Moving from Small to Medium: The Questions Nobody Tells You to Ask

There’s this odd space between running a small business and becoming a proper medium-sized enterprise. It’s not quite David versus Goliath, but it’s definitely uncomfortable. You’ve outgrown your scrappy startup phase, but you’re not yet the well-oiled machine you see in case studies. And honestly? This is where most business owners either thrive or quietly struggle for years.

I’ve worked with numerous SME owners navigating this exact transition, and what strikes me most is how similar the challenges are - yet how differently each business handles them. That’s where coaching comes in, because the questions you need to answer aren’t always obvious until you’re already knee-deep in the mess.

The Identity Crisis Nobody Mentions

When you’re small, you know everyone. You probably hired your team yourself, you’re involved in most decisions, and there’s a certain energy to the chaos. But as you grow, something shifts. Suddenly you’ve got people you’ve never met working for you, departments that need coordinating, and processes that… well, need to exist in the first place.

The first question I always ask is: Are you still trying to run a medium business like a small one? Because that’s the trap. You can’t be in every meeting, approve every expense, or personally onboard every client anymore. But letting go? That’s terrifying. Through coaching, we work out what you genuinely need to control and what’s just habitual interference masquerading as involvement.

The Money Gets Weird

Here’s what nobody warns you about - your relationship with money completely changes. When you’re small, cash flow is straightforward (even if it’s tight). But as you scale, you’re dealing with bigger overheads, longer payment terms, maybe external investment or loans. The numbers get larger, the stakes feel higher, and suddenly a bad quarter isn’t just disappointing, it’s properly scary.

You need to answer: What does financial security actually mean at this size? Not the textbook answer, but for you, your business, your sector. I’ve seen owners paralysed by growth because they’re terrified of the increased exposure. Coaching helps you build a framework for decision-making that balances ambition with pragmatism - and your own sanity.

People Problems Multiply

This is the big one. When you’re small, personalities matter but they’re manageable. At medium size, you need actual management structures, and this is where things get properly complicated. You might need to hire managers, which means you’re managing people who manage people. Your mate from uni who was brilliant when you started might not be the right person for the role anymore.

Who do you need to be as a leader now? It’s not the same answer as two years ago. Some founders make this leap naturally; others need to consciously develop new skills. The honest truth is that you might need to have difficult conversations - about roles, performance, or even whether certain people fit your future. Coaching provides a confidential space to work through these challenges before they become crises.

Systems Before You Think You Need Them

If I had a pound for every time someone told me “we’ll sort out proper systems once we’re bigger,” I’d be retired. The problem is, you can’t grow without systems, but implementing them feels like it slows you down. It’s a proper catch-22.

The question is: What’s the minimum viable structure you need right now? Not in six months, not when you hit that revenue target - now. Because the alternative is that thing where everyone’s frantically busy but nothing quite works properly. HR, finance, operations, sales - they all need some framework, even if it’s not fancy.

Watch Out For These Traps

A few things I see repeatedly: overtrading (growing faster than your cash can support), hiring too quickly then having to make redundancies, losing your core culture in pursuit of “professionalism,” and my personal least favourite - making decisions based on what you think medium businesses are “supposed” to do rather than what works for you.

Also, watch your own wellbeing. This transition is exhausting. You’re building the plane while flying it, except now there are more passengers.

Why Coaching Actually Helps

Look, I’m biased, but here’s what I’ve observed: the business owners who navigate this well usually have someone to talk things through with. Not a consultant who’ll sell you a solution, not a mate who’ll just sympathise - someone who asks awkward questions and helps you figure out your own answers.

Because ultimately, there’s no single blueprint for going from small to medium. There’s just your business, your market, your capabilities, and the decisions you make. Coaching helps you make them more deliberately, with less panic and more confidence.

And sometimes, just having someone say “yes, this is properly difficult and you’re not imagining it” is worth its weight in gold.