to really looking at especially sales from this lens?

Brown: Yeah. I think the first part of my technology career was really in marketing, but prior to that, I was a clinical psychologist. For me, it was really interesting to study how people behaved online, what essentially triggered their reactions, what got them interested in particular pieces of content, and then, ultimately, what drove them to an action. From a marketing standpoint, it was really important to understand attribution.

From an ROI standpoint, it was really great to see that we were generating leads, but then what happened once those leads went over to sales?

Micalizzi: Right.

Brown: It was sort of the unknown. What got me really excited was, rather than creating this argument between sales and marketing, let’s figure out the best way to study what changes behavior. Is it context? Is it coaching? Is it behavioral science? Is it the chemistry between the two individuals who are actually having a conversation?

Micalizzi: Now I want to know. [Laughs] What is the answer?

Brown: Well, it’s all of that. It really is. If you think about interpersonal communication, interpersonal relationships, it’s really about two people. We make a lot of assumptions about people based on how they look or what they first say or what they’re wearing.

It’s the opening to any conversation. It’s your ability to ask questions. It’s your ability to be open-ended, your ability to talk to people and really understand them, just like any relationship, whether it’s father and son, mother and daughter, a couple. Their ability to communicate and the narrative between their relationship is really critical. The more information I have about you when I’m walking into a conversation, the better our conversation will be.

You and I barely spoke before this particular interview, so right now we’re sort of feeling ourselves out.

Micalizzi: Right.

Brown: We’re trying to find that common ground so that we can have a real fruitful conversation. In sales, the more information you know about your prospect, the more context you have, and the more you know about what they’ve done prior to your interaction with them, the more powerful, the more connection will be created.

Micalizzi: I recently had a conversation with Shari Levitin.

Her focus is very much around kind of the behaviors and attitude that you bring to the transaction. Having the selling skills is great, but at the same time, you truly have to have empathy and be engaged there. I’m curious, in the research you’ve done and the work you do, when you’re engaging with someone — what I’m trying to ask you here, Howard, and I was trying to dance around it to be nice.

Brown: Don’t be nice.

Micalizzi: So many people get into conversations, especially with a prospect, and the whole time, what’s going through their head is, “Okay, how do I plug in what I’m selling?”

Brown: Right.

Micalizzi: “How do I fit myself into this narrative?” as opposed to truly taking that narrative in and making sure they understand and are really looking for holistic and fulfilling ways to help that prospect.

Brown: How do we approach a relationship without a predetermined outcome?

Micalizzi: Yes.

Brown: I think that’s really what you’re talking about.

Micalizzi: That’s far more succinct and better said than I was going down.

Brown: Well, I think that’s critical, and I think it’s critical to any relationship, whether it’s a sales relationship, a customer success relationship, or relationship with your children. If you’re just trying to get to a desired outcome to prove you’re right, you’re really missing the point, and people sense that. People get a real sense of “Do you care?” Are you being empathic?

I talk to some sales reps from time to time, and I’ll listen to their calls. I’ll listen to recordings, and I’ll hear them. What they’re trying to get is “What is the pain that this individual prospect or customer has, so that they can solve it?” That’s fabulous. They’re asking questions and they get that person to open up. Almost immediately, they go from having this great conversation, open-ended questions to finding the pain point, and then immediately, “So how many seats do you need?”

In the therapeutic world, we call that empathic failure. The person opened up. They trusted you, and you immediately turn that information on them for your benefit. It’s the same thing we’re talking about. If all I’m trying to do is get there, [I’m] missing the point. As salespeople, our job is to help. Our job is to understand it may not be to sell my product. It may be that what you need is somebody else, and if I’m doing my job as a sales rep, as a support rep, it may be to push you off to somebody else.

Micalizzi: Right. Not every customer is a good customer.

Brown: Most customers are not good customers.

Micalizzi: Okay.

Brown: Yeah.

Micalizzi: Even broader than I would have phrased it.

Brown: Yeah.

Royal Oh, I’ve got a question, Howard. It sounds like a lot of your work is related to emotional intelligence and helping sales reps develop the emotional intelligence they need to interact with prospects successfully.

What are specific EI skills that you’ve seen reps needing the most help with developing?

Micalizzi: Ooh, I like that.

Brown: Yeah, I like that, too. That’s a tough one, though. I think that it comes down to finding what works for that individual rep, where their skills lie today, and where we can see improvement.

For some people, and millennials in particular, they’re very used to “We have Alexa devices. We sort of order it what to do. We have chats. We quickly text. We send emoticons.”

So our communication, in general, has been diminished to something that’s one way and just getting what we need. I think figuring out how to come at a relationship, at a conversation, and thinking of how — I guess it’s what we learn in kindergarten. How do we want to be treated by others?

What does this person need? What do I need in this conversation or transaction? I think that’s the healthy approach.

A lot of reps, a lot of salespeople, they’ll go right in and they’ll ask questions that are closed-ended. We analyze conversations. If you look at a conversation and you see that there are 55 questions in a conversation and 49 of them were just answered yes/no, that’s not a healthy conversation, and that’s not a healthy relationship.

You’re just trying to get through it. When you see a conversation that has 10 to 15 open-ended questions with two-minute answers, you know that there’s a true interaction there. I think open-ended questions, the ability to listen, to find out what that person’s basic human need is because we all want to be heard, we all want to feel important, we all want to be recognized.

I think one of the basic things is just saying the other person’s name during a conversation. If I just say your name, Justin, while we’re talking, you’ll remember to pay attention. If I leave you out of the conversation, it starts dulling really quickly.

Royal: Awesome. Yeah. That’s real interesting. I actually had a background in psychology before I started at Salesforce, so I’m totally nerding out on everything you were talking about today.

Brown: Awesome.

Micalizzi: It sounds like what you were saying around the open-ended versus closed-ended questions is you actually have to have some genuine curiosity in what your prospect is going through, what they need, to really explore that well. I mean, the closed-ended questions, to me, says you kind of know what your destination is, so you’re just trying to lead the prospect there versus truly trying to feel and be a part of whatever the prospect’s challenge is.

Brown: Yeah, and you have a wonderful way of actually mirroring what I’m saying. After I’m done answering a question, you’ll say “What you’re trying to say” or “What you just said” or what you think. That’s actually a great way of communicating. It’s not just asking open-ended questions, but it’s confirming that I was seen, that what I said mattered to you and that you heard it. Really important.

Micalizzi: I do avoid saying, “What I’m hearing you say, Howard, is” [laughs] because I was taught to do that years ago, and it’s a really hard habit to break once you’ve started it.

Brown: It is. I think, with technology today, look, technology has allowed us to test and measure everything, right? Testing and measuring things, optimizing performance, automating things. What’s going to separate the world of great salespeople and not great salespeople is their ability to have great conversations.

Because, let’s face it, the reps and below, there’s going to be chatbots. A lot of that will be automated out.

I don’t want to talk to a sales rep. Most people don’t wake up and say, “Hey, I’m going to have a great conversation with a sales rep.” It doesn’t happen, but what I would like is, I’d like to talk to somebody who’s going to add value to my profession, add value to my life, help me solve a problem. So we have to come at it as, “How are we going to help you?”

If you can’t bring that, if you can’t bring that curiosity, if you can’t bring the problem-solving, if you can’t be someone who wants to add to other people’s lives, you probably shouldn’t be in sales. You’re going to be automated out.

Micalizzi: Right. I want to ask, on the technology side, how are you finding that people are kind of bridging that gap and creating that authentic engagement that, if I’m not on the phone or not seeing you, we’ve just completely cut off any kind of nonverbal feedback.

So if I’m texting with you, I’m emailing with you, I’m instant-messaging, any kind of chat like that, there are no cues that I have to go on or that my prospect has to go on. What are you finding is either working or not in that space? How are people getting that connection they need?

Brown: Yeah. Well, I think a lot of people are avoiding that connection at all costs until it’s absolutely necessary.

I don’t have time for another relationship. We’re very busy. I just want to get to the answers as quickly as possible and move on. That’s why it’s even more important that, if you’re going to establish a relationship, whether it’s a support rep, customer success, or a sales rep, that’s a brand experience. If that brand experience is not excellent, I as a consumer, I’m going to go somewhere else. So it’s really powerful.

I don’t know how to increase the number of conversations that I necessarily have with people that have impact, if they’re not interested in talking to me, if they simply just want to text with me. I have to move them towards a conversation, which means I have to utilize those technologies to generate interest, to make them feel like what I have to offer is worth taking the time to actually talk to me or meet with me face to face.

Micalizzi: Okay.

Royal: Here at Quotable and just in general, you’ve certainly seen a lot of work about AI taking over a lot of the manual tasks involved in being a sales rep and AI being more and more a part of sales reps’ lives. Since I feel like now, more than ever before, this emotional intelligence and this human factor is becoming really important in sales, in your work, how have you seen the importance of that human connection change over time?

Or are your clients acknowledging that it’s more important?

Brown: Yeah. I think that, because there’s so much cadence out there and, like, “follow this recipe to get somebody interested” and artificial intelligence, those sort of things can actually decrease the connection, the actual connection that people have. It’s like you’re talking all this technology is creating a bridge in between us and the people we’re trying to connect with.

Micalizzi: Right

Brown: I think that there will be fewer and fewer reps that are actually employed because of the technology, and those who are employed are those people who in fact have the ability to connect. It’s people who are coachable. When we think about sales reps, they have to be extremely coachable. When we think about sales leaders, they have to be coaches. How do we use artificial intelligence to surface those coachable moments?

If I can listen to a million conversations manually, I would do it, but instead, we apply artificial intelligence to listen to those conversations to surface areas that need improvement. If my team doesn’t know how to build rapport, I need that surfaced. If they don’t know how to ask questions, I need that surfaced. If they don’t know how to answer questions or deal with pricing objection, I need to know that.

I think, in a lot of ways, the artificial intelligence that’s starting to evolve allows coachable moments to be surfaced and allows us to help people be better salespeople, better communicators, better educators.

Royal: If I’m a sales rep, what should I be doing to ensure that I am truly adding that value that you were talking about earlier?

I guess I think of it in terms of, “Is this a quick transactional interaction?” Or if this is the complex sale, then you and I are going to need to have many conversations and really have a strong level of trust and a strong understanding of each other. What should I be doing as a sales rep to make sure that I am in that position? Whether it’s new chatbot technology or AI coming in and filling in some of those gaps, where I’m doing activities, but not really adding value.

Brown: Yeah.

I’d say one of the most valuable things in my personal and professional career that I have ever had done was when I was a therapist and they set up a video camera and they videotaped me doing a session with a client. I had no idea that I had all these nervous habits. One of my habits was, when the material got heavy, I’d shake my foot or I would tap my knee.

It’s that sort of insight into our behavior that’s so critical, because what I was doing in the room was actually making the client more uncomfortable, more tense, by my nonverbal cues.

When I think about your questions and sales reps, how do they stay top of game? They need to observe. They need to listen to recordings of their calls. They need to have feedback on how they’re interacting as much as possible by those who can provide a somewhat objective feedback on their process and how they’re performing.

To me, the most important technologies out there are really those that will help us observe how we behave in certain circumstances. Everything else we do, whether we’re athletes or other professions, we have a way of looking at how we perform and improving on it. Within sales, it’s really hard. It’s “Did you make enough calls? Did you send out enough emails? How are your pipeline reviews?” How about “How is your ability to build rapport? How is your ability to handle this type of problem?”

Micalizzi: All the metrics we look at, they’re backward-facing and they don’t get to these underlying behaviors and attitudes — 

Brown: That’s right.

Micalizzi: — that you need or the self-awareness that you were just talking about.

Brown: Yeah. “Were you efficient?” as opposed to “When you were efficient, how effective are you?” and “How effective are you by making a connection? How effective are you by actually coming from a place of understanding, empathy, compassion?”

Somebody is sharing with you their pain point. Their pain point actually causes them pain. They may go home and not be the best father. They may go home and not be the best spouse. They may lose sleep. They have real challenges. They’re not meeting their number. They’ve shared that with you. Your job is to help them. If you can’t help them, get out of sales. Find something else to do.

Micalizzi: Right.

Royal: That self-observance element that you were just talking about, it reminds me almost of you hear about football coaches going back to watch games, like after the game is done.

It almost sounds like you’re suggesting that people do go back and actually pinpoint the exact moments of a sales interaction with a customer that might have positively or negatively impacted the outcome of the sale and sort of use those moments to improve on future efforts. I know, for me personally, that would be really hard to just watch myself do that and to pinpoint those moments.

But is that something that you would advise your clients to do?

Brown: It absolutely is. We also advise their coaches that do it for them. If my coach can listen to my recording and annotate a part of my recording and then go back and help me learn about how I can improve that moment, it’s massive.

Micalizzi: Because it’s keeping it in context.

Brown: You got it.

Micalizzi: So I’m not giving you general advice and —

Brown: Right.

Micalizzi: — you have to figure out how to apply it to your —

Brown: Right, and you’re not overwhelming. The typical coach or trainer will come in and say, “I listened to your calls, and these are the 47 things you did wrong.”


Brown: No. I can’t learn with [that]. I’m overwhelmed. That means just I’m not okay. But if you come and show me specifically how I handled something and how I might have done that better and I can feel that and we can talk through that, next time that happens, I’m going to handle that better.

We’re prediction machines. We learn from our experience. We can learn from other people’s experience, so that, when it happens again, I can improve, but unless I have somebody who’s helping me through that, I’m going to stumble.

Micalizzi: Or you’re going to repeat the same behaviors.

Brown: Exactly.

Micalizzi: Because it’s already your pattern of behavior.

Brown: That’s right.

Micalizzi: Right.

Brown: Like we talked about, there’s very little training out there for most sales reps. I said six weeks. You said probably a lot less.

Micalizzi: I said six weeks is very generous.

Brown: Right. So send them on the front lines to make mistakes with no feedback other than, “Why aren’t you making your number?” or “Did you have enough activity metrics?” It’s tough.

Micalizzi: From the sales leadership perspective, we talked about the importance of coaching, and you not only have to have reps who are willing to be coached, but all your leaders need to be coaches. On the metric side, what would you recommend people be measuring to try and encourage these behaviors? I mean, I tend to use the mantra “Whatever’s measured is what gets done.”

Brown: Mm-hmm.

Micalizzi: If we’re always using those kind of backward-looking metrics and it’s strictly activity-based, then I think you’re missing an opportunity here. What would you recommend, or what have you found works, in terms of what kind of targets to set to encourage this behavior?

Brown: Well, I think it’s always really important to set a culture, and a culture of coaching and training and learning is critical.

Having the ability to raise your hand during a call and say, “Hey, I would like some coaching on that” and have a management team that supports that culture — that not only supports it, but creates metrics around it. As a VP of sales, I have regional sales reps or sales managers. How many calls did they listen to? How many coaching opportunities did they create? How much feedback did they provide that individual rep? You could track that.

If I can track that and I can say, “Oh, this RVP happened to listen to two hours of calls every day and actually spread that out amongst 15 reps,” how is the performance of that rep both before and then after those coaching sessions? It’s amazing.

Once they see that their coaching is valuable and made a difference, wow, now you’ve created something. If you could take those moments, not only the ones that need coaching, but take those great moments, those best practices, and create libraries around them, where we can actually train people on what’s done well, that’s powerful as well.

Look, we all like to be rewarded. That’s gamification. If we can have recordings where you handled this, great, and now it’s in that public library that we use to train all our other reps, that’s motivation.

Micalizzi: Right. I kind of want to emphasize what you were just saying, though, because we always talk about what metrics we’re measuring the rep performance by.

I love the fact that you’re shifting the onus of responsibility onto the managers. If they’re not doing the coaching and they’re not exhibiting the behaviors they need to, then obviously the culture won’t change and reps won’t improve. I just totally want to highlight that, because I love the fact that you’re shifting that focus to, I would totally agree, where it needs to be.

Brown: Mm-hmm. I’ll tell you what just happened to me. When you reinforce what I said with “I love that” and you did it with enthusiasm and feeling, I light up. I loosen up. I literally feel my body loosen up. That sort of feedback, both positive and constructive —

Micalizzi: Constructive. Yep.

Brown: — is critical, and it means you care. It means we’ve connected. We’ve now made a connection. When you look at organizations — we work with companies that are very large, that are very vertically integrated, that have management up and down — how do I measure my middle managers?

Are they participating in creating a culture of learning? Are they creating a culture of training? Are they taking accountability and responsibility? Because, guess what, they may not be the best coaches, so I need to train them. They need coaching as well. So it works from top to bottom. If you don’t have metrics for your supervisors or coaches, that’s not going to work, either. They have to be held accountable to the coaching and the training as well.

Micalizzi: Right.

Royal: Howard, in terms of metrics, it’s easy to envision a scenario in which a sales manager would say, “Your calls are averaging this amount of time. They need to be shorter,” or, “You’re making this number of calls. You need to make more calls,” like, very numbers-based metrics. If a sales manager was offering feedback that you need to be more empathetic or be more of an active listener, how can that actually be quantified?

In terms of, if the feedback was, “You need to be more empathetic,” how is a quality like empathy actually measured for a sales rep’s performance? Is it based on client rating or the manager rating? How do you actually go in and assess? Obviously, we don’t have a clinical psychologist observing the interaction and providing their own rating.

Brown: Yeah, and it’s actually where we apply some AI, because I think that there are certain ways that we mirror.

For example, if I say a sentence and you repeat that sentence or you say a portion of that sentence in the transcript, that can be pulled out. In other words, if you say “I hear you saying this” or you repeat some of the same words I use, that in a way is empathy. If you ask follow on questions that have some of the same words in them, that also shows that you’ve continued the dialogue and created a connection.

Then you take the human intervention. If my managers are actually annotating a certain section of a recording, so they’re writing “Great job in building rapport,” and they tag that as rapport-building positive, you’re essentially training a machine [to know] what a positive rapport-building sounds like. So that’s one part of it.

There’s also simple things like, “Is the rep talking 60% of the time?” or are they listening?

We look at optimal as about 42% of the time. A rep should be talking 42% of the time for most B-to-B sales. Are they talking 60%? Great. Flag it. I need to talk to that rep and have a conversation. Let’s listen to the call. If they’re talking that much, chances are they’re probably not building rapport.

Micalizzi: You said 42%. Have you found that there is a particular pattern? Does the rep need to be speaking a little bit more at the beginning, middle, end? Does it vary?

Brown: Yeah. It does vary quite a bit. We like to see a lot of open-ended questions up-front and we like to see them doing far less talking at the beginning of the conversation. Once they’ve built rapport and they’re into a process where they can provide some solutions, they should be talking more on the tail end. Things like that actually make a difference. That’s what’s so incredible.

You can theorize about anything and test it. Does it matter? Yes. Let’s take a million phone calls. Let’s look at how the rep performed. Let’s look at, “Did this conversation’s lead status change, move forward? Did the opportunity get won and then come up with some answers?”

Micalizzi: Does it vary? In a complex sale, you and I will most likely have multiple conversations.

Brown: Yes.

Micalizzi: Does that timing or that percentage of timing vary?

Brown: Completely, and that’s where you track opportunity stage.

Micalizzi: Interesting.

Brown: I know, at early opportunity stages, I should be asking certain types of questions. I should be talking for a certain amount, doing certain things. At later stages, I should be looking to talk about other things.

Some people would say, if you’re talking about competition at the very early stages of an opportunity, that’s okay. If you’re talking about competition when you’re about to close a deal, that’s a problem. They’re negotiating price.

So in certain conversations you should be looking for certain things, and other [things, like] tracking lead status changes, call dispositions. You need to be tracking opportunity stages and then pulling up. The more data points you have, the more you’re able to analyze the conversation and pull out some true facts.

Micalizzi: Right.

Royal There’s many generations of sellers in the workplace right now. Have you found any interesting research?

Brown: This was an interesting study we had done.

We had heard that the use of um’s or like’s, filler words during a conversation, would in fact negatively impact building rapport. What we studied was: Does it negatively impact rapport between somebody who’s millennial and somebody who’s, say, 50 years old? Absolutely.

We also discovered just the opposite is true when a millennial is speaking to a millennial. It’s actually rapport-building. They say “like” to each other all the time.

In a sense, they’re mirroring each other. When we look at how we study this stuff, we have to have all the information. It’s like research methodology. You have to look at the various data points and see.

You have to test and measure it; otherwise, you’re going to make false assumptions. Actually, if you tell a millennial, “Stop saying like’s,” and they’re reaching out to millennials all day long, you’ve just negatively impacted their ability to build rapport.

Micalizzi: They’re hurting themselves in it.

Brown: Yeah, and you’ve hurt them by giving them the wrong advice.

Micalizzi: Yeah. If somebody’s listening right now, they’re going for a run, doing the dishes, cooking dinner, whatever they’re doing — as soon as they finish, what’s the first thing they need to do to try and get themselves on the right path to take a better approach to their selling?

Brown: I think the first thing they should do is commit to wanting to improve in their skill. You find tools that they can utilize to help them improve.

It’s like anything. If I want to get strong in my biceps, I’m going to do curls. If I want to get strong in my chest, I’m going to do bench press. If I want to become a better conversationalist, a better problem-solver, a better sales rep, focus on what we do as salespeople. We communicate. We build rapport. We have relationships. Focus on that part of it.

Micalizzi: Excellent. I love it. I want to ask you the lightning-round question.

Brown: Uh-oh.

Micalizzi: If you can take all the knowledge and experience you have now, go back to the beginning of your career, and give yourself one piece of advice, what would you tell yourself?

Brown: Listen more.

Micalizzi: I love it. It’s super concise, and I totally agree.

Brown: This was a blast. Thank you for having me.

Micalizzi: Yeah. No. Thank you so much for joining us in the studio.

And, Justin, thank you for jumping in.

Royal: Yeah. Thanks for having me, guys.

Brown: Yeah. It was great having you, Justin, as well.

Royal: Thanks.

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