Hilary Silver Says Ordering Nine Women to Brag Left Them Teary and Cheering

In Hilary Silver's telling, drinks and an opening toast came before the assignment. Silver, a mentor to high-achieving women, had brought nine clients together for a weekend in a large house, and she had saved something special for the first dinner. The group had settled in at the restaurant, and Silver said she felt giddy, like a child about to hand over a gift she knew they would love.

Then she gave the order. One by one around the table, Silver recalled, each woman had to brag on herself and tell the real truth about how successful she was, without downplaying, brushing it aside, or retreating into false modesty.

That, Silver said, is what made the night different. Most of the women, in her account, had never done that as adults. And they had much to tell. One had just retired as chief financial officer of one of the nation's largest and oldest firms, in a field where men still hold most of the power, after spending many years often as the sole woman in the meeting. Another had recently earned the top sales ranking nationwide for the large company she worked for, beating thousands of colleagues. A third had started her own high-end home-selling firm in Atlanta from nothing, without inherited wealth and relying only on her own drive and commitment.

As their mentor, Silver said she knew the full backstory for each woman, not only the final titles but the hard climb behind them, and she wanted the women to know it about each other. So whenever someone hesitated or tried to shrink what she had done, Silver stopped her.

"Say the whole thing," she told them, urging them to spill it all. She added details herself, bragging on each woman as she went.

What followed is why Silver still calls it one of her favorite nights. She said there were tears and cheers as the women shared what she called their deep secrets about themselves. Silver said every woman got to be fully seen by people with no motive to flatter her and nothing to gain, only pure admiration.

As the evening closed, she said she watched nine near strangers bond like longtime friends, and stay lit up for each other. She said knowing those stories changed the rest of the weekend, as the women pulled each other aside for sidebar talks about business ideas, problem solving, and relationships.