Some of the most challenging situations I’ve faced in accounting have not come from tax codes or reconciliation software, but from the clients themselves. It’s surprisingly common to encounter business owners who cannot clearly explain their own finances. One particular case involved a client engaged in inter-company trading who simply could not say how much he owed to his own business partner. It wasn’t dishonesty — it was a genuine lack of clarity that had become embedded in how he operated.
When faced with this kind of financial fog, the only responsible path forward is to ask the hard questions. These aren’t meant to embarrass anyone, but to protect them. If your accountant is asking, “Where did this money go?” or “Who exactly paid for that?”, it’s not nitpicking, it’s risk management. Without precise answers, even the best bookkeeping system will eventually collapse under the weight of assumptions.
This is why early engagement and expectation-setting matter. Before we get into numbers, we must ensure that the business owner understands the story behind them. As part of my client onboarding, I now insist on a core set of clarifying questions that must be answered before we begin any meaningful work:
What exactly do you sell, and how is payment collected?
Who do you owe money to, and who owes you?
Are there transactions between your businesses, or with related parties?
Do you know the current balances of your main bank accounts and credit lines?
It’s not about perfection. It’s about honesty, structure, and collaboration. A client who cannot answer these questions at the outset is not ready for an accountant — they’re still sorting out their business. And that’s fine, as long as we’re honest about where we’re starting from.