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    • You’ve worked with some iconic brands along your professional journey - General Electric, Google, Nike, Warby Parker, The United Nations, the Obama Administration. What are some key learnings you gathered along the way?

    • I think one of the things that comes up a lot with organizations of any size - GE, which is 100+ years old, or Warby Parker, who may be 10 years old - a lot of similar DNA strands in both. One of the things we find with respect, particularly, to our work, is someone inside who’s willing to act bravely in the best interests of the company. And that, I think, is an important characteristic of any organization that’s looking to effect change - either within their four walls or the larger ecosystem they operate in. And so I think there are organizations that will do the pro forma work of “hey, we need to bring in an agency partner, to work on this thing” and then it goes into a file server and never is seen again, but they ticked a box and did a thing. And there are plenty of organizations who do that sort of work every day, and there’s no shame in that game, but for us, one of the things we’re really conscious of is that we’re working with a client team who’s willing to not necessarily take big bets every time, but sometimes the brave thing to do is the simple thing, or the incremental choice, not the big bets. So when I say “brave” it doesn’t mean “foolhardy” or “acting in an overly aggressive way” but someone who’s willing to really be thoughtful, mindful about what choices they make, and that those choices are in the best interest of the growth of the business. 

    • Sub Rosa was founded by you in 2009 and one of its mottos is “Meaningful Work starts with Applied Empathy” - with the context of “Applied Empathy is a design methodology, pioneered by Sub Rosa, that empowers leaders and their businesses to explore, learn, and grow through deeper understanding.” To help do that, you developed the Questions & Empathy deck to enable empathic thinking. Can you share more information about what went into building the Q&E deck and process?

    • We were looking to use a colloquial term an “empathy gateway drug.” Because there are a lot of people who talk about the idea of empathy, but don’t know where to start. So we wanted to find a way to make an experience for people that lets them “try on” empathy in a safe-ish context. So we developed these cards to ask provocative questions that aren’t designed for short answers. Because what happens with most people is you get asked a question, and even if it’s a non-binary question, something that requires a 1-2 sentence answer, often we have that as a canned answer. If I asked you “tell me about a time you’ve failed,” you’ve probably been in enough bad interviews to have a stock answer! But what this deck encourages is that each answer should be no less than four minutes long. So you might have that quick 2-3 sentence answer, and then the conversation goes quiet, so it’s incumbent on the question-answer to go deeper, learn WHY. And all of a sudden the conversation isn’t about the question anymore, it’s about the two people. The question is the threshold you walk through to get to a deeper conversation. If I walked up to you at a coffee shop and asked “When have you made a brave choice in your career,” you’re going to close your laptop and walk away from me! But if the CARD asks that question, it’s a permission granting tool. The question isn’t coming from me, and you know you can ask an equally-provocative question to me too, so the cards become a facilitation tool for deeper, more meaningful conversations. 

    • I love this reasoning behind why empathy is a valuable skill, and not something that is intangible or has no direct value correlation: “the words business and empathy are rarely used together—in fact, for some of us they might even sound oxymoronic, but there are incredible benefits to taking on others’ perspectives in the context of our professional lives. That’s what Applied Empathy is about. Empathy is not some out-of-reach mystical power. Instead it is a skill that each of us can make a part of our daily practice and ultimately bring into the organizations we serve.” What have been some of the most surprising organizations that have contacted you about learning more empathic techniques?

    • Well, one of them for sure would be the US Military Academy at Westpoint! The conversation we had with them was really enlightening. The superintendent of the school, who’s a 3-star general, I asked him “why am I here? What makes empathy so important to you that you’d bring an outside civilian consultant to teach it to cadets?” And he said “You know, there are 2 immediate things that come to mind. The first is we are a military governed by civilians. If we don’t know how to take perspective of congress, or the commander in chief, or the general population, if we can’t understand why we are being deployed, what political situation is taking place, then we’re blindly going. So perspective-taking is critical for us, because we need to know why and understand the context. It’s not enough to just be told, we have to understand at a deeper level.” The other thing he said was in his entire career, the number one skill that any great leader has exhibited with him was the ability to be empathic - to connect with someone else, to use that information and perspective to gain richer and deeper understanding and connection. He said “I’m acutely aware that many of our cadets will not be career military people. They may do a couple tours, then go into the private sector. So I want to make sure when someone scans a CV, and they see they are getting a graduate of Westpoint, they know they are getting an empathic leader.” So I was pretty surprised when he called, because my perspective of the value that empathy might offer to a military academy was flipped on its head. 

    • Why do you think people oftentimes go straight to “niceness” or “kindness” as an association with empathy?

    • I’m so glad you asked this, because it’s the thing that comes up so often in our conversations when we meet someone new and talk about empathy. THere’s often someone in the room who I refer to as the “tooth sucker,” the person who leans back in their chair, sucks on their teeth, and is the skeptic in the room. Oftentimes people equate empathy to being nice. And being nice, or kind, is not empathy itself: empathy unto itself is something entirely different. It’s important to note that there are 3 primary types of empathy: there’s affective empathy, what I sometimes call “Golden Rule empathy.” It is “I was sad before, you are sad now, I would have wanted to be treated like this, so I will treat you that way.” While it’s a critical and beautiful human behavior we have, it’s hard to train, you have to have a degree of EQ, challenging to measure, and doesn’t always have a direct line to helping an organization work through a problem or evolve. Another form is somatic empathy: that’s when a spouse has sympathy pains when their partner is pregnant. When you physically feel something someone else is going through. That’s not what we are doing. The third type is where our work begins, and that is cognitive empathy. This is about projecting yourself into the mind of somebody else. How we define applied empathy is as “self-aware perspective taking to gain richer and deeper understanding.” And what we do with that - empathy onto itself is neutral, but it’s in the applied where the rubber meets the road. So it’s our tools and methodologies that lets you take that understanding and put it into meaningful action with your colleagues, customers and partners. 

    • You state that “Cultivating an empathic practice isn't always natural or easy, but the first step is beginning to recognize specific empathic strengths and deficits in yourself.” And to help people do that, you outlined the seven empathic archetypes:  


      * Sage: Be present -- inhabit the here and now.

      * Inquirer: Question -- interrogate assumed truths.

      * Convener: Host -- creatively anticipate the needs of others.

      * Confidant: Listen -- summon the patience to observe and absorb information.

      * Cultivator: Commit -- purposefully nurture and actively develop.

      * Seeker: Dare -- be confident and unafraid to take risks or pivot.

      * Alchemist: Experiment -- constantly test and try.



      And “as a starting point to figuring out which archetype you default to, ask yourself: Which of these archetypes am I more naturally inclined to? Which ones feel less natural?” Which archetype(s) do you find yourself naturally leaning towards? Do you see that certain archetypes are attracted to specific types of roles or businesses? How can we better expand our perspectives to understand other archetypes?

    • So unlike a Myers-briggs test or a strength finder test, what we’re desirous with this archetype test is for people to gain comfort with all seven so people can switch from one to another depending on the circumstances you find yourself in. So for instance, I am naturally inclined toward a couple - the Seeker. You find that in a lot of entrepreneurs, because you’re wiling to go out on a limb, to be daring. Another one I find for me personally is the Convener - the person who cares about placemaking, creating an environment where people are comfortable, relaxed and willing to be fully themselves. There are others of course, but those 2 are pre-existing strengths. There are instances where those have value. Another archetype I don’t have as naturally abundant is the Alchemist: they are great experimenters, they thrive in the failure of something, they like to prototype, test, and learn, and that’s how they gain richer, deeper understanding. One of our clients is a large technology company that operates from the perspective of the Alchemist: they told us “don’t come with a deck or a prototype. Every meeting should be a workshop.” We had to un-train our behavior as a consultancy and design studio to shift into that of a real alchemist mindset in order to build a good relationships with them: we would have lost the business and them in the room. So the ability to shift our perspective into that of Alchemist and then say to ourselves “OK, if we were Alchemists, what would we want to do in the next 90 minutes?” And then design the meeting and run from there. We found it was very successful, as we were able to meet them halfway. We all have the capacity to operate in all of these, but we all have strengths and weaknesses. We want everyone to be more comfortable with all of them, so that ultimately we can have more cohesion, collaboration, and effectiveness. 

    • The idea that you can grow your ability to exercise empathy is super-interesting. One reviewer I found online referred to you as the “Brene Brown of empathy”! Do you feel like it’s been a driving mission for you to enable people to explore these ideas and empower themselves with these skills?

    • First of all, that’s super-high praise, I hadn’t read that quote before. That makes me feel like I’ve done something right with this, because Brene is pretty spectacular, so that’s nice. I think that we all have a capacity to be empathic in this way, cognitively. The work that we’re doing is really designed to wake that up, and give people useful tools to make it part of their every-day life. So I do think in some ways we’re the pollinators, the stewards of this message, and we’ve been given the opportunity to carry it into some interesting corners of the world. What’s interesting is some organizations you might think we might not work with, or that place would be known for having a tough workplace environment. And our belief is as long as we’re being asked to do work that’s meaningful and productive, we’re open to going to do work with places that people may cringe at. My belief is that if you help a bad actor work 15% better, you’re made a difference. I’d love to work with Patagonia, but they are highly empathic to their environment, employees, the issues that are being thrust upon us in the political climate we live in, and they’re doing it right. So would we like to work with them? Of course. But there are other organizations that are seeking our help, and we have a responsibility, provided they are asking to truly change and showing up for their customers or consumers, to do that. If we can help a bad place behave better, we can tip the balance of power in this world towards the good. 

    • You say that “Good bosses know that empathy is one of the best tools to have.” Do you think it’s a chicken / egg equation? That one starts out as a good leader who when empathy is added, becomes even MORE dynamic and extraordinary, or can someone start out as a less-emotionally resonant leader and by adding empathy increase their effectiveness?

    • Yes, definitely both. Without a doubt. Someone who’s already pretty high on the emotionally intelligence scale and brings more empathy will be able to use it more regularly and with more effectiveness, which is a plus. And for someone who this is new for, trying to figure out how this fits into their organization, there are a couple of ways we’ve found going into these conversations you can excite them about the potential for success. Some leaders want to be excited about how this will impact their hard business numbers - and we’ve found it does. When workplace cultures are built on empathy, workplace effectiveness improves. When you listen to your customers or B2B partners, and then build solutions on those needs, you’re more effective. If you have a diversity or inclusion issue that’s been been persistent, and you listen, and the workplace becomes a more safe and comfortable place to be, all of those are direct ties to practicing empathy. So whether it’s an uptick in profitability or psychological safety, this can be a tool to help get there. 

    • As it becomes increasingly easy to silo oneself off into custom-curated groups both on and off-line, do you feel that we should look at applying empathy beyond our business or organizations to larger settings?

    • Absolutely. The common misnomer is that too often, we see employees as employees, not as people. And I might be sitting inside an office right now, but I’m many things over the course of a day. I’m a commuter. I’m a coffee shop patron. I’m a CEO. I’m a husband. I’m a dog dad. I’m all of these things. So if we’re focusing only on the time we spend sitting at a desk, or in a conference room, we’re selling these folks way short. What we need to do is that this has an effect in people’s entire lives. I had a funny circumstance where I was with someone I was working on a one-to-one basis, they are a very senior leader, and I was connected to them by another very senior leader in the organization, and he said “You know, so-and-so resigned the other day.” And I said “Oh that’s interesting, good for them.” And he raised an eyebrow. And I said “Well, because they realized who they want to be!” And he said “Well, does that mean if we continue to work together, I’ll change my career too?” And I said “You might, but that’s not the point of this. The point of this is to get you connected to the real you, and the real intuition and insight that you need to know, and then the right answers are going to emerge.”

      And a few hours later, I got a note from that person that had announced their departure. They said “This has helped me clarify what I’m looking for, and where I want to be, and I decided to make a change, so thanks.”

      You never know how this will have a butterfly effect in all the nooks and crannies of someone’s life. But it’s a valuable tool to be able to take perspective, to see yourself with fresh eyes, and in doing so, hopefully a new you emerges. 

    • You created a podcast to accompany Sub Rosa’s events with some super-interesting guests. What’s the reaction you’ve gotten from listeners?

    • I think a lot of people really like the balance of intimacy that comes from listening to a podcast - it’s happening in your ear, and you get a truth that sounds different when you’re listening to a podcast, so I think we get a lot of good feedback because exploring empathy is meaningful. Historically we record it live, although we’re working on a second show now that’s more formatted in a booth, interview-style, but the live audience makes it interesting. The environment plays a role in the conversation, so when someone says something and you can hear the audience laugh, or a pin drop, it’s an important layer to empathize with the story in some way. And we’ve been fortunate to get an interesting cross-section of thought leaders who share vulnerably how empathy has or hasn’t shown up in the work they do. 

    • When we had President Obama - and boy, do we miss him - he said “we are suffering from an empathy deficit in America.” I think he was accurate. Unfortunately, also, foreshadowing a lot of what has happened since he’s left office, where we’ve become more divided, less willing to see the other side, and we have become labeled, and compartmentalized, and opaquely walled-off to the voices that don’t sound like our own. And that is not a world I want to live in. And a lot of the work that we’re doing is desirous of trying to wipe clean, or at the very least, be a bellwether for a different way of showing up in the world that can hopefully bring us back into a more united United States. 

    • Fun. Hands down, the most fun. It was a challenging project in many ways, because we were starting at the ground level with a man who’s seen the highest highs and the lowest lows in a career. It was important that we didn’t avoid the things that were uncomfortable to talk about. And considered all of the different scenarios for how his career might play out. At the time we were working together, it was unclear if he’d ever return to the game of golf due to his injuries and all of the pressures that had been put around him as a result of his back injuries and the scandal in 2009. And to watch a man who knows how to work a plan work this plan we put together, and to come back, fumble in coming back (it wasn’t a meteoric return - he came back, hurt his back, had a surgery, came back - it wasn’t easy), he persevered. He had a playbook. He knew what he needed to do. And to see him with the Masters a few weeks ago was so amazing, to see two years of thinking, and practice, and dedication on behalf of him and our teams come to life. 

    • I would say - that’s a good question. The unexpected insights that we glean from someone you’d imagine is going to have a certain perspective on the work they do, and then they surprise you with something completely insightful and unexpected that has helped them do their job more effectively. A quick example: Rob Gore is an emergency room doctor in Brooklyn. And we had him come on the panel to talk about what it’s like having empathy being an ER doctor, dealing with trauma of that degree every day. And the conversation took an amazing turn where he started talking about an insight he picked up, which is that so many young men of color were coming into the ER with brutal either gunshot or knife wounds, because of the early experiences they were having entering gang life. And what he realized is that particularly in low income communities, these kids need to be treated like at-risk youth with more mental health services, because they don’t have role models at home or around them that are necessarily showing them another way to be a man. So he actually created a nonprofit that is designed to provide a mentorship role to these kids, so he doesn’t see as many of them on his operating. And that was all born out of empathy.

    • Nobody likes to hear me say this, but I actually really enjoyed it! It was due in part of the fact that I had a pretty rigorous process that we put in place, which is that I would write every Friday. No meetings, no other things I let encroach on my schedule. And if Friday went well, then I’d carry on into the weekend, and spend 3 days writing. If Friday was terrible, I didn’t put any pressure on myself to make Saturday a makeup day, I just said “See you next Friday.” So there were weeks I didn’t write because Friday wasn’t a good day. I could have sat down some Saturdays, but I thought if I’m on a roll, I’m on a roll, and I won’t force it. And that process got the book done in 4.5-5 months. 

    • The only reason those brands are still in business is because they are good at listening to the marketplace, and evolving with its needs. So with an organization like Nike, our role as a strategy partner is really to help ensure that as many fingers on pulse that can be out in the world are there, providing insight and research and direction, to continue to let an organization that’s really good at moving with trend to continue to move with the trends as they change. So just because they are good at it doesn’t mean they can slack off. I think it means if you’re good at it, you have to keep working on it, in order to be better, because the market is always changing, and if you’re not changing with it, you’re losing ground. 

    • I already did! It's up on Audible. I did read the book, and it's out there somewhere.