Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
With no glibness intended, the answer is a dysfunctional childhood.
My childhood formed career aspirations that were not authentically my own. My plan coming out of college was the same as it was going in: make as much money as possible — how didn’t really matter.
Over the next few years chasing that goal, I kept finding out that’s not who I am. So, my career path correlated closely to the long process of self-discovery often experienced in therapy, which is why I have taken so many extreme career pivots.
But like most things in life, a traumatic childhood is a double-edged sword as we are only as strong as the holes we climb out of. In my case, my childhood circumstances required me to pay extremely close attention to the emotional states of very unhealthy people. And it usually fell to me to talk them off the ledge, despite my very young age.
So, the upside is that now my superpower is understanding what’s happening with people emotionally and what they need to hear and feel to be OK. Everything worthwhile that I have ever done is because of that.
Can you share the most interesting story that happened to you since you started your career?
That’s like asking me to choose a favorite song. From what year?
I will give you two because owning a music venue in Hollywood probably gives me more unusual stories than are usually found in business interviews.
Story #1 — Right around the time I opened the Vanguard, I became a huge action figure collector. It all started with a single action figure: Dr. Hibbert from the Simpsons — I thought it was funny that a lesser character would get an action figure. Lo and behold, every Simpsons character ever has an action figure, and before you knew it, I had every one of them displayed on huge shelves in my office. (Which eventually led to my Muppets collection. Which ultimately led to my…everything.)
Every year, The Simpsons kicks off their season with the Treehouse of Horrors episode, and they hold a massive party for the cast and crew to watch it live together.
In either 2007 or 2008, they were supposed to hold their event at my competitor, Avalon. But someone told the booker about my office. So, she called me up to ask if she could see the venue. She walked through and loved the place. But then she asked me, “Is it true about your office?”
We went to my office, and she gasped as she walked in — everyone did. She took out her phone, snapped a picture, and texted Matt Groening, who said, “Let’s have the party there.”
Sure enough, we got the gig, and about 1000 people came to my office that night. It was one of my top five all-time favorite events.
Story #2 — When we first opened, Vanguard had a “middle-class” sound system for DJs. Everyone I met with any experience in hospitality told me, “If you get a top-quality sound system, you’ll raise your average bar spend by 20%.” But no one could ever explain why, and we weren’t about to plop down $125,000 because people thought it would be cool.
Nonetheless, I rented a high-end sound system for a month, and sure enough, bar sales increased by about 20%. I didn’t know why, but I didn’t need to know why. We installed a FunctionOne sound system, which increased our bar spend and made every DJ in the world want to play our venue. It was the best investment we ever made, despite the fact that we couldn’t explain why bar sales increased.
Several years later, I met an ENT who was a huge fan of electronic music. I asked him if he knew why bar sales increased when the sound system was improved.
“The better the sound system, the more the bass travels through the floor. When the bass travels through the floor, it vibrates the pelvis. That sensory stimulation motivates people to drink.”
I love the story because it demonstrates the levels at which our behavior is being affected without our awareness of it.
What do you think makes your company stand out? Can you share a story?
Our clients become very empowered as a result of working with us because we understand how to provide them with guidance that reaches them and leaves them intrinsically motivated to embrace it.
For example, whenever I meet with sales leaders, I tell them, “You’re already great at behavioral science. You’ve been experimenting with it since you were a kid, and given your position, you are necessarily great at it.
The only thing is, you’re great at it intuitively and instinctively, which has served you incredibly well. But you can’t do instincts on purpose. Great leadership requires intentionality.
So today, we’re here to learn names, like “loss aversion.” Because once you can name something, you can do it purposefully.”
Just framing it that way almost guarantees my success at triggering intrinsic motivation, which is the only thing that matters. And then you get to see what happens.
I always regroup with clients following training sessions for smaller group discussions, which allows me the opportunity to see how the training drove impact.
One leader told me about how struck he was thinking about referent power and how shared interests drive liking. He had one direct report about to be put on a performance plan. Prior to meeting with them about it, he watched two episodes of their favorite TV show, which he had never seen before.
In the meeting, they talked about the show for ten minutes, and it transformed their relationship. The rest of the meeting was the best they’d ever had (despite the performance plan), and ever since then, the report has been killing it.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
- Empathy — People were often intrinsically motivated to work with me because I consistently made them feel understood and validated. That, respect and fairness are all people need to run through a brick wall for you.
- Humor — Sometimes work can be a drag, with nothing going right. The ability to make people laugh is hugely important when you need to keep the wheels turning without any inertia.
- Servitude—I was a servant leader before I knew such a thing existed. I could not have emerged from my childhood (in a healthy state) without an orientation to helping people.
It’s hard to share stories about characteristics because they are so ingrained in my behavior. So, maybe it’s better to share the evidence of their outcomes.
When I was at Juno, I was in my 20s and leading a group of 40 young salespeople, and I found myself in one of the most challenging leadership jobs, exacerbated by the ambiguity of sales in the Internet 1.0 era. Throughout it all, I listened to my team, provided what they needed to succeed, and generally created a positive culture. In a company of 400 people, I got the highest upward review scores, and we always beat our numbers. Although, to be fair, many of those salespeople have gone on to spectacular careers, so I also had the benefit of some spectacular talent.
At Vanguard, I ran a massive venue for a decade, employing 48 security guards and 24 bartenders on a sold-out night. The hospitality industry is notorious for massive turnover, yet the voluntary turnover was non-existent at Vanguard. We built a culture that had 150 people treat Vanguard like their family business for ten years, which played a massive role in its success. Thirteen years later, people still talk (fairly frequently) about the magic of the Vanguard being the staff.
But I’ve learned that as good as I may be as a leader, I’m even better at talking about it and helping others improve. With Compass, we managed to get a 70% read rate on our coaching emails, and leader scores increased on average by 10% after receiving eight emails. And I can tell you that getting people interested in reading the emails was infinitely harder than helping them improve as leaders.
Leadership often entails making difficult choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.
At Juno, I had to buck a century of media industry sales culture, going around the ad agencies and engaging directly with the client. Traditionally, doing this meant being blacklisted by the ad agencies and ending your career. But because I wasn’t burdened by the “curse of knowledge,” it was evident that Internet 1.0 companies that relied on selling to ad agencies would go out of business because the agencies were clearly dragging their feet. (Which is another interesting conversation about vested interests and change.) Any Internet 1.0 company that sold ads and survived did so by going direct to the client and calling it business development. This taught me the importance of knowing when to rely on history and when to ignore it.
At Vanguard, we needed to sell alcohol to be profitable operationally. But for concerts to be profitable, you have to sell tickets to all ages, including teenagers. In California, the only way you can sell alcohol and allow underage people on your premises is to sell food. And to ensure people don’t try to take advantage of the loophole, more than 50% of your sales have to be food. This is one of those laws that is impossible to follow and never gets enforced unless an influential person wants to mess with you. So, it creates a stressful state of existence. But in addition, the expenses of opening and running a kitchen were very high, and the concerts were proving to be breakeven. So, I ditched the food, went 21+ for all events, focused on electronic music DJs and special events, and it significantly increased our profitability, despite the painful personal loss of identity as the owner of a concert hall. It taught me the importance of abandoning your original ideas based on what is actually happening right in front of you.
At ADP, when we first designed Compass, I was sure to make the coaching opt-out (as opposed to opt-in). We knew definitively from the data that asking people to opt into the coaching would get us about a 10% sign-up rate, while asking people to opt out from receiving the coaching would get us about a 95% sign-up rate. Unfortunately, despite my best efforts, one level up decided that the coaching should be opt-in. I was stuck. I knew the product would fail if coaching was opt-in and would be a massive success if it was opt-out. I also knew that if I went high enough in the organization to make my case, I’d make a lot of enemies and possibly bring my ADP career to a swift end. But I found my courage. I decided I didn’t want to stay if it meant making such fundamental compromises in the absence of a compelling reason to do so. So, I took the risk and jumped three levels to make my case. Thankfully, it went our way, and the product was a success. It taught me the importance of understanding where you set your boundaries and then honoring that in the moment of truth.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?
Empathy is the capacity to understand and relate to what another person is feeling in real time and in general. It allows leaders to understand what their people need and when they need it. When leaders act in accordance with their empathy, they create environments with very high employee engagement, discretionary effort, and performance.
The reason that empathy is so important for leaders is because the psychological contract of the 1950’s and 60’s, which was responsible for employee motivation and engagement, has been systematically disassembled and replaced with nothing. The only thing left to drive employee motivation and engagement are the human relationships with their leaders and colleagues. But without empathy, those relationships are transactional and worth very little.
Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?
I was a counselor at a camp years ago and there was a lot of bullying within my camper group. So, I got the three most influential campers in the group together and asked them, “Imagine your life as a movie. Do you want to be the character that bullies the wimpy kid, or do you want to be the one that protects the kid from bullies? Because I only respect one of those two.” After that conversation and new perspective, they made it a mission to protect their bunkmates from bullying, which spread from my smaller group to the entire age group at the camp. I got so many thank you’s from parents and campers then, and I continue to get surprise notes here and there thanking me for how I helped them that summer. I may be prouder of that than anything else I have ever done.
How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?
Transparency, honesty, and active listening. If a leader is making an unpopular decision, there has to be a defensible reason behind it. It is incumbent on the leader to help the team understand the rationale behind the decision, even if they disagree with it. However, it is even more important that the leader makes each team member feel heard and considered. People are generally OK with a decision with which they disagree if they feel their perspective has been given due consideration and respect and if they can understand the rationale behind it. It certainly helps to have a trusting and inclusive dynamic beforehand, rather than wait until the moment of truth to try and chase it.
How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?
Sympathy is feeling bad for someone. Empathy is understanding what someone is going through. You can sympathize with someone who has lost a pet, but unless you’ve lost a pet yourself, you can’t empathize with them because you can’t understand what they are feeling.
When I lost my first pet as an adult, someone said to me, “You knew one day this would happen. You knew you would experience terrible pain. And you chose to do it anyway, so you could give your pet the most wonderful life.”
It’s the only thing anyone ever said to me that made me feel better, and I now repeat it to everyone who just lost a pet. And it has helped every single one of them. There’s no way I could have known that’s what I needed to hear until I experienced it.
And that’s why sympathy isn’t enough, because sympathy doesn’t help you know what to say or expect. As a leader, you need to know what to say and what to expect.
What practical strategies or exercise employ to cultivate and enhance their empathetic skills?
In my experience, the more empathy you feel for others, the more politics become unpalatable. It’s like the quote from Ender’s Game – I’m paraphrasing here: “To defeat my enemy, I must understand him. But the moment I understand him, I no longer want to defeat him.”
This is an unpopular opinion, but I think people have a choice to make, like those campers years ago.
Do you want to be the leader that people remember for the rest of their lives with gratitude, or do you want to get as far ahead as possible in your career? Because the more empathy you feel, the harder it becomes to prioritize your own advancement. The good news is that helping other people advance is much more satisfying than advancing yourself.
How can empathy help leaders navigate the complexities of leading diverse teams and ensure inclusivity?
Sometimes, our capacity for empathy is limited by our life experiences, such as an earlier example of never having owned a pet. In cases in which we do not have direct experience, we often believe our best option to express empathy is to guess how people are feeling. As well-intentioned as that may be, it is terribly ineffective. **** Remember what they say about assumptions? The best way to display empathy towards people with vastly different life experiences is to acknowledge your lack of understanding and demonstrate curiosity to know how people feel.
It is never a good idea to fake empathy. You’d be better off saying nothing. When there is no empathy to express, the best thing you can say is something to this effect, “I cannot pretend to know what you are going through. But I am curious to understand you better and how best to validate you. I’ll try my best. I’m sorry in advance for the mistakes I will make. I have the capacity to be an unbelievable idiot. So I hope you’ll help me to be as effective in this regard as I possibly can because I very much want to be there for you.”
Based on your experience and research, can you please share “5 Ways Empathy Will Affect Your Leadership”?
1 . Your teams perform better. Empathy will get people to work harder for you. My teams have always thrived, and I have had a surprisingly large number of people tell me they worked harder for me than anyone before or since – the reason is because our relationship supported their best life. Everyone can think about how their lives were different under the best boss they ever had. Your mission at work gives you purpose. Your role at work gives you pride. Your relationships with your teammates provide you with connection. And when you’re at home in the shower, you’re thinking of creative ways to problem solve instead of ruminating over the latest sleight at work. Empathy makes that happen, and it produces transformative results for organizations.
2 . You make better people decisions. People complications are the most ambiguous, complex and unexpected challenge in every organization. What happens to the people who didn’t get promoted? What happens to team morale after a key departure to another organization? How does the team respond when a new hire turns out to be toxic? How about when the organization’s stock takes a hit and there are rumors of layoffs? Any attempts to address these situations without empathy will almost certainly fail spectacularly. It is only by understanding what people are likely to experience that the most effective strategies can be formulated in advance. It is only with empathy that it is possible to understand what people need in any particular context, from the mundane to the troubling. Reacting to people’s issues without empathy is like choosing a torch over a flashlight in a fireworks warehouse: you are maximizing the likelihood of the largest possible explosion.
3 . You design better operations. As companies grow, keeping everyone rowing in the same direction becomes increasingly difficult. Designing effective operations within and between teams requires tremendous empathy. It is only in understanding the needs and experiences of various stakeholders that a holistic plan can succeed. Whether that means providing clear roles on individual teams, or clearly negotiated standards between teams, success is only possible when each party understands, considers and values the experiences of all the others. Organizations who think they suffer from a silo problem actually suffer from an empathy problem.
4 . You make better business decisions. You want to formulate a value proposition that is going to resonate? You want to formulate marketing copy that is going to cut through the noise? You want to create a client success strategy that will earn you a high NPS? You want to design a product that is going to drive engagement from users intrinsically motivated to use it? How can you possibly do any of the above without understanding what your customers are feeling and experiencing? A lack of empathy places a very low ceiling on a very high number of contexts. One could argue that all business boils down to a single question: how would people react if I did this? Without empathy, you have no shot at answering that question.
5 . You become a better and more fulfilled human being. Climbing up Maslow’s hierarchy, we find the need for connection is even more fundamental than the need for self-esteem. Everyone I know agrees with the following sentiment: accomplishment is underwhelming. The only thing that accomplishment accomplishes is moving the goalposts to some other future accomplishment that will supposedly make you happy, but won’t. However, as our careers progress, the way we evaluate ourselves begins to shift to how we have affected others. We think about the people we helped, and not achievements, as we seek to articulate the meaning of our lives. Simply understanding other people makes us feel more connected and happier. But the behaviors driven by our empathy become the behaviors we use to define ourselves. I can’t say it any better than The Beatles. “And in the end, the love you take, is equal to the love you make.” Beginning right this moment, the more empathy you show others in life, the more joy you will experience in life.
Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?
Omigod yes. In today’s world, leaders have to worry about strategy, execution, and team engagement. The amount of time and focus required to show sufficient empathy can make it very difficult to attend to the other aspects of the job. It makes having to deliver bad news gut-wrenching. It makes you easier to take advantage of by manipulative people. It makes it much harder to prioritize the organization’s health over the needs of the individuals you empathize with. It makes it harder to play politics, and harder to prioritize your own career advancement.
But my life experience tells me empathy is an 80-20 proposition. The rewards far exceed the costs, and the challenges you get from showing empathy are the types of challenges you want.
Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?
The answer is totally context-dependent. Even differentiating between my professional experiences wouldn’t allow me to answer that question. “When” during a venture would dictate what my biggest fear was at the time. But if I had to name the most common worry, it would be involuntary turnover. And I’m quite proud of that, because involuntary turnover is what you worry about when things are going great.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
Kindness is cooler than coolness.
The human condition requires talk therapy.
The purpose of capitalism is to produce equilibrium at the point that maximizes the public good.
How can our readers further follow you online?
Follow me on LinkedIn.
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!