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How to / Lead with Empathy

6 years ago by

Within five minutes of meeting Michael Ventura he made a joke at my expense. That’s my kind of person. He also happens to be someone who, on paper, you wouldn’t believe is real — at least I didn’t.

In 2005 Michael founded Sub Rosa, which is a strategy and design firm that counts Nike, G.E., and even the Obama White House as some of their clients. What makes Sub Rosa stand out from the rest is their insistence on bringing considered empathy to understand a problem and offer a solution.

As if that wasn’t enough, Michael also hosts a podcast, is a guest lecturer at Princeton, a practitioner of Chinese medicine and a healer. Oh, and runs an amazing store in the West Village, Calliope, with is wife Caroline. (You might remember the two of them from this post…)

Well, to top it all off, Michael recently published a book, Applied Empathy, that draws upon his experiences of applying empathy to his own leadership roles as well as the experiences with his clients.

After spending an hour chatting with Michael about all things empathy I can attest, he’s beyond real. He’s eloquent and funny and heartfelt and most of all, empathetic. Read on to see for yourself..


… on how he faced his biggest fear…

I went to business school so my undergrad was a business degree. The school is called Babson, it’s a tiny little business school outside of Boston and year after year it’s ranked the number one entrepreneurial program in the country.

What Babson knows how to do better than anything else, is train people on how to run a business. But when I got there, despite the fact that I was student body president and captain of sports teams in high-school, I was still deathly afraid of public speaking.

In one of the required freshman classes everyone has to get up and present an idea for a business and the school will give a few students up to 3k to start the business.

And so I got up as one of 60 kids and said, I think a good idea is to sell water — because the water on campus sucked — so we’ll do a delivery water service to people’s rooms. Then the idea stuck and got to the next round.

You build your team the first semester as ideas get voted off the island and you draft fellow classmates into your business. At the end of the first semester you’ve got two teams of thirty and then the second semester is just running that business. And I was the CEO of one of those businesses. So I had to give weekly reports to a couple hundred people, so I got thrown straight into the the fire of public speaking.

I went from complete and total crippling fear to this is something I have to do everyday.


… on when he started to identify with empathy…

I would say I’ve always felt I’ve embodied empathy, but I didn’t use it as a word, or identify with it, until 6 years ago. I started this business when I was 23, I’m 37 now, and for the entirety of running this business we put out good work but we didn’t call it “applied empathy” and then about 5, 6 years ago we said “we need to declare a major” so we all sat down and said, “what were our best projects the past 3 or 4 years?” We pulled out the case studies and said, “what did we do right here?” “Why was that interesting?” “What did we love about that?”

And what we started to see is that our best work wasn’t when we sat in a room and shut the door and said, “wouldn’t it be cool if?” but when we opened the door, walked out of the door, and went out into the world and met with people and asked questions and experimented with things and really engaged with people to gain an understanding for the problem we were trying to solve.

And then we brought all of that information into the kitchen and cooked something with it.

It was then that we discovered — oh, that’s empathy. But empathy onto itself can be passive. You can have a lot of empathy but do nothing with it. Just sit on it.

We wanted to figure out how you build a process for applying and understanding empathy. What might that process look and feel like? We wrote a 40 minute talk that I started giving and then I got asked by Princeton to write a curriculum and we did a 12 week curriculum and taught that curriculum three times at Princeton and that led to another thing, which led to another thing and all of a sudden we were like, oh, we’re the empathy people now and that’s kind of awesome.

… on applying an Eastern philosophy…

I’m a big proponent and practitioner of Chinese medicine and alternative medicine. There’s a difference between Eastern and Western medicine. In Western medicine, you’re going to come in and say my throat hurts and they’re going to give you something for your throat. In Eastern medicine you’re going to come in and say, my throat hurts and they’re going to figure out what aspect of your system is causing your throat to hurt. It might be the food in your stomach that’s bubbling up, it might be that you’re not verbalizing feelings that you’re having that you need to say. They’re not just going to leap to treat the issue. They’re going to try to find the root cause and I think that approach is in a large part of our work.

…. on who he admires for their empathy….

It depends on the context, I think there’s this misconception that empathy is being nice, right? And it’s not. Really at it’s core, empathy is just about understanding and truly connecting with the views of others and frankly, with your interior self to such a degree that you can know something more deeply than you once did.

So in a business context, if I say Elon Musk, people will say, he’s an asshole. Sure, he might be, I don’t know I’ve never met him but he’s also fucking empathic. If you look at the business he’s built, PayPal, Tesla, The Boring Company, all of these things are looking out into the world and understanding the context, the needs, the desires of people and what’s in their mind and then building smart, implementations of it.

All of these things he’s created have been predicted businesses because he’s understood the rising tide before it hits high tide.

I think the best empaths know how to deliver what people want.

How to / Lead with Empathy

… on his definition of a leader…

You can be a leader of one. Most leadership starts at an individualized, personal basis, if you are not aware of who you are and how you show up and conduct yourself in the world it’s impossible to lead anyone else. It’s impossible to trust the person who questions themselves all the time. Leadership starts inside. Leadership is also a very tacit acknowledgement of our own imperfections. No leader is flawless. Every leader is flawed, the best leaders just know where their flaws are and empower others to compliment those flaws with their strengths.

I’m a great generalist, not a terribly powerful specialist. I can see a lot of different things and I can help connect dots, but then specialists are actually needed to go do the thing, and I think that’s what makes a good CEO.

For example, I know enough finance to be just slightly dangerous when I look at a PNL. If you made me a CFO I would fail at the job everyday. But I have a great CFO, therefore I can continue to lead in the way I lead, because she leads the way she leads.

… on his approach to helping companies build their empathy…

We’re typically brought in from a fairly senior level. Someone at the organization says, we need to solve a problem. Depending on who they are, the problem is often very different. Sometimes we get brought in to build culture and capability. The company tells us, we want to be a more innovative place to work, we want to be more diverse and resilient place to work — or sometimes it’s more external, we want to engage this new audience we’ve never reached before and we need to figure out how to do that. We want to grow into southeast Asia. How do we do that?

So we get asked to bring in an idea to help solve a problem and then use empathy to make it rich and executable.

Particularly in the large organizations, there are a lot of bottom up moments we seek out, even if it’s contrary to their existing culture.

For example, there’s a bank that we worked with that has 450,000 employees around the world. And they have a mission, like every company, and that mission was from an unaided perspective. And if you walked up to anyone of those 450,000 employees and asked what’s the company’s mission without giving them a prompt, only 1.5% could give you the right mission. Which is terrifying.

If only 1.5% of your entire workforce at their core, know why they come to work for you everyday, that’s horrific. So how do we, from the bottom up, pinpoint where are the wheels are falling off the bus. Where’s the disconnect. Does it fall apart in the middle, or higher than that? Or lower that that?

Sometimes I think about it like exploratory surgery.

Nobody wants to have exploratory surgery, but that’s kind of what you have to do sometimes to find the root cause.

…on working with Obama’s White House…

It was really nice being on the right side of history.


You can order a copy of Michael’s book and learn more about Applied Empathy, here!


Add yours
  • He is my dream person! Where can I meet someone like him??!!

  • JustAGirl June, 1 2018, 7:36 / Reply

    He is dead right. Too many people confuse niceness and charisma with empathy and they are very different. I really enjoyed reading his profile.

  • empathy – maybe. compassion?

  • Nancy V. June, 2 2018, 3:43

    I thought that exactly! It is the same meaning ,only empathy is a word of greek origin which means compassion

  • Paula Martin June, 2 2018, 11:10 / Reply

    If this is the definition of empathy, then 45 is an “empath”.

  • Yuna Trong June, 2 2018, 4:28 / Reply

    There’s something about this viewpoint that doesn’t sit right with me. I feel that he, like many westerners I’ve come across are fetishizing our methods. The term “Eastern medicine” has become some a catch all for anything that’s non-western, that the nuances needed to define certain practices get jumbled in practices that really reflect new age spiritualism that has nothing to do with traditional chinese or asian medicine.

    His description feels no different from the way westerners misuse Buddhism to satiate their moral/spiritual relativism, or with the way westerners have diluted nuances of vedic astrology to make people believe that astrology is only about sun signs, vapid retrogrades and daily horoscopes.

    Eastern medicine definitely has great benefits (acupuncture and tai chi being great examples), and you could certainly take herbal ingredients to help soothe a sore throat, but please don’t place ” it might be that you’re not verbalizing feelings that you’re having that you need to say” in the same space or realm as eastern medicine.

    Having maintained residencies in both the east and west, even if I did go to remedy something like bronchitis, my herbalist would never tell me, “oh you have a sore throat, it’s because you’re not verbalizing something that needs to be said.” His speech would more or less be the same as how a western doctor will speak to you, the only difference being that the remedy is herbal.

    If anything, the greatest thing about eastern medicine that I don’t see westerner’s speaking about as much is the accessibility to facilities and the universal health coverage.

    Instead of exhausting your willpower and privilege to make sure everybody can afford and get healthcare, so many westerners are concerned with making their maladies seem “special” “alternative.”

  • What a great man and a great post . So many people speak hollow words on the subject of empathy . What I gained in this post is the idea that empathy is really about understanding at a new level . I have mastered sympathy and only slightly understand empathy . But both have a path , I will try and follow. Thanks
    Dress The Part

  • Sophie June, 3 2018, 3:55 / Reply

    Article vraiment passionnant,
    je suis étudiante en école de commerce en ce moment, et c’est marrant nous avons eu un “Leadership Seminar” la semaine dernière où on nous expliquait ce qu’était un bon Leader. et évidemment, l’empathie est une qualité qui revenait essentiellement. Et la différence entre un manager et un leader c’est aussi que le leader est capable d’avoir une véritable vision, d’avoir des objectifs sur le long-terme; alors que le simple manager va en quelque sorte effectuer les tâches pour y parvenir.
    Et je trouve que c’est clé de se connaitre parfaitement soi-même afin de pouvoir manager les autres.

  • esther June, 13 2018, 9:34 / Reply

    thanks so much for these empowering interviews.!!! I love this blog.

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