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Transit CEO Interview Series: Brad Sheffield (Jaunt)

Insights from Insight

Brad Sheffield, Executive Director at JAUNT

December, 2016

The Insights from Insight interview series aims to gather the collective wisdom of the most accomplished and seasoned General Managers and CEO's in transit and transportation. These are men and women who have spent entire careers leading and managing steeped in the dual challenges of daily chaos and daily execution. Insight Strategies works in many industries; none are quite like transportation.

We are of the opinion that it takes and extreme talent to just make it in this industry. The people we interview have not only "made it" but have thrived. Their stories and the lessons we can gain from them are presented here.


Brad Sheffield was elected to the Albemarle County Board of Supervisors to represent the Rio Magisterial District in November 2013. Professionally, Brad serves as the Executive at JAUNT Inc., a Charlottesville Virginia based rural public transportation system. He has been working in the transit industry for 16 years, in both public and private transit planning roles.

Brad earned a Master's degree in Urban and Environmental Planning from the University of Virginia with a focus on transportation planning. He began his career in the public sector developing a regional rural transit program for 14 counties in Southwest Georgia. In 2005 he became the Transit Planning Director for Tallahassee's transit system, StarMetro. In 2008 he moved to the private sector and began working with Renaissance Planning Group as a transit planning project manager. In 2011 he returned to the public sector, joining JAUNT.

At his core, Brad is a transportation and land use planner. He has focused his career on community development. He has worked on projects ranging from regional transportation planning and transit projects to urban community design and rural land preservation. He is passionate about helping communities foster the traditional characteristics that make places great to work, raise a family, and retire.

The Interview

Kevin Catlin: The idea for these interview is that a young Brad Sheffield could pick this interview up and hear from an older, wiser Brad Sheffield, to learn what he would do differently, what he did right… or wrong in his opinion. Do you think it's valuable to have interviews with working CEO's/General it Managers where a younger executive or a future executive could hear from someone in transit about what it takes?

Brad Sheffield: Yes, I think so. I think the audience has got to be receptive to wanting to get that sage advice of what an older executive has gone through, tempering that with what has changed in the industry. What an older executive went through 10 years ago may not be what a younger executive coming through the ranks is going through right now, but still understanding what they have to offer and what they have to say could be put to use. It's like going to conference or meetings, or the analogy of stepping into a library: You're not going to be overwhelmed with knowledge and information just by walking into a library, you have to find the book you want, check it out, read it and absorb it, and then learn to apply it. I think a lot of young leaders forget you can't just be told; you have to learn from it.

KC: That leads me to my next question. Are there any 2-3 pivotal experiences that you have learned a lesson from or that you wish you could've been prepared for or handled differently?

BS: I didn't know much about the politics of transit when I was getting started. When I was in Southwest Georgia, I had a person, who is now a good friend, a county manager, call me up, and he asked "What are you doing to my county?" and there was a little more profanity in the conversation than what I'm giving. (Laughs). And he was upset. I was trying to create a rural service in his county and I had no idea that I probably should've sat down with the county leadership and actually tell them what I was doing before I started doing it. So that they knew when constituents would come to him with questions, that he would know how to respond. I don't know if any education would've helped me with that, but it's where getting some seasoned advice from a veteran would've been great. Someone could've told me that I should talk to those county managers or the local leadership involved with the project, to let them what I was doing. That conversation was very eye opening, and like I said he's a good friend now, but they say the best friendships are forged in fire, I'm sure we'll be friends for a long time.

Some of the other things I wish I was better prepared for that someone could've told me about was the way bureaucracy and government works, from the federal to the state, the regional entities in between. Everyone is looking at the same project through a different lens, and what may be important to one entity may not even be on the spectrum of what's important to another, and it's always a challenge to see where those things overlap and keep a focus on the endgame to provide everyone with the results they're looking for. I didn't really have anyone in my experience step forward and help me with that, it's something I had to learn on my own, but it was worth the lesson.

KC: Excellent, you just saved someone some a headache by sharing that story. They'll make sure their constituents are on board and that will most certainly help someone. Have you had a mentor or even a book-mentor that has guided you as a leader?

BS: Yes, I've had a lot of guidance from friends, family, and colleagues, you know, you get little nudges along the way, like a ball rolling down the road. One that stands out to me is a gentleman named Gary Oakerland, he was an urban design professor at UVA and as I stepped into planning my graduate degree I came in with a very technical mindset. Numbers and engineering, if the two lines weren't equal they weren't parallel, that kind of stuff. And he offered a different way of looking at things, a more conceptual view. What that did challenged me. You know you take a road or street map and every curve or turn is the true road, but when you look at a subway map you're not going to be able to capture every turn in the route and on the line. What he did is help me understand how that relates how people look at the maps, how they understand where they're going, and how to communicate ideas to people. It's a longer conversation but he helped me learn how to take that data driven information and make it more easily digestible, for example when you take ridership numbers, just data, and how you can convert that data into something you can better communicate to whomever your audience is.

Another aspect to leadership is how we present ourselves and ideas. I have another person who was a mentor. A guy name Whit Blanton from my consulting years. He taught me that it is not about prepping for a presentation, it's about knowing your material. The better you know your stuff, the better you can present and engage your audience. My audience these days might be a board or a group of coach operators. This guy could go into a meeting and blow away everyone with his knowledge, and how he connected with the audience. To this day I still strive to make that level of connection with my constituents.

KC: What do you think every leader needs to know?

BS: Wow I don't know if I've even filled in my toolbox to even know what every leadership position should have, but mine is the ability to know yourself and where your strengths and weaknesses are. As you know for me – very technical, very project, very task oriented. I think knowing where you are and who you are, if you're able to surround yourself and build your core network with whatever staff to help compliment you so you can be a stronger team, I think a leader needs to understand that. You can't be a leader unless you know where you need to build up your support from others, and how you can support others, and vice-versa. I think that's the #1 thing that I will look at going into any leadership position in the future was going forward, looking into how I fit into the puzzle.

KC: So I was going to ask what advice you would give to someone new to leadership.

BS: Well, the first advice I would say is jump in feet forward. It's like having kids; nobody ever thinks they're ready. You never feel 100% ready to jump into a leadership role; you're worried you won't know everything that you'll have to know. If you know you want to be a leader, I would advise you dive into it all the way, bring people along the way with you, and as you learn, you become stronger. I think some people want to build up enough experience or don't feel quite ready, all those excuses you make for yourself before you pull the trigger, but the worst thing that would happen is you make a mistake, and when you do that, you own up to it and you move on.

KC: What role do you think that culture plays in a transit organization?

BS: I think transit has multiple cultures, that's something I've learned, not just from what y'all had to offer in the class (Eno) I took, but even before the class, understanding what that meant to an organization. It's probably one of the understated aspects of leading your organization. It's not just telling people to be safer, it's creating a culture of safety. If you lay an electrical cord down a hallway, it doesn't matter if you're a receptionist or in a management position or you're in maintenance, you should see that cord and think, "someone's going to trip on that," and that's a culture reaction. And you can have many cultures in an agency. A culture of safety, a culture of family, a culture of listening, it depends on the organization and what that organization's needs are. In the past year, I've understood that more, it's more than a mission statement or a goal. If an employee can't instinctively react in that cultural context, then they're not getting it. And as a leader, you need to instill that culture into your organization and your people. That's definitely, I think it's about the only way you get people inspired because again it becomes who they are. When they walk in the door to do their job it's part of who they are.

KC: Brad I can't add anymore to that than what you've said. I think it'll help anyone who reads it and I appreciate your time and your expertise.

BS: You're welcome! I would add just a little bit, in reading the other blogs and stuff one interesting aspect to what you're doing is there's only a handful of big leadership positions in the transit industry, we've got WMATA's and things like that. But the transit system is made up of lots of smaller systems, and the leadership positions they have are very different. Those positions are saturated with so many responsibilities. In a big agency they get to delegate some of the responsibilities and some of the leadership. I think it's important for people becoming stronger leaders, you go back to the strategic vs. tactical, and the people in those smaller organizations can struggle a bit more than those in larger organizations, because they have to wear a lot of hats. I think why this is important, because it bridges that gap and shares different thoughts on leadership, it spreads the knowledge that can help those in the industry.

KC: And that's exactly why I wanted you to be a part of this. I think your insights are so valuable because of the different perspective and I appreciate so much you sharing your time.

BS: You're welcome.

KC: By the way what's with the Storm Trooper outfit?

BS: It's Halloween! Who doesn't love Star Wars!

Final Thoughts From Insight Strategies

We met Brad originally at the Eno Center for Transportation Transit Senior Executive Program. He had self-enrolled in order to continue his development as a leader. A testament to his character. I had the pleasure of having him in what we call our Insight Group. His manner was thoughtful, wise with a big dose of humor and humility. In no time he was being asked his perspectives on all manner of concerns by our small group and the entire cadre of up and coming leaders. He was gracious with his time to all and to my thinking epitomized the gracious leader and continuos learner. He is a teacher and his lessons can serve all who might listen

Kevin Catlin

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