What every aspiring business owner should ask before taking the leap.

"Can I do this myself?"

For many people, the dream of owning a business is incredibly appealing. More freedom. More control. The opportunity to build something that's yours.

But “Are you running towards an opportunity... or simply running away from your current job?”

There's a big difference.

Many successful businesses begin with a great idea, specialist skills or a genuine passion. Others begin because someone becomes frustrated with their employer or feels undervalued.

Neither reason is right or wrong. But neither guarantees success.

Here's a question every Owner, CEO and Manager should ask themselves:

Do you genuinely deal with poor performance—or do you simply learn to live with it?

Many businesses know they have an underperforming employee. Yet instead of addressing the issue, they hope things improve. Or hope the employee resigns. Or quietly move work to others.

Sometimes they even consider a restructure to avoid dealing with the real problem.

What is that approach actually costing your business?

Poor performance doesn't just affect productivity.

It impacts customer service, profitability, team morale, culture and your credibility as a leader.

Here are three key questions every business owner and CEO should ask themselves:

Is my business profitable and does it actually have cash?

If you hesitated before answering, you are not alone.

Many owners use the terms profit and cash flow interchangeably. They are not the same, and misunderstanding the difference can lead to poor decisions, unnecessary stress and, in some cases, business failure.

Profit measures how well your business has performed over a period after deducting expenses from income. It's an important measure of performance and ultimately determines your tax obligations.

Cash flow is very different. It measures the actual cash moving into and out of your business.

Business ownership can be rewarding, exciting and fulfilling.

It can also be one of the loneliest jobs in business.

As owners, CEOs and leaders, we spend much of our time helping others. We support customers, guide employees, solve problems, manage risk and make decisions that affect the future of our businesses.

But here's a question worth reflecting on:

Who's looking after you, particularly when times are tough?

The most successful business owners I've worked with rarely try to navigate challenges alone. They seek out trusted advisors, mentors and sounding boards.

Business owners spend much of their time helping others.

They help customers solve problems. They help employees develop and grow. They help suppliers, stakeholders and their communities.

But here's a question that often gets overlooked:

Who helps the business owner?

In challenging economic times, that question becomes even more important.

Many owners carry the weight of major decisions alone. Cashflow pressures, staffing challenges, growth opportunities, succession planning, governance issues and strategic direction can all become overwhelming when there is nobody independent to challenge your thinking or provide perspective.

The most successful business owners I have worked with over the years have one thing in common. They rarely try to do everything themselves.

A simple, but perhaps uncomfortable question, to start with...

Are you building the business you want, or are you simply getting better at doing what you have always done?

Many business owners, CEOs and managers spend most of their time focused on operations, sales, customers, staff, cashflow, and solving today's problems. All important activities, but how much time do you spend thinking strategically?

Ask yourself:

• Do I have a clear vision of where the business will be in 3–5 years?

• Have I clearly defined what success actually looks like?

• Does my team understand that vision?

• Do my business goals align with my personal values and ambitions?

• Am I intentionally building the future, or simply reacting to the present?

Ask yourself a simple question:

What does your business stand for? And perhaps more importantly, would your customers, employees, suppliers, and community answer that question the same way you would?

Many business owners think of branding as a logo, colour palette, slogan, or website. While these things matter, they are not your brand.

Your brand is the promise you make, and the experience people receive.

Mistakes in business and leadership are inevitable.

The real question is not whether you will make mistakes, it is how you respond when you do.

Too often in workplaces, people fear making mistakes because they worry about blame, embarrassment or judgement. Yet some of the greatest growth opportunities in business, leadership and life come directly from getting things wrong, reflecting honestly, and learning from the experience.

Of course, there is a difference between careless mistakes caused by repeated lack of effort or attention, and genuine mistakes made while making decisions, taking initiative, solving problems or stepping outside your comfort zone.

Inspiration vs. Motivation – Where Does Responsibility Lie?

Leadership articles often focus on one question, “how do leaders inspire and motivate their teams?” But the more important question is this, “should motivation rely solely on the leader?”

In business today, Owners, CEOs and managers are expected to create vision, culture, and energy within their organisations. They are expected to inspire people through communication, integrity, leadership, and example. Great leaders create environments where people feel valued, challenged and connected to a bigger purpose.

But motivation is different.

Motivation is deeply personal. It comes from within (or should). It reflects attitude, accountability, ambition, and personal responsibility. While leaders can encourage, support and coach people, they cannot permanently “manufacture” motivation for someone else.

When people talk about governance, what do they actually mean?

Is it a board meeting, a neatly filed minute book, and a few policies? Or is it the way an organisation is directed, overseen, and held accountable? It is both. Good governance is the framework that gives clarity to decision-making, oversight, risk, reporting, and stakeholder trust.

Does good governance look the same in every business? Not at all. A small privately owned company may rely on one director and occasional and informal strategic reviews. A small to medium sized business with multiple owners usually needs clearer rules around rights, planning, approvals, and reporting. A larger corporate, listed company, charity, or incorporated society will typically need a more formal structure, including constitutions or rules, shareholder agreements, board or committee charters, delegated authorities, policy statements, registers, minutes, and regular reporting to stakeholders.

When pressure builds in your business, what really shows up?

Your strategy… or your leadership or both?

In times of economic uncertainty, rising costs, shifting demand, and reduced confidence, every business feels the strain. But the real test isn’t the conditions. It’s how you lead through them.

So here’s the first question to consider:

Are you leading your business or reacting to the environment around you?

You can’t control the economy. You can’t control global events. But you can control your response.

And that starts with leading yourself.

• Are your decisions calm and considered or are they rushed and reactive?

• Are your behaviours setting the standard or are they adding to the noise?

• Are you focused on solutions or are you distracted by problems?

I was struck recently while working with a client who runs a successful business with over 20 employees that despite their success, they were almost paralysed when it came to addressing an underperforming staff member. Their concern? Taking the wrong step and ending up in a grievance over a “process flaw” that could cost, in their words, “three months’ salary.”

That fear was real and it was stopping them from acting. The result? Ongoing underperformance that was impacting the business, customers, and the wider team. The reality is, many businesses simply can’t afford that cost, so the issue goes unaddressed.

Here is a question for every business owner and CEO:

Do you genuinely believe you have all the answers right now?

Or are you open to the idea that better decisions might come from better input?

Strong leaders understand something simple, but powerful, “they don’t know everything.” And more importantly, they are prepared to seek out advice when it matters most.

Here is a question every business owner, CEO, and manager should ask:

Are you truly rewarding performance—and equally holding people accountable?

Or is one happening without the other? Most leaders will say they value high performance. But ask yourself:

• Do I actively recognise and reward my top performers?

• Do they feel valued—or just expected to keep delivering?

Because when high performance goes unnoticed, motivation quietly erodes.

In business, the difference between success and regret often comes down to one simple question. Are you reacting… or are you responding?

Most leaders have been there. Firing off a frustrated email, making a rushed decision under pressure, or assigning blame when things go wrong. It feels justified in the moment, but more often than not, it comes at a cost, financially, emotionally, or in damaged relationships.

Reacting is instinctive. Responding is intentional.

Buying an existing business can be one of the fastest and most effective ways to become a business owner. However, many new owners later reflect, “I wish I had known that at the time.” Asking the right questions upfront can make the difference between a rewarding investment and an expensive mistake.

Interestingly, challenging economic conditions can present exceptional opportunities. Buying a business when times are tough or the outlook is uncertain may allow you to negotiate a favourable price, as sellers look to exit under pressure. With the right strategy and leadership, you can navigate those challenges effectively and secure the future upside when conditions improve.

Before committing, consider these ten essential questions:

Have you ever caught yourself saying, “I’ve been thinking about that”? Good. Thinking is a start.

But here is the real question:

Is thinking enough to change your business or your performance?

Are you simply replaying the same ideas in your head — or are you genuinely open to new perspectives? Are you willing to be challenged? Have you sought guidance, feedback, or support?

Most owners think about exiting when they are exhausted or constantly thinking about their future. That is human, but it is rarely optimal. The best exits are planned while you still have the energy (and patience) to keep standards high, not when you are quietly Googling “how to sell a business” at 11pm or thinking about what next! 

A sellable business is mature, profitable, and transferable. In plain English, it still performs when you are not there. Buyers do not want to buy a job, and they can’t buy you. So, the goal is to shift value out of your head and into the business with documented processes, clear roles, a capable leader or leadership depending on its sizer, clean financials, and customers who stick around because the company is great, not just because you are. 

Business owners often talk about strategic plans and business plans as if they are interchangeable. But are they? And more importantly, does the difference actually matter?

Let’s start with a simple question:

Do you know where your business is going and how you’ll get there?

What is a Business Plan?

Ask yourself:

• Have I clearly documented how my business operates and makes money?

• Do I know who my customers are, what I sell, and how we generate profit?

• If I needed funding tomorrow, could I confidently present the numbers?