Should my spouse and I write our Letter of Wishes together or independently first?

Independently first, then together. Kris Kluver, in The Dysfunctional Family Office, gives the process directly in the Letter of Wishes template. Each senior family member writes their own version individually. The independent step is what surfaces blind spots and protects the output from one spouse quietly going along with the other. Once both letters are done, the spouses sit down together with curiosity and a desire to understand each other's perspective. They compare. Where they agree, the language gets sharpened. Where they disagree, they listen to understand before responding. They eventually produce a jointly written letter that captures both voices. Couples who skip the individual step usually end up with one spouse's letter and the other quietly nodding. The whole exercise loses value. The independent draft is the part that produces the real conversation. Most spouses discover something about each other's hopes and fears they hadn't known after thirty years.