The Chief of Staff as Empathy Whisperer


Can a leader actually gain more empathy? The jury may still be out, but a critical role the Chief of Staff can play is that of “empathy whisperer.” Providing an empathetic viewpoint to a leader who may not otherwise see it that way.

Many powerful leaders can lose sight of reality. They’ve become successful because of their instincts, smart decision-making ability, strategic skills, and tenacity for their business. But life at the top can be isolating. Without someone to keep them grounded, executives often confuse their ability to make smart decisions with delusions of invincibility.

Dacher Keltner, a psychology professor at UC Berkeley, found in studies spanning two decades, subjects under the influence of power acted as if they had suffered a traumatic brain injury—becoming more impulsive, less risk-aware, and, crucially, less adept at seeing things from other people’s point of view. Let’s be clear, not all people in power act this way and you can’t expect to change the behaviors of your boss. However, you can promote empathy by showing it to others, including people in positions of power. These tactics may help.


Some leaders grow accustomed to being treated with deference. The business accommodates their schedule, their preferences, and their whims. They usually get their way because they are the boss. Of course, any leader deserves your respect, but so does the most entry-level employee in the building.

As Chief of Staff you can counteract a developing “Ruler of the Universe” persona by developing a close rapport that allows for back-and-forth conversation and banter – whether work-related or not. Effective Chiefs of Staff are not yes-people. You must be comfortable telling your executive when you disagree. Playing devil’s advocate or challenging ideas can only be done when trust and rapport is established.


Hectic schedules and a stressful workload aren’t the only things that disconnect a leader from the work force. Their socioeconomic status can drive a wedge as well. It’s hard for employees living paycheck to paycheck to see how their boss, who drives a luxury car and lives in a fancy house could have any worries. Conversely, it may be difficult for a leader to recognize how and why their employees’ family, health, and financial issues are having an impact on their work (and ultimately, the business).

While they don’t need to know all the water cooler chatter, it’s important for the CEO to have a pulse on the attitude and back stories of their employees. Your awareness and sensitivity to these personal situations can go a long way in helping the leader understand that “the average employee” does not have a personal assistant or laundry service.


Your boss ends a meeting and leaves the room frustrated that, yet again, after asking for ideas from others, no one said a word. She tells you that the team is “too execution-focused” and “does not understand the big picture,” hence why no one can ideate on command. However, you saw the meeting run differently. Prior to your boss asking for new ideas, she singled out one team member for making a mistake. By nit-picking this person for a minor mishap, the tone of the meeting changed. Faces went from attentive to anxious that they would be singled out next. When the time came for ideation, no one in the room felt compelled to say anything.

This perspective is important to share with your leader. It matters. An executive can develop a sort of “tunnel vision” when it comes to thinking through matters like these. They may fail to see their role in creating what they don’t want. As a Chief of Staff, you can shed light on how the same situation can be viewed differently by different people – and why these differing viewpoints are important to understand to get the best from people.


In a recent meeting, your boss is deciding between two options. You go back and forth and neither agree or disagree on a direction. It may be time to invite others into the decision-making process. When a leader opens up a decision to their staff, they can be amazed by the rich feedback and viewpoints received. While you can’t force a leader to listen, you can remind them that they hired their team for a reason, and they should utilize those people to their fullest potential by hearing what they have to say. It just may spark the next great idea for the company.

It is true that the skills needed to get a CEO to the top may end up backfiring on them once they get there. As Chief of Staff, you have the ability to inject more empathy into situations and help your leader refocus their vision on what’s best for your organization as a whole.  

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