An operating business is the most difficult asset in an estate, and the planning belongs in the company’s documents as much as in the owner’s.

Buy-sell agreement. A funded obligation to purchase on death, with a defined price. Without one, an estate holds an illiquid minority interest and a family member becomes an owner of a business they cannot run.

Transfer restrictions preventing an interest passing to persons outside a defined group, with the estate obliged to sell.

Valuation for estate tax. A buy-sell price is respected for estate tax purposes only if the agreement meets conditions — it is a bona fide business arrangement, not a device to transfer to family for less than full consideration, and its terms are comparable to arm’s-length arrangements. Family businesses fail these tests regularly.

Succession of management distinct from succession of ownership, with an interim decision-maker identified.

Entity documents. Operating agreements should address what happens on a member’s death — whether the successor becomes a full member or only a transferee entitled to distributions — because the default rules often frustrate the plan.

Liquidity. Estate tax on a closely held business may be payable before any liquidity event, and deferral elections have conditions worth confirming in advance.