Every business goes through difficult phases as it grows. In the early days, the challenges are obvious.
You’re finding your feet, proving your model and working out your next steps. Later on, the challenges shift again as the business matures and you start to think about exit.
But the stage that often gets overlooked is the one in between: the messy middle.
This is the point where you’ve moved beyond being a start-up, but not quite reached the next level. You have solid foundations, plenty of opportunities and a real potential for growth. But at the same time, it feels a lot harder than you expected.
Capacity is tight. Systems that once felt perfectly adequate are starting to strain and decisions carry more weight because they affect more people. You’re no longer asking whether the business works, but whether it’s ready to become something bigger.
In this blog, we will explore what the messy middle actually looks like in practice, why it can feel so uncomfortable, and how leaders can navigate it with greater clarity, control and confidence.
What the messy middle actually looks like
The clearest sign you are in the messy middle is when opportunity begins to outpace capacity.
You’re winning more work, but the team is busy. You could hire, but aren’t certain revenue is predictable enough. You could invest in better systems, but that means taking time and money away from day-to-day delivery.
Take it from me, this is not a bad place to be. In fact, it’s usually a sign that you have built something valuable.
The discomfort you’re feeling comes from tension. You can see the potential ahead of you and you’re keen to get there, but the infrastructure underneath is still catching up.
The bigger picture: capacity, clarity and finance
There are typically three pressures sitting beneath this stage: capacity, clarity and finance.
Capacity becomes a leadership issue very quickly. When a business is small, everyone gets involved. Communication is simple and decisions are fast. As you grow, that simplicity starts to fade. Roles blur. Founders carry too much in their heads. Teams become reactive rather than proactive.
Clarity can also start to drift. In the early days, your “why” is obvious. You’re focused on survival and traction. As the business stabilises, novelty wears off and operational demands take over. If the purpose is not clearly defined, growth can start to feel like pressure rather than progress.
Finances often become more complex at this stage too. Revenue may be increasing, but so are costs. Hiring decisions feel weightier, cash flow becomes more sensitive and without clear financial visibility, even good growth feels risky.
None of this means you are doing something wrong. It just means the business is evolving.
Working your way through the messy middle
The biggest mistake leaders make at this stage is assuming the answer is to push harder, with more sales, more hires and faster growth. These things can definitely help, but more often than not, what you really need is intention.
Reconnect with your purpose
When you’re deep in delivery and firefighting operational issues, it’s easy to default to chasing revenue or headcount as the next marker of success.
Take a step back and ask yourself what this growth is actually for. What do you want this business to look like in three to five years? What kind of culture do you want to build? What impact are you trying to create?
Revisiting your longer-term strategy and aligning it with clear goals and measurable KPIs can bring valuable perspective. When leaders and teams understand what progress really looks like, day-to-day decisions become easier and more consistent.
The messy middle often exposes weak spots. Reporting might be inconsistent. Roles may overlap. Processes might exist in someone’s head rather than on paper.
Instead of short term fixes, now is the time to invest in the systems, processes and people that enable long term, sustainable growth. That might mean investing in better financial reporting, clarifying responsibilities across the team, documenting key processes or improving forecasting.
These changes aren’t always glamorous, but they remove pressure from individuals and build resilience into the business.
Be deliberate about culture
In smaller businesses, culture often develops naturally. As you scale, it needs to be articulated and protected.
If you don’t define what matters, it’s easy to lose sight of it. New hires bring new behaviours, expectations start to shift and before you know it, your internal comms have broken down.
Take the time to define the values and behaviours that have made the business successful so far. Be explicit about what you want to preserve as you grow.
Strengthen financial visibility
Many leaders feel the strain of the messy middle most clearly in their numbers. Scaling requires investment in people, systems and infrastructure. Without forward-looking visibility, those decisions can feel uncomfortable.
Clear cash flow forecasting, scenario planning and regular KPI reviews provide confidence. They allow you to see how decisions today will affect the business in six or twelve months’ time. When you understand the financial implications of growth, you can move forward deliberately rather than hesitantly.
Growth is not just about getting bigger
The challenge now is not just to grow, but to grow well. Leaders who navigate this stage successfully tend to slow down before they speed up. By slowing down, you can build a business that can sustain growth rather than chase after it.
If you are in the messy middle and want a clearer view of your financial position or support shaping your next stage of growth, we’d be happy to have a chat.
