Why Lawyers Make Exceptional Business Operators: Insights from Helen McGrath

Our 2025 white paper posed the question, “Why are lawyers underrepresented in CEO roles?” The response to the publication was so overwhelmingly positive that the team decided to continue the conversation. We launched an interview series with Heads of Legal and General Counsel to explore what it truly takes to step out of one’s comfort zone and progress up the in-house career ladder. Although these legal leaders offered a wide range of perspectives, common themes emerged throughout their stories: pushing past fear and remaining open to the new and unknown.

In this latest interview in our in-house legal series, we’re joined by Helen McGrath, Head of Global Payment Methods Partnerships Program at Stripe.

Helen highlights that the transition from law into a non‑legal role often brings internal uncertainty, particularly around identity, credibility and the fear of undervaluing years of legal training. The biggest challenge is recalibrating from being the adviser - the person who identifies and frames risk - to becoming the decision‑maker who must weigh competing priorities and act despite ambiguity.

Many lawyers also struggle with the cultural shift away from perfectionism and the instinct to always “be right,” which can hinder their ability to admit knowledge gaps when entering a new domain. To combat this, Helen advises adopting a strong growth mindset, embracing the discomfort of learning, and seeking targeted mentorship from people who excel in specific skills you want to develop.

She also highlights the importance of doing the homework required to articulate how legal strengths, such as negotiation, structured analysis and regulatory understanding, can translate directly into business value. Ultimately, she encourages lawyers to embed themselves deeply within business teams, to shift perceptions from “legal blocker” to “strategic enabler,” making the transition into non‑legal roles far smoother.