iscoverThis is free. My scripts on how to gain more traction with clients in conversation. Most accountants are having the wrong conversations with their clients. Here's how to fix it.
The questions that actually get clients talking
29 September 2025
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10 minute read
Your best advisory opportunities are walking out the door every day.
They're sitting across from you in client meetings, giving polite one-word answers to your questions, then paying someone else for the strategic advice you could have provided.
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"How's business?" "Fine, thanks."
"Any problems?" "Nothing major."
"Need any help?" "We're all good."
Conversation over. Opportunity missed.
I see this constantly in my business recovery work. By the time I'm called in, it's usually too late for prevention - I'm there to manage the aftermath. But as I review these failed businesses, the same pattern emerges: the conversations that could have saved them never happened.
After 30+ years of liquidating businesses, I've learned something: the difference between businesses that survive and those that fail often comes down to whether someone asked the right questions at the right time.
The conversations that should have happened
Recently, I was called in to handle the liquidation of a construction company. The usual story - cash flow problems, mounting debts, trading while insolvent.
But as I reviewed their situation, I realized this entire crisis could have been prevented. Here's the conversation that should have happened in their accountant's office two years earlier:
"How are you, Bede?"
"Oh, I'm okay, yeah, business is getting tough, it's not like it used to be!"
"What's different?"
"Oh, a lot of new players in the game, people looking for work, so they are pricing unders, and I can't find the right people… That's all."
"What do you usually charge, I mean, what is your margin?"
"I mean, I always try to hold out for a markup of 20%, you know, but lately I have had to drop that rate."
"Okay, so your margin should be around 16%, but it could now be lower?"
"No, no, my margin is 20%..."
"Bede, you know margin and markup are two different measures right?"
"I don't understand."
This fundamental misunderstanding was at the heart of his business failure. He'd been making pricing decisions based on incorrect assumptions for years, gradually eroding his actual margins until the business became unsustainable.
His accountant had been doing his books for over a decade. The warning signs were all there in the financial reports. But this conversation - the one that could have saved the business - never happened.
When I explained the difference between markup and margin during our final meeting, Bede asked the question I hear in almost every liquidation: "Why didn't my accountant ever tell me this?"
The pattern I see everywhere
This isn't isolated. In nearly every business failure I handle, I discover fundamental knowledge gaps that should have been addressed years earlier:
• The retail owner expanding into three unprofitable locations because revenue was growing, not realizing margins were declining
• The manufacturer making expansion decisions based on bank balances rather than sustainable profitability
• The professional services firm losing 60% of revenue when their major client moved to a competitor
In each case, their accountant had the data. They could see the warning signs. But the conversations that could have prevented disaster never happened.
Instead, I have these conversations during liquidations, when it's too late. And always, the same response: "I wish someone had explained this to me earlier."
What these conversations should look like
If Bede's accountant had engaged with his pricing concerns, the conversation could have continued:
“A 20% mark up is a 16% margin. If you want a 20% margin you need to mark up 30%.”
“No way, I wouldn’t win any work.”
"Well, what sort of work do you want? What does your best client look like?"
"What do you mean? Any work mate, it's all work."
"Well, it's not all work. Are you curious to understand more?"
Then they could have discussed specialisation. Extensions vs. renovations vs. custom homes. How focusing on one area builds expertise, reduces competition, and allows for better margins.
They could have covered breakeven analysis, cash flow management, strategic positioning - all the tools that could have prevented his business failure.
The questions that reveal real problems
The difference between surface-level compliance work and business-saving advisory relationships often comes down to the questions you ask.
Instead of "How's business?" try:
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"What's keeping you busy at the moment?"
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"What's different from last year?"
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"What's your biggest challenge right now?"
Instead of "Any problems?" try:
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"What decisions are you avoiding?"
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"What keeps you awake at night about the business?"
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"Walk me through how you make pricing decisions."
Instead of "Need any advice?" try:
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"What's the cost of getting this wrong?"
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"What happens if you don't address this?"
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"If you had unlimited cash flow, what would you do differently?"
These questions invite real answers, not polite responses. They create opportunities for you to provide guidance that could prevent clients from ending up in my office.
Why this matters more than ever
The accounting profession is changing rapidly. AI can process transactions. Offshore providers can prepare compliance reports.
I've been saying for a while that Xero isn't just accounting software - it's positioning itself as much more than that. They're building an ecosystem that handles more and more of what accountants traditionally did.
But here's what AI and platforms like Xero can't do: sit across from a client and ask "What's different?" They can't have the conversation that reveals a client doesn't understand their own pricing strategy. They can't engage deeply with people.
The businesses I liquidate often had accountants who could have saved them with timely strategic conversations. But those accountants were focused on historical compliance rather than forward-looking advisory work.
Here's what I find most frustrating: during liquidations, clients frequently ask if I can recommend an accountant who thinks strategically about business, not just compliance. They're looking for someone who will ask the hard questions and help them avoid the mistakes that destroy businesses.
The challenge
Look at your next client meeting. Instead of accepting "business is tough" as the end of the conversation, ask "What's different?"
You might discover they're making fundamental errors in business logic. You might uncover strategic challenges they've been wrestling with alone. You might find opportunities to provide guidance that transforms their business trajectory.
Because here's the reality I see every day: the conversations I'm having during liquidations should be happening in accountants' offices years earlier, when there's still time to change the outcome.
The question is: will you be the accountant having them?
Or will you be the one your clients wish they'd talked to sooner?
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