An IT Leader’s Empathy Exercise Bootcamp

Co-authored by Chris Kondracki and ChiChi Lu.

Understanding and empathizing with others helps IT leaders navigate complex business environments. Empathy enables us to better understand a situation, relate to other people, and view issues from different angles.

Here’s why it works, and how to put it in practice.

Empathy is underrated.

There is an unfortunate stereotype that high-level executives are all ruthless. So ruthless that they will work their way to the top regardless of who stands in their way. Although this might be true for a small minority, the research shows that empathy is the stealthy quality shared by the most effective leaders.

Empathy is more than just relating to or understanding someone—it’s a genuine need to treat people how they want to be treated and to accept their feelings for what they are. Empathy is important for a leader navigating complex business environments because it makes them relatable and allows for an understanding of needs beyond their own.

“Though the concept of empathy might contradict the modern concept of a traditional workplace—competitive, cutthroat, and with employees climbing over each other to reach the top— the reality is that for business leaders to experience success, they need to not just see or hear the activity around them, but also relate to the people they serve.”

Jayson M. Boyers, Forbes.com, Why Empathy Is The Force That Moves Business Forward

An empathetic approach is especially effective when managing IT professionals, who tend to be more introverted than the average sales rep or marketing associate. Practicing empathy will allow quieter personalities on your team to contribute even more. You’ll become sensitive to unique work styles and understand how to solicit a range of input more effectively.

Practicing empathy can also improve productivity and efficiency simply because people respond better to working with coworkers and managers who treat them with respect.

“A study shows when leaders are fair to the members of their team, the team members display more citizenship behavior and are more productive, both individually and as a team.”

Emma Seppala, Harvard Business Review, The Hard Data on Being a Nice Boss, citing The Effect of Interactional Fairness on the Performance of Cross‐Functional Product Development Teams

In an ever-changing business environment, any edge that may help a team be more productive is valuable. The first step for leaders to practice empathy more effectively is to understand their own biases.

Snap judgments cloud our interactions.

It’s critical to develop the ability to take a step back and consider what unconscious biases are shaping your thoughts and behaviors. If you can understand your own feelings without judgment, you may be able to do the same for others.

Imagine arriving on the first day of a new job and meeting a high-level executive in their office. You see something on their desk that upsets you. A piece of memorabilia related to a hot button issue. A deal-breaker from your last romantic relationship. It might be a Red Sox hat for a Yankees fan, a Big Mac wrapper for a health nut, or a hunting trophy for an animal lover. The object makes you judge them immediately.

In this moment, can you pause and ask yourself, “If this object were not on the desk, would I feel differently about them?”

Questions like this help you reflect in the moment and notice your own bias. This is also how to start understanding why someone else might have an affinity for something you’re extremely opposed to.

This way of thinking allows for more clarity when a complex situation arrives. It also slowly begins to break the habit of judging people who are different. Differences are rich sources for personal and organizational growth.

Empathy takes effort.

Think of practicing empathy as if it were a physical fitness routine. Below are some exercises that help strengthen the empathy muscle, or the neural pathways in the brain that view issues from various angles. Once a leader is able to actively notice their own biases (see prior section), the following exercises become a bit easier:

Exercise 1. Put yourself in someone else’s shoes.

Goal: To step away from your own perspective and assess a situation from another person’s point of view.

Activity: Recall a recent interaction that was unpleasant. It could be as simple as someone bumping into you without so much as an apology. Think through how the other party may have perceived the same event.

From your perspective, you might have thought: Unbelievable. Not only did he plow into me, but he made me spill my coffee! Meanwhile, he was thinking: This idiot is standing in front of the only exit, staring at his phone. I’ll just squeeze around him to catch the door…. Oops did my bag catch something?

Reacting without empathy will lead to assumptions, ambivalence, or even malice. In any given conflict, most people think they are in the right and the other is in the wrong. But both parties can be right—it just takes a change of perspective.

Exercise 2. Listen actively.

Goal: To be completely present and non-verbal.

Activity: The next time you enter a conversation, simply concentrate on the other person. Truly listen. Absorb what they are saying.

When responses or unrelated topics pop into your head, notice that there’s a competing thought and quickly redirect your attention back to your conversation partner. Notice how soon after the person starts speaking that you trip over to response mode. Is it before the person finishes a thought? Can you wait longer and longer before you think about what you’ll say next?

If the person knows you well, you may want to reveal that you are practicing active listening. This way, if your natural conversation style is to chime in frequently, they won’t think something is wrong.

Pro tip: Active listening is especially challenging when a smartphone is present. Silence it and remove it from your line of sight.

Exercise 3: Get curious.

Goal: To better understand the other person by asking insightful questions.

Activity: The next time you’re tempted to jump into a conversation with your own anecdote, ask a question instead. Keep asking questions until you learn something new.

The key to asking questions empathetically is a combination of active listening (see above) and genuine curiosity. It’s difficult to ask questions that are relevant when you have been distracted. You’ll risk asking something that was already addressed or changing the subject. Being sincerely curious allows you to be more creative in your questions and bring up perspectives that might have been missed prior.

During this Q&A session, a great outcome would be for you to better understand the person you’re speaking with, as well as uncover some new assumptions and biases you might have.

Exercise 4: Ask others what they want.

Goal: To understand how another person wants to be treated and what that looks like.

“Do unto others as you would have them do unto you” would work fine in business if everyone had the same set of motivations and workstyle. Instead, treat people how they want to be treated. Communicate and collaborate with people in the way they want to communicate and collaborate.

Activity: On your next project, go beyond the golden rule. Instead of proposing how a collaboration phase will happen or what the communication channels will be based on your preferences, ask team members what would work best for them personally. Be aware of how your defaults might be affecting other people or the project as a whole. Don’t assume that how you’ve been managed in the past is how others want to be managed.

Exercise 5: Connect with people you disagree with.

Goal: To handle situations with less judgment.

There are more than 7.5 billion people in the world, many with beliefs vastly different than your own. It’s impossible to change the minds of everyone you meet, and arrogant to try. But it is possible to open your own mind, to try to understand why other people’s beliefs are different than yours.

In a business setting, occasionally there are forks in the road where one path is clearly correct and the other is incorrect. More often, the path forward is ambiguous. It is up to us and our team to choose which direction to take.

Activity: When we disagree with other people on the approach, apply empathy to understand their rationale. Look for points of agreement. Listen actively. Even if you still disagree, you’ll change the focus of the conflict from the person (who just doesn’t understand) to the issue (which may be a flawed approach). The shift is nuanced, but it makes for a more productive decision-making process.

Empathy is a habit.

Empathetic behavior is not a skill you can learn once and move on. It’s more like a muscle that needs to be continually strengthened over time. The exercises above are healthy for leaders and team members alike to revisit time after time.

There’s no shortage of frameworks for how to be the best executive or develop the most productive team, but a foundational and often overlooked method is to simply practice empathy. The empathy habits of leaders have a noticeable impact on work cultures and business outcomes.


ChiChi Lu

ChiChi Lu's profile picture

Leave a Reply

Your email address will not be published. Required fields are marked *