Working in the trenches, negotiating with labor unions, correcting design flaws, meeting deadlines and dealing with vendors, contracts and client issues aren't foreign to him. He too can look you in the eye and tell you firsthand how he feels your pain and what he will do to minimize it. Let's get real here. When we're told this empathy is generated from having been in the same trench, burdened with the same problems, we believe it. In large part, this characteristic is more prevalent in women than in men.
Women tend to see issues, work or personal, in the context of personal impact on their values.
To illustrate my point, consider the following example. A woman in the audience cited a torturous decision, as she saw it, to accept a top executive position being offered or to decline in expectation of starting a family. She worried that her career would be stymied, and that her hard work getting to where she is would be for naught. As she explained her personal crisis to all, she lost her fight to ward off a flood of tears. What I heard was a bright, energetic woman approaching a bigger issue from the bottom up.