Each of us, especially those in leadership roles, has had to have difficult conversations along the way. Difficult conversations may need to be conducted with supervisors, colleagues, clients and/or subordinates. Some of us seem to be able to conduct difficult conversations with ease, approaching the task head on and working through it to achieve the desired outcomes. Many of us, however, struggle with difficult conversations. We procrastinate or falter, impeding change. This can result in lack of recognition or advancement, poor morale, poor customer service, lack of trust in teams, diminished financial results, and poor performance. Even when we do have the hard conversations, we may end up with unexpected or undesirable outcomes. Mastering the art of difficult conversations is essential for everyone, whether you are delivering a poor performance review to a staff member or asking for a raise from your boss.

Learning Objectives

  • Recognize what makes some conversations difficult
  • Understand why having a difficult conversation is important
  • Understand different types of difficult conversations
  • Know how to prepare for a difficult conversation
  • Use a structured framework to conduct a conversation
  • Explore different ways to deal with defensive reactions


Mary Antonetti

Tax & Business Services Partner, Marcum LLP

Mary Antonetti is a partner in the Firm’s New Haven office, specializing in tax compliance and consulting services to not-for-profit and healthcare organizations. She has more than 30 years of public accounting experience with national and international firms. Her extensive experience includes for healthcare and other tax-exempt organizations and their for-profit affiliates, including higher education institutions, NGOs, hospital systems, title holding companies, Official Catholic Directory entities, and private foundations.

Ms. Antonetti’s expertise includes consultation on the implications of tax reform, unrelated business income, alternative investments, foreign reporting, joint venture transactions, Section 501(r) of the Internal Revenue Code, restructuring, application for exempt status, IRS audit support, and private inurement issues.

She has also has experience providing middle-market companies with general tax compliance and planning services focused on corporate acquisitions, dispositions and reorganizations of entity structure, including consolidated groups, S-Corporations, and multi-tiered partnerships with domestic and foreign operations.

Charles M. Smith, MBA, CPC, SPHR, SHRM-SCP

President & Co-Founder, OnwardDelta, LLC

Charles M. Smith, MBA, CPC, SPHR, SHRM-SCP, is President and Founder of OnwardDelta, LLC. He provides a variety of management consulting and human capital organizational development services. Charley has provided a broad range of organizational development, business management, human resource management, and operations experience in addition to his public accounting expertise. He has been involved in the management of closely-held businesses for more than 30 years and has held leadership positions in Fortune 100 and large international accounting organizations, including founding and directing a new internal audit department. Lending his expertise in the field, he has written numerous articles on leadership and organizational issues.