Humility, Vulnerability and Leadership with Mark Ippolito
Mark Daniel Ippolito, it’s fair to say, is a long-time friend. I was delighted when he agreed to do this. I know Mark, please, tell us about yourself.
Passion for music and photography
I started my career way back in the 80s in New York City. I had a deep, deep passion for one of two things in life: music and photography. I wound up choosing photography as my professional vocation. Music is still very much a part of my life. As you know, I released my debut album last year, which I’m very excited about.
In the 1980s the photo industry was going through massive transformation. Carlos and I were involved in a cutting-edge company that was really taking the best of what was known as “direct marketing” and catalog marketing, and bringing that to an industry that really had not had those capabilities and that ability to reach customers on a broader scale. We wound up being at the epicenter of what became a multibillion-dollar industry called stock photography.
Well, that industry transitioned from film to digital, and so, again, we were blessed that we were on the cutting edge of that technology. Our employer at that time, a company called Comstock, was an early, early adopter of the personal computer revolution and putting computers on every desktop, and we wound up putting images on every desktop as a result - first through CD-ROM and then through online delivery. I was part of that transformation, and I was fortunate to be involved with an organization that evolved quickly and adopted those technologies.
Recognizing a change-worthy future
Moving forward to where we are today in 2022, I’ve been privileged to pivot from those early experiences in working online to moving to the Cloud. In the early 2000s, Cloud computing became really the dominant force. We moved from desktops to Cloud computing, and that’s really been where I’ve focused my career over the last 20 years, helping organizations move - first to that migration from desktop to the Cloud, and now that we’re squarely there, with major reorganizations in corporations worldwide, centering their ERP, CRM, point-of-sale systems in the Cloud. At my current company, Avalara, we help those organizations calculate all of their sales tax, both domestically here in the US as well as globally. As director of our strategic accounts group, which focuses primarily on Fortune 1,000 customers, we really help facilitate transactions around the world through those Cloud-based ERP systems, CRM and point-of-sale, and provide our customers with those compliance requirements.
So that’s kind of the brief history of Mark Ippolito. I’ve been privileged to see many, many changes in the workplace as a result of these capabilities, and hopefully I’ve adapted well enough to get to where I am today.
Stumbling into a leadership role and humility
Mark and I were peers at the photo agency back in the day, and then I was promoted and I was Mark’s boss for a while. That wouldn’t last very long. I make no claims about being a very good boss. Back then, you were a customer service and sales guy, and photo researcher. You were not long out of Fordham University when you got the job at Comstock. You lead people to this day. What did you learn about working with other people that you carry 35 years later?
This is a common story especially among sales professionals. I remember our CEO, and mentor, a guy by the name of Henry Scanlon. I was fresh out of college, hungry to have an impact, make a difference, and quickly became one of the top salespeople in the company. One day, Henry came up to me and said, “Hey, Mark, I want you to go and speak at a conference.” And I was like, “Well, why me?” And he said, “Because you are the first person in this industry who’s ever sold more than a million dollars in stock photography in a single year.” And I didn’t even know this. And that became kind of the impetus for him then coming to me shortly thereafter and saying, “By the way, since you do this better than anybody else, why don’t you train and manage these two, three, four people,” whatever it was at that time. So I was thrust into this leadership role that I absolutely had no preparation for. None whatsoever.
The lesson from that was, first and foremost, remain humble. ‘Cause I was all of 24, 25, and the company was hiring people who were, in some cases, much older than me and had much more experience, be it in sales or other service industries. I immediately had to humble myself and realize there is so much that I know I don’t know about leadership, about managing and creating a great environment for people within which to succeed. I’m not saying I was always successful - I certainly made mistakes in not practicing humility - but I think one of the things that allowed me to be successful was to listen first, then think before I act.
Acquisitions foster continued humility
Now I’m part of a multi-national company; there’s about 4,000 employees at Avalara. We've grown tremendously. There were about 400 employees when I started here nine years ago, so I’ve seen tremendous growth in that time. Our valuation is a multibillion-dollar company, I think we’ve acquired something like 13 new companies. And so, as a result of this rapid acquisition pace, we’re bringing in this incredible talent - people who’ve founded other companies, who are now becoming part of our organization, who have tremendous credentials in subject matter and domain expertise that I certainly don’t have. What I do have is the experience of nine years of selling sales and use tax solutions to customers worldwide. But the reality is that I still have to remain humble, because these people are coming into our organization with expertise that I need, and I need to let them know that. So that’s something that I’m keenly aware of to this day.
Align team on the company’s strategic intent
You are a member of the leadership team with your organization. You worked for Bill Gates for a period of time; you’ve got broad experience. How does it change from that front-line kind of job to this more senior, more strategic role?
One of my best bosses that I ever worked for was a woman by the name of Sally von Bargen. She was a senior vice president of sales and marketing for a company called Getty Images, which in the early 2000s was the preeminent player in the digital stock photography arena. She put a mantra in my head that I live by to this day: “A manager’s job is to see the future and make it happen.” And that’s really what leaders do. At the leadership level, be it at this organization or other organizations where I’ve had the privilege of being a leader, it really is about that. It’s about seeing the future, and then taking that information and that vision, those insights, and sharing it with the team to empower them, so that they can execute it. Because it’s one thing for a manager to see the future; it’s another thing to execute on it. In a leadership role, that’s what we focus on: empowering our people to execute.
I’m always shocked - and disappointed, quite frankly - when I talk to other team members who are not direct-report to mine, and I’ll share with them an insight that we are clearly instructed as leaders to make sure we share with our teams, whether it’s a growth initiative or whatever it may be, and I’m shocked when I hear employees say, “Well, I was never told that. I didn’t know we had that guidance.” And I’m sitting there saying, “It’s your leader’s job to share information that is of strategic importance to the company so that you can execute on it.” Because if you don’t have that, you get into questions of, “What’s my role? How am I being evaluated? Where am I being measured?” And that’s just a recipe for all kinds of bad things to happen [laughs].
Difficult conversation: Trusted colleague/teammate - a trust-building opportunity
George Bernard Shaw said, “The single biggest problem in communication is the illusion that it has taken place.” You’re chatting with an employee a level or two down, and you’re talking about this initiative that is a leadership mandate. Do you pull that colleague, your fellow leader, aside, and say, “Hey, I was chatting with one of your folks, and they don’t seem to be up to speed on this. What’s going on here?” It’s the sort of conversation that trusted teammates have with each other.
So, Carlos, there are two things I do in that situation.
I ask the employee to please go back to their manager and ask them to be briefed on whatever the topic is.
I reach out to that manager and say, “Hey, I just heard from employee so-and-so. Can you please take time to brief your team, because it impacts our collective performance.”
I think when you do that as a leader, there’s always some risk in taking that bold stance, but I think that’s the way you build trust because I would ask the same of them. I would say, “Listen, if you hear something from my team, or learn about an action someone took that’s inconsistent with guidance that we’ve provided as a leadership team, please tell me so I can be proactive in correcting that.” I think over time, that’s the way you build trust, and build, frankly, great teams.
I’m sure you’re a reader of Patrick Lensioni’s books on leadership. I wholly subscribe to much of the philosophy that he shares there. You have to have open dialogue to build trust. When you don’t, you really don’t have high-performing teams.
That kind of candor is a hallmark of the highest performing teams that I’m aware of. And I think you’re right; the way you build it is not on a ropes course or at the company golf event. It is just digging into the tough issues. I have a lot of bones to pick with people in my field who I think purvey team-building that’s of questionable value. I love to talk to my guests about their worst team-building experience ever.
the failures of team-building events
Do you have any memory of a time when any team you were a part of tried to do some team-building and it just wasn’t working?
We were actually joking about this with some colleagues the other day. It was with my current employers, so I’m not embarrassed to talk about it. We were still relatively early stage, pre-IPO, and we’d have our annual sales conference. But there would always be this team-building component, which would be multiple hours during the course of the day. And, I mean, they were just exercises in pain and futility. They really did not help. They created some funny stories down the road, and I guess if that’s the objective of team-building…
We were joking the other day about this scavenger hunt. We’re here in Seattle, Washington, and it’s the second week in January and we’re kicking off the new year. It’s still chilly here, and usually wet at that time of year, and the scavenger hunt was completely outdoors. Now, you had people traveling from the desert, from Southern California, from the Southeast, who are completely ill-prepared to deal with any kind of chilly weather, because they’re thinking they’re going to a conference and they’re going to be inside a hotel, or inside of a conference room for a couple of days, right? So we get thrown out onto the streets of Seattle, and the distance that we had to cover was multiple miles. By foot.
So these people are outside, no taxis–We’re supposed to go from one location to another - go to this bar, go to this park, go to this landmark, whatever. Read this thing and record it and come back. It literally took, like, half the day. By the end of it, we were just so exhausted and, frankly, pissed off that we had to go through this useless exercise.
We couldn’t wait to get back to the learning sessions, where we could actually get some value out of this time that we were spending at our sales kick-offs. And it was all done with this idea of, “Meet your colleagues and have this great time together.”
But it really just became this kind of senseless activity. We were like, “Boy, we didn’t really get anything out of that except a couple of funny stories to tell each other.”
Effective way to build teams
Then what’s an effective way to build teams?
We’ve done some really great ones at Avalara. Harkening back to my days at Getty Images, Getty was also very acquisitive. I think we did 23 acquisitions, total, in the four years that I was there, and I was a VP of sales at that time.
Business conversations on horseback and the power of vulnerability
One of the things that we did in order to bring on board all these new leaders who were quickly joining the company through the acquisitions was we went out to Park City, Utah. A bit of a boondoggle, but in the time that we spent together there, we really engaged with one another through facilitated exercises to really draw out both our commonalities as well as our differences, and get them on the table. Through the course of those two days, we did some fun activities together - a horseback riding exercise, which, still to this day, is one of my treasured memories in my career because we were having these deep conversations about what can make us a better company while we’re riding bareback on horses, going through this alpine meadow in Utah.
We were side by side, having this experience, and I was incredibly afraid of horses at the time, too. I did not want to be on a horse. But I think that vulnerability, sharing that with my colleagues - who were new; these were not people that I had long relationships with. We immediately bonded. And then the conversations during the exercise, during the facilitated discussions, over dinner, etc. were real and meaningful. And I gotta tell you, in that 48-72 hour period that we were together, we came away a changed team.
Really?
A really changed team. And the communication and the effectiveness of our execution of our strategic plan was remarkable.
What I get out of this is that your fear forced you to drop your defenses. You were doing fun stuff, but you were talking about real stuff.
Absolutely.
Is there any other attribute to that stretch of time that you think made it effective?
First and foremost, you’ve gotta create that safe space.
I’ve had the privilege of facilitating those kinds of sessions in different organizations that I’ve been a part of. I was part of a digital ad placement startup back in the early 2000s, and it was a much smaller organization - only a couple hundred employees - but there were 50 people in the sales organization, and the first thing we had to do was create a safe space where people knew that they could come out and share their concerns, their risks, and also where they saw opportunities.
I started the session by playing Bob Dylan’s song, “The Times, They Are A-Changin’,” and I asked them, “Please, listen to this lyric, because we are in this transformative period. Our time is changing, and we either take action and be part of the change, or we get left behind.” And I gotta tell you, it was like– there weren’t a lot of folkies in the room. It was mostly twenty-somethings who’d never even heard of Bob Dylan. But yet, when they listened to the lyrics, they understood, “it’s up to me now to be part of that change.” The conversations that emanated over those next two days with that relatively small group of people - the seed of that was built in just allowing people to be in a safe place, be vulnerable. Let them know it’s okay to talk about change, it’s okay to talk about your fear, because it’s through that that we will get to a better place together. That’s the key.
Too many times in my career, I’ve worked with leaders who have said, “I want to create a safe space,” and what they end up with is a space full of people trying to be nice to each other. I think what you need is a courageous space. Brené Brown talks about the courage to be vulnerable.
Creating a psychologically safe space
When you think about creating a safe space - psychological safety, where people feel they can speak up without risk of being put down - what do you do?
For me, it just comes back to doing what I say I’m going to do.
So, if I say I’m going to create a courageous space - I like that attribution, Carlos - then I need to be courageous as a leader. I have to show that. I have to demonstrate that behavior. I have to be willing to go there myself. If the other people that you’re asking to go on this journey with you don’t see you take that first step in an honest, authentic way, they’re not going to go there.
Be a model of vulnerability
Can you think of a time when you were with a group of people who report to you where you were able to be vulnerable and model that kind of behavior?
Well, I like to think I do it every day. And I do it with customers as much as I do it with my team, by just simply saying, “I don’t have the answer.”
In this complex world that we live in today, employees, leaders, customers, shareholders - we all have opinions, and we all have experience we draw from, but, boy, I tell you, in so many industries, we’re creating new pathways, new endpoints. So we all have to be willing to say we don’t know the answer. When I lead my team meetings, I’ll ask people specifically,
where are the gaps?
What is it that we’re not talking about?
What are we not addressing that we need to address in order to accomplish this goal, this initiative, whatever the topic is on the table?
I’m very intentional about asking that because I want to eliminate as many blind spots I have. And I know I’ve got them. We all do. So, I think it’s really being in that mindset of being willing to admit. Be vulnerable. Together, we will create a much, much better output than any one of us trying to pursue an answer on our own. Does that mean that people don’t come up with individual moments of insight and inspiration? Of course not. But now we allow, at least, that collective of ideas to come forward so that we then choose the best path.
Artificial Intelligence is here, but only humans can connect the unrelated stimuli
“Be surprising, social, and scarce.” Walter Lippmann said, “You cannot endow even the best machine with initiative. The jolliest steamroller will not plant flowers.”
You recommended a book to me recently. “Futureproof: Nine Rules for Humans in the Age of Automation” [by Kevin Roose]. You’ve given it to your current team. It’s a book about being a human being in the age of AI and machine learning. The first half of the book is chilling, as he talks about how AI is transforming the work and our work lives, and the second half of the book is nine strategies for how to be a person in the midst of all that. What’s your takeaway, as a leader, from that book?
The point that the author makes in the book that really resonated with me is, look, machines, AI - it is here, it is now. It is not some future state, it’s not something that you should be thinking about and planning for in five years, no. It’s right now. It’s transforming our lives today. So just (a.) recognizing that, but (b.) not being afraid of it. We’ve seen this before. We’ve seen technology transform our business, our society, our culture at large. He draws some wonderful analogies to everything from the cotton gin to the industrial revolution to the PC. We’ve seen this before, so it’s not like we’re not equipped to deal with it, and the way through it is really to your point.
Machines are wonderful at doing repetitive tasks quickly, accurately, and at scale. But machines are unable to deal with unconnected or unrelated scenarios, which we humans do very instinctively. We’re designed to do that. The wind is picking up and the light is hitting your head in a stronger way - oh, I need to adjust for that. Better put on some sunscreen or some sunglasses, right? Machines don’t know how to deal with unrelated stimuli. As business leaders, we are often being confronted with unrelated tasks, trends, issues.
Mental acuity and emotional intelligence: be human
That’s the thing that I’ve asked my team to focus on. Let’s use technology to alleviate ourselves of the mundane, the repetitive things, the things that really do slow us down, and let’s focus our mental acuity, our emotional intelligence, on the things that machines just simply cannot and will not do. And that is: be human. Recognize the humanity in other people. Recognize the different scenarios that you find yourself in, and bring those links together.
I recently went through the CliftonStrengths finder exercise. I’ve done similar things in the past, but CliftonStrengths was new to me. My number one strength is actually the strength that is least identified amongst leaders: connectedness. And I kind of put that in the context of what we were just talking about. That’s how you make yourself valuable: seeing the connections between events, people, places, scenarios. That’s not something that computers can or ever will do. That’s the piece that I walked away with from that reading, and have been sharing with my team. Identify how you can be connected, how you can be aware, and how you can have an impact as a human, and you will absolutely not only preserve your value, but grow your value to the organization and to your life as a whole.
Advice for the new manager
If you’re bringing in your successor, what’s your first piece of advice?
Recognize others’ strengths
First and foremost, recognize the strengths of the individuals that you have the privilege to lead. Recognize and celebrate the strengths. It’s far too easy to call out weaknesses and gaps and mistakes and shortcomings. That’s easy. Real leaders, those of us who have the privilege to influence the behavior of others, focus on strengths. Focus on what it is that you are uniquely bringing to this organization, and how we can expand that. That would be the coaching that I would give. I have the privilege of working with an incredible group of people who I’ve been able to build and grow over my nine years here in my current role, and that’s a place of privilege to be. They all have incredible strengths. They all have weaknesses. But I think the reason why we have been able to sustain one another and sustain our growth as a team is because we focus on strengths.
Know your own strengths and weaknesses
I have strengths. I have weaknesses. I’m very clear about where they are, and I articulate those to my team all the time. And what I reinforce with them is, “You have strengths.” And it’s different for each individual. That’s what I would really coach any leader who’s going to take my role - focus first on strengths. Focus on what you can enable this team to do, and then put all of your efforts - all of your efforts, all of your intellect, all of your emotion, all of your heart - into supporting those strengths and letting those people flourish around their strengths. I think if you do that, you’ll achieve not only the goals you set out, but much, much more.
C: I don’t think that it can be better said than that, Mark. Thank you so much for taking time out of your busy schedule.
M: Carlos, you’re very welcome. And thank you for the opportunity.
You can follow Mark Ippolito on LinkedIn.