Allison Cannella is Senior Vice President and General Counsel at the largest private owner and operator of wireless communications infrastructure in the United States, where she leads legal, regulatory, risk and compliance for operations across the country. Allison stepped into the General Counsel position in February 2024, at a company that was in a period of significant growth.
Over fifteen years of practice, Allison has been involved in negotiating and closing more than thirty billion dollars in real estate, corporate, and strategic transactions. Allison combines strong commercial and business acumen with legal judgment to close deals quickly while managing risk appropriately.
Allison has approached the General Counsel role with an emphasis on authenticity and humility as she has built out the company’s legal function. She leads not from behind a title, but by showing up as herself; a quality that has helped her foster a culture that develops, lifts, and engages employees.
Allison earned both her Juris Doctor and her undergraduate degrees from the University of Florida.
What is your typical day, and how do you make it productive?
As a working mom of three, no two days look the same. My grandmother used to say, “You can’t get done in a day what you can get done in a morning,” and I live by that advice. My days are noticeably better and more productive when I stick to my morning routine. I wake up early and start each day with at least 30 minutes of meditation, journaling, and a gratitude practice. I also try to fit in at least 30 minutes of exercise before the morning rush of getting kids ready and out the door. I’m typically in the office by 9 a.m. and rely heavily on my calendar. Early in my career, I took a time management course that taught me a valuable lesson: respect your calendar. Everything gets scheduled, including focus time and personal commitments. If a meeting runs over, I excuse myself. If someone drops by during blocked time, I ask them to schedule time later. I’ve found that once you stop protecting your calendar, every other commitment starts to suffer. Evenings are reserved for family time, along with the usual chauffeur duties that come with having a child involved in sports. It’s a full life, but having structure, routines, and clear priorities helps me stay present and productive both personally and professionally.
How do you bring ideas to life?
For most of my life, I brought ideas to life the same way I approached everything else: set a goal, create a plan, and work relentlessly until it was accomplished. As a classic Type A personality, I became very good at checking boxes. Give me a list, and I will make sure every single box gets checked. More recently, I’ve shifted my approach. Instead of forcing an idea into existence through sheer will, I try to visualize it and then let it be. It sounds a little “woo-woo,” I know, and my younger, list-loving self would have rolled her eyes at me, but I’ve learned that not every idea needs to be forced or controlled. I still think big and work hard, but I spend more time getting clear on what I want and less time obsessing over exactly how it will happen. I’ve found that my best ideas emerge in quiet moments, not from a spreadsheet or a to-do list. Once I have clarity, I put energy behind the idea, take action, and trust the process. Ironically, giving ideas room to breathe has often been more effective than trying to force them across the finish line.
What’s one trend that excites you?
People seem to be putting self-care and wellness first more than ever. Burnout is no longer a badge of honor. I feel like there’s a real understanding that a healthy mind, body, and spirit isn’t separate from success; it’s actually what drives it. Take care of yourself first, and the rest follows.
What is one habit that helps you be productive?
Saying No! If its not a heck yes, it’s a no. I have been so much better about ruthlessly guarding my time, declining meetings that don’t need me and saying no to both personal and professional obligations that are not my highest and best use.
What advice would you give your younger self?
Your authentic self is your superpower. Stop trying to polish it away. For years, I thought success meant fitting a mold: being buttoned-up, guarded, saying the “right” thing. What I’ve learned is the opposite is true. People do business with people they like and trust, and you can’t build real trust being someone you’re not. Stop editing yourself down to seem more palatable. Bring your full self to the table. Your humor, your convictions, even your quirks, because that’s exactly what makes people want to work with you, and it’s what makes the work sustainable over an entire career.
Tell us something you believe almost nobody agrees with you on?
Hard work isn’t actually the key to success. I was raised to believe I could outwork anyone, and honestly, I still believe that’s true. But over the course of my career, I’ve learned that working smarter, not harder, matters far more than sheer hours logged. What’s made me successful as a c-suite executive isn’t that I grind the longest; it’s that I’m efficient. I know how to prioritize what actually matters and execute on it. I’ve watched so many talented people spin their wheels or over analyze, mistaking motion for progress. The people logging the most hours aren’t necessarily the ones who rise to the top. The people who know exactly where to spend their time and energy are.
What is the one thing you repeatedly do and recommend everyone else do?
Pay attention to what fuels your energy and what drains it. In your career, when you’re working on something that genuinely excites you, it stops feeling like a job and starts feeling exhilarating. You naturally bring more creativity, resilience, and enthusiasm to the table. The same is true in your personal life. Surround yourself with people, activities, and commitments that energize rather than deplete you. Whenever I’m faced with a new opportunity or decision, I pay close attention to how it feels. If it gives me energy, I lean in. If it consistently leaves me drained, I take a step back and ask what needs to change. This doesn’t mean avoiding hard things. Some of the most worthwhile pursuits in life are hard. It simply means being honest about what’s worth the hard. I’ve found that following what energizes me has been one of the best guides for making career and personal decisions, while staying fulfilled over the long term.
When you feel overwhelmed or unfocused, what do you do?
My first step is to slow down and reconnect with myself. I’ve learned that stress can easily pull us into fear, worry, or worst-case scenarios, which rarely lead to good decisions. Instead of immediately reacting, I pause, get quiet, take a deep breath and reconnect with what I know to be true. I’ve found that clarity, peace, and focus come from looking inward rather than outward. Outside opinions, judgments, and noise are often just reflections of other people’s fears, experiences, and expectations. While feedback can be valuable, I’ve learned that not all voices deserve equal weight. The faster I can tune out the noise and reconnect with what I know to be true, the more grounded, confident, and effective I become.
What is one strategy that has helped you grow your business or advance in your career?
Become a genuine champion for the success of others. The best way to grow your power is to give it away. Early in my career, I was often intimidated by people who seemed smarter, more experienced, or more accomplished than I was. As I moved into leadership roles, however, I realized my success wasn’t dependent on being the smartest person in the room. It came from surrounding myself with talented people, empowering them to succeed, and creating an environment where they could thrive. The stronger my team became, the stronger our results became, and ultimately, the more successful I became. That shift in mindset changed everything. Rather than comparing myself to others, I began seeking out people who would challenge me, teach me, and bring strengths that complemented my own. Over time, that philosophy expanded beyond my team. I’ve found that approaching others (even my competitors) from a mindset of abundance rather than scarcity creates more opportunities for learning, growth, and success. When someone does something better than I do, I see it as an opportunity to learn, not a threat.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
For a long time, I would have said I hadn’t experienced many meaningful failures. Then someone I trust challenged me with a simple observation: “If you’re not failing, you’re playing it too safe.” That made me realize that my biggest failure wasn’t a specific event. It was staying too comfortable and not pushing my own boundaries enough. Since then, I’ve intentionally taken bigger risks, pursued bigger goals, and stepped into situations where failure was a real possibility. The interesting thing is that I’ve failed more often, but I’ve also grown more than ever before.
What is one business idea you’re willing to give away to our readers?
This is a tough one. If I come up with a truly great business idea, I’m probably going to keep it and build it myself! But broadly speaking, I believe the next wave of successful businesses will be focused on helping people reclaim time through automation and AI.
What is one piece of software that helps you be productive? How do you use it?
It’s probably cliché at this point, but I’ve fully embraced AI in both my professional and personal life. I often describe it as the equivalent of having a talented junior associate and personal assistant available at any time. It helps me quickly analyze and synthesize information and draft communications, contracts, and presentations. I also now use it to build underwriting models in Excel for my real estate projects, which takes minutes, saving hours of manual work. Personally, it has been just as transformative. AI has become my primary tool for meal planning and grocery lists, coordinating family schedules, planning travel and vacations, and creating workout plans and routines.
What is the best $100 you recently spent? What and why?
The best $100 I’ve spent recently wasn’t on a single purchase, but on a collection of small investments in my health and well-being. As a working mom, I’ve come to realize that my mental, physical, and spiritual health directly impact my effectiveness in every area of my life. Lately I’ve been very focused on strength training and increasing my protein intake. I supplement my diet with protein bars and shakes that allow me to hit my protein goals (where it used to feel impossible!) I see a wellness doctor that prescribes me peptides and vitamins that are tailored to my wellness goals. My husband and I are also big fans of Tonal. I’ve tried just about every workout class and fitness trend out there, and I’ve found nothing more efficient than a 25 to 30-minute weight lifting routine on the Tonal that I can do in my house. I also subscribe to the Waking Up meditation app, which has become an important part of staying grounded and focused.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
My favorite books are Wishes Fulfilled by Wayne Dyer, A New Earth by Eckhart Tolle, and Big Magic by Elizabeth Gilbert. Each challenges you to think differently about purpose, mindset, creativity, and how you show up in the world. I also enjoyed The 7 Rules of Power by Jeffrey Pfeffer and Good to Great by Jim Collins. Both offer valuable insights into leadership, influence, organizational success, and what separates high-performing individuals and companies from the rest. And purely for pleasure, I recently read Theo of Golden and absolutely loved it.
What’s a movie or series you recently enjoyed and why?
Lately, my biggest TV obsession has been cooking competition shows. Give me Bobby Flay, Tournament of Champions, Top Chef… all of it. Maybe it’s because I’m a horrible cook and enjoy watching people accomplish things I could never do. Bobby Flay, if you’re reading this, let’s discuss a mentorship opportunity. 😉
Key learnings
- Wellness is not separate from success. Sustainable success is driven by a strong foundation of mental, physical, and spiritual well-being, rather than burnout.
- Authenticity builds trust and stronger professional relationships more effectively than trying to conform to a predetermined mold.
- Follow what fuels your energy. The work, opportunities, and relationships that genuinely excite you are often where you’ll have the greatest impact, fulfillment, and long-term success and are usually worth the hard work they require.
- The greatest clarity, confidence, and effectiveness come from looking inward. Tune out the noise and outside opinions and trust your inner wisdom. True clarity comes from within, not from external validation.
- The best way to grow your power is to give it away. The strongest leaders grow their influence by investing in and championing the success of others.