What questions should customers think through before talking to professionals about their project?

Unrealistic expectations should be addressed first. Always ask what is the worst case scenario first. This way you don’t spend 90 minutes in your initial consultation getting pumped up (sales trick) and you start writing $1000s in checks (consumer reinforcement). Get the bad news first then have your advisor work backwards to a realistic resolution.

Risk verses reward should be the second question. It does not make any sense to solve a $5,000 tax problem if it costs $6,000 to hire someone to solve it.

Also, keep the five-headed dragon in mind. For example, a typical non-filer (someone who hasn’t filed a tax return) has five areas of concern: (1) record keeping, (2) tax return preparation, (3) audit potential, (4) the appeals of such an audit; and (5) the collection actions of the tax agencies. Other pitfalls are employment taxes, sales taxes, penalties and interest assessments, state tax agencies, professional licensing agencies, business entanglements and/or marital-family entanglements. Every obstacle will cost money to solve.

Ask for the bad news first. It may be worse than you think.