The Hardest Part of Running a Business for Owners and Managing Directors

There’s a moment most Managing Directors don’t talk about.

It usually happens early in the week. The emails have started arriving. A couple of decisions are already overdue. Something small has escalated quietly over the weekend. Nothing is on fire, but nothing feels settled either.

On paper, the business looks fine. Headcount is stable. Revenue is broadly where it should be. Clients are being served. Yet the sense of pressure feels heavier than it used to.

Not louder. Heavier.

This is the point where many owners and directors assume they need to work harder, be sharper, push faster, or finally “get on top of things”. It feels logical. It also misses the real source of the strain.

For most owners and Managing Directors of growing businesses, the hardest part of the job is not the workload itself.

It is the accumulation of decisions, responsibility, and consequence, without enough structure to absorb the weight.

Why Pressure in Growing Businesses Has Less to Do with Hours and More to Do with Decisions

In the early stages of a business, effort solves most problems.

If something needs fixing, you step in.
If a decision needs making, you make it.
If a gap appears, you fill it.

That approach works remarkably well for a long time.

Then the business reaches a point where effort alone no longer scales. Somewhere between 25 and 150 people, complexity quietly overtakes visibility. Decisions start to overlap. Responsibilities blur. Risks become harder to spot until they are already close.

Pressure no longer comes from long days. It comes from carrying too many unresolved decisions at once.

Not dramatic decisions. Ordinary ones.

Who signs this off.
Who owns that risk.
Whether this exception is acceptable.
Whether that role still makes sense.
Whether a problem is operational, people-related, or structural.

Each decision on its own is manageable. Together, they create a constant background load.

Why Business Leadership Feels Harder Now Than It Did a Few Years Ago

Many leaders will say, “It was never easy, but it didn’t feel like this before.”

They are usually right.

What has changed is not resilience or competence. It is context.

Costs move faster than planning cycles.
Compliance expectations are less forgiving.
People issues escalate more quickly.
Tolerance for mistakes has narrowed.
Visibility has increased, even when clarity has not.

Decisions that once had local impact now have wider consequences. A small people issue can become a legal risk. A delayed decision can affect cash flow months later. A vague responsibility can sit quietly until something goes wrong.

The business does not collapse. It simply becomes harder to carry.

A Common Scenario for Managing Directors of 25–150 Person Businesses

Consider a Managing Director of a 60-person business.

The company is profitable. Clients are satisfied. Growth has been steady.

Over the past year, decisions have begun to gravitate upwards. Managers hesitate before acting. Questions that used to be resolved lower down now land on the MD’s desk “just to be safe”.

One employee issue feels uncomfortable but not urgent, so it sits. A process exception becomes routine. A compliance requirement is technically covered, but no one is quite sure who owns it day to day.

None of this triggers an immediate crisis.

What it does create is a constant mental backlog. The MD carries decisions that should be distributed. Managers carry uncertainty they shouldn't. The organisation feels busy, but oddly fragile.

This is not a capability problem. It is a structural one.

Why Motivation Alone Doesn’t Fix Structural Problems in Businesses

At this point, many leaders reach for familiar tools.

Clearer goals.
Sharper messaging.
More accountability conversations.
Another push for ownership.

These help, but only temporarily.

When roles, decision rights, and expectations are unclear, motivation increases effort around a broken shape. People work harder, not cleaner. Leaders intervene more, not less.

Over time, this creates pressure not just operationally, but around role clarity, accountability, and who is actually responsible for what when things get difficult.

That is usually the moment when leaders realise the problem is not effort or intent.

It is the system through which the effort flows.

In many growing businesses, this shows up as blurred responsibilities, informal expectations, and uncertainty around who owns people decisions when pressure increases.

The Hidden Cost of Owners and Directors Carrying Too Many Decisions

Most Managing Directors underestimate how much risk they personally absorb simply by being the default decision-maker.

Not because they want control. Because gaps exist.

When the structure is incomplete, the leader becomes the connector between people, risk, timing, and consequence. That works for a while. Eventually, it becomes unsustainable.

The cost shows up quietly.

Delayed decisions.
Reduced thinking time.
More reactive days.
Less space to plan properly.

The business keeps moving. The leader feels permanently behind.

How Well-Run Businesses Design Decision-Making as They Grow

Well-run businesses that feel calmer at scale are not led by more driven or more intelligent people.

They have done one thing particularly well.

They have deliberately designed how decisions are made, owned, and reviewed, rather than leaving those questions implicit.

This design work is rarely glamorous. It sits between strategy, people, risk, and operations. It does not neatly fit into one function. But it is what allows leaders to step back without things falling apart.

When decision-making is designed properly, responsibility is shared. Risk is visible earlier. Leaders regain space to think rather than constantly react.

The Question Owners and Managing Directors Rarely Give Themselves Time to Answer

There is one question many leaders sense but rarely articulate.

What is genuinely the hardest part of running this business right now?

Not what sounds acceptable. Not what appears on the board agenda. The real answer.

For some, it is carrying people decisions they were never trained for.
For others, it is living with unresolved risk.
For many, it is making trade-offs without enough clarity.

The answer almost always points to structure, not effort.

When External Decision Support Becomes Necessary for Growing Businesses

At a certain level of complexity, thinking harder inside the same system does not produce better outcomes.

It produces better rationalisations.

This is where structured decision support across the business becomes valuable. Not to replace leadership judgment, but to help owners and directors step back, untangle priorities, and redesign how decisions flow across people, compliance, and operations.

This is the role ProgressA plays for many growing businesses. Providing calm, experienced support when decisions are interconnected, consequences matter, and informal ways of working are no longer enough.

You can explore how that support works across our Services if and when it is useful.

A More Sustainable Way to Lead a Complex Business

Running a business at this level will never be effortless.

But it does not have to feel constantly heavy.

When decisions are clearer, ownership is defined, and structure absorbs pressure, leaders regain space to think. The organisation becomes more resilient. Progress stops when one person holds everything together.

That is usually when the hardest part of the job begins to ease.

Not because the work disappears.
Because the system finally supports it.