Empathy building at work

A simple exercise to improve communication

I’m a big, big proponent of cultivating empathy. It’s the single most important value that I have personally, it was one of the core company values at Penny, and it’s even one of four company values at Credit Karma (although I can take no credit for that).

There are actually two different classes of empathy: emotional empathy, and cognitive empathy. When I use the term “empathy,” I’m typically referring to cognitive empathy, which can be summarized by the following definition from Wordnik:

empathy [n] - the intellectual identification of the thoughts, feelings, or state of another person

Note that having cognitive empathy does not involve an emotional response (e.g. pity), as is the case with emotional empathy. It simply means identifying another person’s perspective or mental state.

Empathy in this form is a powerful muscle. It can be used to improve communication, facilitate negotiations, or develop relationships. In a work environment, use of empathy can easily cut through a whole class of problems, from the classic speaking over each other in meetings to getting several interconnected teams moving in the same direction.

And as with any muscle, empathy can be strengthened through deliberate practice.

Predicting people’s responses

With that context in mind, here’s one simple exercise you can use to build cognitive empathy:

Before your next meeting, try to predict how people are going to react (beginner mode) or what they’re going to say (expert mode) during the meeting.

Beginner mode

The beginner version of this exercise is to predict how people will react in a meeting.

The exercise itself is relatively straightforward: open up your calendar for the day and write down how you expect each attendee to react in each meeting you have. You can start with basic emotions like happy, mad, or neutral and build into more nuanced reactions like eager, disinterested, surprised, or frustrated.

Make sure to write your predictions down! Then, after each meeting, grade yourself against your predictions.

If you thought Alice would be happy when you delivered your project ahead of schedule and she was, you win! If you thought Bob would be frustrated by the team’s new priorities and he was, you win! If you thought Carol would be eager to work on the new project and she wasn’t, that’s where the muscle-building happens!

In those situations, reflect on the missed prediction:

  • Why didn’t the person react the way you expected?
  • What context might you be missing?
  • Could you have known the person would react the way they did?

As you get better at predicting your coworkers’ reactions, you can even start layering on predictions of the magnitude of reaction. When you’re consistently predicting both — that Alice would be mildly upset by a new deadline — it’s time for the next level.

Intermediate mode

The intermediate version of this exercise is to not only predict how people will react in a meeting, but also why they will react that way. Write down a few bullet points on why you expect Alice will be happy, or why you expect Bob will be frustrated.

You might have already started doing this as part of the first version of the exercise. If so, that’s great! You can quickly advance to the expert version.

Expert mode

The expert version of this exercise is where things really get interesting. Your goal is to predict what people will actually say in a meeting. That involves not just understanding the what and why of their reaction, but also the how: how will that reaction translate into words?

This isn’t as straightforward as it might seem. People don’t always say what they mean or feel, especially in a work setting. Work communication tends to involve more subtlety or nicety, not to mention body language. Therefore, even if you understand the what and why of a person’s reaction, predicting how that translates into what they say can take serious practice.

Maybe Bob suddenly starts agreeing with Carol despite appearing frustrated by her proposal. Why might that be? Perhaps he’s placating Carol but actually intends to escalate the issue to their boss.

Putting empathy to work

As you develop the ability to predict the what, why, and eventually how of people’s reactions, you can start putting that empathy to work.

For example, if you have a good idea that Bob will try to deflect the ask you have for him because he doesn’t think the work is part of his team’s charter, get ahead of it! Use your cognitive empathy to figure out how to disarm Bob’s resistance before he even raises it. In this case, how might you position the ask in such a way that Bob feels it is part of his team’s charter?


By practicing this on a weekly or even daily basis, you’ll soon be adept at not only having cognitive empathy, but also putting it to productive use in a work environment. Just remember: with great power comes great responsibility 😉