The hardest part of choosing advisers is that evaluating expertise usually requires the expertise you are trying to hire. You cannot assess a tax strategy without understanding tax.
Incentives are different. Anyone can evaluate an incentive, and incentives predict behaviour better than credentials do. These questions are all answerable in a sentence by someone acting in good faith, and awkward for someone who is not.
On how they are paid
- How exactly are you paid, and by whom?
- Does what you earn change depending on which option I choose?
- Is anyone else paying you in connection with me or my decisions?
- What happens to your income if I do nothing at all?
On duty
- Do you owe me a duty of loyalty, in writing?
- Whose interests come first if mine and yours conflict?
- Who else at your firm sees my information, and why?
On the work itself
- What falls outside your scope, and who is handling it?
- What would make you tell me not to do something?
- What does leaving look like, and how long does it take?
How to read the answers
The content of the answer matters less than its shape. Direct, specific and slightly boring is a good sign. Vagueness, deflection into how well they know the industry, or mild irritation that you asked at all are worth taking seriously — not as proof of anything, but as information.
The last question is the most revealing and the least asked. People who expect to earn your continued trust describe leaving calmly. People who expect to rely on inertia do not.
None of this replaces engaging independent licensed professionals. It is a way of deciding which ones.
