Investigations - Training - Consulting


 Experience Expertise Diligence Professionalism

Kevin D. O'Leary

Kevin O’Leary has practiced law for over twenty-five years, focusing on employment and education.  From 1989 until 2002, he was an associate and then a partner in the Labor, Employment and Benefits group at Cummings and Lockwood, a full-service law firm based in Connecticut.  Kevin spent the next 15 years as Associate General Counsel at Dartmouth College, where he was the attorney principally responsible for responding to employment related issues involving the faculty and the staff, as well as focusing on student affairs matters. In addition, he served as an important part of the team that responded to reports of sexual misconduct, including assault, involving students as the reporting and responding parties.  Kevin has experience advising senior leadership on the development of an effective response to critical issues, taking into account the interests of all parties to the dispute and protecting everyone involved. 

Kevin’s practice has always included investigative work of some form. While in private practice this included helping his clients determine the facts necessary to respond to an internal or an external complaint. At Dartmouth College, he assisted in preparing responses to concerns raised by or about employees, faculty members, coaches and students, relying on his own review of facts in dispute.

Kevin now focuses his work on conducting investigations and providing training that allows organizations to effectively respond to allegations of misconduct and proactively train its staff to avoid these behaviors.  Kevin is trained in conducting forensic, trauma informed interviews.  

Throughout his career, Kevin has been involved in preparing for litigation in state and federal courts, before administrative agencies and before arbitrators.  With decades of experience and a deep understanding of how to conduct a balanced, thorough, credible investigation, Kevin is uniquely suited to advise senior leadership on how to respond to complaints about conduct.  His track record of success includes the supervision of high-stakes investigations which produced effective and reliable results.

Kevin is also an experienced trainer in one-on-one and group settings.  He understands how to combine his practical experience and deep knowledge of legal requirements with interesting specifics to engage his audience and deliver a well-received training program.  Kevin began providing sexual harassment prevention training to his private practice clients in the early 1990’s in response to a mandate from the Connecticut Legislature.  When he left private practice to join Dartmouth in 2002, clients trained by Kevin had an impressive record of avoiding sexual harassment complaints in their workplaces and responding to allegations in an effective way.  At Dartmouth, Kevin led training on a variety of topics, including preparation of an employment law primer as part of the  management training program and Title IX compliance training. 

Kevin received his B.A. in Political Science, magna cum laude from Tufts University, and his J.D, with honors, from the University of Connecticut School of Law.  He is admitted to practice in Massachusetts, New Hampshire and Connecticut.  Kevin is a member of the Labor and Employment Sections of the New Hampshire Bar Association and the American Bar Association.   Kevin is also member of the Boston Bar Association College and Universities section and a former member of the National Association of College and University Attorneys.

References, including those from senior leaders at Dartmouth, available upon request.