Why Scaling Staff Is So Difficult For Many Businesses (James Dooley Interviews Mads Singers)
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What Does “Why Scaling Staff Is So Difficult For Many Businesses (James Dooley Interviews Mads Singers)” Talk About?
In this episode of the James Dooley Podcast, James Dooley sits down with management consultant Mads Singers to explore why scaling a team is one of the most challenging aspects of running a business. Mads outlines three distinct growth stages where companies commonly stall: the founder-led stage of up to eight direct reports, the middle management stage around twenty-five to thirty people, and the multi-layer management stage at fifty to sixty employees. Each stage demands a fundamentally different leadership approach, and Mads explains how failure to adapt at each threshold is where most businesses get stuck.
The conversation digs into the psychology of founders who struggle to delegate, with Mads challenging the common assumption that founders are simply unwilling to let go. Instead, he argues most founders still think like individual contributors and do not realise they are holding the business back. James shares his own perspective on the difficult desert phase between eight and twenty-five staff, which he describes as too small to be big and too big to be small. The episode also covers practical topics like when to hire a management consultant, how to approach recruitment as a learnable skill, and the importance of interviewing forty to fifty candidates before making a hire.
The episode closes with a focused discussion on AI and automation, where Mads cautions against over-automating too early. He advises business owners to first build and understand their processes with people before layering in automation, warning that automating something you do not fully understand will only amplify problems rather than solve them.
“Do not automate something you are not already doing. If you do not know what good output looks like, automation will fail.”
— Mads Singers
Who Are the Guests on “Why Scaling Staff Is So Difficult For Many Businesses (James Dooley Interviews Mads Singers)”?
Mads Singers is a management consultant and coach who specializes in helping business owners navigate the challenges of scaling teams and developing leadership skills. With extensive experience working with founders at various stages of growth, Mads focuses on mindset shifts, delegation frameworks, and recruitment strategy. He is known for his practical, experience-driven approach to management and can be found at madsingers.com.
James Dooley is an entrepreneur and investor who hosts the James Dooley Podcast. Having scaled multiple businesses himself, James brings a firsthand perspective on the difficulties of moving through growth phases, particularly the challenging middle stage between eight and twenty-five staff members. He also approaches business scaling from an investment angle, making his insights relevant to both operators and investors.
What Are the Key Takeaways From “Why Scaling Staff Is So Difficult For Many Businesses (James Dooley Interviews Mads Singers)”?
Here are the key points discussed in this episode:
- Businesses typically stall at three predictable growth stages: managing up to eight people directly, transitioning to managing managers around twenty-five to thirty staff, and navigating multi-layer communication at fifty to sixty employees.
- Most founders do not fail to delegate because they are unwilling, but because they still think like individual contributors and do not recognize that they are the bottleneck holding the business back.
- Recruitment is one of the most critical skills in business, and owners should treat it as a learnable discipline by interviewing forty to fifty candidates to understand what good actually looks like through comparison.
- Automation should only be applied to processes that are already working and well understood, because automating a broken or unclear process will only scale the problems rather than solve them.
- Sustainable business growth comes from building systems, developing trust in others, and increasing the value of your own contribution rather than staying busy with tasks that could be delegated.
“Start with people. Learn the process. Then automate intelligently. That approach almost always gets you further, faster.”
— Mads Singers
Is “Why Scaling Staff Is So Difficult For Many Businesses (James Dooley Interviews Mads Singers)” Worth Listening To?
This episode is particularly valuable for any founder or business owner who feels stuck despite working hard, because Mads Singers reframes the scaling problem in a way that is both honest and actionable. Rather than offering generic leadership advice, he maps out specific growth thresholds and explains exactly why each one breaks down, giving listeners a clear diagnostic tool for understanding where their own business may be struggling. The conversation between James and Mads feels grounded because both have lived through these stages personally, which adds credibility to every point they make.
The discussion on AI and automation is especially timely and cuts against the hype. Mads makes a compelling case that many business owners over-automate out of a fear of managing people, which actually slows growth rather than accelerating it. This honest counterpoint to the prevailing rush toward AI adoption makes the episode stand out. Whether you are hiring your first employee or managing a team of fifty, there are specific, practical insights here that are immediately applicable.
Who Should Listen to “Why Scaling Staff Is So Difficult For Many Businesses (James Dooley Interviews Mads Singers)”?
This episode is ideal for:
- Founders and entrepreneurs who are approaching or stuck in the eight to twenty-five person growth phase and struggling to let go of day-to-day tasks.
- Business owners considering AI and automation tools who want a grounded perspective on when and how to implement them responsibly.
- Investors and operators who evaluate businesses and want to understand the common management failure points that limit company growth.
- First-time or early-stage managers who want to develop hiring and delegation skills before making costly mistakes with their team.
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What Are Listeners Saying About This Episode?
“The breakdown of the three growth stages was something I genuinely needed to hear. I am right in that desert phase James described between eight and twenty-five staff and everything he said about things starting to break rang completely true. Really practical episode.”
“Mads making the point that most founders are not unwilling to delegate but just do not know how was a lightbulb moment for me. I have been telling myself I am a control freak when really I just never learned the process. Changed how I am thinking about my business this week.”
“The advice on automation was the highlight for me. I have been rushing to automate everything and Mads calling out that people over-automate because they are afraid of managing staff hit very close to home. Simple but genuinely useful reframe.”
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.
Creators & Guests
Host
James Dooley is a UK entrepreneur.