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Not because they’re wrong, but because they’re not doing their job properly.

A good accountant reports what happened.
 

A great accountant helps you see what’s coming.
 

But the best accountants — the ones who change the trajectory of a business — are the ones who ask uncomfortable questions. They don’t flatter you. They challenge you. They make you think.

Why comfort kills progress

Most small business owners want harmony with their accountant. Understandable — it’s nice to feel supported. But too much comfort breeds complacency.

The danger is that your accountant becomes a technician, not an advisor — someone who tidies up the numbers instead of interrogating them.

I’ve seen it many times. A business owner proudly says, “We had a great year — sales up 25%!” and their accountant replies, “That’s fantastic.”
But the real question should have been:

“So why hasn’t your cash gone up?”

That’s where growth and reality often part company.

The job of a trusted advisor is to speak truth, not reassurance. And sometimes truth stings.

The most valuable question an accountant can ask

The best accountants don’t start with “How did the numbers look?”
They ask:

“What are you not looking at that could hurt you?”

That question changes everything. It forces reflection. It stops you coasting on good results and ignoring weak signals.

I once had a client — a successful e-commerce founder — who boasted that her sales had tripled. But she hadn’t noticed that her customer acquisition cost had also tripled. Her growth was unsustainable.

When I showed her the data and asked that question, she said quietly, “I thought profit would catch up later.”

It wouldn’t have.
 

She made tough changes, cut wasteful marketing spend, and the business became stronger than ever. That’s the power of a well-timed challenge.

Why most accountants avoid hard questions

There’s a reason many accountants don’t push clients. They’re afraid — afraid of losing the relationship, afraid of being seen as critical, afraid of not having the answers.

But the role of an advisor isn’t to have all the answers. It’s to ask better questions.

Business owners need perspective more than praise. The right question, asked at the right time, can save months of drift or thousands in wasted effort.

Here are a few of my favourites:

• “If you stopped doing this tomorrow, what would really happen?”
• “Is this activity building equity value, or just keeping you busy?”
• “If this customer wasn’t already on your books, would you take them on today?”
• “Are you leading your business, or is it leading you?”

Each question challenges the assumptions that keep owners stuck.

Tough love is still love

Challenging clients isn’t about criticism — it’s about care. When I question a client’s decision, it’s not because I want to prove them wrong. It’s because I care enough to help them see the risk they’re ignoring.

A good accountant doesn’t sugar-coat reality. They interpret it. They connect cause and effect.

Telling a client that they can’t afford that new hire, or that their margins are eroding, or that their pricing strategy is broken — that’s not negativity. It’s honesty. And honesty is what you’re paying for.

The courage to disagree

I once told a long-standing client that his business model was broken. He didn’t take it well. Then he went away, thought about it, and called me back a week later.

“You’re right,” he said. “I didn’t want to hear it, but I needed to.”

Six months later he’d restructured the business and was making more profit on fewer sales.

Sometimes the job of an accountant isn’t to say what the client wants to hear — it’s to say what they’ll thank you for later.

A challenge for business owners

If you’re a business owner, ask yourself this:

• When was the last time your accountant really made you think?
• When was the last time they challenged your assumptions, questioned your strategy, or asked what you really want your business to achieve?

If the answer is “not recently,” you’re getting numbers, not advice.

A great accountant isn’t there to please you. They’re there to stretch you and make you think.

They bring objectivity when you’re emotional, realism when you’re optimistic, and clarity when you’re too close to the problem.

So don’t just look for an accountant who’s easy to work with. Look for one who’s honest enough to ask the hard questions.

The ones who challenge you are the ones who’ll help you grow.

If you or someone you know needs to be challenged by their accountant lets have a chat.

To your success

Noel Guilford