HOW TO START A HARD CONVERSATION
Rabbi Michael Whitman

The Jewish calendar is not just a way for Jews to mark time. It is also a textbook, a source of universal lessons about every aspect of life relevant to each of us. We are currently experiencing one of the most important lessons our calendar teaches. We are approaching the Jewish High Holidays (Rosh Hashana, the Jewish New Year; and Yom Kippur, the Day of Atonement), with its heavy subjects of judgement, apologies, and forgiveness. Each of us has moments in our lives where we need to express to someone we love our expectations and disappointments. How can we do this more effectively? How does God do it?

The Jewish month before Rosh Hashana is the month of Ellul. We recite extra prayers to allow this month to prepare us for the challenges and potential uplift of the High Holidays. Our rabbis teach us that the Hebrew word Ellul stands for an acronym, a quote from Shir HaShirim (Song of Songs) that can be paraphrased as, “God loves us, and we love God.”

The first step for any hard conversation, in effectively holding someone responsible for their actions, or expressing our expectations, is to convince the other that we love them. Only when they are convinced of our love beyond any doubt, and convinced we would only do what is best for them, can we say what might otherwise be harsh, and probably ineffective.

Our calendar teaches is that the first step God takes, before the heavy conversations He will have with us over the High Holidays, is to give us a month to remind us of His love for us. Only when we are assured of that, can we accept God’s words in the spirit they are truly given.

This is a crucial lesson we can emulate in every relationship – between spouses, between parents and children, between a community and its leaders. First convince your listener that you genuinely love them, and then, gently start the hard conversation you need to have.

For Jews, Shabbat is a particularly suitable time to transmit this. Many parents have the custom on Friday night just before Kiddush, to give a blessing to their children. You can find a traditional blessing in any prayer book, or you can express your own thoughts and words. This is a custom that can be adapted to any religion in any family. What you say is less important than conveying your absolute and unconditional love for your child, just what God feels for us. When that is clearly understood, everything else you say is heard differently.
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