Robert B. Carter is a visionary technology executive whose pioneering career and accomplishments have set the standard for IT leadership excellence. He served as the CIO of FedEx for almost a quarter of a century, six times the average tenure of a CIO, and led his global organization to a remarkable 27 straight CIO 100 awards. While he was inducted into the CIO Hall of Fame in 2007, his greatest impact came in the 17 years that followed.
Carter joined me on a recent episode of the Tech Whisperers podcast for a wide-ranging conversation about his leadership story and legacy, the guiding philosophies and principles behind his myriad successes, and the indelible mark he has left on FedEx and the broader IT landscape. Afterwards, we spent some more time exploring Carter’ s innate ability to zero in on the specific areas that really matter when it comes to building a world-class culture and future-ready workforce. What follows is that conversation, edited for length and clarity.
Dan Roberts: Relationships, both inside and outside the organization, matter. What are some ways relationships have proved instrumental in helping your technology organization fuel business growth?
Robert Carter: My predecessor at FedEx, Dennis Jones, taught me something important: You’ve got to establish relationships with people who are on the edges of technology. In 1994 Bill Joy of Sun Microsystems came to Memphis to meet with Dennis and me and a couple of our key folks. Five minutes in, he says, ‘Tell me about your website.’
In 1994, that wasn’t really a thing, to be honest with you. We were busy trying to figure out how to deliver some of our client-server stuff. So we said, ‘Well, we don’t actually have a website yet,’ and he immediately interrupts, saying, ‘You need to go build one and build it quickly.’
So we did. At that time, everybody’s page was brochureware — an about page, a picture of the company’s headquarters warbling in over a 1200-baud modem. But it didn’t do anything. We had already launched FedEx tracking as PC software, a little diskette you’d pop into your IBM PC and it would bring up a simple interface for tracking. It was an LU0 backend to an IMS database on the mainframe. So we got together some of our advanced technology team members, led by Miley Ainsworth, and they built the very first fedex.com.
The graphic was this flying FedEx box leaving an arc behind it. It was an HTML page with a little blank field on it that said, “Enter your tracking number here.” When you entered your number, it would do the same thing the PC software did, connect with the mainframe through this LU0 backend, get all the tracking data, reformat it into an HTML page, and redisplay it on your Internet screen at fedex.com.
We won a Smithsonian award for this for being the first website that actually did business transactional work, and the reason I tell that story is because relationships matter. It wouldn’t have been possible were it not for Bill Joy being willing to come spend some time with us and challenge us on what he knew and could clearly see, and then also to have a landing place for it with people like Miley and his team, who were skunkworks people. They weren’t building big, bolted high transaction systems; they were figuring out ways to invite the customer into the mix and be part of this.
Just a few years later, we’d taken half the calls out of the call center, because you could schedule a dispatch on fedex.com, you could order supplies, you could track your packages. And then that just grew and grew and grew.
I’ve heard you reference the ‘two wings of innovation’ when explaining how to anticipate where the customer is going. What do you mean by that?
One wing of innovation is your outside connections, and how you interface with a world that you don’t know, because you don’t know everything you need to know and can’t see around that corner by yourself. But if that’s all you do, the bird can’t fly. It flaps around in a circle on the ground. But if you connect that to the other wing, which is your innovation people inside the company, now you can get speed and lift and altitude. Now you’re flying.
The two wings of innovation are replete in that story about Bill Joy and Miley Ainsworth and creating a connection because of relationships.
You talk about how tech is a people business. Can you expand on that and how this emphasis came about?
It became clear to me early on that the problem with most technologists and technology leaders is that they believed that the speeds and feeds in the machine in the back was what the conversation was all about. That was never what the conversation was about. Those were just enablers. It always takes people to make great things happen.
When I was learning and growing as a manager, and eventually as a director, I realized these people didn’t have any fun. So on a Friday, we’d say, ‘Bring your family,’ and there would be 300 of us out at a big picnic playing volleyball and doing the Macarena. We’d go fishing, we’d have bowling leagues, and we’d celebrate the people.
The beginning of my mantra is ‘work hard,’ but what follows is ‘lead a balanced life.’ People respond to that. And it’s still true to this day when you see what I would call average to subpar technology leaders. They’re too focused on the tech. They’re not focused on the people that make it happen.
It’s a little bit like that conversation you and I had about the tale of two CIOs, where one leaves a wake of bodies in their path and maybe accomplishes something for a while, but it’s not lasting. If I get the luxury of being an example of the other CIO, then this quote becomes the hugest part of that. This is a people business, and it includes those external relationships. That was something I learned from Dennis, because I had a couple of bosses before that who said, ‘You just don’t need to waste your time talking to these vendors.’ Well, these are people, too, and they actually have good ideas, and the reason that their companies have been so impactful is because they’re changing the world.
At the CIO100 Awards event two years ago, I had the honor of leading the ‘Leadership Masterclass,’ and you were part of my faculty. Your team let me know you would need to leave right after your session due to other commitments, but after the session ended, I saw you find a seat in the front row for the remaining two and half hours. This was such a rich reminder of how humility matters and continuous learning matters. How has this been integral to the success you’ve had and the impacts you’ve made?
In that instance, the conversation was superb. I also looked at the agenda for who was coming, including Cisco [Sanchez, Qualcomm’s CIO], and so it was about learning and respect. It’s important to realize you don’t know it all, that there are going to be other people with other contexts and other learnings, and folks like Cisco who have different ways of thinking about what their world is. One of the things about that is, you’ve got to be adaptive. You can’t be too rigid.
You also learn from people you don’t expect to necessarily learn from. I’m not a fan of his politics, but I was at a Fortune event where Bill Clinton was one of the speakers. My wife and I are waiting for the elevator to go to dinner on night one, and the doors open, and inside is a secret service guy and Bill Clinton. We step into the elevator, and he is the most charming, gracious, charismatic, captivating person. Yes, we’re the only people in the room because we’re in an elevator, but he’s introducing himself, as if we needed to be introduced to him. And then that night, there’s a hundred people at this conference, and more than once he comes up to us and remembers our names, talks to us, and you just can’t help but be impressed by this guy. He gets up and plays saxophone with the band. He’s just kind of an amazing person.
Later, I heard his definition of leadership is to walk slowly through the room. You don’t come barreling into a room. I’ve met a lot of presidents, but I’ve probably met Bill more times than most, and he exemplifies that. When he’s shaking your hand, he’s going to look you right in the eyes to make you feel like you’re the only person in that room. He’s probably going to ask you a question, where are you from.
Michael Dell is someone else who’s come so far since the early days of growing a company to now being evolved as a leader, always listening, always curious, always adapting. And he has that same focus-in-on-you charisma. ‘Be here now’ is what Larry Senn called it. So one of my leadership lessons is that I could come in heels and elbows and set that example for the room, or I could walk slowly through the room and sit there and listen and learn.
Talk about how being able to communicate a vision and lead people through change matters. What’s your perspective on that?
Peter Senge’s notion of shared mental models was something I absolutely took to heart. The idea of putting people in the seats of the cathedral before it’s built is all about having a shared mental model and a way to communicate it. Over and over again, we would work our tails off, and it’s hard because you’d never know it until you saw it. The shared mental model was an abstraction — it was never the thing — but it was something on paper that you could get people to buy into, whether it was part of a journey or the destination.
I remember reading a book, I think it was called Change Monster, and the point was that you have to get 5% of the people to buy into the change vision and be your influencers. You’ll never get 100% of the people, but you start with 5% and equip them to tell the story, too. It’s sort of like an apostle. You have to bring them into the fold and have a group of apostles that can go tell the story.
Something else that Fred [Smith] taught me about change is that words and names matter. Once we decided on what we were going to call something, if people used the wrong name or put it in the wrong order, he’d correct them. This is part of commander’s intent and being clear. Don’t let words confuse people. Let words be clear, let them be consistent. He’d say, ‘Tell ’em, tell ’em what you told ’em, and tell ’em again. Sometimes you’re going to feel silly, like you’re just repeating yourself. But trust me, they’re not hearing it as clearly as you think they are, or they’ve never heard it.’
Today more than ever, courage matters. What words of advice do you have for CIOs about courage and its counterpart, fear?
Fred would say, ‘When asked to lead, lead,’ and man, there’s something so powerful about that, when you say, ‘I’m kind of struggling with this,’ and he says, ‘When asked to lead, lead. It’s on you. I’m not going tell you how to do it. If I need to do that, then I need to find somebody else to run technology.’
Part of having courage is knowing someone’s got your back. It may sound like I just said he didn’t have my back, but the reality is, I knew he absolutely had my back. But that didn’t mean that I’d walk two steps behind him. That meant that if I had to have some air cover, I could count on him. But only after I had done the work.
I also think about Brad Martin’s book 5 Smooth Stones about David and Goliath. The book explains that sometimes we tell this story like it’s the most improbable thing ever to happen. But when you really unpack it, here’s a young guy who killed a bear this way. He’d killed a lion this way. He’d killed innumerable wolves and foxes this way. He had prepared himself with mad skills when it came to using that sling.
Courage requires a great deal of preparation, and David was well equipped. Just like that bear, just like that lion, he knows, I’ve got skills necessary to do this. And I don’t just have one stone, I’ve got five. If I miss, I’m going to fire another. But I’ve chosen these stones because I know what flies right, and I know what doesn’t. So ultimately, courage is about preparation. And it comes with purpose and conviction and belief.
For more insights and advice from Robert Carter, certainly one of the greatest-of-all-time CIOs, tune in to the Tech Whisperers podcast.
