#90 Spotlight: Velocity Coaching – Helping Hyper-Growth Founders Scale with Edward Sullivan

Edward Sullivan is CEO and Managing Partner of Velocity Coaching, an executive coaching firm that helps founders scale their businesses. In this episode, Edward and Daniel discuss the journey of leadership coaching and how to lead with heart.
Last updated
August 13, 2023
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Edward Sullivan has coached and advised start-up founders, Fortune 500 executives, and political leaders for over 20 years.
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#90 Spotlight: Velocity Coaching – Helping Hyper-Growth Founders Scale with Edward Sullivan

“The reason compassion is so important is that we are all human beings—we are all emotional, alive human beings who need psychological safety. We need to feel belonging, we need to feel trust, we need to feel trusted. We need to believe that people think we're competent.” – Edward Sullivan

Velocity Coaching works with hyper-growth companies, helping founders who have found product-market fit scale their businesses 10-100x. Their clients include DoorDash, MasterClass, Airtable, Google, and Apple, and they’ve worked with some of the biggest names in tech, including Tony Hseih of Zappos. Edward Sullivan has coached and advised start-up founders, Fortune 500 executives, and political leaders for over 20 years. At Velocity Coaching, Edward Sullivan serves as the CEO and Managing Partner for a team of over 25 coaches located around the world.

Topics discussed with Edward Sullivan

  • 00:02:37 – Background on Velocity Coaching
  • 00:06:17 – Velocity’s philosophy when working with clients
  • 00:19:04 – The current state of executive coaching, and how leadership coaching differs from life coaching
  • 00:25:02 – The coaching journey
  • 00:27:43 – Focusing on compassion
  • 00:30:59 – Constructive vs. deconstructive conflict
  • 00:39:12 – Common themes in coaching
  • 00:45:29 – Work self and home self are one
  • 00:51:31 – Leading with heart

Edward Sullivan Resources

Books Written by Edward Sullivan

Learn More About This Topic

Spotlight: Chris Sparks of The Forcing Function

Check out our interview with productivity coach Chris Sparks for another perspective on executive coaching.

Want to get great at something? Get a coach

This talk from Atul Gawande hammers home how important it is to get help from a coach when trying to improve ourselves and our work.

The Courage to Be Disliked: The Japanese Phenomenon That Shows You How to Change Your Life and Achieve Real Happiness by Ichiro Kishimi
Edward recommends this book for anyone ready to move forward and get past the need to impress others.

Alan Watts Org
One of Edward’s favorite writers, Alan Watts was a writer and speaker whose works have been aggregated at this site. 

Velocity Blog

Check out Velocity’s own blog for articles on everything from self-care to running successful board meetings.


Daniel Scrivner (00:06):

Hello, and welcome to another episode of Outlier Academy Spotlight series, where every week we sit down with a founder or investor that's working at the edge of what's next. I'm Daniel Scrivner, and on the show today, I sit down with Edward Sullivan, who is the CEO and managing partner of Velocity Coaching. Velocity has a team of over 25 coaches located around the world and they work with the world's best hyper growth founders to help them scale their companies and their leadership skills. Velocity has worked with most of the biggest names in tech, including DoorDash, MasterClass, Airtable, Google and Apple.

Daniel Scrivner (00:38):

Over the years, we've profiled many of the world's best coaches on Outlier Academy, including Jessica Hansen at NPR, and Chris Sparks at the Forcing Function. And one truth we've observed is that the world's best founders and teams are heavily coached, just like the world's best athletes. As Edward says in this interview, the best founders are going for gold, they all recognize that if they want to get there, they need great coaches to help them.

Daniel Scrivner (01:01):

This episode is our definitive guide to transitioning from the search for product market fit to hyper growth. Velocity Coaching specializes in helping founders 10 to 100X the size of their business, and in this episode, we dive into a lot of their tactics. We cover the state of coaching and the different models in the market today. The difference between good and great coaches and why the best address the root of problems, rather than just coaching the symptoms. We talk about some of the most common challenges that founders and companies face during the hyper growth phase.

Daniel Scrivner (01:31):

And finally, we go down a bunch of rabbit holes to explore how Velocity works with founders on everything from blind spots and delegation to micromanaging and engaging in constructive conflict. You can find the notes and transcript for this episode at Outlieracademy.com/90, and you can learn more about Velocity Coaching at Velocitycoaching.com. With that, please enjoy my conversation with Edward Sullivan of Velocity Coaching. Edward, thank you so much for joining me on Outlier Academy, I'm super thrilled to have you on. So thanks for the time.

Edward Sullivan (02:03):

So happy to be here. Thanks for the invitation.

Daniel Scrivner (02:05):

We're going to spend today talking about coaching, which is something that I'm really excited about. We've had a couple of people on the show, but you have a very different take and focus at Velocity Coaching, and you guys are specifically focused on hyper growth companies. You have an incredible list of companies you work with, some of them, DoorDash, MasterClass, Airtable, as well as top executives at companies that are a little bit later stage like Apple and Google. So, just to start, can you give everyone a quick background of Velocity Coaching, how long it's been around and how you got there?

Edward Sullivan (02:37):

Sure. Yeah. Velocity has been around for about seven years, and I've been with Velocity for six. So my business partner, John and his former partner started the company seven years ago to bring top flight executive coaching, that at one point was really reserved for like the Fortune 100, Fortune 500 companies back to startups. John, I consider him a national treasurer, he's one of the greatest humans I've ever met. He's 78 years old. He's been in the coaching business for close to 40 years, and he was coaching in the C-suite of places like Apple and Nike and eBay and others.

Edward Sullivan (03:15):

I think he got to the point in his career and he said, "I'm going to work with founders here, and I want to work with startups. And at that time I was living in New York, working on my own as a startup coach, founder coach, and John and his business partner called me, and they said, "Why are we doing the same thing on different coasts, let's join forces." And since that time we've grown Velocity into what it is today, and we're very lucky to be able to count all the clients you mentioned among our friends and clients, and it's really a word of mouth business. We do very little marketing. I think this is the third podcast I've ever been on. So, I appreciate the invitation, and do what you can in editing to make me sound smart. Will you?

Daniel Scrivner (03:58):

I think we'll be okay. I think we'll be okay on this one. Before doing startup coaching, did you have a period where you did larger company coaching as well too? And can you maybe talk a little bit about the difference?

Edward Sullivan (04:10):

My intro into coaching actually began in politics. So in my late twenties, early thirties, I got picked up by a political consulting firm in Washington, D.C., and was traveling around the world advising candidates, like local candidates, the man who wanted to be president of places like Honduras or Bolivia or the Ukraine. I did a lot of work in Ukraine. So now is a pretty interesting time to see what's going on there. I was hired as a pollster, like an ad guy, I'd write speeches and make television ads, but really most of my clients just wanted to talk. They just wanted to talk about leadership, they wanted to talk about the challenges of getting people motivated and focused and crafting a message, creating and communicating a vision.

Edward Sullivan (04:57):

I guess I got pretty good at that, fast forward a couple of years I was living in Silicon Valley, working in a number of startups, very senior positions. Wherever I worked, I always ended up being the CEO whisperer. I was like the person who was the confidant, the consigliere of the CEO. So when I was doing a mid-career business degree, my classmates heard these stories. I would share about politics or about working with CEOX or CEOY, and they just started asking me to coach them, and it happened very organically. I didn't want it at first. I was like the reluctant coach, and then it just started snowballing from there.

Daniel Scrivner (05:38):

Super interesting. What was it that pulled you into that work in the first place? Like, even hearing you describe your work with politicians, it does sound very similar in many regards to coaching a professional. What do you think that draw was innately? What excites you about it?

Edward Sullivan (05:53):

I think I've just always been fascinated by how people work, how we inspire each other, how we choose to motivate each other authentically, not through fear, but through vision and excitement, and ultimately love, right, and heart. And I also saw a lot of bad leadership out there, and I wanted to work with people to help them be more effective and authentic.

Daniel Scrivner (06:17):

So one of the questions that I wanted to ask was, and you're getting into some of it like the heart first approach, which is, I think going to be a theme that comes up again and again and again. But talk a little bit about some of the philosophical underpinnings or the things that you have very strong beliefs about at Velocity Coaching that might not be shared by other coaching firms. How do you guys show up in the world and what motivates you?

Edward Sullivan (06:39):

I would say philosophically first and foremost, we believe that the best answers always lie within the client. Right? So, we come in with a lot of experience and everyone has a background in business, and we certainly have opinions, but we're going to do our best to get the best solutions out of the client, him or herself. So we believe people are inherently resourceful and inherently wise.

Edward Sullivan (07:05):

We also believe that the business and the client need to succeed for it to be a successful coaching engagement. So we always hold the company and the client in almost equal parts. The client is the individual we're working with and we want to make sure that they are using themselves well and not overusing themselves, no martyrdom on our watch please, no burning out on our watch. But at the same time, they have to be working in service of the business. So sometimes when we're working with clients, it is of greatest integrity from our perspective, to help them make a transition out of the company. Right?

Edward Sullivan (07:41):

We've helped various founders and CEOs make transitions when they had reached the limit of either their interest or their ability. Ideally we help people grow with the company and grow through the different stages of development of the company. And it's really fun to work with the client for three, four years, take them from series A all the way through IPO and just watch how one human being can go from being a green or almost insecure founder to being this incredible CEO with gravitas. That transformation's incredible to watch.

Daniel Scrivner (08:17):

And one of the things that is so interesting is your focus on hyper growth, we talked about this a little bit before you came on the show, but loosely, that's this idea that there's this initial stage of your company, where you're just trying to honestly find a hole in the market. You're trying to figure out product market fit. Then once you have that, one typically the fundraisers start to get much bigger. The team starts to get much bigger, and you typically go from tens of people to hundreds and thousands of people.

Daniel Scrivner (08:43):

That moment in time, I imagine is really unique. So you're working with a founder that has already spent maybe years crafting this business and working really hard inside it, but now they're entering a phase where both themselves and the company are going to have to scale incredibly, like you just talked about. Talk us through when you arrive and you meet a founder for the first time that's entering this new phase, what do they know? What maybe don't they know yet? What does this moment in time feel like, and what does it feel like for you on the other end of the table talking with them and working with them on this?

Edward Sullivan (09:16):

Yeah. You kind of pointed at it. It's one thing to build a product, it's another thing to build a company. And most clients come to us when they have gotten to the point where metaphorically, as they say in Silicon Valley, the dog is eating the dog food. Like they've reached product market fit, they've figured out what the recipe is and Sequoia or another large venture firm will come in and say, "Great, here's 25, 50 million dollars to build out a company around this idea, right, that you've proven out."

Edward Sullivan (09:46):

At that point they often say, "Well, wait a minute. I know how to build a product. I don't necessarily know how to build a company. I don't know how to think through culture, I don't know how to think through how to hire in professional management. Sometimes layering the people who've been with me for the last three years as we try to figure out this product." So, whereas the early stages of company building or product building are about interacting with the customer, trying to figure out what they want, trying to figure out how to build a product that you can sell reliably and replicably, building the company is suddenly a lot of difficult conversations, learning how to disappoint people well, learning how to inspire people well. Right?

Edward Sullivan (10:27):

Learning how to think through the complexities of a very vast and large decision making organization. How can we in the C-suite push more decisions down into the company as quickly as possible? We find that series A founder still wants to hold onto the baby, wants to hold onto every decision, keep it really close, and that becomes the bottleneck. So often that C-suite starting with the founder needs to learn to let go.

Daniel Scrivner (10:56):

One of the things we talked about before, and quote, you said that I had never heard it said that way, but it was just brilliant. It's just this notion that, as humans, it's very unnatural to be in a position where you're responsible for say 2000 plus people. Because number one, yes, in many ways you're dealing with individuals, but more than that, you're dealing in the system. It's a very large interconnected complex human system.

Daniel Scrivner (11:21):

Why is that so difficult? And talk a little bit about some of the push and pull that goes on inside people's heads when they're trying to move from feeling like they know everyone in the company to now they need to operate this giant machine. And a lot of it happens without them knowing or seeing anything.

Edward Sullivan (11:36):

Yeah. Yeah, you're right. I do say that leadership of large systems is an unnatural act. Right? And I say that because, well, first and foremost, we were not evolved, our brains are not evolved to manage 2000 relationships. Dunbar's number is 150, the traditional tribe size when we were still hunters and gatherers was up to 150. And after that, the tribe would split into two. Right? And now we are managing hundreds of relationships personally. I live in New York City, I have hundreds of friends in New York City. I don't know how it happened, but if you look in my phone, I may have like 300 active conversations over text at any one time and hundreds of conversations over email with business. And it's very unnatural.

Edward Sullivan (12:20):

Take that to the level of a company, a CEO who has 2,000, 5,000 employees, it can feel completely overwhelming. So they have to think at a much different level. They have to think about systems, they have to think about culture, they have to think about norms. And one of the smartest things a CEO or founder can do in a company that is growing past that number is very public displays of the behaviors that get rewarded here. That's how you set the norms for culture. You can put it on the wall. You can say, we have got these values, here are 10 principles, et cetera. But by showing people, by holding up individuals and holding up stories, that this is what good looks like here, that is how you scale culture and scale leadership way past 150.

Daniel Scrivner (13:10):

Yeah. Which is really interesting. Phrase that back, see if I'm saying it accurately. You're basically starting to teach via stories and developing this shared language internally of one, how do we talk about work? How do we talk about our values? How does that show up in projects that get rewarded? It's really interesting because it's ... Yeah. And to your point then, I guess one, that's much more high fidelity than a single page notion doc that says here's our values and go and read them, and here's our mission, which is, I think a lot of people think that that's the solve. Why is that not the solve and why are stories so powerful? Why do you think that those scale to a different degree?

Edward Sullivan (13:46):

We are naturally as a species, we're storytellers, we connect to emotion and it's very easy to want to hide behind a listicle, to hide behind a notion document as you said. It's a dry fix. People want emotional connection, they want to connect at a heart level. You mentioned this at the top of the session, we'll be mentioning heart a lot in this call. My business partner and I just finished a book called Leading with Heart as you know, and the premise of the book and the premise of our work is that we need to connect at a human level to be able to connect at a more intellectual level and build great companies and build great products.

Edward Sullivan (14:24):

And I think the mistake we often make is thinking that we can just keep it transactional. We can make it all about work. We can make it all about the rules. Did you read the memo? Did you get my document? And people leaving in droves right now during the Great Resignation, because they don't feel seen. They don't feel understood. They don't feel any real connection. People say it's about money, they say they want to go on vacation, but it's really, they don't feel like they belong to anything anymore.

Edward Sullivan (14:52):

And I think part of that has to do with the pandemic. Everyone's been working from their little home studios. I like my little apartment here in New York. But also leaders have started to abandon those stories. Right? They've abandoned the responsibility of being the holder of those narratives and the communicator of the stories and being vulnerable and getting out there and showing up authentically and sharing a story that's hard to share. That's what opens people up. That's what gets people feeling connected to bring it back to your question, it's all about the story, it's all about the emotional connection at the end of the day.

Daniel Scrivner (15:28):

Yeah. I love the way you walked through that because you made the point, which I've often found incredibly true that, with the people we work with, we're connected in two ways. And one is obviously mentally where I can make an argument to you or I can say, "Hey, can I need this? Or I need this tomorrow." But the point being that if there's not something real and rich and heartfelt that's underlying that, then number one I think we can misinterpret one another, we can come across being overly transactional. Yeah, I think I would say that there's a pandemic of work being more and more transactional over time, not having enough time spent in person.

Daniel Scrivner (16:06):

I was having this conversation recently with someone who's planning an offsite for their company, and in my perspective, and it's almost heretical, the point of an offsite is yes, you should ideally go and you should definitely do some business stuff together, because why not? You're doing that normally day to day in a distributed way, you're going to be together, sure. But the real point is just to build that trust and to build that rapport with one another and to know who each other is and build that almost safety net underneath that.

Daniel Scrivner (16:31):

But I think for a lot of people they're like, "Well, no, let's just go and work and let's have working blocks." It's almost like they're trying to squeeze the productivity juice out of an offsite as opposed to just saying no, go and spend time together, develop relationships. Any thoughts on that or a commentary on that?

Edward Sullivan (16:47):

A 100%, violently agree with that, because we run a lot of offsites for companies, and yes, the CEO often come to us and say, "Okay, great." So for 80, 90% of the time we spend together, we need to do strategic planning and roles and ... Right? And we'll back them up and say, "Actually, I think we need to flip that. Let's spend 60, 70% of the time having fun, helping you all get to know each other, helping you build trust, telling stories about where you come from, helping understand what your quirks are."

Edward Sullivan (17:16):

Sometimes if we'll do like a CEO or a C-suite weekend at dinner, I'll bring like a very old bottle of wine, very old as like the nineties. If it's too old, it's meaningless because it'll be older than people at the table. But it's like, "What were you doing in 1998?" Some people at table will say, "I was in kindergarten." Others will say, "I was in college." More senior person on the team will say, "I was at my first job at X, Y, Z."

Edward Sullivan (17:40):

Just help giving people some convention, some anchor to hang a story on is a really easy way to start making those emotional connections. It's convenient in a way for us to think that work is just about work and our lives are something separate. I think that's one of the great myths of our time. I think gladly, it's a myth that we're starting to work our way out of. Over the last two years, we've had an eye into everyone's home. Some people working from the bedroom rooms. Early in pandemic I did calls from a bathroom in a group house I was staying in Tahoe.

Edward Sullivan (18:14):

We've laid down our armor a little bit during this time, and I think that now is the moment to take advantage of that and actually build real relationships around that moment where we've speared into each other's lives, this work life balance, this work life myth, we talk about, we wrote about that in the book. I don't think it's really helpful. It's not helping any of us. People feel like they need to suit up. We used to suit up physically, we literally wore suits and now we suit up emotionally.

Edward Sullivan (18:44):

My hope for all of us is that we can show up more and more as ourselves at work because that's where the juice is, that's where the great ideas come from, that's what gets our prefrontal cortex firing. That's what bathes us in great hormones like oxytocin and serotonin to help us feel creative and help us feel connected.

Daniel Scrivner (19:04):

There's a ton that we're going to dive into in a second. I want to go much deeper into tactics, how you guys typically work with clients. But I want to pause for a second and just talk about state of coaching, because on the one hand, at least from my perspective, I feel like coaching now, absolutely the vast majority of CEOs, I know founders have a coach, they likely have multiple coaches. It's just something that's talked about much more. And so it would suggest that maybe it's becoming more popular, becoming more accepted. What is your vantage point, what's your take? Where are we in the state of coaching and the good, the bad and the ugly?

Edward Sullivan (19:36):

Yeah. Well, I think the good news is, coaching has become normalized as a positive and proactive thing to engage in. I think 20, 30 years ago, coaching was something that like, "Oh, he had to get a coach." It's like, "It was part of a performance improvement plans." The last thing you did before you fired someone is you invested in a coach so you could show and document. "We did everything we could, but Jim had to go. We even got him a coach." Right? It was all remedial. It was like, "There's a huge problem we need to fix."

Edward Sullivan (20:04):

Now most coaching and exclusively the coaching we do is proactive coaching, leadership, coaching. We're building something that we don't exactly know what the future holds, but we know we don't know everything and we want support. Right? An Olympian would never go to the Olympic games or an athlete would never go to the Olympic games without a coach. You want to win the gold medal? You get a coach. It's just table stakes. Well, I think we've entered into that phase in Silicon Valley and in most companies that coaching is something that is reserved for the high performers. It is what the people who really want to win the gold medal go and get.

Edward Sullivan (20:44):

Our coaching is specifically around leadership. We work mostly with CEOs and in the C-suite, sometimes VPs and directors in larger companies that are working on really important projects. We don't do career coaching as much as I love helping my friends figure out what they want to do next in their life. We don't do that professionally. And we don't consider our work life coaching. A lot of life coaching can be like directional, it's aspirational, I'm so happy there are so many people doing that kind of work now and seeking that out. I know I need it at one point in my life as a younger man, but a lot of coaching now can also be stress management coaching. It's like coaching as an employee benefit.

Edward Sullivan (21:26):

So a lot of the coaching for everyone in the company, I think, it's tremendous that companies are able to offer that now. It's not always leadership coaching. It's often a rather inexpensive benefit that the employer will share so that the employee can manage completely unmanageable workload. Right? I think there's another conversation we need to be having. Right? We need to be having conversation with leadership about realistic expectations, about setting appropriate deadlines.

Edward Sullivan (21:57):

We hear a lot in some of these hyper growth companies of unnecessary urgency, everything's an emergency and delivered by Friday, but then it sits in someone's inbox for three weeks until the next person has time to take it down the work stream. Why was it due that Friday? Can we get better coordination and lower the temperature and lower the sense of urgency for everyone? So then we're not simply managing for stress, we're managing for success. So, it's a little bit of how I think about coaching right now.

Daniel Scrivner (22:29):

No, I think that's great. I mean, you covered the whole space. I want to talk now specifically about how you work with your clients, and I think part of why I want to ask that is I know there's people listening. I know a lot of people listening have worked with a coach, likely one coach. As you alluded to, there's all sorts of different types of coaches. I've worked with a productivity coach, I've worked with performance coaches. So maybe actually, before we go on, maybe I'll have you just define, when you talk about leadership coaching, what does that entail and what's in and what's out. So you talked obviously about, it's not a life coach, it's not a career coach. What isn't under that umbrella?

Edward Sullivan (23:02):

Yeah. Yeah. It's funny, as soon as I said, it's not life, it's not career, depending on the client, almost anything could be on the table. One of my clients, we spent half of last year talking about a relationship that he had because that relationship and him dedicating so much Headspace to his relationship was preventing him from dedicating more Headspace to the company. Right? So it was almost like, we had to triage, like let's get this off the table so we can get to the deeper work. Often with clients in the beginning of a relationship, we'll ask the basic questions around performance like, "How are you sleeping? How are you eating? What's your morning routine?" To establish a baseline.

Edward Sullivan (23:44):

We don't want to spend all of our coaching talking about that. I'm not going to be your accountability partner about how much sleep you got or whether or not you meditated in the morning. But we are going to establish a baseline of these are healthy habits that create and make you available for deeper work around leadership. And when we talk about leadership coaching, it really is developing the ability to be in touch with your own needs and in touch with those of others, having conversations about fears and what's blocking people, having difficult conversations about feedback, it's about identifying gifts in people that they're not even aware of themselves, and it's about connecting people to purpose.

Edward Sullivan (24:25):

And often we manage to the task and not to the relationship. It's really easy in a company to get super tactical and to be working off of to-do lists and say, "But did we get this done?" Let's ask the question. Why isn't it getting done? Why do we have to follow up so many times? Is there something going on in this individual, are their needs being met? Are they blocked by fear? Is there some toxic relationship in the system? Do they have an abusive superior? Are we having those levels of conversations to really create scale, to create flow in the company?

Daniel Scrivner (25:02):

Yeah, that makes sense. So I'm curious, you talked about, obviously you'll sit down with someone you're going to develop a baseline, and this can either be a made up example or you can just make it anonymous, take a client you've worked with and anonymize of it. But I'm curious, what does a traditional journey look like with you and a client, from the first meeting to then how often do you meet, and how does a relationship happen, flow or change over time?

Edward Sullivan (25:27):

Sure, sure. I have this conversation a dozen times a week now, because we've got so many potential clients coming to talk to us. So, the basic format is, in the first month of an engagement, we try to get to know the client as quickly as possible. And we want to get to know him or her through their eyes and experiences, and also through that of their colleagues, board members, people who are reporting to them. So it's probably no surprise we do a very deep 360 in the beginning of any engagement.

Edward Sullivan (25:55):

We want to figure out what are the blind spots, what are the unsung strengths? Maybe Daniel is really good public speaker, but he doesn't think he's a great public speaker. So he never gets in front of a microphone. I know that's not true about you, here you are in front of a microphone. But oftentimes, they don't give themselves enough credit. So, we use that opportunity to give them more credit. And we also want to talk about the larger business goals. What are we trying to accomplish at a big level? You just raise the series A, you're going to be raising series B, C, D.

Edward Sullivan (26:28):

We're experienced with taking a company through that pathway, done it dozens of times. Here's what you might expect. Here's what you're going to be hiring for this position. You're going to be thinking about this. You're going to be having these kinds of conversations around this time. Private equity is going to be coming in and trying to ... Like, we want to help them think through, not simply how do I get through today, but who do I need to be in a year or two years or three years at that next level? Who do I need to be in four years when we IPO? So we'll set near term and long term goals with our clients and figure out a pathway to get there.

Daniel Scrivner (27:08):

Yeah. So I want to talk now just about a couple of themes that I know show up. I know that's either from my own experience, just because it's thematic with a lot of people that I know that are high performers, and the first one is actually something, I don't think it's talked about enough, and it's the balance between being compassionate both with yourself and the people on your team, and this idea that compassion is actually a net negative, and actually what I need is, if I'm always saying, thank you, maybe I'm not pushing people enough, and I actually need to be more demanding, more pushing, more, I don't know, driving.

Daniel Scrivner (27:43):

I had this experience once where I had a coach call out that I was not compassionate with myself, and I needed to be much more compassionate. And honestly it was one of the most profound conversations and realizations I had ever had. How does that show up in your work? And do you have a similar conversation with high performers around why is compassion important? Here's how to bring it back or here's how to bring it back into the fold?

Edward Sullivan (28:04):

Yeah. I mean, going back to the conversation about things are getting very transactional now. I think one of the reasons is there's a lack of compassion and it's very easy when we don't see each other in the office to not experience each other as human beings anymore. I only see you an hour a week. We go through our tactics or we go through the to-do list. These are deliverables. This got done. Why didn't that get done? Okay, get it done next week. It's very easy to make it all about the work, and no longer about the relationship.

Edward Sullivan (28:36):

But the reason compassion is so important is that, we are all human beings, we are all emotional, alive human beings who need psychological safety, we need to feel belonging, we need to feel trust, we need to feel trusted. We need to believe that people think we're competent. And when we're working with someone who is only hard driving and only talking about the task, frankly, that's when people bounce. That's when people say, "I don't think I need this job anymore." So the leaders who try to be very, very hard, especially in this environment when we're still not back together, many of them they haven't earned the right to be hard.

Edward Sullivan (29:17):

I think about these famous basketball coaches, the collegiate basketball coaches who the players always say, "No one's ever driven me harder, but no one's ever cared as much." You have to invest for sometimes months or years in the relationship showing how much you care, showing how much you are interested in this individual being a success and you're interested in their career, and you're interested in them learning and developing, not just interested in them getting the job done.

Daniel Scrivner (29:50):

Yeah. It seems like another way to describe that is, this concept of focusing on first order outcomes or effects versus second and third order. And in that example you gave of, okay, I want to get more done. What should I focus on? Well, clearly I'm just going to focus on here's the things you need to get done, why aren't they done? [crosstalk 00:30:05]

Edward Sullivan (30:05):

[crosstalk 00:30:05]

Daniel Scrivner (30:05):

Yeah. But if instead you focus a little bit longer term on, I care maybe less about this person, their productivity over the next 30 days, I care a lot about it over three to six months, so what does that look like? How does that change my approach? You would do things very differently.

Edward Sullivan (30:21):

Right. Right. And if you're only driving to the task, you're training people to not be creative. You're training them to not think for themselves. They're like, "All right, well, there is a to-do list, I'm just going to knock off the to-do list. I'm being told what to do. I'll just do what I'm told." Right? As opposed to, "I'm going to think creatively, I'm going to think of a new way of doing this. I'm going to surprise someone." Right? People who only-

Daniel Scrivner (30:44):

Yeah. I'll surprise myself.

Edward Sullivan (30:45):

I'm going to surprise myself. Right? Exactly. Managers who only manage to the task are rarely surprised. And then they say, "I'm surrounded by these people, they're not problem solvers, they're not creative." Right? And it's a system that they've created.

Daniel Scrivner (30:59):

One of the other things I wanted to talk about is, because I know you've obviously brought this up many times before, but yeah, I know from my own experience that this is a huge area of learning and growth as you scale up, which is engaging in constructive conflict. And I know it's also not a simple topic. So maybe first, can you share your take on what constructive conflict is? How is that different than destructive conflict? And then why it's important that people lean into that?

Edward Sullivan (31:27):

Yeah. If you think of sometimes a two by two or the little X, Y graph, is a simple way to explain something. If you think of a bell curve, and across the bottom, you have tension or conflict, and on the Y axis, you have performance. That is how we map out conflict relative to performance. If you have too much conflict, you're fully polarized, toxic behavior. People are no longer thinking straight. They are in fight or flight. Right? They've activated their amygdala, they've prefrontal cortex shuts down and they're in defensive mode, posture, finger pointing. It's no longer fun, it's no longer productive.

Edward Sullivan (32:09):

At the other end of the spectrum, where there's no conflict, there's no stress in the system, people are bored. People aren't even showing up. They have what we call artificial harmony. Right? It's just, "I'm not even going to bother, I'm just going to show up to the meeting and call it in. I'm just clicking off my to-do list." In the middle where there's a little bit of heat in the room and the leader is able to get people engaged and say like, "Hey, well, what do you think? He said that, what do you think?" But the leader is creating an environment of safety that allows for rigorous debate. That rigorous debate builds trust. It allows people to take risks. Right?

Edward Sullivan (32:48):

When people come in with a bad idea, the leader says like, "That's not the direction we're going to go, but I appreciate the insight. I appreciate you taking the risk. Let's go with Sally over here." That is what creates the heat in the room. And it also demonstrates for people, this is the kind of behavior that we should be engaging in, even when the leader's not in the room. So that's how you create scale as well around constructive conflict. When the leader is modeling it, honoring a risk, saying to someone, "I'm glad you ran that experiment, I'm glad it failed, you failed fabulously. We lost a couple thousand dollars, but what did we learn?" Modeling that behavior is then replicated throughout the business.

Daniel Scrivner (33:31):

I love that. In that example again, you said obviously people in the room, building an atmosphere of safety where people feel like they can express themselves and they can express even polarizing opinions or strong opinions. It just seems like constantly leadership is about and and not or, so it's about embracing the positives and the negatives and doing it once as opposed to just leaning in one direction.

Edward Sullivan (33:52):

Absolutely. Absolutely. There are no polls. Right? There's no black and white in leadership.

Daniel Scrivner (33:57):

Yeah. It's a giant messy spectrum trying to pick the right shape [crosstalk 00:34:01]

Edward Sullivan (34:01):

[crosstalk 00:34:01] Four dimensional spectrum.

Daniel Scrivner (34:04):

At every point in time, which is difficult. You talked about modeling, which is really interesting because obviously as a leader, I'm sure a lot of coaching is, in a lot of ways, it's building up a model in the company. So you have somebody who is the leader doing behavior that they want replicated as opposed to behavior that they might see positively, but they wouldn't want done to them by another teammate. How much of working with clients is one opening their eyes to how other people see them? And I'm sure this goes back to that 360. And then how do you thoughtfully, carefully, methodically, I don't know, get people to recognize the things that they're doing that aren't perceived the way they would like them being perceived and correct some of those behaviors? What does that look like in practice?

Edward Sullivan (34:53):

First of all, I'll just say that most leaders are completely unaware of just how observed they are. People are watching every move of the leader, what their preferences are, how they speak, what their slang is. I don't know if you've ever worked in a company where everyone uses the same words. A lot of that came from the early team. This is just, again, old tribal behavior. We signal off of the alpha, right, as mammals.

Edward Sullivan (35:21):

When a leader comes to us, we do the 360, and they learn that there are all these negative behaviors they have and not constructive ways of giving feedback. They are very testy, they're angry, they're bitter, they're demanding. How are they then surprised when they've built a company where all of those behaviors are exactly, they see them everywhere. Right? Every other manager or leader is mimicking what they see from the CEO, from the founders.

Edward Sullivan (35:51):

So, it's really important for people to get clear how they want their company to behave is how they should be behaving. And what we often do is to help them establish that norm. Since they know they're going to be the role model for the company, we ask them to think of their role models. So we'll do an exercise with a CEO and say, "Who are the four leaders who you most admire and why? What are their attributes? So we might take like the speaking style of this one, the creative thinking of this one, the first order principles of this one, and we'll bring it all together. Right?

Edward Sullivan (36:28):

And we put this amalgamated idea of what leadership looks like for this individual, and we make sure it's authentic. Do you actually think that you can demonstrate this? You can live this way? And then we'll coach to that norm. Right? We'll coach that ideal. Where are you today, and where do we need to get to? To help you transform authentically, I want you to own it, I don't want you to feel like you're acting or faking it, but into the leader that you need to be for this company to be what it needs to be to succeed. Yeah.

Edward Sullivan (37:00):

And it's a really interesting exercise to go through, right, because you see people suddenly developing this gravitas or developing this ability to communicate, and it's like, "I never thought this was available to me. I thought it would feel like faking it to act this way or to speak this way. But I actually own it. I found it at a different part of me that I was telling myself a story, self limiting belief." What we call it in coaching, that I wasn't that person. It turns out I can be that person if I want to be.

Daniel Scrivner (37:29):

That seems super helpful in that it also gives people, one, it makes it objective. So, we know what you're working on then becomes like, "Well, yeah. I wanted to become that way, and it's less focused on what's right or wrong about them." Then it's more a shared division, a shared direction about where they want head, and being objective because of that, I'm guessing allows people to process feedback about themselves maybe a little bit more positively. One of the questions I want to ask on the 360 is how often do you find that you need to convince people that a 360 is a good thing to do, and what do you tell people who are maybe resistant or hesitant about that?

Edward Sullivan (38:06):

If somebody is resistant to a 360, I'll just ask them what they're afraid of. "What are you afraid of hearing? What do you think these people are going to say?" Right? I mean, the 360 is a very private document. Right? It is a 100% confidential. First of all, it's anonymous. We get feedback from everyone. We anonymize and aggregate it. We take out hard and identifying information. And then it's handed only to the client. Right? We don't give it to board members. Whoever's paying for it, we don't even give it to them. It's up to the client if they want to share it with other people.

Edward Sullivan (38:38):

So we try to set some safety with them around that, but the client who's really resistant, there's a deeper conversation to have there. Are they not self aware? Are they're not curious? Do they think they're perfect? Anyone who thinks they're perfect is actually hiding a very deep sense of insecurity, and we try to dig into that, and we try to do that with compassion, sometimes with ice cold bucket of water. Right? Sometimes people need to hear the thing that's really hard to hear. And as coaches, we're often paid to communicate that.

Daniel Scrivner (39:12):

So, what themes show up again and again and again? And I think what I'm asking there is, I'm sure at this point, when you sit down with a client, you can also anticipate some of the conversations you're going to be having, but also knowing that you guys now have a team of 25 plus, you've got a massive client roster, the number of data points has just grown. So what shows up repeatably and reliably across all the different companies and founders?

Edward Sullivan (39:36):

Yeah. I mean, you're right. I try to treat all of our clients as very unique individuals and I let them know that they will be given a very bespoke coaching experience at Velocity, and they can also have the confidence of knowing that we've probably seen it all before. Some of the things we see frequently, you're probably not surprised, are micromanagement of a founder staying too close to the product, right, too close to my baby. Right?

Edward Sullivan (40:04):

We see executive teams holding this OG, mafia status a little bit too tightly, and they spend all this money recruiting and hiring professionals, recruiting people in from Google and stealing people from Salesforce, and then they bring them in and don't give them any work. Right? They don't give them any power. It's a waste of money and it's a waste of great talent. So we work with executive teams as well to help them push more decisions down into the organization.

Edward Sullivan (40:31):

The executive team shouldn't be making a decision on the color of a package for a CPG company. They should be thinking much more higher level, making strategic decisions. I think sometimes there's a discomfort with founders, with the founding teams, in letting go of too much power. How can we trust these people? They just started two years ago. We've been here seven years. Right? They started two years ago. They've got a lot of experience. They're closer to the customer now. They're closer to the product. So, a lot of that work is around letting go, building trust. It's also around emotional regulation. Right?

Edward Sullivan (41:10):

Again, this is an unnatural act. It's really stressful. It's really hard to lead a company. There's so many moving parts. There's so much going on. We have to help our clients elevate emotionally so they can stay above the fray. It's not baseline stress management, it's very different in terms of helping them develop an emotional distance, an ego distance from themselves, and disambiguating themselves from the company, from the product itself. Because a lot of people experience terrible stress when something goes wrong with the company as if it is a problem with themselves. Right? We have to help them establish a deeper understanding there.

Daniel Scrivner (41:56):

How do you help people with that? Because I've had that experience before knowing that you're in charge, it's incredibly easy to take it all very personally, because one, you think that every data point that you see about the company in many ways reflects on you. There's also the sense of just a deep sense that you don't want to mess it up and that you want to do right by the team and do right by your vision and all the work you've done today. So there's so many things that are swirling around in someone's head that make it really difficult I think to one, see information as non-threatening and then just to be able to be objective. How do you tangibly help people get that distance? Because I imagine that can be very hard.

Edward Sullivan (42:35):

It is harder for some than others. I think the first step is often helping them identify individuals in the company who they really feel they can trust. Right? And also helping them understand that their task is not so much to make sure the product turns out perfect or that every decision is made perfectly. But their job is to help others in the business, see the product, see the press release, see the brand and the messaging with the same lens of quality that they have. That's really what it comes down to.

Edward Sullivan (43:11):

No one knows this product better than I do, is what the CEO will say. No one knows the customer better than I do. Okay. Well, then teach them. Once the client or the CEO has spent time with their team coaching people, we really turn the CEO or the founding team into coaches because they need to build scale in decision making and in quality identification and helping everyone in the company see through their lenses. If we can do that, then suddenly the founder can let go and be like, "Oh my gosh, they're doing it better than I would have." I gave them a little bit of coaching, I put them in the right direction. We hired the right people. They're actually really smart. They're doing great job. Right? They can finally be surprised.

Daniel Scrivner (44:00):

Yeah, and I'm sure some of that is allowing them enough time to be able to get comfortable, flexing new muscles, because I think about a lot of that as, you've been used to doing this, let's try this. Also, one, it's going to feel really unnatural, and two, it's probably going to take you a while to get comfortable doing it. But I think it sounds like it's one part getting them to take the leap and make the switch, and then second part, allowing them to fall in love with this new approach or this new way of seeing the world or this new way of acting.

Edward Sullivan (44:29):

There's a grieving process that also goes on sometimes with a, let's say a founder who is very product focused. That founder letting go of the product, that's the thing I'm best at. I built my entire career as a product designer or as a graphic designer working on brand, and now you're telling me I can't do that anymore. I don't have any confidence in leadership, I don't trust myself as a coach of these people in the C-suite, how am I supposed to experience myself as good? Right? We all love being great at our jobs, and we love nailing that design or writing that script that runs perfectly, and now these leaders are challenged with, "I don't get to code anymore, I don't get to design anymore, I have no purpose here."

Daniel Scrivner (45:14):

It's a huge part of their identity. I feel like a lot of times too, it's like ego death.

Edward Sullivan (45:17):

Ego death. And they have to develop a new competency, they have to derive joy in the work from the joy of others, not from the doing of the work themselves. It's a completely different thing.

Daniel Scrivner (45:29):

Yeah. I want to go back to one of the points you brought up earlier that just the perspective and the belief that there isn't a home you and a work you, or a personal you and a work you, that it's all the same. Why is that so important? Why do you feel so strongly about that? And then, how do you help founders work with that? And I guess be able to internalize that idea because I still think by and large, that's a very common way of looking at the world.

Edward Sullivan (45:56):

Yes, it is a very common way of looking at the world and we are proudly fighting against the norm in that way. The reason we think it's so important is because if you are showing up as work self, you feel like you need to constantly be suppressing what's actually going on for you. Oftentimes it's almost weird to find out later that I didn't know someone's parent was sick. Right? I didn't know someone was going through a divorce or a breakup. They were just like stuffing it down the whole time, and everything we know about emotional regulation and dealing with trauma is, we need to let the things out, we need to talk about it, we need to feel supported.

Edward Sullivan (46:36):

And only by sharing these stories of what's actually going on for us can our colleagues make space for us. "Oh, Edward's going through a hard time. Edward stay home this afternoon, call your mom, whatever's going on, I'll cover for you." Right? Then we develop more trust. We can feel taken care of, we can feel seen. If I'm hiding who I am the whole time, by definition, I cannot feel seen. And all we want is to feel seen. That's what makes us feel safe, that's what makes us feel like we belong. That's what creates psychological safety. I can take risks. I know that I can show up as I am.

Edward Sullivan (47:15):

And I feel there's a larger conversation in society right now, which is actually very helpful in terms of more and more people showing up as they are, more and more people being very clear about how they identify from a gender or sexuality standpoint, more and more people being very clear about how they identify in other ways and showing up as they are boldly, bravely, courageously. More of us need to do that. I think it creates better conversations, I think it ultimately leads to better ideas being surfaced in the office and it ultimately leads to better business outcomes.

Daniel Scrivner (47:51):

And it makes work, I think, feel like not too dimensional. I think when you have actual deep connection and relationship with your colleagues, things are very different. I think to that point. So I want to ask two closing questions, and one is, for people listening who maybe have gone through a coaching experience before, or listened to this and are interested, I wanted to ask your take on what makes a great coaching client and just advice for anyone, on the other side of the table for people listening like myself, when we reach out to a coach, how should we expect to show up? I think part of that is, in your best relationships, what is there that's maybe not there otherwise. Then I think the other piece is just obviously coaching is a two-way street, and let's talk about that and what that takes from the client's perspective.

Edward Sullivan (48:42):

I think that the best clients are the ones who show up with a lot of willingness, they show up with a lot of curiosity, they show up knowing that there are many things they don't know they don't know. Right? There's a humility to the act of asking for help. That's very beautiful, and it's very vulnerable, and we try to honor that in our work.

Edward Sullivan (49:03):

Sometimes clients will come to us and say, "My board said I need a coach." Right? "Or everything's falling apart at the company, I don't know if you saw Businessweek that I was written up in this terrible article. Like, I need help." We don't take those clients on. We don't take clients on who are assigned to coaching by their board or dealing with some PR nightmare, and they need to show that they're seeking help. We take on clients who are proactive, they're excited, they have raised some money and they want to build a great company and they want professional support to do that. Right?

Edward Sullivan (49:41):

In terms of, what I call the show up ins of a client, they need to show up, they need to show up for the appointments that we set, they need to follow through on any assignments. Sometimes if a client is really trying to work on a breakthrough with a specific habit or a specific bad habit, I'll have them text me every single day. Every day at six o'clock, you need to text me X, Y, Z. How you did in that meeting, how you showed up with this person, how you gave that other person feedback. And if they're not showing up for the work, there are many other potential clients that will. Right?

Edward Sullivan (50:14):

We want to work with clients who are engaged, who are excited, who are digging in. That's what fulfills me, is to work with a client who's so excited like, "I took what we talked about last week and I put it to work immediately and this next meeting was magic. I can't believe it." It's not magic. A lot of it is common sense. But sometimes we just need to have a conversation with someone to come to that conclusion.

Daniel Scrivner (50:39):

Yeah. Well, I'm sure for the people that then commit and show up, it truly feels like each week you can build off of the last, as opposed to reiterating the same concepts and feel like you're just in a loop.

Edward Sullivan (50:50):

Yeah. As soon as it turns into like, "Hey, what's going on? What do you have for me this week?" And we're not building a longer arc, it might be time for a new coach. Right? Or it might be time to bring this coaching experience to an end. Coaching shouldn't be something that goes on perpetuity. Right? It should be a defined period of time, we're working on specific goals. Sometimes new goals present themselves as the company grows. We pride ourselves in being able to scale the coaching with the client. We can go from series A to IPO. We can deploy 10 more coaches onto the executive team if that's what's required, but there have to be new challenges. Right? If it's the same thing over and over, maybe it's time to move on.

Daniel Scrivner (51:31):

Yeah. Last question. I know you have a book and I'm going to hope to have you back on the show in June after it's released, that's coming out all around heart first leadership. For everyone listening, paint a picture of what a great heart first leader looks like. And this can be historical figure or just somebody, I think, that you've encountered in your own work, but I think everyone can latch onto the idea. What does it look like embodied and what are some of the major traits? Why is it important?

Edward Sullivan (52:00):

So, I appreciate that question and thank you for the little mention of the book, it's called Leading with Heart, and it will be out, published by Harper Collins, in June of this year. So we're very, very excited.

Daniel Scrivner (52:11):

Can people preorder it now?

Edward Sullivan (52:12):

People can queue to preorder it now at Leadingwithheartbook.com.

Daniel Scrivner (52:18):

I'll put that in the show notes.

Edward Sullivan (52:19):

Thank you. Thank you. So the opening of the book, spoiler alert, the opening of the book is a walkthrough a client's office, and the client is Dave Heath, the CEO and founder of Bombas, the socks company. He says they're cornering the market on comfort, and we see Dave walking through the office and having conversations. And there's this incredible vibe in the Bombas office. Now this is pre pandemic, this is their old office, this specific vignette. Everyone is excited, no one's approaching him with fear or trepidation, he's very open.

Edward Sullivan (52:55):

And his head of marketing comes in and asks him a question about how to deal with a specific employee who is not really performing right now and having a tough time. Instead of jumping in with advice, Dave jumps in with questions, "Tell me about this person. Are their needs being met? What are the fears that are coming up for them? Are they really feeling connected to the purpose of the business? Do they have unexpressed gifts that they really think that they could be deploying in a different position?" When you're leading with heart, you're always starting with questions. You're always trying to have the conversation that is difficult to have. The conversation that's almost unexpected to have. How often is a CEO asking about the fears that are coming up for an employee or-

Daniel Scrivner (53:39):


Edward Sullivan (53:39):

What's that? Zero?

Daniel Scrivner (53:40):

I said zero. We're almost there.

Edward Sullivan (53:41):

Never, never. Right? How often are they asking the question, what are we doing enough to get their needs met? Maybe it might be their physical needs, might be their environmental needs. There's too much noise in their home office, we can help them with something. Might be their emotional needs. Are they really feeling a sense of belonging here?

Edward Sullivan (53:59):

And that ultimately is what the book is all about, is helping people have the conversations that unlock creativity, purpose, and results. That's the little subtitle, and it's not a listical book, it's not a hacking leadership book, it is a deep dive into the emotional side of leadership that helps us all show up with open hearts, helps us show up armed and feeling a little bit more able to have these sometimes awkward conversations. But the more you have those conversations, the less awkward they are.

Daniel Scrivner (54:30):

Yeah. Well, thank you so much for joining me, Ed, it's been incredible to have you on. For anyone listening, you can learn more about Velocity Coaching at velocitycoaching.com. Any closing thoughts, closing words, closing messages?

Edward Sullivan (54:43):

I'm just really happy to be here, and I just want to tell you, and all your listeners, how honored we are as coaches to be able to do this sort of work. My main values in life are service and freedom, and doing this work allows me to be of great service to many people, and it also affords me the freedom to live life the way I want to. Right? And I think that's my hope for everyone, is that they can live a life of service, but not be so service that they can't experience the joy of life as well.

Daniel Scrivner (55:12):

Yeah. That's a perfect note to end on. Thank you so much for the time.

Edward Sullivan (55:15):

Thank you.

Daniel Scrivner (55:17):

Thank you so much for listening. For links to everything we discussed, as well as the notes and transcript for this episode, visit Outlieracademy.com/90. At Outlieracademy.com, you can find more incredible interviews with the founders of Superhuman, Levels, Rally, Commonstock, Primal Kitchen, and so many more, as well as many of the world's best selling authors and some of the smartest investors.

Daniel Scrivner (55:40):

You can now also find us on YouTube at youtube.com/outlieracademy. On our channel, you'll find all of our full-length interviews as well as our favorite clips from every episode, including this one. You can also follow us on Twitter, Instagram, and LinkedIn under the handle Outlier Academy. From our entire team, we hope you enjoyed the show and we hope to see you right here next week on Outlier Academy.

On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. 

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Daniel Scrivner and Mighty Publishing LLC own the copyright in and to all content in and transcripts of the Outlier Academy podcast, with all rights reserved, including Daniel’s right of publicity.

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