Listen Well And Tell The Truth: How To Lead With Empathy

Three NYC tech leaders share their wisdom on empathetic leadership.

Written by Dana Cassell
Published on Dec. 11, 2023
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Ted Lasso, the hit tv show about an American football coach moving to England to coach European football, has become a goldmine of leadership case studies. Ted, honest, humble and bumbling, leads his team with clarity and empathy. He understands that what matters most is not winning or losing (much to the chagrin of the team’s owners and fans), but how the players and staff live and work together.

Ted, a model of empathy, tells his team in a locker room speech, “I want you to know, I value each of your opinions, even when you’re wrong.” And while the line is typically cheesy, it is also deeply instructive for leaders aiming for empathy in their work.

Empathy begins with listening and genuinely appreciating what another person shares. Jessica Scott, vice president of talent at VTS, told Built In that honest listening creates safe space in her team. “This safe space allows for creative conversations and invaluable feedback that positively impact our work,” she said.

Listening is one half of empathy. The other half is being honest in response. Telling the truth creates trust and makes way for productive discussions about growth and change. When leaders tell the truth, people feel secure,” said Catherine Pavlov, managing director at Enfusion.

These leaders are far more refined than Ted Lasso, but their lived wisdom around leading with empathy is even more potent.

 

Image of Stephanie Gossage
Stephanie Gossage
Chief People Officer • Madhive

Madhive is the leading technology company engineered for modern TV advertising. 

 

How do you practice leading with empathy on a day-to-day basis? 

It has been an honor to lead the people and culture team at Madhive for the last four years. We are a lean company that has experienced a lot of growth and change during my tenure. As we scale and evolve, leading with empathy has been a key tenet of our culture.

Empathy starts with vulnerability and trust. I make it a priority to share my personal experiences to create an environment where team members feel safe to do the same. By being candid about my personal successes and failures, I aim to encourage a safe and open space for discourse. 

Championing employees is the cornerstone of empathetic leadership. I advocate for my team and my employees at all levels. When presenting to our executive team, I make sure that my team not only receives the recognition they deserve but also has a platform to showcase their expertise and contributions.

 

How has being an empathetic leader created a stronger culture on your team? 

We use empathy to promote a culture where employees can share ideas and disagree respectfully and openly. This aligns with one of Madhive’s core principles: “strong opinions loosely held.” 

An example in action is our annual Hackathon. Our engineering team runs a competition where everyone in the organization is encouraged to submit ideas to improve our products. We foster innovation by championing an environment where every team member feels safe to share their ideas. 

Another critical element to building a strong culture is maintaining an open door policy, something to which our entire leadership team is committed. Leading with empathy means understanding the needs of all team members, from those who recently joined to those who've been with us since inception. By maintaining direct lines of communication, we have been able to preserve the best parts of our culture and evolve as we grow.

 

What advice would you give to other leaders interested in strengthening their approach to empathy? Are there any resources you find particularly helpful?

As a leader, I’ve learned that embracing challenging conversations is paramount to an organization's success. If you build authentic relationships with your team, they will be more open to receiving direct and constructive feedback. This elevates performance across the board. 

 

As a leader, I’ve learned that embracing challenging conversations is paramount to an organization's success.”

 

Startup life is challenging and constantly in flux. In order to get the best out of people in this fast paced environment, you need to take a personal approach to leadership. Taking the time to look at situations from an employee's perspective and to consider differing viewpoints will guide you to make better decisions, and is critical to earning respect as a leader. The success of your team is a direct reflection of your effectiveness as a leader.

 

 

Image of Jessica Scott
Jessica Scott
VP, Talent • VTS

VTS is a real estate CRM software company bringing together landlords, brokers and tenants to make deals happen.

 

How do you practice leading with empathy on a day-to-day basis? 

As a leader, I think it is important to understand the individuality of my team members and naturally take that into account; to understand individual needs and how they can show up while maintaining an expectation for work productivity is crucial to success. 

For example, if there are members of my team that need flexibility around work hours, I always try to lead with trust and empathy. I always think about how I would want to be treated.

 

How has being an empathetic leader created a stronger culture on your team? 

I think it has created trust and empathy in the way we work with one another. I also think that because there is that space, folks can share how they feel and where they are. I will always listen because this is a partnership. 

This safe space allows for creative conversations and invaluable feedback that positively impact our work. When you have an investment as a human being, you do more. You step up as an employee in a different way because you know that who you are authentically as a human matters.

 

This safe space allows for creative conversations and invaluable feedback that positively impact our work.”

 

What advice would you give to other leaders interested in strengthening their approach to empathy? Are there any resources you find particularly helpful?

As a partner to leaders and executives within VTS, a lot of it is finding a person that can act as a trusted resource, share a different perspective and play devil's advocate. This has been very helpful to me as it helps me see and understand other potential outcomes, some that I hadn't anticipated. 

Though there isn’t a "magic book," there is an author I would recommend: Patrick Lencioni. Some of his books that I have enjoyed are The 5 Dysfunctions of a Team, Death by Meeting and The Advantage.

 

 

Image of Catherine Pavlov
Catherine Pavlov
Managing Director, Head of Content • Enfusion

Enfusion is a provider of a cloud-based portfolio management and risk system, as well as middle and back office services.

 

How do you practice leading with empathy on a day-to-day basis? 

When I hire, I talk to candidates about the importance of being authentic, of feeling at ease with who they are as people. I add that it’s important for them to recognize when people with whom they’re working may need them to adjust their approach, but we discuss the difference between adjusting behavior to build rapport and sacrificing one’s values. 

The former is a display of empathy, which most often results in understanding that leads to a connection. That leads to collaboration, and — you guessed it — that leads to happy, motivated people who deliver inspiring work. 

One of my direct reports became frustrated with a stakeholder who seemed unwilling to work with him. When he shared the issue with me, I listened to how not being able to establish a working relationship made him feel hurt.

I acknowledged that and showed I understood. I asked if we might try to understand the stakeholder’s frame of mind. He realized he had focused on his feelings and hadn’t considered what she might need. We ended up with full-circle empathy.

 

How has being an empathetic leader created a stronger culture on your team? 

When leaders practice empathy, we create a kind environment in which people trust and support each other. Generosity, gratitude and transparency are keystones of an empathetic culture. 

When leaders tell the truth, people feel secure. When people are secure, they are open-minded and open-hearted. We are a strong community of people with a shared objective, and our actions align with our words and values.

 

When leaders tell the truth, people feel secure.”

 

I lead the way I want to be led, and I recognize and let people know that I am wrong half the time. Acknowledging that I am only right half of the time opens me up to new ideas and gives others the freedom to present their ideas. It’s an almost accidental, very simple expression of empathy, which creates a collaborative culture.

 

What advice would you give to other leaders interested in strengthening their approach to empathy? Are there any resources you find particularly helpful?

Sometimes, as leaders, we’re taught not to be soft. My guidance is to remember that being kind is a strength. Showing empathy does not mean you stop managing and delivering work; in fact, you manage stronger teams and deliver more creative, sustainable solutions. 

You don’t stop telling the truth; you tell it more clearly and in real time. Identify your guiding principles as a team and be relentless about pursuing magnificence with the group of humans who bolster you.

I take advantage of whatever resources I can get my hands on, and there’s no shortage. I’ll just name a few of my regular stops. These include: Sahil Bloom (newer on the scene, a Warren Buffet favorite), Brene Brown (of course), Hidden Brain (no more secrets), Seth Godin (tried and true), Daniel Pink (love the Pinkcast), Heather McGowan (all-in empathy), Andrew Huberman (whole health), and lots of fiction (develops empathy). 

Finally, I watch and try to emulate people who make me feel seen, heard, and valued. These are the true leaders.

 

 

Responses have been edited for length and clarity. Images provided by Shutterstock and listed companies.