When you work in-house for many years, it can be easy to forget about the networks you have from school or previous jobs, but these are all important connections to maintain. Staying in touch with people outside of work is critical — a great reason to serve on boards, do nonprofit work and join extracurricular clubs.
The important thing, Reg says, is: “You want to be the first person on someone’s mind for an opportunity. You can be really good at what you do, but if you do not have the network, then you are stuck. Get involved outside of work and build that network so you will be the one who gets called when there is an opportunity.”
Reg stressed the importance of thinking systematically to keep your networks fresh by having regular tasks built into your routine. In his case, he spends an hour every Friday calling people in his network just to catch up. The consummate career person, he gets a lot of this kind of “work” done when he is on vacation and has more time to catch up with old friends and colleagues.
You need a cabinet, and you have to build it yourself
One of the reasons networking is so critical is because being an in-house general counsel can be lonely. You have to proactively build a team of advisers from your network, people to bounce ideas off, and that means keeping in touch with colleagues from previous positions — a continuous theme throughout Reg’s career.
Having a cabinet of advisers doesn’t just give you experienced people to bounce ideas off, it also gives you the exposure you need to continue to grow your career. Reg refers to assembling this team of advisers as “creating your own kitchen cabinet” and says it’s an important element of professional growth and mobility. Saying yes to relationship building and fostering the relationships you already have positions you to meet the right people to add to your cabinet as you move through your career.
For this reason, Reg says, as you are rising to the role of general counsel, it is important to be consistently available. “When someone asks you to go to an event or attend a board dinner, the answer is always yes,” he says. “Those in the know want to meet and develop the next generation of talent.”
Do not compromise on what you are worth
One of the biggest risks you take if you are not actively out there cultivating connections is getting stuck in a comfortable corporate world where you do not take risks.
At one point in his career, Reg learned of an in-house role at a financial services firm, but the offered compensation range was below what his experience and skill level could command in the market. Although the job was attractive, he took a risk and said no. In the end, holding out for what he was worth paid off, as ultimately, the company came back with a higher offer.
“It is really important to know what you are worth,” he says. “And not be afraid to say it.” This means being willing to walk away from subpar offers. That first “no” allowed Reg to hold out for a better title and bigger portfolio.
How you show up in crisis is everything
Reg has made a name for himself as a “crisis person” since his days at the White House. When clients come to him, it is typically to get out of a bind or navigate a high-stakes situation. Early on, he learned the importance of having a cool head while handling crises in the moment. “I had to make a lot of decisions without having perfect information,” he says.
Throughout his career, he has advised many CEOs across different sectors on how to navigate messy situations. This skill was especially valuable as he was under consideration for service on the board of Blackstone. In particular, his background in regulatory matters made him valuable as a board member, and his advice for those on the path to general counsel is this: “Do not sell yourself short on what skills you bring to the table.”
During the Florida recount in 2020, Reg was deputy general counsel to the governor. He remembers vividly how leaders on all sides of the crisis displayed varying reactions. The one that stood out most clearly to Reg was the senior law firm partner who, despite the demanding days and long nights the work required, made his own health and well-being a priority — hitting the treadmill in the middle of a crisis. For Reg, the takeaway was this: in order to be successful, you need to know what you can delegate to other people so you can take care of yourself. He says of his colleague, “He knew he needed to stay active, and I took that as a lesson in being a good people manager. He did the macro things and let other people do the micro things.”
Pay attention to new technologies and trends
Law school teaches you how to think and communicate like a lawyer, but it does not always effectively prepare you for the current landscape, which inherently includes a lot of advancements in technology, notably including AI. Companies of all kinds are currently investing in AI and scrutinizing how they can use their existing data to capitalize on the new technology possibilities.
For deputy general counsels, this is an opportunity to get ahead of an evolving trend. As Reg noted in his talk, AI and other emerging technology trends have the ability to disrupt the practice of law and other industries, but they also present a fantastic opportunity for young lawyers to become leaders in this space. He said, “Raise your hand, volunteer, ask to be sent to advanced courses and become the expert, creating a need for your skill set.” Pointedly, he also noted, “The worst thing you can do is remain static.”
Draft your resignation letter long before you need it
One of the most poignant pieces of advice from Reg’s breakfast dialog was about the importance of imagining your eventual resignation ahead of time. His advice: “Think about what you want people to know you accomplished while in the role. What do you want your farewell letter to say? What do you want people to remember about you, in terms of integrity?” His future-planning exercise can serve as a blueprint for your current actions.
At this point in his career, Reg has assisted leading institutions and high-profile individual clients with more than 150 congressional inquiries and hearings, and many other regulatory inquiries. He has carved out a pretty remarkable place for himself in the canon of regulatory, enforcement and reputational matters for high-profile clients, including banks, hedge funds, asset managers, private equity and venture firms, energy companies, technology and social media firms, healthcare institutions and government contractors, as well as individual CEOs and high-ranking public officials. It is safe to say his resignation letter would be impeccable.
But as Reg humbly phrases it, “I would like to say my journey was planned, but serendipity was the plan. It all worked out.”