Name: Alessandra L. Simons

Category: Law Firm: Thought Leadership

Firm/Company: Goodwin Procter

Title: Partner

Time in Position: Since 2016

What was your route to the top?

After figuring out I wasn't going to be a doctor, I entered the legal world where I became very well-versed in large and sophisticated M&A transactions, both buy and sell side. I joined Goodwin in 2014 and my practice has since expanded to include a variety of transactional work. I still do large M&A deals regularly—that's my bread and butter—but I've developed significant experience counseling startups, venture firms and family offices.

My days often include a board meeting in the morning, marking up secondary documents around lunch and negotiating an acquisition in the afternoon. Add in an appointment for one of my kids, a Women's Initiative meeting, identifying a CEO for a HimforHer dinner and grabbing coffee with a friend and then drinks with a client.

What keeps you up at night? 

Because of the 24/7 nature of my transactional practice, my work literally keeps me up at night. The hardest, yet most rewarding, part of my job is managing personalities on multiple sides of a deal, all of whom want to see a successful outcome but may view the business or legal issues from a different angle. My job is a lot like playing poker where reading the table is important. Beyond that, I spend a lot of time thinking about the development of my team and what I can do to advance their careers and lives.

What is the best leadership advice you've given, or received, and why do you think it was effective?

Share yourself with your team. Encourage them to do the same. Letting people see your emotions, your struggles, your successes, your life brings them closer to you. It is a risk to share yourself with others—it requires you to trust them with those parts of you. That trust is a huge responsibility. In turn, I practice and preach work-life integration. I want my team to tell me when they have a date, need a night off, don't feel well, had a great win or are frustrated with me. If we share our lives with each other, then we can cover for each other, care for each other, and teach and learn from each other. I will make sure they get to their date, get the night off, get sent home with some chicken soup, celebrate with a glass of champagne or two or listen and learn from their frustration. But I can't do that unless they tell me. And they won't tell me unless I tell them.

Looking back, what do you wish you had known when you started out in the legal profession?

Just because you are good at something doesn't mean you want to do it for the rest of your life. Growing up, I was good at math and science, so I went to Johns Hopkins. Turns out I don't actually enjoy math and science; I just happened to be good at them. My best classes in law school were litigation-focused; but turns out I don't enjoy reading case law and writing briefs. I happened into transactional work through a summer associate assignment that I enjoyed. When you enjoy the work, you'll do it enough to become good at it.

What is the most valuable career advice anyone has ever given you?

The best advice I've received is to spend time learning to do your craft the right way. Become an expert in doing one thing exceptionally well, at a world-class level, before branching into other areas. I'll always be grateful for the way I was "classically trained" to do M&A, but I've also learned to adapt to the times and the needs of clients today. In addition, at Goodwin, there is a very clear pragmatic business approach to practicing law, and that has guided me well. I am in many ways more business person than lawyer—this makes me far more valuable to my clients than my classical training alone could afford me.