A New Playbook for Today’s Best Leaders: A Conversation with David Cuthbert of Wine to Water

I spoke with the CEO of Wine to Water, David Cuthbert about the evolution of leadership and team dynamics. Wine to Water is an organization that brings clean water to those that need it most.

Steve: In the business context, what is the thing that stops people from doing the next thing they want to do? Personally, my theory is that’s usually us. How we show up as leaders, essentially. Things like compassion, empathy, etc. are all necessary to get toward that goal you’re shooting for. Tell us a little bit about what you’ve learned about leadership and how you got started.

David: My leadership training started when I was in the Naval Academy. We had classes on leadership training, so I started pretty young in the sense of formal leadership training. If I’ve done anything right in this world, it’s that I have constantly sought out learning opportunities. I don’t think I’ve stopped doing that, either. Leadership today is dramatically different than it was 25 years ago. And that’s a good thing! We’re having different conversations today about inclusion, diversity, awareness, and things in that vein. As much as we would like to think that we’ve figured leadership out, we haven’t. It’s continually evolving.

Going back to my story personally, much of my time in the Navy taught me the logistics of everything. How to get from point A to point B, execution of a mission, etc. Following my time there, I went into corporate America and joined a start-up company around 2006. I learned business at a very high level while I was there. It wasn’t just about the success of the technology, it was about the organization’s culture. I carried this with me into my third career, Wine to Water. I’ve been here for about 5 years now. The balance between the success of the company and the culture of the company is crucial. During my time as a leader at Wine to Water, keeping that balance has been my focus.

Steve: I’m glad you brought up culture. It can be a touchy word in business, with people either overusing it or not using it at all. In the military, was there a culture component that you had to uphold, and if so, how?

David: Definitely. Whether I was selling technology at the start-up, leading Wine to Water, or disarming bombs in the military, culture still played an important role. It’s all about the team environment. If you ignore the culture and the team dynamic, you’re essentially building a house of cards. My primary focus has always been building the right team. Because if you do that, you’ll always execute your jobs at a very high level. I firmly believe that. This was even more so the case in the military, where one person’s life literally depends on the other’s. That’s a kind of culture in and of itself. We had to pay close attention to the relationships that we were building in order to keep that clear communication and complete our missions effectively. It’s why you see so many military and ex-military people become like brothers and sisters.

Steve: I can see how that would lead to a strong sense of camaraderie. Were you able to replicate that kind of bond in your technology career or now at Wine to Water?

David: It’s really this concept of interdependence. What we’re talking about is a high-level trust of each other. The idea that you’re going to your job well and understand that I need you to, and vice versa. Where organizations tend to fail is when only one of those two things is happening. Your job as the leader is to instill the idea that you need them as much as they need you. If your team doesn’t feel supported by you or is afraid to speak up and be vulnerable, it starts to create a cycle of independence. This can work for some time, but at some point it will limit everyone’s success (and wellbeing, for that matter).

Steve: I love that. What about when people are underperforming or are no longer on the same level as the other team members? How do you handle that?

David: When you evaluate where someone is, you should also evaluate where you are as a team.

Does the team still have that trust in each other?

Do you all have the same vision for where you are going?

Does everyone have access to the same information and learning?

Are people empowered and given the authority to do their jobs well?

These are the things you need to look at in this scenario. I’ve found that when I have a situation like this with a team member and I go through those questions, you can usually spot where the problem is. A lot of the time you might wonder why they’re having these problems, but when you take a deeper look, maybe it was you that didn’t provide them with the right information or didn’t instill that trust in them.

Steve: Building that trust is vital, I agree. How do you go about doing that?

David: There’s a reason that having universal trust is the first thing I look at. As much as we want there to be this amazing hack for building trust, there simply isn’t. You have to show up every single day and be consistent so that people can trust what they see in you and what you say. Beyond that, it’s availability, vulnerability, the willingness to have both personal and professional conversations. Knowing that you can count on your team and they can count on you is a cool, beautiful thing.

Steve: I’ve been rereading How to Win Friends and Influence People and have pulled some great things from it on my second go-around. Are there any books you’ve read that you recommend?

David: I actually love that book as well. It really reminded me and my team that we don’t HAVE to do the work, we GET to do this work. I think that can really be applied to any field. Everyone has customers and everyone has the opportunity to impact their customers’ lives.

As far as books go, I recommend Team of Teams. It’s rooted in military tradition but it really applies to everyone. Extreme Ownership is another great one and it focuses on a high level of accountability, which is crucial for leaders.

Steve: I loved Extreme Ownership. It was especially helpful at a time where I was struggling with our performance as a team at one point and was like “How is the military able to get a bunch of 18-year-olds together to complete these missions and I can’t get that same kind of camaraderie?”

What I learned from that book is that your growth will be stunted if you’re the leader with a thousand little helpers. But if you have a team that has leaders at every level, the growth possibilities are endless.

David: Definitely. Especially with the younger generations, they’re so smart and so aware and can lead us in so many important conversations. To your point, we have to hear these voices. They’re changing companies, markets, etc.

The last book I’ll recommend is The Boys in the Boat. It’s about a rowing team from the 1900s that went on to win Olympic gold. It talks about the teamwork involved in the sport. While not everyone can be the strongest or fastest, if the team is entirely in sync, they can be the best. Carry that over to the idea of having these different voices in your organization. If you as the leader are too far ahead, it’s a waste of time.

Steve: I’d like to talk about Wine to Water. When we first met at the coffee shop, I had done some personal giving and had an idea of what corporate giving was. To some extent, I thought it could be a negative thing if you were too promotional about it (“Hey, look at us! We donate to charity!”). You helped me changed my perception of that. Can you explain what you told me for our listeners?

David: Of course. If you notice, you can’t go on social media anymore without seeing some sort of corporate giving going on. Which is great, people are getting the word out there. Quite frankly, this, along with the pressing issues going on in society, is demanding a response from all corporations. People, whether it be the employees or the customers, are holding them responsible for more than growing their own profits. Being a good citizen to the world is now just as important.

To your point of bragging or being too promotional, you should be posting about what you’re doing. Let people know what you’re participating in and tell them how they can take part in it. That’s what it’s about, raising awareness. I think where some companies get lost along the way is that they don’t actually see where their money is going and it gets forgotten about.

Steve: You nailed it. What you really instilled in me is that it’s not okay to just sit on the sidelines. If you care about these global and community issues, you have the ability to make an impact. On top of that, the giver should feel that impact as well. One thing you’re doing well with Wine to Water is including your donors in the process and sending them updates and showing them how these things work.

David: Without companies like Good Life and our other partners, Wine to Water couldn’t do what we set out to do. It’s these partnerships that help us thrive. Positive and sustainable change happens when companies and charities align and have that partnership where they’re continuously involved with each other.