Robert H. Flynn

Flynn Law Firm, P.C.

1042 North El Camino Real
Natick, Massachusetts 01760


Accident, Construction, Employment, Inheritance Disputes, Medical Malpractice, Nursing Home, Partnership Disputes, Personal Injury, Real Estate

Attorney Robert H. Flynn provides Alternative Dispute Resolution (ADR) services to other lawyers, including arbitration, mediation and neutral evaluation.  Bob Flynn has served lawyers and their clients for fifteen years as a mediator and arbitrator in real estate cases, construction cases, partnership disputes, serious injury and death cases, business disputes, employment cases, contract and commercial disputes, insurance and business bad faith and 93A claims serving as a neutral in these types of cases. Bob Flynn brings more than 40 years of experience preparing, trying, arbitrating, mediating, negotiating and settling these types of cases for insurers, self-insurers and claimants.

Profession: Mediator & arbitrator, acting as a neutral in the following cases and claims:

  • Real estate, buyers, sellers, agents and brokers disputes
  • Lease, commercial and residential, HOA and condominium disputes
  • Partnership and trust disputes
  • Construction disputes between owners, generals, suppliers, subs and professionals
  • Insurance, bad faith and insurance coverage disputes
  • Accident, tort, negligence, product liability, construction, transportation, aviation and maritime cases
  • Professional negligence including legal, accounting, engineering, nursing home and assisted living, medical and dental malpractice claims
  • Employment cases
  • Error and omission cases including architects, engineers, insurance and real estate broker cases
  • Business, commercial and contract cases

Experience: Fifteen years as a neutral in dispute resolution: mediation, arbitration and discovery master. Court appointed in Suffolk, Worcester and Middlesex Counties in Massachusetts as an arbitrator and discovery master. Formerly, on American Arbitration Association panels. Decades of experience preparing, trying and settling civil cases for insurers, defendants and claimants. Fifteen appellate cases before the United States Court of Appeals, 1st Circuit; the Massachusetts Supreme Judicial Court; the Massachusetts Appeals Court and  one Application for Certiorari to the United States Supreme Court. Practical trial experience and a skill at listening and seeing where to build agreement is the key to guiding parties to case resolution.

  • AV rated Martindale Hubbell
  • Super Lawyer Designation 2011- 2014
  • Perfect 10 rating AVVO

Professional History: Trial lawyer representing insurers and claimants in real estate, construction, professional, employment, tort and insurance cases since 1973.

  • Coast to Coast ADR, 2014 – present, Principal
  • Flynn Law Firm, P.C., 2002 – present, Principal (MA only)
  • Fay, Flynn & Fay, P.C., 1982 – 2002, Partner
  • Hale, Sanderson, Byrnes & Morton, 1973 – 1982, Associate and Partner

Bar Admissions:  Supreme Judicial Court, Commonwealth of Massachusetts, 1973; United States District Court, Massachusetts, 1975;  United States Court of Appeals, First Circuit, 1977; United States Supreme Court, 1995.

Professional Associations: American Bar Association (past TIPS Committee Chair); Massachusetts Bar Association; Boston Bar Association; San Diego County Bar Association; North County Bar Association; Formerly member of the following: Defense Research Institute (past Committee Chair); International Association of Defense Counsel; Professional Liability Underwriters Association; Massachusetts Defense Lawyers Association; Norfolk Bar Association; Metro West Bar Association; American Association for Justice; Massachusetts Academy of Trial Attorneys; and Transportation Lawyers Association.

Education: Boston College, AB, History, 1970; Boston College Law School, JD, 1973; Staff, Boston College Industrial & Commercial Law Review.

Publications, Appellate Experience and Speaking Engagements: “Essential Litigation Skills for Massachusetts Paralegals”, Institute for Paralegal Education, 2003, 2004; “The Legal Investigator as a Witness,” THE LEGAL INVESTIGATOR, August, 2000; “Organizing the Defense File,” THE PRACTICAL LITIGATOR, July, 1995; Speaker and Chair various seminars, programs and presentations at ABA Annual Meetings (TIPS), at DRI Annual Meetings and at local meetings and conferences including MATA and the Massachusetts Licensed Private Detective Association.

Community Activities:

  • Director, Northeast Accessible Golf Association (Past Chairman, Board of Directors)
  • Host, “Talking about the Law”, weekly on WCRN, Radio 830 AM
  • Wellesley Little League Parent, Coach, Manager and President
  • Town of Wellesley, Town Meeting Member for many years; Affordable Housing Committee member; Town Finance or Advisory Committee member

Experienced. Prompt. Effective.

What is Mediation/Arbitration?


A mediator’s goal is to help disputing parties arrive at an agreement. A mediator is a skilled neutral; someone vested in seeing the matter resolved by way of settlement. A mediator’s methodology ranges from the facilitative to the evaluative or judgmental ends of the spectrum. A skilled mediator does not impose the mediator’s views, particularly at the outset; a skilled mediator facilitates the parties’ examination of their own cases, their own exposures, risks and likely outcomes absent a settlement. A skilled mediator guides the parties towards  consensus, letting the parties achieve settlement, reserving more evaluative comments for the end of a stymied mediation. Mediation offers the parties a great deal of control over the venue, the process, the timing, the expense and the final outcome.

See Mediation Fees


Arbitration is at the other end of the spectrum from mediation. Once the parties agree to arbitrate a matter, they have left the decision making in the hands of a third party, an arbitrator in a multi-arbitrator panel or three arbitrators. An arbitrator acts as a judge and jury, making findings of fact and rulings of law, and reading a decision.

See Arbitration Fees

Neutral Evaluation

A neutral evaluation, like mediation, is non-binding but, in a sense, is a bit like arbitration if both parties agree to do it. Both parties submit materials simply by a representation of what each witness would say to the arbitrator and can actually submit testimony by deposition, affidavit or in person if credibility is thought to be an issue, and the neutral is then asked to evaluate the realistically likely outcomes. The parties and the evaluator can structure the process to their liking. The parties can request a suggested settlement figure, a range of numbers from least likely to most likely found, no commentary on liability or damages, or some commentary on liability and damages, as the parties choose.

Mock Jury

A mock jury can be conducted with six to twelve jurors to represent a typical jury panel with a one day, soup to nuts, presentation of each side’s case, followed by an hour or so of deliberation, a vote and a Q&A with the jurors and neutral who acts as a judge. This is a solid way for a plaintiff and defendant to test their case, see what holes might exist, what strengths exist and what the realistic outcome ranges are.

P: 781-239-1005
E: [email protected]