Show Notes

In this episode of the Coach Factory podcast, Brent “Spillly” Spilkin, a business coach, discusses his unique coaching approach with business owners and how he established himself in a niche market. Howard Mann, coach and entrepreneur, shares the influence his personal experiences had on helping him develop tools and practices to share with other entrepreneurs.

Brent “Spillly” Spilkin, a popular business coach, discusses his unique blend of coaching and consulting, and how he established himself in a niche market. He goes on to talk about starting his business in South Africa and how he discovered the pains of running a business early on when establishing his niche.

Brent highlights that measuring growth is the key to understanding how to coach businesses to their ideal success.

Howard Mann, coach and entrepreneur, shares how his personal experiences helped him to develop tools and practices he shares with other entrepreneurs today.

Brent returns to talk about the importance of referrals, how credibility grows in different business structures, and the power of credibility in establishing coaching relationships.

Howard builds off this idea and points to trust as the first key part of coaching, especially working with entrepreneurs. This practice Howard describes takes time. He walks through his two-step process for developing trust effectively in a coaching relationship.

Brent breaks down his coaching structure and describes how he borrows inspiration from the structure of law firms into his service packaging. He explains how this works better both for the coaching process and the client’s business.

He then shares the challenges of remaining relevant with clients through this structure and highlights the relationship between coach and business owner.

Howard discusses how pride can become a roadblock in business coaching and shares how it’s a unique obstacle for business coaches to overcome.

He describes the freedom you can gain from admitting you don’t know everything about the business you run, and the assurance that you’ll learn as you grow. Hiring others to take on certain roles is a powerful tool that Howard encourages business owners to leverage so they can focus on the vision of the company.

Brent points to his clients as his key source of learning and explains how he carries experiences with various business owners into new industries. He talks about how he measured his time learning new things early on, and the mindset shift that happened when he made it a part of his pitch process.

Closing out the episode, Howard shares how business coaching inspires him and the many ways working with entrepreneurs challenges him. He highlights the journey of learning business and working with start-ups.


Brent ‘Spillly’ Spilkin:

So every client is obviously unique in terms of the way they’re brought up, the way they’re educated, their current state of mind, and that’s based on personal things happening in their life, as well as the business itself. So there is no average obviously to start off with. So to understand where they are today is the first piece of work.

Shawn Hesketh:

When it comes to coaching business owners, Brent Spilkin, or “Spillly with 3 Ls” as he’s affectionately known, has built his entire niche by blending coaching and consulting, to solve the practical and personal challenges entrepreneurs face when their business growth becomes stagnant.

Welcome to the Coach Factory Podcast. I’m your host, Shawn Hesketh, and in today’s episode we’re taking a deep dive into the niche of business coaching. We’ll take a look at how to establish yourself as a business coach and then explore the different approaches to connecting with and retaining clients. Spillly has strong brand recognition in his market of South Africa, and he’s learned that to enter the business coaching niche, you first need to understand the pains of running a business.

Brent ‘Spillly’ Spilkin:

The challenge of running a business is obviously it’s hard. You go through phases where things are easy and you don’t really appreciate it, but more often than not, it’s difficult, but the ability to push through, almost embrace that pain, and come to terms with it, is a very immediate factor in terms of deciding whether this person will grow a more substantial business. You often see guys will get the business out the ground quite quickly to a point of sustainability, but then cannot grow it further because it’s too difficult. And it’s too difficult from a mindset perspective. There’s too much work or there’s too much stress, or “I can’t get my head around employing a more expensive person than me,” or there’s a mental block. But then again, if the business owner upfront is going, “I just want to earn X thousand dollars a month and live a good life,” as opposed to grow a behemoth business, then let’s get you to that point and figure out how to maintain that, as opposed to growth for growth sake.

So it very much depends on the individual, where they are in their current state, and what their aspirations are and how quickly they want to get there. I think the one big trick is what are they measuring? They’re measuring where they are to where they want to be? Or are they measuring where they are versus where they came from? And having the ability to self-reflect backwards and go, “Oh, I have accomplished a lot. I have come a long way in the last three months or the last 12 months or the last three years.” Versus, “I’m not there yet.” That I’m not there yet creates a lot of frustration, where looking backwards helps you realize you have come a long way because daily, that incremental growth, you don’t see it, you don’t feel it. But when you look back at the numbers or the headcount or the revenue, whatever that is, over long periods backwards, you realize that you are climbing that hill and that you have achieved some level of success.

Shawn Hesketh:

Looking back on your growth may give you a lot of confidence, but it can also be a starting point for changing your market. That’s why Howard Mann, a business coach and President of The Business Brickyard regularly uses his own experience running a business to inform the work he does with entrepreneurs.

Howard Mann:

In the first half of my career, I was the owner of a mid-sized freight and logistics company that went through really difficult times in the recession of the late ’90s and I spent three to four very lonely worry filled years bouncing around the world and the country trying to fix it, and finally got that business to a place where we could sell it in January of 2000.

And looking back on it, I wanted to find a way to give meaning to those hard years, give meaning to that dark time. And I felt that if I could help other business owners never have to go through that hard time, that would be great, and to never have to go through it alone. And so for the last 23 years, I have been doing business turnarounds, coaching business owners, working with their executive teams, advising businesses to think bigger and to get really honest and open about what a business owner wants from their business and probably ask questions that they don’t want face and how they’re feeling and to help them turn that around.

Shawn Hesketh:

Credentials carry a lot of weight in both the business and coaching markets, and credibility is at the core of any coaching relationship. It can even be a tool for coaches looking to evaluate whether a client’s business matches their target niche.

Brent ‘Spillly’ Spilkin:

One of the best indicators for me of someone that’s doing something right with their business is that credibility piece and that often materializes as a referral. When a client of yours is passing your name around, that means a series of things need to be good enough or great for that to happen. Some people have a natural instinct in terms of EQ and managing relationships and dealing with their clients. And again, it depends on the kind of business, whether it’s a widget business that’s B2C or whether it’s a consultation business, B2B. So it depends on the kind of business and the levels of client in terms of the way they engage. But I think that in terms of building credibility, it starts with the formula of understanding who you’re selling to? What are their drivers? So what does your client want? Do they want increased communication? Do they want faster turnaround time? Do they want value from money or a beautiful quality product?

Understanding the human you’re dealing with, and again, my expertise is very much B2B, so most of my clients sell to other businesses. So what are the tools that you can give someone to understand and unpack the person they’re selling to. And then tailor your offering and your service levels to that person. What you’ll often find is that you could have a fairly mediocre product or service, but if you wrap it in the right level of service and engagement and the right level of communication and you speak the right language, you build credibility or trust very quickly.

Shawn Hesketh:

Turning credibility into trust is like balancing a scale of human nature on one hand and expertise on the other. And as Howard often experiences, it takes time.

Howard Mann:

The first step for any coach is to spend the time to create trust with their client. I don’t care if it’s a business client or any client, that you have to be willing to invest in a truly deep, honest conversation, so that trust is built, so that whomever you’re talking to is willing to say the magic words of, “Okay, let me tell you the truth of how I’m feeling.” And I will often say to somebody, “How are you feeling?’ And you get that knee-jerk reaction, “Oh, great.” That’s the first one. “How are you feeling?” “Oh, you know. Business is business.” I get that sort of response. But what I’m trying to get at with somebody is if you can build up trust, and empathy will help because they don’t feel they have to be so proud because they can understand that you’ve had some of the same life experiences and that you know how they feel and you know it’s not always great, that it will allow them to begin to open up to you and tell you what’s really going on.

Shawn Hesketh:

But how do you build that credibility and connection with your client? Howard’s two-step process for this builds on emphasizing the humanity of a business owner and the goals they have for their business.

Howard Mann:

One, paint a really vivid picture about their life today. “Tell me about your day. Tell me how you start your day. Tell me what time you start. Tell me how you feel when you come home at the end of the day. Tell me how you feel during your day. Do you feel angry? Do you feel exhausted all the time? Do you get up each morning dreading to go to work or you can’t wait to get to work? Do you feel drained by what you’re doing or do you feel super excited by, and nothing’s perfect, do you feel the super excited 75% of your day or 75% of your week or month or year? And if not, why not?”

And then the flip side question to that is, and I often say this is my magic wand question, “If I hand you a magic wand, and we’re sitting here three, five years from today, now tell me about your perfect day. Tell me what’s happening in your life and paint as vivid a picture as you’ll let yourself in this early long conversation that we’re having. Tell me what a perfect day looks like.”

And they find that very difficult. I find people, I think, in this situation, or people just do, if they’re beaten down by life and we’ve been through some really stressful hard times over the last few years, it’s hard for people to dream. It’s much easier for people to just batten down the hatches. So it’s a good and important and a hard process to work people through, “It’s okay to dream. I’m not telling you I’m going to snap my fingers as a genie and make this happen, but why not dream a little bit?” And what I find is that people come in very light on their dreams. They’re almost afraid to think big. They’re afraid to truly say what it is that they’d want out of their life, maybe because it doesn’t sound like what they think an entrepreneur’s supposed to say. There’s all this hustle culture that says, “Well, I want to grow 10 times and then I want to go public or I’m going to sell for a hundred million dollars.” Or that’s what they think they’re supposed to say.

But when I get a lot of people to really say it, they say, “I’d love to spend more time with my kids. I’d like to take two months off every year. I’d like to not have to think about work on the weekends. I’d like to have people in my business that are so great that I’m not spending as much time on the business and I’m enjoying the life that it’s giving me.” They almost feel a bit ashamed to admit that, but getting that level of trust and telling them that that’s an okay want from your business. You don’t have to wait for selling it when you’re 65 or 70 or wherever you’re thinking it is that you’ve worked out with your financial planner, that it’s okay to make enough money from your business to give you the life that you want. And that number’s going to be different for everybody. But to probe with somebody and get them to finally say, “Yeah, when I think about this life that you just helped me describe, I feel pretty excited about that.”

And then the only question set for a coach to then ask when you get to that point, and you have to be willing to have the patience and time to get there, is, “Would you like me to help you get there?” And if there’s enough trust built, they will say, “Yeah.”

Shawn Hesketh:

Your coaching packages can play a big role in establishing this trusting relationship. And Spillly pulls back the curtain on how his structure, which blends both coaching and consulting, helps him to meet the unique needs of business owners.

Brent ‘Spillly’ Spilkin:

So the one secret weapon that I learned from the non-coaching environment which I think all coaches should learn from, comes out of the lawyer legal advocate space. Large businesses have advocates or lawyers on retainer with zero deliverable expectation. It’s, “I need to have a lawyer on call. Should I need someone, I get the priority and I know they will represent me and they won’t represent my opposition. And there’s a sense of comfort in knowing that I’m paying someone to be there when I need them.”

What I’ve done is I’ve built that into my method. So what I now do is it’s a monthly coaching program with a guaranteed X amount of my time set up on a monthly basis and then access to me, buffet style, through the month at additional fee, built into my package. And with that, yes, some clients will abuse me, some clients will use me through phases where they use me a lot in the month and some others won’t. But on average, my breakage, that’s how much people don’t use me, far outweighs the cost of those few clients that do use me for that buffet style, the guys that will eat too much. On average, I know how much people will eat before they put down their plate.

So part of the value that I have is that my stance in terms of who I am, the relationship with my client, is not of a coach, but as a silent business partner. And you would like to be able to phone your business partner whenever you want, within reason. There are some turnaround times. And for that access, I’ve studied from lawyers and I charge a retainer where I’m available to you should you need me.

Shawn Hesketh:

Being credible as a business coach is more than just being a trustworthy person. Your expertise in business and a deep knowledge of your client’s unique field is what allows you to speak with some authority.

Brent ‘Spillly’ Spilkin:

The way I remain relevant with my clients for extended periods of time is twofold. The first thing is I set that expectation upfront. I don’t say, “Guys, this is a six-week engagement, and at the end, we can reevaluate and decide whether you want to continue with me.” I’m looking for clients that are looking for long-term partner discussions, guys that don’t have boards in their business, or don’t have partners and have no one else to speak to. They’re looking, they’re lonely at the top, they’re looking for someone to engage with. So the first thing is set an expectation up front to go that, “Even though you can fire me at any point in time, my intention is to be with you for a period of time. And the more I learn about you and your business, the more value I’ll be able to add to you and your business because I’ll see repeated mistakes or patterns that are happening in the way you run your business or your performance that I can then start reflecting back on you.”

And the second thing for me is that even though there is a defined engagement per month, i.e., I’m on a call for an hour or in the room for two hours, whatever that agreed actual coaching session looks like, I have a series of automated triggers behind the scenes that prompt me to reach out to my clients between sessions if I haven’t heard from them between sessions to just go, “Hey, it’s been 10 days. I haven’t heard from you. Have you taken my thoughts any further? Have you actioned anything off? Can I help with something else?” So I prompt them to go, “I’m still here. I haven’t forgotten about you. You didn’t just buy that hour of my time. You’re actually buying bandwidth in my brain.”

Shawn Hesketh:

When it comes to coaching business owners, there are unique challenges that can block both the coach and the owner from growing professionally and personally. Howard’s experience shows how being convinced you have to know it all at the beginning can actually hold your business back and keep you from reaching your full potential.

Howard Mann:

When I was struggling with my business, I was struggling for a couple of years, long before I asked for help. And if I’m being honest, the reason was everybody saw me as this smart young entrepreneur and I felt that meant that I had to have all the answers and that asking for help would be a sign of weakness. And what would people think if I said, “I don’t know how to get out of this mess. I don’t know how to make my business double or grow or whatever it is.” And so pride is a terrible insidious way of rationalizing not asking for help and feeling that you just have to figure it out on your own.

And there is a stigma across lots of things, lots of areas of life, that showing vulnerability and saying, “Listen, I’m an incredible salesperson, but I don’t know the first thing about hiring,” just to pick an example. “Or, I’m an incredible creative and I love working on creative projects with my clients, but if you stick a P&L or a monthly budget in front of me, my eyes glaze over. And I shouldn’t be doing it.” And there is enormous freedom from just saying, “You know what? I can own this business, but I don’t have to know every single aspect of business. I just have to be smart enough to say I don’t know? Who can help me? And hire somebody that loves looking at financial numbers, hire somebody that loves hiring people, and who loves talking to people about their issues and who loves digging into health insurance,” all these different things that you might not like.

And realizing that just being the visionary leader and the cultural champion of a company, who is pointing people to do great work and is pointing people to be their best and is spending most of their time being an example of what it looks like to practice your craft? That that gives tremendous freedom and gives leverage over your time and it almost starts to feel effortless because you’re now actually being an entrepreneur. You’re actually now doing the things that you’re supposed to do. But it starts at saying, “I don’t care about my pride. I care about my business. I care about building a business that makes me proud.” And if they can do that, then so many good things happen. But it can’t happen if somebody just feels, “I don’t need any help. You don’t know how to run my business better than I do. You don’t understand my business. So I’m just going to just keep going it alone.”

Shawn Hesketh:

Spillly believes that even if you’re an expert in business, there are always new things to be learning, because the business world and its various sub-markets, are always shifting and changing. And he’s absolutely right. And what I find interesting is that he points to his clients as the place he learns the most and that knowledge he can carry to other clients.

Brent ‘Spillly’ Spilkin:

I would say that a lot of the information I learned is actually from my clients. My clients make me smarter because they are solving stuff and talking about new tools and new languages and new systems and structures and constructs within their environment that they’ll name drop things and they’ll put the new acronym into my conversation. I’ll then go and research that. So they’re planting enough seeds for me to go, “Oh, I don’t know what that is. I better go read the article or prompt ChatGPT to tell me what the hell they’re talking about.” So I’m permanently trying to almost play catch up with them. But as soon as someone says to me, “Oh, here’s a new tool,” and I go research that tool, then I can mention that tool to the next 20 clients, and my next 20 clients think I’m smart as hell. So my clients make me smarter.

But the next piece that I’ve put in place is that I have a full-time virtual personal assistant. So she understands me. But what I will do is that when a client suggests something to me and says, :”Oh, I’m considering playing with this or doing that,” I will send her a voice note via WhatsApp. I go, “Kim, please go do some research for me on the following things. I want case studies. I want videos, blogs, books, vlogs, whatever that is. Send me 10 things to read.” And she doesn’t know who it’s for, but she’ll send me stuff that force feeds me information, and then I will read it and sift through it and figure out what parts I like and don’t like. But I tend to do that almost after every session because there’s always something that a client is asking me that I don’t know technically or that may have changed from a legal perspective. So I’m learning about the greater environment and my client’s business all the time.

Shawn Hesketh:

Keeping up to date with advancements and changes in the business market can be really time consuming. But it’s also critical because it shows up in both your sales pitch and interactions with your long-term clients

Brent ‘Spillly’ Spilkin:

For a long period, in my initial phases, I’ve been doing this almost 11 years, but the initial few years, I was quite regimented with time tracking to understand where I spent my time. And I’ve stopped doing that because the average is mostly true. So I try to understand how much prep time, how much time in the room, how much post time was being spent on a client, understanding in order to remain relevant what the techniques I could do to remain relevant. And that was very often slotted in. So I read stuff when I have time. I don’t allocate hours in my day to read information for self-improvement. I’m driven from a understanding what my average conversion rate is of sales.

So I’ve been running a CRM system for eight years. I know exactly how many sales meetings I’ve had, how many I’ve won, and how many I’ve lost. I know what their conversion rate is. I know how many people I need to be speaking to on a month in order to keep my pipeline full. And the way I position myself within the local market is I’m absolutely premium. So I know that the hours that I in theory waste on my self-education are then extracted out of my client pricing, and I can command that price because I have the value and the information within the industry that I practice.

So it is a little bit of a fine balance, but I do think that if you want a career as a coach as opposed to a part-time side hustle, this is what I do eight hours a day, five days, the last 11 years. This is my job. Then I take it seriously to be the best that I can possibly be. And not without fault. I absolutely drop balls. There are things that I do not know. But I do believe that I know more than my clients and it’s my job to know more than my clients in order to retain them. And everyone knows the old adage, it’s cheaper to keep a client than to win a new one. So that is am I being effective? Am I learning stuff? Do I know more than my client, within reason? So the investment in myself pays dividends.

Shawn Hesketh:

Business coaching has two distinct cores, knowledge and empathy. That’s why specializing in the business niche requires a special type of coach. Howard shares how this particular market and the clients he works with every day personally inspire him.

Howard Mann:

I found in coaching, empathy is a very important superpower that is not usually talked about or used. And my understanding of the pain and stress and all the little details of owning a business has been incredibly helpful for me and my clients over the years, because if they know that everything didn’t go perfect for me and that I know that stress of that drive home or the proverbial waking up at 2:00 AM or that feeling, there’s just a feeling in your gut that your business should and could be more. And once they realized that it wasn’t perfect and it wasn’t a perfect journey, then they feel more comfortable about saying, it’s like they see their shoulders drop and the sigh and say, “Man, I haven’t had fun for years. This thing started out as me.” It’s just the typical entrepreneur journey. They were good at something. They were good at selling or they were creative or whatever it was, and then they got a client, then they got two, then they got three.

And all of a sudden, “I guess I got to hire a few people and I got to hire a few people more.” And next thing you know, they’re negotiating a lease and they’re spending all this time hiring people, and they got to fire some people. And then they got client complaining and they look up 5, 6, 10 years later and say, “Wait a minute. I have this big business. I’m not making nearly as much money at this when I was just working this on my own. Or I’m not certainly making enough reward for the risk that I’m taking here. Instead of spending 80% of my time doing what I love to do, where I create the most value, I’m spending 20% of the time there and I’m spending most of my time doing running the business type stuff that I absolutely hate. And somewhere because of all the books that I’m reading and the social media and all these things, I’ve come to believe that that’s just the entrepreneurial journey. It’s supposed to suck and be hard and be lousy. And you’re supposed to say to people, how’s business? Well, this is business. It’s going to stink. And then someday I’m going to sell. And then it’s all going to be okay.”

And I think that that entire line of thinking is broken and my job as a coach is to come in and sort of hold up a mirror and say, “Stop. Look at yourself. You’re not happy. You’re not as happy as you want to be. And you have this business that could do whatever you want it to do. It’s your business. And if it’s not fulfilling for you during the day, and if it’s not giving you the life that you truly want, if you take a pause enough to think about it, then why isn’t it? And why don’t we get to work on getting it there?”

Shawn Hesketh:

The way Howard suggests looking at your business can help you evaluate your own brand as a coach and build it into the work and business you want to create. And if business coaching is the right specialization for you, Spillly’s steps for building your structure and practice can help you build your clientele and your brand.

A huge thank you to Brent “Spillly” Spilkin and Howard Mann for sharing their insights about the world of business coaching and their experiences having personal conversations with clients.

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Until then, thank you for joining me on this episode of the Coach Factory Podcast. I look forward to hearing about your experience as you explore the niche of business coaching.

This episode of The Coach Factory Podcast was produced with the support of Come Alive Creative. To hear more episodes, get the show notes, and learn how to start, run, and grow your coaching practice, visit

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