I was recently exploring a new coaching relationship with a high achieving, successful executive. Paul insisted that he wanted to ‘bring his game to another level’ and thought I might be a catalyst for his professional development.

As I listened to his background and his amazing career trajectory a funny thought occurred to me: I wished I was him! He was outgoing, unpretentious, self-aware, and possibly the least neurotic person I’ve met in a long time. I wondered how I could possibly support him. Then he told me a story about one of the vice presidents who reported to him.

Sheila was a very capable rising star in the Company so Paul had challenged her to ‘step up’ more in high stakes meetings with senior executives and peers. He said he cared about her and wanted her to advance in the company, as he had over the past several years. But, he said, he wasn’t seeing much progress despite the feedback he gave her. The situation was feeling awkward and he didn’t know what to do.

Her shoes, his feet

I asked what Sheila might say about this topic if she was sitting with me. He replied, “Well if I was in her shoes I’d jump at the chance to get more exposure. She is obviously not confident and I think this might hold her back.”

I thanked him for answering a different question and again asked what she might say.

His response improved: “If I was in her shoes I might feel a little intimidated. Not only by the seniors in the room but perhaps even by me with the expectations I have of her.” That’s when I realized Paul might have an opportunity to ‘take his game to another level,’ but perhaps not in the way he anticipated.

I noted that in both of his answers he used the phrase ‘put myself in her shoes’ as a way to frame his understanding of Sheila’s situation. I said this sounds good on the surface but was actually self-limiting.  After all, it was still him wearing her shoes.

To make this tangible, I asked, what if Sheila had ambitions different from Paul’s? Or, what if she saw these meetings as a ‘boy’s club’ that was hard to penetrate (a scenario that might be invisible to him)? What if she valued speaking only when she had something she judged significant to contribute, which would differ from his more extraverted style?

His shoulders, her head

I was simply pointing out that he was coming to the situation from the perspective of his own ego, projecting onto her what he had wanted for himself. I suggested that his opportunity for development was to become more deeply empathetic toward Sheila, and perhaps, towards others.

I asked what would happen if instead of ‘putting himself in her shoes’ he would try to put ‘her head on his shoulders?’ In other words, could he imagine what she might actually feel and think without projecting his own ego on to her? His inability to do so, I said, was a failure of imagination.

I thought my challenge might upset him but he sat back and asked me to elaborate.  “Most of us think we are being empathetic but frequently we don’t attempt to see the other person in their full humanity,” I said. “Rather, without knowing it we see them as objects, sometimes as supportive, sometimes as obstacles.”

I continued,  “But if you invested your energy differently, by stepping back and occasionally just imagining what someone at that moment is thinking and feeling, you would have more insight and potentially more positive influence.”

“But if my imagining is wrong, then what?” Paul asked. I said that he probably would be wrong, at least some of the time. The power of deeper empathy isn’t just in one’s imagination, it is interpersonal in nature: you need to check with people about whether your assumptions are correct. It’s in the checking that they know you care.

With that we discussed some situations where he could conduct ‘empathy experiments.’ As part of these experiments he would check afterwards to see if what he was imagining might actually be true. His goal, he said, would be to more clearly feel what it was like to be someone else. Of course, he wanted to start with Sheila.

Highly successful executives (and the rest of us, for that matter) often have an unexplored leadership frontier to explore. This is not a frontier of ever higher personal achievement. Rather, it is a frontier revealed when we experience people as humans rather than as projections of our own aspirations.  While it only takes a small dose of imagination to try to see people clearly, it takes a larger dose of compassion to feel their experience. Now that’s a leadership challenge!