The Role of Empathy in Leadership with Chris Steer

Empathy is not niceness, and Christopher M. Steer spends a fair amount of his working life correcting that. Chris is founder and CEO of Steer LLC, an organizational advisory firm working with leaders, boards, and teams on leadership development, strategic planning, and organizational excellence. He brings more than 30 years as an entrepreneur, an attorney, and an operator, and describes himself as a chief energy officer. He joined hosts Stephen Sakach and Tullio Siragusa.

In this episode we explore:

• A definition of empathy a leader can actually operate on

• The two ways leaders over dial it and lose clarity

• The two moments in a day where its absence does the most damage

• Building empathy with reps instead of hoping for the right personality

• Why organizations break in the middle layer

• Accountability as the clearest form of care

Chris starts from the job, not the feeling. If your role is getting results through other people, you cannot be optimized without seeing what they see. His definition is the ability to see, understand, and live in someone else’s perspective, and he is careful to note that he barely used the word 15 years ago.

The misuse is where he gets pointed. Leaders learn empathy matters, over dial it, and start substituting kindness for perspective taking, or accept an idea without questioning it just to look empathetic. That is not empathy, it is avoidance, and it costs clarity without buying anything.

He makes it concrete in two moments. The one on one, where a leader can shape someone’s trajectory and instead broadcasts. And the team setting, where everyone is reading the leader’s questions, tone, and body language for whether ideas are welcome. His line for both: you cannot suck the air out of the room and expect to know someone’s story.

Then the systems question, which is what happens when the one naturally empathetic person leaves. His answer is athletic, which is that you need reps. Behavior change becomes habit change becomes mindset change, and only deliberate practice gets you there, built into management development, one on ones, reviews, and 360s. Executives take it back to the plan, teams reward it, and the middle layer is where it usually breaks. That is the same thing a brand faces between its promise and the experience it delivers, which is the gap Zero Company works in.

Key Takeaways

• (3:15) The operating definition: empathy is “the ability to see and understand and really live in the shoes of someone else’s perspective,” and without it “you will never be fully optimized” in an organization that gets results through people.

• (7:02) The correction he keeps making: “empathy is not being nice. That’s not the essence of this. And it’s not a proxy for performance.” The failure mode is over dialing it until kindness quietly replaces perspective.

• (9:04) Where it shows up or fails: the one on one, when a leader makes it “broadcast only,” and the team setting, where everyone is watching. His test: “you can’t suck the air out of the room and expect to know someone’s story.”

• (15:45) How it survives the person who leaves: “You need reps.” Neuroscience backs the sequence he uses, that “behavior change to become habit change, to become mindset change,” and the only route there is deliberate practice.

• (19:43) The scaling problem, named precisely: “where do organizations often break? They break in the middle.” Executives take it back to the plan, culture rewards it, and middle management is where the aspiration usually stalls.

• (35:04) The reframe worth keeping: “accountability is love. If I didn’t love you, why would I try to hold you accountable?” Withholding information that would make someone better is the unloving act, not the hard conversation.

FAQ

Is empathy in leadership the same as being nice?
No. Christopher Steer draws a hard line: empathy is perspective taking in service of the mission, while niceness is a substitute that costs a leader clarity. Empathy without standards is avoidance wearing a friendlier name.

How do you keep empathy in a culture after the empathetic leader leaves?
Build it with reps rather than personality. Christopher Steer puts empathy into management development, one on one structures, performance reviews, and 360s, so behavior becomes habit and habit becomes mindset across the team.

Can you measure empathy without it becoming a checkbox?
Christopher Steer suggests asking directly whether people feel their manager listens, asks good questions, and values their input, alongside 360 reviews. Those answers are more useful than folding empathy into a general engagement score.

Empathy without accountability is not kindness, it is a missing conversation. Hear the full conversation with Christopher M. Steer, watch it on the video page, hear Sherrill Kaplan on building leadership feedback loops, and find more on the Bliss Businesses series.