Why Scaling Staff Is So Difficult For Many Businesses (James Dooley Interviews Mads Singers)

James Dooley Hi, today I’m joined with Mads Singers and today’s episode is about why scaling staff is so difficult for many businesses. Mads Singers Yep. And scaling staff can be difficult. Reality is running a business and scaling a business is not easy. As you and I have both done it many times, there are a lot of traps people fall into. From a management standpoint, the biggest issue I see is that there are three clear growth stages. The first stage is when you go from managing everything yourself. As a founder, you can manage five, six, maybe eight people directly. But eventually, every new hire just makes you busier. You hit a ceiling. Getting past that stage requires learning how to delegate, give ownership, and hand over responsibility. The second stage is usually around twenty five to thirty people. At this point, you are no longer managing individuals. You are managing managers. You need to communicate direction clearly and trust others to execute. This stage is all about management skill development. The third stage tends to happen around fifty to sixty people. Now you are managing through multiple layers. As a CEO, what you say at the top is not what people hear at the bottom. Messages get distorted. Learning how to communicate clearly through layers becomes critical. These three stages are where most businesses struggle, and that’s where I help clients the most. James Dooley Yeah, that lines up perfectly with what we talked about in the book, especially the military style framework. For me, the hardest period was always that desert phase between eight and twenty five staff. Too small to be big, too big to be small. That is actually the stage I look at most now from an investment perspective. That middle phase is where things start breaking. The founder has to let go and introduce middle management systems, which is uncomfortable. On your first phase, founders often struggle to delegate. They are perfectionists. They believe they can do everything better than anyone else. From your experience, how do you get founders past that mindset when they are the bottleneck? Mads Singers My experience is slightly different. Most founders are not unwilling to let go. They simply do not know how or do not realise they are holding the business back. They still think like individual contributors. They believe the business grew because of what they personally did. In reality, it often grows despite what they are doing, not because of it. That is the mindset shift. I explain business growth as building a pyramid. Early on, it is small. As it grows, each stone needs to become more valuable. If a founder keeps doing the same tasks repeatedly, they are not increasing the value of the business. The key question becomes what can I let go of so I can focus on higher value activities. Entrepreneurs always feel busy, but being busy is not the same as being effective. Even in client delivery, people obsess over perfection because they fear losing clients. But if letting go of that perfection frees you to work on something far more valuable, the trade off is worth it. Successful entrepreneurs are not driven by fear of losing customers. They grow because someone trusted them once, and they built from there. James Dooley That makes sense. From your consultancy perspective, when should a business owner actually bring someone like you in? Should they wait until they are struggling, or is that already too late? Mads Singers It depends on how fast you want to grow and what resources you have. If you hire a personal trainer from day one, you grow faster, but it costs more. Businesses usually struggle either with time or with money. Ideally, you should have some experience managing people before bringing in a consultant. Even managing one or two people gives you context. That way, you get value faster because you understand the challenges. Recruitment is one of the most critical skills in business. Success or failure often comes down to hiring the right people. Many owners say they are bad at hiring after hiring one or two people with no process. Hiring is a skill. You have to learn it. When I first hired, I studied it. I talked to experienced managers. I learned how to reduce risk. Even if you are good, you will not get it right every time because you are dealing with humans. My advice is simple. If it is your first time hiring, interview forty or fifty people. It takes time, but comparison teaches you what good actually looks like. James Dooley That’s powerful. Now with AI becoming more common, at what point should business owners consider AI agents instead of people? Can they come to you for guidance on that as well? Mads Singers Yes, absolutely. In online businesses, people are usually further ahead with AI than they think. It is a balancing act. Learning AI systems takes time. Even in our businesses, we often hire specialists to build automations rather than doing it ourselves. I always say do not automate something you are not already doing. If you do not know what good output looks like, automation will fail. Automate proven processes that are already working. Many people over automate because they are afraid of managing people. That often slows growth. Automation works best when a human already understands the task and can explain it properly. If you try to automate everything from day one, you will waste a lot of time. Start with people. Learn the process. Then automate intelligently. That approach almost always gets you further, faster. James Dooley Brilliant. For business owners struggling to scale staff, how can people get hold of you? Mads Singers madsingers.com or just search for Mads Singers on social media. I’m still the only human with that name. James Dooley Anyone watching, leave a comment with your biggest challenges. Head over to madsingers.com if you need help with management consultancy or coaching. Appreciate having you on, Mads. Mads Singers Thank you. Pleasure.