CIO Gray Nester on fostering a culture of success

Brown & Brown Insurance EVP and CIO Gray Nester leads with intention. In heading up people, strategy, operations, and processes for the world’s seventh-largest insurance brokerage, he instills in his team the courage to challenge the status quo and explore solutions that will further differentiate the firm in the marketplace. 

Like all the best CIOs, Nester doesn’t allow himself to lose focus or get thrown off course by setbacks or the latest distractions. Instead, he’s locked in on what I call the seven Cs of great leaders: culture, cultivate, communicate, collaborate, customer, courage, and change.

On a recent episode of the Tech Whisperers podcast, Nester and I discussed his intentionality as a leader in the context of that model. Afterwards, we spent some more time unpacking Nester’s people-first approach to leadership. What follows is that conversation, edited for length and clarity.

Dan Roberts: A key aspect of your leadership approach is building internal partnerships with other disciplines to ensure you’re asking the right questions, communicating across the organization, and doing what’s necessary to recruit, develop, and retain talent. Why do you think building these partnerships is so important to achieving your broader technology vision?

Gray Nester: I think it’s really about culture, collaboration, and another C, curiosity. We hire a lot of really smart people. So, who am I to tell Jenny [Goco], my awesome communications partner, the best way to communicate? I can ask lots of questions, and be inside of how we drive results, but when I’m working with really talented people, I don’t want to tell them how to do their job and only get the best of me.

Sometimes, we feel like because we have ‘the job,’ we have to be the decision-maker. There are very few urgent decisions in our lives that we actually have to make. For example, think about how this conversation between us was orchestrated. Jenny did it. I didn’t do it. When you thanked me for my hard work, it wasn’t me. I hadn’t done anything. She did it. Whether it’s TR [Team Resources — Brown & Brown’s name for HR], finance, communications, or information security, it doesn’t matter what the discipline is inside of this business I’m responsible for. If I’ve hired people that I trust and believe that they’re intelligent, then I need to get out of the way and give them what they need to succeed. So, my job is a support role. My job is not actually the delivery role.

When it comes to customers, many IT leaders focus on internal ones alone. But you have direct interactions with external customers. How does that impact your approach as a CIO?

We often say that, until somebody sells something and somebody pays us, nothing actually happens. Our leadership team thinks about that in a few ways. Number one, we think about how you are engaged with your customers and ensuring that our delivery of technology is aligned with the appropriate business outcomes and business strategies.

Number two, I think about how many customers I meet with every year who are not customers that I generate.

And number three, as an organization, we don’t like ‘vendors.’ That’s not to say we don’t have any, but we don’t like them. We like partners. So, for anyone reading this who happens to be plugged into the tech space and selling something to Brown & Brown, they will likely tell you that somebody on our leadership team, not necessarily me, has asked them for the opportunity to earn their business because everybody’s buying insurance.

Our business is engaged differently with us because, in a lot of places across our footprint, you’ve had somebody work on an account that they didn’t have to generate. Everyone inside of Brown & Brown has the opportunity to sell, whether it’s homeowner’s insurance for a neighbor or property and casualty coverage for a large company that they happen to be connected to. For example, our chief security officer, Barry Hensley, has a new business target inside his world. My goal every year is to cover my own cost — to sell enough insurance to cover the cost of what it takes for Brown & Brown to keep me on. 

In this job, courage is a big factor because every day we see things we’ve not seen before. How do you enable and build courage within your people so they’re more resilient in the face of constant, accelerating change?

It’s easy to be courageous when you’ve already achieved more than you ever thought you would. I don’t have to be afraid to fail because I’m successful in the things that matter — my family. That’s where my love comes from.

As a leader, courage and always doing what’s right equate to being honest but also being kind. There’s a difference between being honest and being truthful. As I have the opportunity to coach people, I have to deliver hard messages, and those are honest messages. I can be truthful with you and never address the opportunity to improve. So, I think courage is the willingness to say things that may not be popular but that help you achieve the goals and objectives you’re capable of achieving.

We all show up here every day for something bigger than ourselves. If you believe in assuming positive intent and believe that people show up every day to be successful, then if you can give them the tough message, you have to believe they’re going to take that and do something with it because feedback is a gift. That doesn’t mean that everybody will be successful in that, but it’s our responsibility as leaders to go out and do that.

That may mean saying, ‘Hey, Business, you’ve got a really bad idea, and this isn’t going to work, and let me tell you why.’ It’s really difficult to say that if you aren’t connected to the business and don’t know whether it’s a good idea or not.

Or it may mean saying, ‘Hey, I know we have a personal relationship, but I’m your leader, and we have to be successful here, and I need you to understand how this action impacts your success inside of Brown & Brown. I don’t want to tell you how to act, but I can tell you that what you’re doing limits your ability to achieve your goals and objectives.’ But if you don’t spend enough time on the people side of things and getting to know your team, then you don’t know their goals and objectives, so how can you help them reach them? 

That is what courage is about for me. But it comes back to something very simple: I’ve already won the game. I have a wife who loves me. I have a son who loves me. I couldn’t be more proud of them. I’ve got two amazing bulldogs that love me to death. I can get a kiss any night of the week, even if I’ve done something wrong or made a wrong decision. Ultimately, this doesn’t matter. It’s very, very important, but it doesn’t define me.

I wanted to talk about a couple of your go-to leadership expressions. You’ve said ‘progress over perfection’ is the foundational cornerstone of your success. Why?

I say that because I’ve had the opportunity to meet so many people from a network perspective, and a lot of people are potentially more talented than me, more gifted than me, and more intelligent than me, but they are afraid to do the next thing. 

I’ve got a business partner here who says, ‘If I can just do three yards every day, I get a first down every time I’m on the field.’ A lot of people think about the Hail Mary, but they don’t think about, ‘I’ve got to get a lot of first downs to be any good.’

Progress over perfection is something that has really defined how we deliver work. Back before Agile was cool, we were out kind of going three yards at a time, just ensuring that we got something done every single day instead of spending time in a sort of analysis paralysis and never achieving anything. So that’s how I think about progress over perfection. And I think over the last four years, Brown & Brown has been a great example of that.

You also like to say, ‘None of us got here without a network and without getting knocked down.’ Talk about that expression and how it helps build resilience.

When I think about my network and the people who help me every day, it’s also about the fact that I haven’t learned anything from being successful; I’ve only learned through my failure. It was great to hear from Jeff [Drye] and Will [Shupe] on the podcast, and there are a hundred more people I could have thought of and brought forward. What’s impactful to me is the fact that these people invested in me and that, through their investment, I’m a better person. 

I also have learned, even through mentoring in the Tech LX program, that as I invest in people, I can’t ‘out-give’ myself. I learn more from the people I give to today than they’ve ever learned from me.

But when Jeff talks about the ability to anticipate and see around corners, all of that comes from the scars that I have. It’s so easy to get knocked down two or three times and go, ‘I don’t like getting knocked down.’ But you only learn from getting knocked down. So, the sooner you get back up, the sooner you engage, the sooner you’re able to re-engage and be super clear with yourself — that self-awareness — determines whether you make it or not in this world. Learning through your failures and being willing to say what you could do differently, even if it wasn’t your failure, that’s what will lead you to a higher level of success. Because you can only control how you accept something that happens; you can’t control the thing that happens. 

For more from Gray Nester and how his intentional approach to leadership is setting him and his teams apart, tune in to the Tech Whisperers podcast.