Howard served as an attorney in the City of Newton Law Department from 1970 through 1978. He was the Assistant City Solicitor (1970 to 1973), and the City Solicitor, responsible for all legal matters for all City Departments, Agencies and Officials, from 1973 to 1978. While City Solicitor, Howard was an active member and regional officer of the National Institute of Municipal Law Officers (NIMLO), Chairman of various of its Committees, and a contributor and participant in its national seminars and publications.
From 1966 to 1968, Howard served as an officer in the United States Army. He served in the Republic of South Vietnam from August, 1967 through August, 1968 for which he was awarded the Bronze Star Medal.
In 2002, Howard resigned as a K&L Gates Partner and he became Of Counsel so that he could accept an appointment as an Adjunct Professor of Law at Boston College School of Law. Howard continues to teach Real Estate Development and Finance and Local Government Law at the Law School. He also supervises Independent Study Programs in Real Estate Development and Finance, and in Municipal and Local Government Law.