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March 5, 2026

Ken Proctor, Founder of The Grey Pointe Group

The Power of Asking Better Questions with Ken Proctor

Leadership is not about having all the answers. It is about asking the right questions.

In this episode of Above the Clouds: Stories from the Boardroom, Richard Byrd sits down with Ken Proctor, Founder of The Grey Pointe Group, to talk about the lessons that come from decades of leadership, career pivots, and helping executives think more clearly about the challenges they face.

Ken reflects on his journey from a long career in the shoe industry to building and selling his own company, and how those experiences shaped the work he does today guiding leaders through peer groups and executive coaching.

The conversation explores why curiosity is one of the most underrated leadership skills, how strong peer networks create accountability, and why the quality of your questions often determines the quality of your decisions.

Full Transcript

Welcome to the podcast Above the Cloud: Stories from the Boardroom. In every episode, we interview business leaders who are navigating the complex world of B2B marketing. Whether you're trying to grow revenue, swoop into a new market, or launch new products, we promise you've landed in the right spot. And now, your host, Richard Bird. >> Welcome to the Above the Clouds podcast. Today, we have a very special guest and somebody not only that I consider my friend, but also a mentor. Today we have Ken Proctor.

And Ken is the longest job title I've ever seen. He's he's uh he has more jobs than anybody. Hardest working man in business, I think. So Ken is a Vistage chair. He is a public speaker, an executive coach, and owner of the Great Group. Please welcome Ken to the podcast. Welcome, Ken. >> Thank you, Richard, for having me. >> Oh, man. I'm really happy to have you here. And also for our viewers that aren't listening, you'll see we're back in the lovely Anthem Studios. So thankful to Nathan and the gang for hosting us here in these wonderful studios.

I I just always feels so nice to shooting. I almost feel like I'm a real podcaster when I when I have this. Well, Ken, as you know on the podcast, we always kick it off with our novelty answer or question and that is if you your company or in your case since you personify your company were a bird, what kind of bird would you be? That's a great question, Richard. One that I've never been asked before. And after deep reflective thought, I would like to be Big Bird. >> Nice. Why Big Bird? >> You know, Big Bird is always affirming.

It It I don't know if it's a he or a she, but it's always positive, uplifting, and I think it helps people feel as though they matter. And I've always appreciated that about Big Bird and Sesame Street. And that's how I want to be viewed. Oh, >> I love it. I love Big Bird. He has mysterious pronouns. I don't know, maybe it's a they them. I don't I'm not >> It's It's androgynous. Yeah, for sure. >> But yeah, Big Bird is great. I think that was one of the things I, you know, I grew up watching that show and I was really happy, you know, for my son to watch it when I when he was a little kid and I always thought that it does make kids feel so comfortable and affirmed as you mentioned.

>> Agreed. >> Usually we say tell us a little about your company, but you have so many companies. Yeah. >> Tell me a little bit about your career, kind of how you got to where you're at and a little bit about about what you're doing these days. >> Happy to. So, I grew up at a time when one of my favorite shows was a show called Lifestyles of the Rich and Famous. >> Yeah. >> And I remember seeing a profile on people like Georgio Armani and Ralph Lauren. And I always had an interest in clothes and I said, "Yeah, I'm going to be a rep someday.

I'm going to be a rep for Giorgio Armani or Ralph Lauren or something like that." And I graduated from college and I went through the Macy's Executive Training Program thinking that that was my first step. Well, I went from Macy's to Sachs and then um I got approached by a head hunter except he wasn't representing Giorgio Armani or Ralph Lauren. He was representing a startup children's shoe company and he was looking for reps. Well, not exactly my biwick because I didn't have any children at the time, but I thought why not?

And I went to work for this company. And from there, I started in the shoe business for 25 years, working my way up from sales rep all the way to the president of a division. And then I was fired from that job. So I started my own company, started it, scaled it, and sold it. And I sold it at age 48. And I didn't know what to do next. So I thought about it, and I hired a career coach. And after four months of very intensive conversations and assessments, he said, "You need to be a coach." Okay. And tell me why.

>> He said, "You're a great listener and you ask great questions." And I got put on the path to Vistage. And for those of you that don't know what Vistage is, Vistage is an organization that puts business owners together in a group and once a month we meet and challenge each other and hold one another accountable. We process issues. It's very confidential. And I started in Vistage about 12 years ago. Grew that to 12 uh sorry to four groups and then started an executive coaching business. And from the executive coaching business I started something called art of the question because I realized through my own failures that I was selling and not asking tough enough questions which is symptomatic of a lot of people in business development.

And then from there I transitioned into keynote speaking and that's basically my career in a nutshell. >> What got you fired from your first job? It probably is the thing that made you successful as an entrepreneur. the the job that I was working for uh when I was the president at the time, this was 2006 and the internet was really coming on um it was kind of in its infancy and the CEO of the company I wanted to go headirs into selling online because Zappos, which was an online shoe retailer, had approached us.

They really didn't have any vendors yet that have signed on yet. And I wanted to go forward with them. And my boss, who is the CEO of the company, said absolutely not. And I went ahead and started business with them anyway. >> Oh wow. >> And he was very unhappy about that until he saw the numbers that we started putting up. >> Yeah. >> And then he started making decisions that were not in the best interest of online. He still believed in brick and mortar, which is fine. we were going in a different direction and finally he made the decision I need somebody that's going to be more of a yes man to me >> and stick with brick and mortar and he fired me and you know arguably he had reason to >> because I had my own ideas of which way brick and mortar were going which way the internet was going.

>> Wow. Did you get to meet Tony Shay? >> I did. Yeah, actually um he came into my booth at a trade show in Las Vegas and uh he came in with a buyer who I knew from a previous relationship at Nordstrom and uh everybody else was escorting them out of the booth. They told me about what they were doing and I said, "Where do I sign?" Absolutely. And I actually started a friendship with Tony Sheay. Went to his um this was years later. He lived in a Airstream in a container park and he had a pet llama. >> Wow.

>> And I He was a little bit of an odd person. Very quiet but brilliant and I really liked him. >> I've read so many case studies about him. How he built the culture. >> That's right. >> Zapos and that just one of those cultures that as a small business owner that I just, you know, would kill to have that kind of amazing customer focused culture that they had. And interestingly enough, he started a protocol that every person, regardless of where you start in the company, you have to spend the first three weeks on the phone talking to customers, regardless of your title.

And he also instituted something that after three weeks of working for the company, you w you got brought into human resources and they offered you $2,500 to quit to see how committed you were to the company. And less than 1% of the people took him up on that. some friends about uh the other night over dinner recently. It's weird because it's a weird case study to bring back that was had was a long time ago. Yeah. >> But but it always that really struck me when I read about that and I thought um so I was telling it to my son's girlfriend who works at Starbucks and they have a hard time when they recruit people there that they get in there and they realize that they don't want to be in the coffee business after a few months but they've already spent all this time training them.

And I said you should do what they did at Zappos. Let them hit the opt out button. You know, the culture at Zapos was really what people would literally break the wall down to go work there. And as an executive coach, I'm very fond of asking my clients, if you back out compensation, tell me why somebody would want to work at your company. And it is literally, Richard, a deer in the headlights moment. >> Sure. >> Because they don't have an answer for that. But I will say Zapos leaned into their employees and always treating them well and investing in them professionally.

>> Tell me your story about Vistage and uh how you wind up choosing that direction. >> So when my coach said, you know, I really think that you should be a coach, I was actually pointed in the direction of Vistage and another company called Focal Point Coaching, >> which was a uh franchise. And I liked both of them. And I got approved to be a Vistage or to go through training for a Vistage chair. At that time, you had to have been in the seuite with at least $10 million of profit and loss responsibility and or start your own company with at least a million dollars in revenue.

I had both. So I got approved for training. in Focal Point, you just had to give them $50,000 and you were a focal point coach. And so I couldn't decide and I finally met with the person from Focal Point. I said, "What do I need to do to be a great focal point coach?" He said, "You've got to be a great salesman." Okay, well, I can sell. And then I asked my colleague at Vistage, "What do I need to do to be a great Vistage chair?" And she said, "You must care deeply about your members." Well, that was it.

So I went with Vistage and the very first day of training I'm in San Diego and honestly Richard it looked like I was attending a Brooks Brothers commercial. All these older gentlemen that were clean and polished and scrubbed and I'm like what am I doing here? And the first thing that they said to us is the chances of launching a group are 22%. It's a 78% failure rate. And I remember thinking looking around and thinking who's going to be in that 22% I'm going to be one of them. >> And that's how I got started at Vistage.

>> Wow. Yeah. That is u it's a discouraging number to hear when you're in that >> first thing. Yep. That's the first thing they said. >> Well, at least that you know they're honest upfront with you about the you know how it was going to you know the challenging how challenging it was going to be >> and it was. >> Well, I'm glad you chose that path because I wouldn't have met you otherwise. That's where we met. Yep. And as you mentioned, it's top secret, so I can't say anything else about it. >> That's right.

>> First roll of Vistage. Never talk about Vistage. >> Las Vegas rules, right? >> That's right. Yep. That is absolutely right. Tell me about when you when you had your own business. What were some of the challenges that you saw as a as a business owner? >> Richard, there were plenty of days that I literally would have traded my company for a $10 gift card to Chick-fil-A. very frustrating trying to scale the business, finding the right employees, finding the right manufacturing, dealing with egos, dealing with retailers.

We're a small business. And at the time, I mean, remember, I started my business in 2007 and we started Yeah, we started growing. And then by 2008, I had a meeting with our CPA and he looked at me and he said, "You're six weeks away from going out of business." And here I was gonna thinking that I was going to take a victory lap because we were growing really quickly. And I said that to him. I said, "But we've got all these POS." He said, "You do, but you're bootstrapping this and you're burning through your cash.

I don't know what to do." And he said, "You got to go get a line of credit or a loan." 2008, I'm sure, Richard, you remember what was happening in 2008. >> Banks were just giving away money for free at that point. >> That's exactly right. And I learned a lesson about banks. Banks loan you money after you prove to them that you don't need it, not when you need it. And so I learned a hard lesson in business, and that is dig the well before you're thirsty. I waited until I was thirsty to dig the well, and we thankfully got a $50,000 line of credit and that saved us.

And then we were a much better financial steward to the business and we created some new payment terms and we were able to scale from there. Somebody told me when I first got in, you know, started my company, they're like, "Well, you know, cash flow is really important." I was like, "Duh." >> Yeah. Right. >> No kidding. That's the biggest understatement. It's like when people tell you when you have kids, it's going to change your life. >> You know, kind of thing. >> Yeah. >> It is. So, it is just everything.

And and like you said, you can things will look great, but if you're burning cash faster than it's coming in, even if you're billing it and you look great on the books. That's right. Doesn't matter if it's not in your bank account. And and I remember very clearly coming home from work one day. Now, at the time, we owed our factory $310,000. Quarterly taxes were due and it was a payroll week. And my wife, I come through the door and she said, "How was work?" How was work, let me tell you. And she held up her hand and she said, "I need you to go pick up Kelsey, our middle daughter, at dance." And I'm like, "I'm dying here.

I gotta talk to somebody about this." I didn't have anybody to talk to. And that's when I those were one of those days where you have a $10 gift card to Chick-fil-A, you can have this company. >> Yeah. And then you can pay the factory $350,000. >> That's it. Yep. That's exactly right. >> Oh man. Well, I think every business owner can relate to that. For sure. For sure. It is. Uh Yeah. I think that is something that people don't fully appreciate about business owners is the how heavy payroll weighs over your head when you own a business.

And you know, I and I'm sure you can relate to this. There were plenty of pay periods that I didn't get paid. We didn't take an income for the first year. And then I think we took I think about $25,000 in salary year two. >> Wow. Yeah. Well, that's the thing. That's the other little sneaky thing they don't tell you about business ownership is that you're the last person to get paid. >> That's correct. That's absolutely correct. Yep. >> Oh, man. That's like, hey, wait a second. This wasn't in the in the brochure about this.

It my dad told me he gave me some great advice about lines of or bank dealing with bankers. And he said that whenever you need money, your banker won't doesn't want to have anything to do with you, but when you don't need them, they're going to be all over you. >> That That's right. And when they when you don't need them, they invite you out to lunch in a golf tournament and you know what? >> When you do need them, >> right? >> Yeah, he was right. >> That sounds like you you learned a lot from, you know, from that that stage in your growth.

How do you think that has influenced the way that you coach business owners? >> You know, I can empathize and sympathize with them. And for those of these business owners that are, you know, having meteoric growth, I always tell them, you have to be mindful of cash. I didn't know any better and thought, but we're growing. What's the big deal? The cash is going to come. Our terms at the time were s 2% 60 days. And the amount of people that paid in 60 days, >> not that many. I mean, it was 90, 120. And then I learned this.

I learned how to identify a lie. When I would call an owner or the credit credit department would call a a store, you're next to be paid. I'm going to be sending you a check on Wednesday, right? That means that none is coming. >> Yes. >> Especially when you hear your next you're on the top of the list. >> No. >> And they said that to the last 30 guys. >> Yes. That that's exactly right. Exactly right. That is another wrinkle to that you don't think about having to do whenever you're in business is the you know even if you have an accounts you know receivable part of your organization which we do but I still have to do collection calls.

>> Yep. >> You know anybody out there if the CEO of a small business calls you to collect money just know uh they they need that cash. >> That's that's exactly correct. I would have to get involved because we needed the cash. they were needing to make payroll and your decision to slow pay them is is hurting a lot more people than than you think it is. >> That's right. >> I think that that I could tell that you know just from our interactions in Vistage that you walked a mile in the >> Oh, absolutely. And you know, it's funny.

I was I was heading out to a trade show in Las Vegas and I had gotten upgraded. I was sitting next to a guy and he was asking me a bunch of questions and he finally said to me, "Man, it must be great owning your own company. I mean, you get to work any hours you want." And I remember looking at him and saying, "That's right. I can work any 17 hours of the day that I want." And by the way, I typically don't get paid. >> So, yes, it's great. >> It is. >> But people don't they don't understand that. >> But that's what it takes in the early years.

But then hopefully one day you get to cash out like you were able to do. >> Yep. >> And it all it all pays off. >> That's right. >> One of the things you mentioned too was uh Art of the Question. >> So as a proud graduate of Art of the Question, but for people who don't understand or haven't heard of Art of the Question, tell us a little bit about about that. >> Sure. Art of the question was born from my own failures because although I launched my first Vistage group quickly with nine members and then I spiked it to 11 and then I dropped to five and I can share with you it was my fault because I was selling what we were doing.

So, I'm at five members and I'm desperate and I'm on my knees begging for members. And let me share with you that desperation is the worst smelling cologne there is. And I was bathed in it. And I remember getting a referral. Another chair called me and said, "You want to talk to this guy? He's in my group. He's not happy. You want to talk to him?" "Sure." And I sat outside in his parking lot and I said to myself, "Don't sell. Don't sell. Ask tough questions." So, I went in and I met with him and I said, "Tell me why you're interested in moving to another group." He said, 'Well, my mother always told me that if I'm the smartest guy in the room, I'm in the wrong room.

H, so you're the smartest guy in the room in your Vistage group. Yes. Okay. Now, how do you know that? And he started telling me about his blue chip education and this business that he has. And I said, "But how do you know you're the smartest?" And I'm starting to challenge him with questions. And the next question I asked him was, "What are your top two leadership blind spots?" >> Now, I'm not telling him all about my group or what. I'm not doing that. I'm asking him tough questions. And he said, "Gosh, I have no idea." So, tell you what, let's ask Elizabeth, your assistant, that same question, but not before you tell her to answer with cander, and then I'm going to send you out of the room.

And at this point, Richard, I am literally having an outof body experience. I'm floating above this person that's asking these tough questions because I'm used to selling. And so I asked Elizabeth, she said, "Oh my gosh, that's easy." One and two are exactly the same. He micromanages the tar out of us. >> Thank you, Elizabeth. Paul comes back in. What do you think, Elizabeth said? No idea. She said, "You micromanage the tar out of them." So we start talking about that and I said, you know, I'm going to ask you one more question.

I'm going to go get a cup of coffee, go to the men's room, think about it. There's an Irish proverb that says, 'When you run from a ghost, it chases you forever. What ghost are you running from? And I left. And I come back after five minutes and he said, I came to this country with $200 in a toothbrush and I'm desperately afraid of going back to that. This guy's running a huge organization. I don't think he's going back to that. But that was his ghost, >> man. >> And I asked him if he could connect the dots between that ghost and his need to micromanage.

And he said, "Yes." And I said, "Are you willing to work on that?" Yes. welcome to the group. And it was at that moment that I realized the power of asking questions, not telling him all about my groups that got him to commit to my group. And then a week or two later, I was asked by another member to evaluate two sales guys presenting to a new prospect in the pipeline inspection business. And it was essentially, this is who we are. This is what we do. This is how long we've been in business. These are the services we offer.

I'll call you next week. >> And my member said to me, how do you think that went? I said, "I think it was not good." And he said, "Why?" And I said, "Well, there's good, there's not good." That wasn't good. What did you learn about the prospect? What metrics are they using to determine which pipeline inspection company? They go, "What do they value? What's the best experience they had?" I asked a bunch of questions. And at that moment, I said, "I am going to start a course called art of the question. It's going to be six sessions, very, very interactive.

I've run it 48 times, 12 people per cohort. I've sold all but eight seats over the last five and a half years. It's become very successful. >> I had a really good experience uh on that. But I I remember it was also painful at times. >> Yeah. Well, >> it seems obvious now that the name of the class is art of the question. That's right. and you would ask us questions and then we would as a person who does sales would just kind of jump in and just start giving my differentiator and hitting you with value propositions.

Sure. >> You know all the stuff that u you learn to do as a you know when you learn about sales >> and you would just bloody our nose for it right there and it's like well you took the bait. Yep. >> Took the bait. You didn't ask any questions and you're going dang it was right on the title of the >> That exactly right. And when um somebody asks me, why should I join your vistage group? Why should I engage you as an executive coach? My stock default answer is this. I don't know that you should. >> Yeah. >> I don't know what you're looking for from a peer group or from executive coaching.

So, let me go ahead and ask you a few questions and then let's determine together whether or not it makes sense to move forward. So, what that does to the trust meter, Richard, it elevates it and people will listen to you if they like you. They buy from you if they trust you. >> 100%. And I'll tell you that is something that I use a lot in our uh sales discovery process because uh I got rid of the sales process. You know, I think at this point we call it a discovery process because >> we had a client that or prospect we were talking to the other day.

I don't know if we're going to win it or not, so I can't tell you if this was successful, but >> they um they're in from Germany >> and so you know, you've worked with Germans before. they were ask firing away all these questions about the company and then uh and then they said why should we work with you and and I used that exact line of well I'm not sure can do you mind if I ask you some questions because I'm not sure if it's a good fit and then I just went straight into consulting mode and started asking all these business questions and things like that and it went the meeting went really really well I said I don't know if we won it yet but we got definitely invited to the next round in fact they sent a follow-up email before we were able to send the follow-up because it was a Friday afternoon meeting.

So, you know, I think that's the kind of thing that really um is great. And I think before that class uh before the question, I would have been like, "Well, let me tell you." >> Yeah. >> Here's what makes us different. Here's why we're better than the last guys that were in here talking to you five minutes before we got here. And you know, and I just um I don't do that anymore. >> It's a mindset shift. And you know, as I always tell people, people care about themselves morning, noon, and after dinner.

And you know, if you ask people, would you rather talk or listen? Everybody's gonna say talk. I I understand that. A successful sales presentation is you're talking 20% of the time and your prospect or customer is talking 80% of the time. They're answering questions because what's people's favorite topic? Themselves. >> Oh yeah. >> They don't want to be sold to. They want to be they want their issue solved. >> Big difference. >> Big time. You know, one of the the games that I like to play that I learned in Art of the Question is I will go to some function, you know, a networking function or some sort of business deal where I don't know anybody at the place and I will play a game where I try to learn as much about anyone, the people in the room without telling them anything about myself >> and I keep a tally and it's really interesting because I've been to I've been to some of those things where maybe I talked to, you know, six six eight people and I learned all kinds of stuff about the you know health problems you name it and I didn't I didn't reveal any nobody in that place could tell one thing about me I think >> that's a successful event because you know what Richard if you ask people about themselves they'll listen for hours and they'll walk away and say boy that guy Richard what a great conversationalist he was you didn't say anything except ask them questions that's how our brains work >> yeah it's really it's fun it's kind of a fun thing to do when you're trying to sharpen that skill or learn to use that muscle because it's hard not to because >> I think one of the examples you gave was like when people say you say, "Oh, you just got back from vacation." They're like, "Oh, I was in Costa Rica.

Oh, I love Costa Rica. I've been to Costa Rica a million times. Did you eat at this place?" You know, all the questions that just jump right in and hijack those conversations. >> That is the most egregious crime scene you can come across. It's the crime scene of hijacking. And I get it because people in an effort to be relatable, they want to tell you about their trip to Costa Rica. But my wife and I raised three kids and we raised them that they have to ask three questions about a person's experience or story before relating their own.

Now, if you're the parent of a 10, 11, 12, 13year-old, go ahead and cue the eye roll, which we got plenty of. But they're all doing adulting really well because they are so naturally inquisitive. And what I tell them, replace judgment with curiosity. And people are far more interested about talking themselves than about hearing about your experience in Costa Rica. >> Well, I'll tell you that is listeners, take note because that is some of the best parenting advice. Uh you you'll get and I wish I would have known that advice before uh before I met you because I love to instill that into a 5-year-old.

>> Yeah. >> Uh would be amazing. You tuned in this to hear about sales and marketing, but you learn about parenting advice on this show. >> That's right. >> Multiaceted. Yeah. >> Tell me about keynote. That's a that's a new one. >> I was once asked a question, when does work not feel like work? >> And for me, it's when I'm speaking publicly because I I don't suffer from stage fright. I really enjoy the opportunity to make a difference in people. And so about a year ago, I embarked on a journey with a company called Brand Builders Group.

And they help speakers sort of refine their message. It's a difficult process because when coming up with a topic for your keynote, one of the questions that they ask in one word, what problem do you solve? >> And I agonized over this for weeks and I kept thinking about it and then I had another meeting with my brand strategist and I I said, I'm really struggling with this because I think I solve a lot of like, you know, about making people feel heard. Well, that's not a problem and that's not one word.

So he said to me, "Tell me a story that happened to you recently that not most people don't know about you." I said, ' Okay. Well, couple weeks ago, I was pulling out of my neighborhood and I saw these two girls about nine and seven and they had a little card table set up. Well, you turn and I got out and I said, "Ladies, what are you selling? Handmade bracelets." Well, I'm interested because my anniversary is next week, so why don't you tell me about these? And they started telling me that they're, you know, they can customize it and make any color you want and on and on and on and on.

And I said, "Okay, how much are they? 50 cents for one, a dollar for two, but if you buy two, you get the third free." >> Bargain. >> Bargain. And I looked at them and I said, "I'm a buyer. I'm going to buy one, but I disagree with the price. I think they're worth $20." >> And they said, "Well, we can't make change." I said, "I'm not asking for change, ladies. You've got labor costs here. You've got your cost of materials here. You've set up this nice store. I'm more comfortable with $20. You can imagine how they felt.

And I told that story to my strategist and he said, "I know what the word is. You solve the problem of people feeling insignificant. You help them feel significant." >> And he nailed it. That's exactly correct. That's what you do with art of the question, executive coaching, things like that. And then it all tied together. So, I just presented a keynote in Nashville. I was selected one of 18 speakers out of 300 that applied to give a 15minute presentation. And then you get right away you get feedback from the owners of the company.

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