Coach: Ken Kilday
Founder: Leaders Cut
Focus: Executive Leadership for Entrepreneurs
Introduction
My name is Ken Kilday, and I’m an executive business coach and owner of Leader’s Cut. I bring simplicity, clarity, and direction to business owners and their leadership teams.
We do this through two categories.
First, we take the processes and strategies in [business owners’] heads and make them visible for everyone to see.
Second, we help leaders articulate their core values and belief systems. This aligns the company around leadership’s “why” and in turn, helps the business run smoothly. It reconnects the team to why they started in the first place.
How Did You Start Coaching?
I had originally been in financial services for 20 years. I started as a frontline contributor and worked all the way up to executive leadership. I had responsibility for designing, building, launching, and growing brand-new products.
Unfortunately, I had a toxic relationship with my boss, and I was hell-bent on divorcing that [relationship] and moving forward.
I had a couple of very interesting leads for similar roles in the same industry. One night at dinner, I told my husband, Mark, “This just doesn't feel right. This doesn't feel like something I want to do. I don't know if I want to be on airplanes every week forever.”
Mark asked, “What do you love doing?” I said, “I have always loved developing my teams. Helping people understand why they're amazing and then unlocking that potential. That's fun.” And he said, “There are businesses that do that. Maybe you explore that and just do your own thing.”
I got busy and started process mapping or, as he calls it, just [putting] a bunch of post-it notes all over the guest room. I wrote down my thoughts, and then I would walk away, come back, and start to organize them. That's how I came up with Leader’s Cut.
How Did You Build Your Coaching Program?
The first version mainly worked with corporate executives who were more like entrepreneurs. They were people who take extreme ownership in a corporate setting: people like me.
“Start with your natural market” is the advice I followed in the beginning. That first iteration was designed around coaching to that [market] specifically. However, life happened, and my program unfolded a little bit differently.
Although my first client was corporate, clients two, three, four, and five were entrepreneurs. Things started to shift. I thought, “What do entrepreneurs need?” and I started seeking resources and certifications to better help them.
It was a cascade of things that happened that first year. Some early advice I got from a coach was to jump in the deep end and start going: don’t wait for things to be perfect, don’t wait to work everything out—just get in there and get busy.
I realized I could help people more than I thought, so I kept the mindset of “I’m here to help,” doing that through good listening and letting the rest unfold. It’s been like that for six years—it has evolved, but my desire and the reward I feel when I help others hasn’t.
How Did Your Coaching Offer Evolve?
The essence stayed the same, but the structure got more organized. I dove into the Entrepreneurial Operating System (EOS) and read Traction [when it first came out]. Even before Gino Wickman formalized it, we’d been selling EOS in a franchise model—I was an EOS implementer way back, and that structure helped me help people.
I’m still a certified financial planner [in financial services], so I was already guiding clients by mapping out a future and bringing it into current action. EOS was the first stage of my development, and I customized it for business owners and leaders. It’s just like financial planning: “Where do you want to be in 20 years, and how do we get you there starting today?”
Business owners do the same thing. They think they’re being illogical, but it’s their baby. My job is to help them see it’s okay to let other people help raise that baby—and that’s what we do in business coaching.
How Did You Land Your First Coaching Client?
The first client was the scariest one because my initial thought was, “I should just coach someone for free, since I don’t know what I’m doing yet. I’ll practice and refine it until it’s perfect, and then I’ll launch the real thing.” But people told me, ‘It’s worth something, so don’t give it away.”
When that first person showed interest, I almost said, “I’ll coach you for free.” Instead, I offered an annual package that I thought was a lot of money—and without blinking, he asked, ‘Do I write a check or something else?’ Right then, I realized he had already hired me. He needed a safe space to talk openly; the support a coach provides.
Asking someone for money was the scary part, especially after years of earning a salary. Suddenly, I was the product, and it felt like a big leap. But it became the first positive mindset component of building a successful coaching business.
How Did You Find This Client?
We worked together for a long time, and when I left, it created a new opportunity for him—so he hired me to do some of what I used to do. It also shows what a powerful leader he is because he recognized he needed help and just went for it.
He’s had his share of promotions and is very much a sought-after leader—people love working for, with, and near him. We were good friends at work, which points to the ‘natural market’ concept: the people who hire you often already believe in you, sometimes more than you believe in yourself when you’re first starting out.
How Did You Structure Your First Coaching Offer?
The first package was structured around four meetings per month. I’ve always made myself accessible outside of formal sessions because I didn’t want clients to calculate what they’re paying on a per-hour basis. Instead, I want them to see it as access to support. We’d have a formal conversation with an agenda once a week or at a cadence that worked for them, but I was also available as needed—because things happen.
Clients often come to me for help with communications, whether it’s drafting remarks, emails, or messages to their team. They’ll run those by me because I already know the message they want to deliver, and we align it with their broader conversations. I also provide templates and deliverables to support their efforts.
I like to think of coaching as a retainer-style service rather than billing by the hour. These days, I’m refining my engagements to be outcome-focused. For example, with a leadership overhaul, we’ll work together for six months, focusing on specific monthly topics. By the end, the team will be more proficient in six defined dimensions, giving clients a clear understanding of what they’ve achieved.
How Did You Find Coaching Clients After That?
It has progressed naturally. My first three clients were men and women I knew from CrossFit. That community is its own little ecosystem—dedicated, disciplined, and heavily weighted towards entrepreneurs, as we all had to get our workout in before a long workday. It was a natural fit because athletes understand the role of a coach, and many were already clear about what they needed help within their business.
That initial work gave me a track record I could build on, helping me market to the kind of clients I enjoy working with.
One of my first networking experiences stands out. I sat next to a business owner at an event who ran a marketing agency. He told me, “All of our friends say we should get a coach, so I’d like to talk to you about that.” I replied, “I have marketing questions,” and he suggested, “What if we trade? You coach me and my business partner, and we’ll do your marketing.”
That relationship unfolded naturally, and it taught me the value of being involved in networking. Sometimes, opportunities appear in ways you couldn’t plan for if you stay open and engaged.
Partnerships
Has The Partnership Brought You More Business?
Yes, they’re a digital marketing company and have built and rebuilt my website. They also help with content. They’ve become so skilled that no one can tell whether I wrote something or if my designer did. They’re that good.
Beyond that, they’ve become my case study. By the end of last year, we tripled their top line with the same number of people. It shows the impact of coaching: they were willing to ‘lift the barbell and eat the right foods,’ and they got the result. It’s not the coach—it’s the people willing to do the work.
How Do You Build a Fair Coaching Partnership?
Start with an open conversation. Talk about what each side needs, the dollar value of what you’re offering, and whether it’s balanced. Be straightforward—don’t discount.
That’s what I appreciated about them. They were transparent and clear, just like me. I told them, “This is what I’d normally charge for a year of coaching,” and they responded with what their marketing package would typically cost. Every year, we revisit what we need from each other. I discuss their coaching goals and how I can help, while they share the marketing efforts they think I’ll need. It’s always transparent and collaborative, so we both feel it’s equitable.
If it ever feels off—like one side is doing all the work—step back and evaluate why it feels that way. A partnership should feel fair.
Early on, I had plenty of unsold coaching hours, so I used that time to coach them and refine my practices. They’ve been my laboratory, where I’ve tested and adjusted my coaching methods. They’re always open to trying new things, which has helped me grow and evolve as a coach.
Any Other Marketing Advice for New Coaches?
In a lot of these ecosystems that coaches join, they're going to tell you to cold call. You don't need to pay someone to tell you to cold call. If you’re good at that, then go crazy, but it’s not something I enjoy. What's the marketing mechanism that you’re good at? Triple down on that one. For me, that’s relationship marketing, networking, & referrals.
It's about finding the thing that you're naturally good at. Whatever you're doing, do a lot more of the thing that you enjoy doing because you love doing it.
I joined LinkedIn in 2003, so I’ve built a lot of content there. When we started, the average cost per click for a LinkedIn ad for coaches was something around seven dollars. We have it down to 75¢. We constantly AB test ads and we know precisely which niche we're designing an ad for.
Which Content Works Best on LinkedIn?
Tips. “My three favorite books, my three tips for communication.” It's always nuggets that a business owner can see and take and use. That's what resonates with people. Just a couple of easy, tangible takeaways that they can go implement their business and see some quick result, because they're busy. We all have to learn how to coach about money, people, and time.
Any Mistakes Along The Way?
One mistake was trying to get things too perfect before launching. Early in my career, I adopted tools or technologies too soon, like an electronic dashboard to support my EOS efforts. I chose a company that was too early to market—the product wasn’t fully vetted, had bugs, and didn’t work as intended. My tendency to adopt technology early cost me time and money, and I often stayed with tools longer than I should have because of the investment.
Another mistake was not trusting my own ability. I thought I needed another brand alongside my own to validate me. For example,I briefly worked with Vistage, a group coaching program with a specific niche. I wasn’t a fit for it, but instead of trusting my ability to create something better, I tried to reorganize their system to work for me. Often, you don’t need someone else’s system to succeed—trust your abilities and avoid unnecessary distractions or costs.
What Does The Future Look Like?
To break through my plateau, I’m planning an updated menu and tweaking how I market, package, and focus my services. This year, I’ve been reading Don Miller’s Coach Builder. It’s a great resource for both new and experienced coaches.
The way I’d describe it is that I already have all the ingredients for my cake. This program is helping me refine my recipe to make it exactly what I want. I’m using it to fuel and organize my growth plan for 2025, where my goal is to double my business. It’s certainly a stretch, but it’s doable with the strategies we’re putting in place.
One of my long-standing ideas has been creating a turnkey platform for independent coaches. I don’t want employees, but I’d love to provide a platform for others—people who, like me, came from a corporate background, aren’t in my specific industry, but have a lot to offer in helping business owners succeed.
We’re designing a system where these coaches can jump onto my platform. They could join under my brand, or they could white-label their own version and just focus on coaching. My vision is to make it easier for them to start and thrive as independent coaches.
How Will You Double Your Business?
The two main drivers will be updating my menu and launching a small business community.
First, the menu update will present what I offer in a way that’s easier for people to understand and clearly recognize as exactly what they need.
Second, the small business community will be my version of an effective resource for business owners—a place where they can get support, share their expertise, and give back to the business community. This will be a major fuel and driver toward achieving my goals.
By maintaining what I’m already doing and adding these new elements, that’s where the new revenue will come from.
What Coaching Business Tools Do You Use?
- CoachAccountable was the first product I signed up for to help me run my business. I have been in financial services long enough to know I needed a form of CRM and having some sort of basis for running the coaching business. I think it's the only product that I've used since launch.
- I'm also a GoHighLevel agency owner, designing the funnels. Super customizable with a lot of flexibility. If somebody's going to jump into it, you want to be one of those people naturally drawn to technology, not someone who struggles with it. I love GoHighLevel for the marketing arm and CoachAccountable for my client experience.
Recommended Coaching Podcasts, Books, or Resources
- My Coach's Coach had a ton of white-label topics that helped me out
- Don Miller's Story Brand is one of the most effective books for designing that story. The story that I tell about myself and the story that help clients tell me back so that I can help them get where they are.
Your Top Advice For Aspiring Coaches?
- You don't have to have it all figured out. Just get going and have a propensity to action. It's never going to be perfect. The idea is to get people to engage with you.
- All you're trying to do is get people to have a conversation with you, and that's where the magic's going to happen if it happens.
Where Can We Learn More?
