If you are an engineer or executive at a Houston energy company with five or ten years of tenure, there is a real chance that more than half of your family's net worth sits in one company's stock.

That can be tax-efficient, emotionally meaningful, and financially significant. It can also be the single biggest risk to the life your family is trying to build.

In every conversation we have about estate planning, two things come up. First, the structural piece: wills, trusts, powers of attorney, beneficiary designations. Second, the relational piece: what you want your family to know, believe, and carry forward.

Most families have given more thought to the structural piece. The relational piece is where the more important work usually lives.

Most families have one financial conversation a year. It usually happens in March or April, around tax time. It is short, transactional, and centered on numbers.

There is a different conversation worth having in May. It is not about numbers first. It is about what the numbers are for.