Remove Fear from the Sales Conversation, Create Human Connection


Kim Orlesky is Founder and President of KO Advantage Group, one of the fastest-growing sales training organizations, and author of Sell More Faster. KO Advantage Group works with small companies selling high value, premium-priced B2B services and helps them expedite the sales process by focusing on building relationships, getting that first handshake with a potential client faster, connecting with the client in an authentic way, communicating value, and sometimes selling a product idea before the product has even been created. Clients of KO Advantage are passionate about helping their clients.

KO Advantage group has one product: a ten-week online sales training course, which has its own “continuous improvement process.” Alumni of the course can login to review course information at any time and read the updated material Kim has “curated.”

Kim spoke on “AI & Sales: What Will and Never Can Be Replaced by Bots” at HubSpot’s Inbound 2019,” where she discussed how sales professionals, business owners, and entrepreneurs can use AI to improve conversations with potential clients. Artificial Intelligence is already part of the sales process, but companies need to be aware of how critical “the personal touch” is to long term success. AI may help find potential clients faster, but she notes that, in the end, “Sales is about conversations and relationships.

Kim can be reached by email at: or on LinkedIn, which has named her one of the Top Sales Leaders to Follow

ROB: Welcome to the Marketing Agency Leadership Podcast. I am your host, Rob Kischuk. I am joined, live and in person, by Kim Orlesky. Kim is the President of KO Advantage Group based in Calgary, Alberta, Canada. She’s also the author of Sell More Faster. Welcome to the podcast, Kim.

KIM: Thank you so much, Rob. I am so excited to be here. I’m so excited about Inbound. It’s so late already, and I still have the energy flowing.

ROB: Yeah, there’s a lot of energy to go around here. Why don’t you start off, Kim, by filling us in a little bit on KO Advantage Group? What is the company? What do you do amazingly well that we should all know about?

KIM: We do a lot of things amazingly well. [laughs] I guess, as agencies, we always have to niche ourselves down. We are one of the fastest growing sales training organizations, specifically for those that are selling B2B high value services for a premium price.

What that means is we help to teach business owners, entrepreneurs, and small businesses how to go through a sales process if they’re selling everything from engineering consultation, business consultation, marketing agencies – how do you drive your customer conversations so that you’re connecting with more value?

ROB: High value, does that connote a particular price point? Or is that just relative to competition? Are you positioning premium versus selling on price versus selling features?

KIM: I think when it comes to the price point, that’s a relative position. When I’m onstage speaking, I say, “Are you positioned as a mid to high to premium level tier?” I don’t think it has much to do about how competitive the environment is or specific features. People buy premium because they believe that “You know my business better than anyone else, and you are the best suited to help me achieve my goals and aspirations.” That’s why people are willing to pay that.

ROB: Right. So, you come in the door, and do they sometimes know everything they need to know to position the product? Or is that part of the process you’re getting into, how to think about increasing that position.

KIM: We don’t talk necessarily about how you position a product. We do talk about what it is that you do. The people that come to us are very passionate about helping their clients.

Why they come to us is because the conversations they’re having are just not connecting with their clients. They have a ton of marketing leads and they’re just not able to turn that into sales, or ultimately they’re saying, “For the amount of sales we are having, for the number of conversations we are having, how can we do that in either less time or how can we save ourselves time?” Like “I only want to work 4 days a week,” for instance,. “How do I create as much revenue in that same amount of time?”

ROB: What are typically some of the first few things that need to happen to start getting more maturity around that process, where you can get the marketing leads and you can actually convert them into business?

KIM: If we’re talking about the marketing side of it, I’m going to leave that to people like you and some of the other experts. Where we want to focus on is how quickly you can get the first handshake with a potential prospect. Where we start and stop the conversation I like to say is from handshake to handshake. How do we get that first handshake to get that initial meeting? How do we get the final handshake that yes, we have a deal, and then we continue on in (if we’re using HubSpot terminology) the flywheel, the entire customer sales journey?

So, how much does somebody have to know about their product or what they’re looking for? I don’t think you need to know a ton. I come from the school of thought of sometimes sell it first, create it later, with the idea that as long as you know what you can do for your client or how you will leave your client better off in the end, we’ll teach you how to have that conversation in a genuine and authentic way. Let’s say you haven’t even made your first sale. How do you eventually get there?

ROB: Right. In some cases, they don’t know what they don’t know. You’re making a mistake, you’re saying, “Help me, I need to know how to be cool and how to sell well and help these customers,” is what it comes back to.

KIM: Yeah. I probably have one of the hardest sales to ever have to do, because marketers are great marketers and they can promote why we should do more ads, why we should promote more pretty quotes on landscape backgrounds and post them on Instagram to help get people to be more “brand aware.” Salespeople, we’re just like, get rid of the fluff. How do you actually get to the source of the conversation?

I mean, if the intention of let’s say an Instagram Story is to get someone to click on your banner to ultimately go to your website and give you their contact information, salespeople are like, instead of waiting for that to come to us, how do we go out there and grab it? How do we start that conversation with ourselves?

ROB: That sales and marketing conversation is always such an interesting one, much less product folks. I think another battle you probably end up fighting is if it’s an entrepreneurial client that you’re working with, they also have to admit that it’s not working.

KIM: They have to at least admit that they can do it better or that there’s a better way of doing it. I’m not saying that it’s not working. Even a broken clock can tell the right time twice in a day. They have to say to themselves, “What I’m doing is just taking up too much energy,” or ultimately, “I’m not having fun when I have to go out and get the business.” So, how do we help them make it more fun in the client conversations before the client ultimately says “Yes, I now want you to produce that service”?

ROB: If we rewind a little bit, what led you to start KO Advantage Group? What is the origin story here?

KIM: I worked for well over a decade in corporate sales – Xerox, American Express. I was doing high value services. We had the woman who wrote Eat, Pray, Love here, and I had my own little “eat, pray, love” moment. I said, “I’m going to go travel the world. I’m going to get rid of this whole corporate mentality.” Over 6 months, I traveled to 17 different countries, and when I came back I was like, I want to do that for the rest of my life. [laughs]

I knew that if I wanted to do that, number one, I was going to have to create my own company. But then through iterations – because we have these massive time gaps – eventually I got to a point where I fell back in love with the sales conversation. I realized that the people that needed me the most weren’t the Fortune 500 organizations. They were the small little mom’n’pops. They were the person that was going out there and eating what they killed every single day, and, “If I don’t make that sale, I can’t feed my family.” My heart went out to that. I was like, “Oh, my goodness, I wish there was somebody out there that was helping all of these little people learn how to sell.”

Over time – it actually started at Inbound, when I came here for the first time, speaking, 3 years ago – I was right near the end of one of my iteration processes, and I had two companies come up to me and say, “We need to hire you.” Over time, we just created everything as it evolved, which then ultimately became an online classroom. So, we can now appeal to business owners from coast to coast.

ROB: It seems like an interesting decision that you have to make at those points where someone says, “Hey, we want to hire you.” I’m sure lots of people want to hire you.

KIM: Thank you. [laughs]

ROB: I’m also sure that you have a high degree of confidence in yourself that in that opportunity, you could go out there and make a lot of sales and have a very lucrative role – assuming in some cases there’s company risk. Some stuff is not sellable or harder to sell, at least. There must be a gift and a drive within yourself to help other people to do this well. There’s more of a teaching gene in there than a “kill all of the deals” gene. I don’t know, a little bit of both?

KIM: Oh, absolutely. Here’s the reality: if my intention was to go out there and get the euphoric high that comes from every time a contract’s signed, I would still be working for American Express on the global corporate payment side.

My euphoria essentially didn’t come from signing these big deals, but rather the moment somebody came back and said, “Oh, my goodness. What you taught me worked. I asked this one question, and it was like magic.” When I felt that, I was like, how do we scale this and how do we create this so that it becomes a movement where people aren’t fearful of the sales conversation, but enjoy it and love it?

Sales is not about the fear of picking up a phone call. It’s about the thrill of connecting with somebody who says, “I’m so glad you called” or “I’m so glad we had this conversation” – and how good does that feel?

ROB: Absolutely great. Interestingly, you get this joy out of those “aha” moments, but you also mentioned that you like to think about scaling it. Sometimes scaling it can take you away from the “aha” moments. As you’ve grown, as you’ve brought in people to certain roles within the organization, how do you still stay close to that while also keeping peace and order?

KIM: There comes a point where you can’t be on top of every conversation at all times. One of those moments happened a few weeks ago. We’re still a relatively young business. We incorporated in November 2017, but we’re already at seven people, which means that we’re not the octopus with one head, many hands. We are independent roles.

I remember signing the graduation certificate of one of our recent graduates. We run through a 10-week program. As I’m signing this, I had this moment where I shed this tear of joy, because the only time I had interacted with this gentleman was well before he had actually ever signed the agreement. The conversation started, he ended up working with one of the people on my team, who ended up nurturing him to the point where he was like, “Yes, this is what I need.” He was taught by one of our instructors, and now the next time, I’m signing his graduation certificate.

At the same time, he writes me an email thanking me personally, “Thank you so much. The connection I had with Kerry, your trainer, and with Katelyn, who helped me through this process – this is unbelievable.”

So how do you stay on top of it? I think your role has to evolve and you have to be okay moving up the levels in the office tower, while at the same time feeling faith and confidence that everyone is doing 100% the best work for what they believe for every client, every time.

ROB: It sounds like one of the things that you’ve found you can do is with a client that you didn’t have a lot of contact with, you can still get joy out of the outcome of helping more people with the thing you want to help more people learn. That’s part of the opportunity of leverage. You didn’t necessarily get to spend the “aha” moments with that client, but it sounds like there was still encouragement from knowing they had been helped, knowing that they were grateful, and knowing that they still felt like you had helped them.

KIM: Yeah. I developed the process. As it has developed, the instructors I have are helping finesse it. We’re shining a stone all the way through. We do one thing really, really, and that is the sales process. People have asked us, “Do you do customer implementation? Do you train in these other areas? Do you work on marketing?” I say, “No. We do one 10-week program. That is it.” When we feel like we’ve mastered it, then maybe we might explore something else.

But I think I would actually be a little bit sad if we ever felt like we had “mastered” this entire process, because it was something so near and dear to our – I would much rather continuously make it better and better and better, because it works. This is about creating human connection.

When people come back like, “Thank you so much for introducing me to this” – this is the same as picking up your favorite book. You didn’t have to meet the author, but don’t you feel well-connected to that person after you have been given that learning and that education?

We talked about this; you’re going to be interviewing Verne Harnish. Scaling Up is a critical book to my business success. Have I met the guy? No, but I feel like I know him. I feel like he has shone a ray of light down on my business and on my brain that has allowed me to grow and expand in the same way.

ROB: Probably a little bit in parallel, one of the things I have found is revisiting some of the different parts of Scaling Up on an annual basis, I learn different things. I implement new processes. My business needs something different from Scaling Up. That’s probably going to be true with your 10-week sales process. It could be 10, it could be 12, but number one, we might need the tune-up. Number two, as you look through it year over year, different parts of it need different nudges at different times.

KIM: That’s absolutely correct. Number one, we’re constantly reiterating the program. When I read books, other sales books, other sales information, I actually use that information to finesse it.

Chris Voss, who wrote Never Split the Difference – I ended up rewriting our entire negotiation module because I was like, “Oh my goodness, this is the stuff that needs to be done.” Dan Pink’s To Sell Is Human – we rewrote the entire elevator pitch.

One of the reasons why we’re also the only program that gives our students lifetime access to the material is for exactly that reason. I’m going back and I’m making the information better, and if that’s a value that I hold for myself, that’s a value that I cherish my students to hold, so they want to go back and take that same information and make it better and better for themselves, for their organizations.

I’m honest to them. I say, “Listen, go use your login. You get one login. Who you want to share it with, I don’t care.” I have no choice but to care, but I’m like, “Go share it. Leverage it, because it helps everyone in your entire company when they’re all speaking the same language.”

ROB: Absolutely. So you’re revising, and one direction you’re probably going to be revising a good bit, your talk here, is a very looking-ahead-to-the-future kind of talk.

KIM: Yeah.

ROB: “AI & Sales: What Will and Never Can Be Replaced by Bots” Tell us what we’re diving into with this talk.

KIM: I love this talk, and part of the reason why I love it is because it is so different than what we teach normally in some of our programs. Every time I create a talk, I have to spend literally months researching, curating, interviewing, finding out as much information. As I go ahead and craft something, then I can go back and teach it.

When I’m speaking onstage, this gives me a first attempt on, is this something that resonates? What’s resonating versus what’s not? I might have started off creating my company as a teacher, but I now consider myself just to be a better curator of content.

With the AI and sales conversation, the generic thesis is that this isn’t about if artificial intelligence is going to take over parts of the sales process. We already know it’s there. It’s a when, and that when is happening sooner rather than later.

So, knowing that that is going to happen, how do we as sales professionals, as business owners, as entrepreneurs, use that and continue to harness that to make the conversation better? Because the reality is that as automation continues to take over, we’re craving more human interaction, not less. We need to use that automation to help us either make decisions faster or to be able to get the information we need.

But the goal as a business owner, as a sales professional, is not to uncover the problem and solve it, as so many salespeople are still teaching. If you’re taking a sales program or something and that’s one of the things they say, I want you to stop, because Dr. Google and WebMD have solved every problem that has ever existed. Your client has found the problem, they’ve googled it, they’ve found their answer, they’re on their way.

Our jobs are now, how do we help people become the highest level of Maslow’s hierarchy, self-actualization? How do we help them achieve their goals and aspirations better and faster than ever? That’s what we need to uncover, because most people don’t know what they want to achieve. Most people don’t know that they’re capable of dreaming bigger.

So, when we are able to interact with that, the automation is going to help us uncover who we should have those conversations with. But when we’re in those conversations, that’s when we really have to embrace the more human aspects, more emotional intelligence.

ROB: Yeah, the bots don’t have empathy. They can’t have empathy, definitionally.

KIM: They will. [laughs]

ROB: It’s still going to feel like what it is. It’s cute that Google Duplex can book a restaurant reservation for me, but I’m not looking for warm fuzzies out of that. You’re talking about a very big goal, to take your buyer on a journey to where you are helping them believe you can help them be the person they want to be in their role, in their career, as a company, etc. That degree of empathy seems like it’s going to be very hard to get some automation to equip a person to do that.

KIM: To a point. At the lowest level of emotional intelligence, it is about being able to articulate an emotion. When you say that, I’d be like, “Wow, Rob, that sounds very frustrating to you.” It’s easy to train a bot to say, whoever comes to our website, “Who are you currently using?” or “Why are you looking for a new service?” and when the person responds, they’re like “That sounds really frustrating.” At the lowest level, that’s how we mimic emotional intelligence and empathy.

On the deeper level, where we’re actually connecting with something within ourselves in order to share that, that’s what we need to do. This is everything from understanding what my client is feeling all the way through what they’re feeling after we’re finished. But then, yes, after you get to feelings, it’s a “be.” What will you become when you’re able to achieve that? Help your client to dream.

Then you get into, when we talk about the changing of that conversation, then it’s taking away the dream, and then they want the dream. [laughs] It’s the new sales, essentially.

ROB: Sure. On the flip side of it, what are the things that, if someone is defining their value as a salesperson by doing these particular tasks, where are they hosed? Where are they just in trouble, where these things are going to be automated by bots? You might have to do them now, but you’re not going to be doing these things in 3-5 years.

KIM: The fastest thing is the logic-based conversations. If you have built your sales process where you are having the conversation of “What is your budget? Are you the decision-maker? How will you determine what is the best solution for you?” – if those are your standard three questions that you ask every client, a bot can take that over. There’s nothing stopping you versus a machine from asking those same levels of questions.

If your questions are about “How do you think” or “How do you know,” get away from that. Let’s dive in as deep as we can into “How would that feel?” and “What would you do with that feeling?” and “How would that help you to become…?” If you are not emotionally charged, either positively or negatively, and your client is not emotionally charged – if they are not leaving that conversation feeling better than, then you have failed your client, and your job is at risk of being completely replaced.

Because that means that your company is training you to be transactional, and the only reason they’re training you to be transactional is so they can extract your information and hand it over to some script company to see the effectiveness of each one of these questions in order to lead to a sale. It gets crazy deep, crazy fast. But at the end of the day, what we all need to focus on is the skill. This is a skill. You have to practice it every single day, and if you’re not asking somebody new, “How are you feeling today?”, then you’re failing that skillset.

ROB: It’s kind of like business sales eventually becomes like vending machines. You used to buy a Coke from a person; now you can buy it from a vending machine. If you’re doing a sales process that is just a fancy version of being a vending machine, then you’re going to be in some trouble, it sounds like.

KIM: Absolutely. If therapists are going to eventually also become replaced by bots, therapists are going to find jobs now as salespeople, because they’re the only ones that are going to have conversations about feelings.

If you can go through there, if you write down say the top 10 questions that you ask, and they either have the word “think” or “know” or they are asking for a logic-based question, change it up. It is time. Otherwise, start developing a brand new skill, because the future’s now. We’re not talking about at some point, 2040. We’re talking about like 2022.

ROB: That skill of figuring out the better questions, that’s still a human thing right now?

KIM: Is the skill of asking better questions a human thing?

ROB: Right now, yeah.

KIM: It could be.

ROB: Do you think we’ll get to a point where you can plug in some tool to your email system and your CRM, it can look at all your conversations and say, “Hey, these are some good deeper questions to ask your clients”?

KIM: Yes. Short stop, yes. I believe that there’s already technology that’s providing that. We just haven’t done the research on finding out what that – I’m sure there’s going to be somebody listening to your podcast right now that’s going to be like, “Here’s the company.” But yes.

ROB: There’s tons of those things. It’s fragmented, and the price points start off high. Then over time we get really amazing stuff for sure cheap. It’s table stakes.

KIM: Here’s the thing. Here we are at Inbound, we’re at HubSpot’s conference. But if you’ve ever written an email out of HubSpot’s CRM, one of the things it’ll ask you is, “Listen, this sounds very one-sided. Would you like to insert a question?” So, they already know that there isn’t a question being asked. Now what they’re going to start to do is continue to use that automation and be like, “How about this question?” Google’s already doing this.

Here’s the thing. Chances are, as well, the technology already exists. They just haven’t released it to the masses yet because we haven’t embraced what we already have.

ROB: And we’re still robo-calling, so they’re like, “You don’t need any of this stuff yet, you’re still robo-calling.”

KIM: [laughs] Yeah. I’m still a huge fan of phone calls. I love the connections that we have. But there will be a point where – I mean, Google Duplex is calling restaurants on our behalf. We’re training our buyers. Whatever phone calls they were picking up, we’re training them now to no longer pick up. That’s the unfortunate reality. If we train ourselves and our buyers on how we want to interact with them, are we training them in the right things?

ROB: Or as we poisoning the well?

KIM: Exactly. Are we training them to actually become more distant? If you’re finding that the conversations you’re having are really hard to extract the information, it’s time to turn the mirror around and take a look.

ROB: Kim, you’ve been building KO Advantage Group for not too long, but a little bit. If you were starting that thing over today, what might you do differently? What have you learned from this process?

KIM: A few things. For anybody who’s brand new or planning on starting, first things first, I probably would have not spent nearly as much time trying to develop my website and create a Facebook group and everything else. I don’t know if you’ve heard that one before, but honestly, I probably spent months creating all that stuff, and none of that actually generated me revenue.

ROB: I don’t think I’ve heard it enough. I think that’s an admission that a lot of people won’t say because they have a bias towards the thing they did. You do like it. You’re glad for what you have.

KIM: I’m so glad. I’m so glad that I have it. But I wish I wouldn’t have spent so much time on it because at the end of the day, what actually brought me in revenue was having the client conversations. When I was able to have those client conversations, when I was able to convert those deals, then I could go back and finesse the things I had written.

Here’s the reality. I have yet to have a single person who I’ve had a conversation with say, “I love you. Whatever you’re selling, I’m buying. But give me one second – I need to check out your website first to find out if you’re legit.” [laughs] That doesn’t happen.

ROB: Right. What people were buying on Day 1 was you.

KIM: Yes.

ROB: And on Day Whatever now, they’re buying your people, your process, your results.

KIM: Yes. But I spent too much time.

ROB: I almost feel like the way I might put this to someone is get to a website and a logo and whatever branding you need to not be embarrassed. Not to be completely embarrassed. Make sure it’s not an obstacle. Once you’re at that level, you’re probably good enough for now, because you’re going to change your mind.

KIM: You’re going to change it, exactly. You’re going to change it. I changed everything from logos to colors to even my incorporation name all the way through it, until I got to a point where I landed on it. Here’s the reality – I’m sure even the biggest companies eventually get tired of a logo from time to time. “Oh, it’s so tired.” But it’s not about you anymore. The clients own that. Once you have given them that gift, that is theirs to enjoy.

ROB: Kim, when people want to find you and find KO Advantage Group, where should they go find you and learn more about this 10-week process?

KIM: Thank you so much. I would love to have as many conversations with people as possible. You can email me directly, Otherwise, find me on LinkedIn. That’s probably my most active social media platform. LinkedIn has already called me one of the Top Sales Leaders to Follow, so I’m constantly putting out information all the time on just how to help you sell more.

ROB: Nice. Any LinkedIn tips for aspiring LinkedIn pros out there?

KIM: Just start posting. Start engaging, and like anything, have fun with it. Don’t spend too much time. Don’t overthink it, at the end of the day.

ROB: Perfect. Thank you for that, and thank you for joining us, Kim. It has been a pleasure.

KIM: Thank you so much for having me, Rob. I loved it.

ROB: Be well. Loved it too.

Thank you for listening. The Marketing Agency Leadership Podcast is presented by Converge. Converge helps digital marketing agencies and brands automate their reporting so they can be more profitable, accurate, and responsive. To learn more about how Converge can automate your marketing reporting, email, or visit us on the web at

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