Harley Green (Moderator, Founder & CEO of Workergenics)
Clay, do you have anything to share about why so many leaders think hiring more people often equals more progress?
Welcome everyone, and thank you for joining us today for the June edition of our Executive Edge Live panel. I’m Harley Green, founder and CEO of Workergenics, where we help executives and leadership teams stay focused on high-impact activities by delegating the rest to highly skilled, AI-leveraged executive assistants. I’m thrilled to moderate today’s conversation with these powerhouse leaders who understand what it means to hire for real strategic impact through intentional hiring strategies.
Joining us today are Clay Posey, CEO and founder of Clearbox Strategies, with over 30 years of experience shaping data-driven growth and effective hiring strategies; Susan Fennema, CEO and founder of Beyond the Chaos, an operations expert helping owners escape the weeds through strategic support hires and planning; and Mike Slinker, CEO of Tennessee Memories and founder of Slinker Consulting, a visionary leader who builds value-driven teams across industries. We also have Jason Rosado joining us shortly.
Our first question is a bit of myth-busting: why do so many leaders think hiring more people automatically means more progress, even when their hiring strategies aren’t clear?
Susan Fennema (CEO & Founder, Beyond the Chaos)
I think a lot of times leaders don’t know how to solve the problem they’re facing. They know they have too much to do, there’s a lot of overwhelm, and they may be freaking out a little, wondering how everything is going to get done. The only solution they see is to bring in more people, believing that will fix it, instead of stepping back to rethink their hiring strategies.
What they’re often not looking at is the overhead that comes with more people, the interpersonal challenges that can arise, and the reality that throwing more people at a problem doesn’t necessarily solve it—depending on what the actual problem is.
Mike Slinker (CEO, Tennessee Memories; Founder, Slinker Consulting)
I think people often take the stance that more people automatically means more work getting done. But when you look at it from a tactical perspective, you forget that where the rubber really meets the road is where vision connects with execution.
That’s where you need implementers versus visionaries, which should directly shape your hiring strategies. If those roles aren’t clearly defined and aligned, simply adding people doesn’t move things forward in a meaningful way.
Clay Posey (CEO & Founder, Clearbox Strategies)
When you said that, Harley, I immediately thought of a story from the very beginning of my career. My first real job was with a retired Marine colonel who was running and growing a business. He talked about how, in the military, they would estimate that a project would take 200 man-hours. A general would hear that and say, “Great, get me 200 men over here. I’ll see you in an hour.”
The fallacy there is assuming that every additional person is going to be 100% effective or 100% efficient. They’re not. We delude ourselves into thinking that if we add more people, work will magically go faster, even when hiring strategies aren’t aligned with reality. But there are diminishing returns with every additional pair of hands you put on a project. Management overhead, training, and coordination all add up.
Harley Green
Absolutely. That management overhead is huge, and it’s something many hiring strategies fail to account for. At this point, we’re joined by our final panelist. Jason Rosado, founder of Distinctive Coaching for Business Success, welcome. Jason helps coaching and service firms scale revenue with lean, empowered teams.
Jason, we’ve been talking about why leaders often believe hiring more people equals more progress. Do you have any insights to share?
Jason Rosado (Founder, Distinctive Coaching for Business Success)
Yeah, the myth is that people want to duplicate themselves. Leaders feel that if they bring in more people—whether at their level or below—they’ll be able to get more work done. That’s often the thinking behind it, which often reflects reactive hiring strategies.
Harley Green
I’d love to shift this into storytelling. Can each of you share a moment when a single key hire—whether entry-level or as senior as a COO—created a real turning point in your business? Mike, let’s start with you.
Mike Slinker
From a pastoral perspective, I once served as executive pastor for one of the largest and fastest-growing churches in the Nashville market. The senior pastor had strong vision and a clear direction for growth, but what he needed was someone to actually implement and execute that vision.
The turning point came when we focused on policies and procedures across all ministries. This applies to nonprofits, churches, and businesses alike. When you allow a visionary—whether a founder or CEO—to focus on vision, you must have key people who can implement. When tactical responsibilities start to outrun the vision, it’s time to hire.
Visionaries often see five miles down the road or from 30,000 feet. You need people operating at 500 feet who can execute that vision. If your tactical work is outpacing your vision, you need to reset and bring in the right person to establish momentum. There’s a big difference between managers and leaders, and understanding that distinction is critical.
Susan Fennema
I can speak from my own business. About four or five years ago, I hired a part-time virtual assistant. She was amazing, and today she’s my full-time director of operations, my right-hand person, and my only full-time employee. She’ll probably be the one who eventually takes over the business.
Watching her grow and developing her over the years has been a joy. When you bring in someone like that, you can immediately see their brilliance and the path ahead. Seeing their commitment to your culture and values—and how they reflect you as a leader—is incredibly powerful and humbling.
That said, I’ve also worked with other virtual assistants, and they are not all created equal, which reinforced the importance of thoughtful hiring strategies.
Jason Rosado
One example that stands out is a client of mine named Andrew, who owned a web design and development firm. He was working 70-hour weeks, pulling all-nighters, and still barely hanging on. He had a team of 20 contracted designers and developers but didn’t fully delegate or trust them.
We worked on clarifying what Andrew truly wanted to focus on and restructured his organization. The key hire was a project manager who acted as a general manager, proving how the right hiring strategies can transform a business. Once that person was in place, Andrew was freed up to focus on business development and the work he loved most.
Within six months, his revenue more than doubled—up 105%—and he cut his work hours in half, from 70 to 35. That one hire completely transformed the business.
Clay Posey
For me, the common theme is hiring that key operations leader—whether you call them a COO, head of operations, or general manager. It’s always scary for owners because it feels like hiring “overhead.”
At Clearbox, bringing in that layer of management freed up my bandwidth to focus on business development, which is what I do best. Even though she’s still ramping up, we’ve already booked as much revenue this year as we did all of last year—and it’s only midyear. The impact has been huge.
Harley Green
That naturally leads to our next topic: when you start scaling your support team, where do you begin? Susan, what’s your take?
Susan Fennema
I have strong opinions on this. I believe owners should get out of operations as soon as possible. As a small business owner, your focus should be on sales and revenue generation. No one sells your business better than you.
You don’t need to hire a $250,000-a-year COO. You can hire fractional operations support or part-time help, even overseas talent, to manage execution at a lower cost. Get out of ops, stay close to sales and finances, and outsource marketing as early as you can afford to.
Jason Rosado
I agree with Susan, but I approach it a little differently. I believe the owner should focus on whatever brings them the most energy and impact. There’s no single right way to build a business.
I start with clients by having them design their ideal role as if they were hiring themselves—title, responsibilities, income, culture fit. This clarifies their hiring strategies early. The business flows outward from the person. You need to put your energy where you’re most effective and outsource or hire for the rest.
Clay Posey
One thing I’d add is that as you scale, you delegate—you don’t abdicate. Regardless of who’s doing the work, the founder is responsible for culture, expectations, and standards.
At Clearbox, we’ve built a culture of excellence over ten years. Whether someone is fractional, overseas, or full-time, if we commit to something, we deliver. That culture has to be measured and reinforced consistently.
Harley Green
Let’s talk about hiring fails. One of the biggest mistakes leaders make is expecting new hires to be miracle workers without providing clear systems or guidance. Clay, why does this happen so often?
Clay Posey
It goes back to The E-Myth by Michael Gerber. Being a technical expert doesn’t mean you know how to run a business. Successful hires require clear systems, roles, expectations, and documentation.
I’ve made the mistake of hiring someone and saying, “Go forth and prosper,” without clarity. That always ends badly—for the employee, the business, and the customers.
Jason Rosado
I coach clients on using a true two-way interview process. Too often, both sides are just trying to sell each other, and nobody is critically evaluating fit.
I ask candidates questions that help them disqualify themselves, like why the role might not be a good fit. That depth prevents misalignment and future frustration.
Susan Fennema
Another common mistake is hiring people you know—family or friends—who you can’t easily let go. Sometimes you outgrow people, and that can damage relationships if you’re not careful. Go in with eyes open and talk about how the relationship might end, not just how it starts.
Harley Green
Before we wrap, what’s one thing you now do before making a key hire that you wish you’d done earlier?
Susan Fennema
I run the numbers thoroughly and consider what happens if projections don’t play out. Last year, I hired too early, and revenue couldn’t support the role. It was a hard lesson, but an important one.
Clay Posey
I make sure the compensation truly supports the employee’s life. If someone can’t live on what you’re paying them, they can’t give you their best work, and resentment will eventually creep in.
Mike Slinker
I’ve had success with pay-for-performance agreements. They keep both sides aligned and ensure accountability while creating shared upside.
Harley Green
Finally, what signals tell you it’s time to hire instead of automating or outsourcing?
Jason Rosado
I work backward from a one-year vision, then look at stress levels, capacity, finances, and emotional readiness. You need to look at the decision from multiple angles—organizational, financial, skill-based, and emotional.
Susan Fennema
I treat hiring as a last resort, which has become a core principle in my hiring strategies. I ask if the work can be automated, outsourced, or handled part-time first. People are the most expensive overhead, and technology usually causes less drama.
Mike Slinker
I look at culture and capacity. If departments are stretched like rubber bands about to snap, it’s time to hire. You must build margin into your business—time, people, and resources—or growth becomes impossible.
Clay Posey
I rely heavily on forecasting data. I hire before the rubber band snaps, so new team members can ramp up without pressure. That requires margin in both budget and planning.
Harley Green (Closing)
Thank you all for sharing your wisdom and experience today. For those listening, take advantage of the generous offers from our panelists and continue the conversation with them.
Thank you again to our incredible panelists and everyone who joined us today. We’ll see you on the next Executive Edge Live session.