The odds against catching Jean's sparkle seemed to me to be high; rare is the family member who doesn't find something not quite right in a family portrait. I asked Tom what it was like to embark on such a skittish marriage every time a new patron signs him up.
"I have to please myself," he said. "That's what I must do. But my job is to please the client. Clients rarely know what they want, but they often know what they don't want. Wives also have very possessive feelings—here's a guy fooling around with my husband's face. But I always make it clear that the painting is for just one person—the client. If it's a portrait of a child, the child's mother can be the client. Mothers know more about how their children look than you do. They'll say, ‘I think George's cheeks are a little fuller than you have them,' or, if I've changed the clothing for aesthetic reasons, ‘He never wears a shirt like that.'
"When a CEO—or anyone else—comes to me to be painted, I'm looking for an idea. This assumes that I've met him; maybe we've had a meal. We chat. I ask questions, see what his interests are, how he reacts, laughs, makes a point. Just who is this person? I study his face. I'm very conscious of his bearing, how he holds himself. Is he old and tired? Is he alive? Is he intellectually curious about the world? One banker who was retiring had a strong idea about the kind of person he thought he was and wanted to be: without a jacket, a hands-on guy. When someone wants to be like something, it tells you a lot about them. I could make an image of you that people would say, ‘He must be a very funny guy,' or ‘He must be a pessimist.'"
"Is it necessary for a portrait artist to like the people he paints?" I asked.
"I've done very few people I didn't like," Tom said. "I think that gives me an edge because your attitude is what you really paint. Some wonderful things happen with portrait subjects. They're out of their depth—they're in the hands of someone else. You really don't want to get arrogant with your surgeon.
"There was one CEO I didn't like. He talked only about himself and his achievements, instead of having a conversation with me. When he saw the finished portrait he said, ‘You don't like me, do you?' I said, ‘I'm sorry you said that. There are many other painters I'd be glad to put you in touch with—the best.' But when he brought his wife to see the portrait she said, ‘You should look so good.'
"Some men refuse to be painted. But most of them are interested. They regard it as a certain kind of mystery. How did it happen? It's a two-person transaction. Painting people is what I most like to do. In one person we see all people, including ourselves."
One question Tom often asks executives and other leaders, he said, is: "Do you want to be painted as someone who has a question, or as someone who has an answer?" It's an elegant question, and I began to wrestle with it. The CEOs, I guessed, were answer types, and I didn't want to be associated with them: arrogant know-it-alls. I wanted to be a man who has a question. Much of what I know I've learned by asking a million questions.
And yet...as I watched Tom studying my face and making judgments of his own, I heard a voice saying, "Not so fast." For much of my working life I've been in a position of authority, starting in my mid-20s when I was an editor at the New York Herald Tribune. Later I edited several magazines and was master of Branford College at Yale. Since then I've kept busy writing books and teaching courses that are taken by people looking for answers on how to write. In none of those undertakings do I remember having an onset of shyness or doubt and thinking, "I can't do that." Obviously, I was also a man who liked to be in charge, and I told Tom he would just have to contend with that ambiguity. I don't think it came as news to him that the human face is a shifting sea of contradictions.
"Actually," he said, "that question is mostly a ruse to get people to think—to start using the muscles in their face. Your face right now is full of all sorts of ripples as you think about the question."