From early role models to boardroom leadership, Pivot team member Chelsea Grayson explains what shaped her journey.
Q: Who or what has had the biggest influence on your career path?
CAG: A huge influence at every stage has been seeing someone doing what I aspired to do—someone whose example felt real and attainable. As a lawyer, that meant seeing people from humble beginnings and women with families make partner at “Big Law.” Later, I looked to lawyers who moved into CEO roles; those examples were harder to find, but they exist—some are even women.
Finding models was toughest when I decided to make a career of board service. Directors tend to be private, and some sit on only one board while keeping an operator role—not the path I wanted. The key was meeting people who’d built full-time board careers, which you usually can’t do until you’re already in those circles. Very chicken-and-egg. Fortunately, I found early examples in my network and proved both my worth and sincerity to them.
Q: What advice would you give to someone starting in your field?
CAG: Whatever the field, get proper training early—preferably on your employer’s dime. Learn how to write, present, stay organized, manage your calendar, and communicate professionally. Know when to pick up the phone instead of sending an email. These basics set you apart the from the many people who came up in non-traditional environments that encouraged entrepreneurialism over formal professionalism. We all have to walk before we run—bad habits early on will trip you up later.
Q: How do you approach challenges or setbacks in your work?
CAG: I keep my eyes on the horizon and keep moving—no panicking or getting stuck. Remember, it’s just a moment in time, and you’ll recover if you stay steady. Make the apologies you owe, but not for someone else’s mistake. Often, what happened matters less than the story told about it later. If you can tell your own narrative clearly and consistently, you can turn a stumble into part of your personal history and journey.
Q: What’s something about Pivot you think more people should know?
CAG: The core group of us has been working together on tough, complicated matters for decades. That history has built trust and “muscle memory” that’s rare today. We deal with each other using a kind of shorthand that saves clients time and learning curve. Each of us has seen whatever a client brings to us many times—and usually together—so we can draw on shared experience to deliver more efficient, effective and seasoned advice than our competitors. This core competency makes up the DNA of Pivot.
Q: What’s your go-to productivity hack or morning routine?
CAG: I schedule daily fitness just like a meeting. It balances hormones, clears the mind, and builds stamina needed to handle the high-level engagements we work on at Pivot. Also, if I’m running a meeting, it starts and ends on time so that all the attendees (including me) can get to the next thing on the calendar on time. That discipline has earned me more than a few Chair roles. I get Wi-Fi on flights and use that time to catch up on email and LinkedIn. And I rarely do breakfast, lunch, or dinner meetings—too much time lost in transit, small talk, and ordering. Let’s get in a conference room or on Zoom and get to work!