Stewart  is a highly experienced business development and executive/leadership coach, specializing in helping lawyers—both in firms and in-house—build long-term, trust-based relationships. With an intuitive and practical approach, Stewart has been coaching lawyers since 1994, guiding them to achieve their goals in ways that feel authentic and natural.

Stewart’s business development coaching with firm lawyers includes tailored strategic and tactical advice, assistance with written and oral communications, creating a business plan, effective cross-marketing, addressing challenges as they arise, networking in one’s comfort zone, and guidance on follow-up actions.  He helps lawyers approach business development in ways that align with their personal style, ensuring they feel confident and not “salesy.”

His practice with in-house lawyers includes helping them enhance their leadership skills, navigate complex relationships, delegate, and communicate effectively with stakeholders, including the c-suite and boards, and career advancement. His coaching addresses real-time challenges such as managing difficult conversations, addressing implicit bias, navigating internal politics, and providing constructive feedback to direct reports. 

His in-coaching often expands into career advancement. He has helped lawyers create Board resumes, evaluate new opportunities, and prepare for interviews.



Stewart has numerous blogs and articles on various topics ranging from networking, being a trusted advisor, becoming a general counsel, executive presence, reducing gender bias, and interviewing.

Before coaching, he was a firm lawyer and then a fractional in-house counsel for about 15 legal departments, from privately held to Fortune 500s, including The TJX Companies, Staples, Welch’s, Cabot Creamery, Dun & Bradstreet subsidiaries, Boston University and others. 

What coaching services do you provide?

I focus on two key areas described above:

1. Business development coaching for partners firms
2. Executive and leadership coaching for in-house lawyers
   

What services do you provide in addition to coaching?

I provide interactive workshops on networking effectively, leveraging referral relationships/internal cross-marketing, creating a business plan and others for firm lawyers, and for both in-house and firm lawyers, executive presence and being a trusted advisor.

What is your coaching philosophy?

My coaching goes beyond achieving typical goals like helping lawyers excel and reach their objectives. I prioritize being genuinely helpful, whether by sharing resources, making introductions, or offering insights. With my clients’ permission, I connect people to foster mutual support and growth. I believe in sharing perspectives, opinions, and information that can be valuable, and my clients appreciate the external viewpoint I bring to their business development and leadership challenges.

What interests or excites you about coaching women lawyers?

The majority of my clients have been women, and I’ve found that women often excel as natural networkers, leaders, and business developers. I enjoy helping them amplify these strengths. I’ve been told that I relate well to women, listen to truly understand, and provide honest feedback—even when it’s difficult to hear—in a way that feels constructive and supportive. I find it deeply rewarding to help women succeed and to be appreciated for my ability to connect, listen, and guide.

Tell us about your training and certifications as a coach.

I was among the first lawyer coaches in the U.S., with over 15 years of experience teaching coaching at the international Refuah Institute. I’ve trained partners to coach associates, marketing teams to coach lawyers (including at the Legal Marketing Association's Annual Meeting), and general counsel to coach their team members. I’ve also led a lawyer coaches’ group for many years. As the lead senior coach for Trusted Advisor Associates LLC, I’ve provided and continue to provide coaching to their clients, grounded in Trusted Advisor principles. My decades of hands-on coaching experience have equipped me with a deep understanding of the unique challenges lawyers face and how to help them thrive.