# Using AI to Prepare for Difficult Conversations Course SHRM PDCs available Canonical URL: ## Overview No magic wand exists for difficult conversations, but this course comes pretty close. Using Claude and other free, publicly available AI tools as your personal preparation coach, you will learn how to prepare for and navigate the conversations many people avoid, delay, or mishandle at work and in life. Hard conversations do not get easier by waiting. Walking in unprepared, or using language that does not sound like you, can make them more difficult. Whether you are addressing a performance issue, navigating conflict with a peer, delivering feedback to someone who does not receive it well, preparing for a high-stakes conversation with leadership, or working through a difficult situation outside of work, this course provides a clear, step-by-step approach to using AI effectively. You will learn how to prompt AI in a way that reflects your voice, anticipates how others may respond, and allows you to practice before the actual conversation. You will leave with a personalized plan and an approach you can use whenever a difficult conversation arises, whether in the workplace or in everyday situations. ## What you'll learn - Prompt AI effectively to get coaching-level guidance, not generic advice. - Build a personal communication style profile so AI output sounds like you. - Anticipate how the other person is likely to respond in a difficult conversation and prepare for it. - Craft and refine an opening and approach that invites rather than inflames. - Practice live using AI role-play and debrief your own performance. - Leave with a complete, personalized conversation plan for immediate use. ## Curriculum #### Module 1: Why AI? Setting the Stage - The avoidance cycle and what it costs us. - What AI can and cannot do in conversation preparation. - Overview of tools: Claude, ChatGPT, Gemini, and Pi. - The personalization gap and why generic prompts produce generic results. - Your first prompt, including unguided practice and debrief. #### Module 2: Teaching AI Who You Are - The four dimensions of communication style: directness, warmth, formality, and emotional expression. - Building your Communication Style Profile. - Putting your profile to work through before-and-after comparison. - Common profile mistakes and how to fix them. #### Module 3: Teaching AI About the Other Person - Why the other person's profile matters. - Building a Person Profile, including style, triggers, interests, and what makes them receptive. - Using AI to anticipate reactions and stress-test your approach. - Understanding the limits: AI sees only your perspective. #### Module 4: Preparing Your Opening Statement - The three-part anatomy of an effective opener. - Five common opener mistakes and why they backfire. - Drafting multiple versions with AI feedback. - Refining your opener through iteration and peer review. #### Module 5: Practice Mode — Role-Playing with AI - Why practicing a conversation is different from rehearsing a monologue. - Setting up a realistic AI role-play. - Running a five-exchange practice simulation. - Debriefing with AI: what you noticed and what to adjust. #### Module 6: Your Personal Conversation Plan - The six-part Conversation Plan framework. - Building your plan with AI section by section. - Using AI after the conversation through the post-conversation debrief prompt. - Closing reflection and next steps. ## Schedule - Jul 8, 2026 9:00am–4:30pm — Live Online - Sep 9, 2026 9:00am–4:30pm — Live Online ## Instructors ### Tara Taylor — Instructor Tara Taylor, MPA, is a dynamic senior instructional trainer, consultant, and nationally recognized conflict management expert whose 25+ year career has been dedicated to helping leaders, teams, and organizations engage across differences with clarity, courage, and skill. As Managing Director of ADR Vantage, Inc., she leads the firm’s strategic direction while designing and delivering high-impact training, mediation, facilitation, and organizational development services for federal agencies, private sector, and nonprofit clients. Tara’s expertise bridges collaborative problem-solving, government relations, and leadership development with a deep commitment to driving organizational effectiveness efforts that build powerful and positive workplace cultures. She has served clients including the TSA, the U.S. Air Force, NARA, EEOC, DHS, and PepsiCo, equipping managers and employees with practical tools to navigate workplace conflict, strengthen team effectiveness, and lead inclusively. Over the course of her career, she has trained a wide variety of professionals, mediated hundreds of disputes, designed integrated conflict management systems, and created and directed Maryland’s first statewide civil rights government mediation program. A highly engaging facilitator and “Top 10 Speaker” recognized by SHRM, Tara is known for her energetic, interactive training style and her ability to translate complex group dynamics into actionable skills. She has taught mediation, negotiation, and conflict management at the graduate level and authored journal articles on dispute resolution and intergroup dialogue. Whether leading in-person intensives, virtual programs, or multi-day strategic retreats or skills trainings, she creates environments where participants feel challenged, supported, and inspired to grow. Grounded in an M.S. in Public Administration from Wilmington University and a coaching certification from the NeuroLeadership Institute (NLP), Tara brings both systems thinking and human insight to her work. She coaches executives, supervisors, and emerging leaders to build cultures of accountability, inclusion, and resilience. Above all, Tara is driven by a passion for helping workplaces and communities move beyond polarization toward productive, mission-focused conversations, turning conflict into an opportunity for stronger leadership and sustainable results. ### Melinda Ostermeyer — Instructor Melinda Ostermeyer, MSOD, is a nationally respected senior instructional trainer and OD expert whose career reflects more than three decades of advancing excellence in conflict resolution, mediation, team effectiveness, and leadership development. As Director of Programs at ADR Vantage, Inc., she oversees complex organizational initiatives while continuing to deliver high-impact training, facilitation, coaching, and mediation services to leaders and teams navigating high-stakes environments. Melinda’s professional journey is defined by both depth and breadth. She has designed and administered large-scale dispute resolution systems, trained and mentored hundreds of mediators and other professionals, and consulted with U.S. government agencies, international justice systems, NGOs, and private-sector organizations to strengthen leadership, collaboration, and resilience. Earlier in her career, she directed the Multi-Door Dispute Resolution Division of the Superior Court of the District of Columbia and the Dispute Resolution Centers of Houston, Texas, training and evaluating the performance of hundreds of mediators and shaping programs that handled complex civil, family, workplace, and probate matters while setting standards for mediator performance and accountability. She has also consulted with the justice systems of more than a dozen countries, establishing mediation programs and training, mentoring, and evaluating the performance of their mediators. A gifted educator, Melinda has taught graduate-level mediation, negotiation, and conflict resolution courses and has served as a senior advisor and program manager supporting global organizational resilience efforts. What distinguishes Melinda is her ability to translate complex human dynamics into clear, actionable skills. Whether guiding leaders through tough conversations, equipping managers to mediate workplace disputes, or helping teams rebuild trust and alignment, she creates learning experiences that are grounded, practical, and transformative. Her work empowers individuals and organizations not only to resolve conflict, but to harness it as a catalyst for clarity, growth, and sustained performance. Her academic foundation, an M.S. in Organization Development from Johns Hopkins University and an Executive Coaching certification from Georgetown University, anchors her work in rigorous theory and practical application. ### Becky Bell — Instructor Becky Bell, Ph.D., is an accomplished organizational development and conflict management consultant with more than 25 years of experience as a mediator, facilitator, trainer, coach, and nationally recognized speaker. A passionate advocate for conflict transformation, Becky designs and delivers engaging, results-oriented experiences that help individuals and organizations move from tension to collaboration, and from impasse to productive action. As a senior practitioner for ADR Vantage, she provides consultation, mediation, coaching, and customized training services focused on strengthening workplace relationships and enhancing leadership effectiveness. Becky specializes in helping organizations manage complex workplace challenges while building the communication and conflict resolution skills necessary for long-term success. Her approach integrates rigorous academic theory with decades of practical experience—ensuring that her clients benefit from both conceptual depth and actionable strategies. Becky previously served as a Mediator and Senior Alternative Dispute Resolution (ADR) Specialist for the U.S. Department of Agriculture, where she was a trusted advisor to senior leadership on ADR strategy, interpersonal communication, team development, and leadership transition. In that role, she delivered comprehensive training programs, provided conflict coaching, mediated disputes nationwide, and guided organizational leaders in strengthening employee engagement and collaboration. She also served as an Equal Employment Opportunity (EEO) Program Manager for both SRA International (supporting the Department of Homeland Security) and the U.S. Air Force, where she developed and managed programs designed to improve employee relationships, accountability, and workplace culture. A retired Air Force officer with numerous awards and commendations, Becky brings disciplined leadership and mission focus to her work. She is a sought-after conference presenter, having delivered sessions at national forums including the EEOC’s EXCEL Conference, the Association for Conflict Resolution (ACR) National Conference, Blacks in Government (BIG) National Training Conference, League of United Latin American Citizens (LULAC), Federally Employed Women (FEW), and Federal Asian Federal Asian Pacific American Council (FAPAC). She holds a Ph.D. in Conflict Analysis and Resolution from Nova Southeastern University, along with advanced degrees in Human Resources Development and Liberal Arts. Certified in mediation and conflict coaching, she is known for her dynamic presence, practical wisdom, and unwavering commitment to helping organizations build cultures where conflict is addressed constructively and leadership thrives. ### Rick Buccheri — Instructor Rick Buccheri, MSOD, is a collaborative strategist, mediator, facilitator, and organizational development consultant with nearly two decades of experience helping leaders and teams navigate complex change, resolve conflict, and strengthen organizational culture. Known for his steady presence and systems-level thinking, Rick partners with passionate stakeholders to improve communication, enhance performance, and align strategy with day-to-day operations. As a senior practitioner with ADR Vantage, Rick has provided conflict management, culture transformation, and strategic planning services to more than 15 federal agencies. He has worked with leaders at every level, from frontline supervisors to executive teams, designing and facilitating initiatives that address deeply rooted cultural patterns, operational barriers, and organizational redesign. Rick has mediated complex workplace and EEO disputes for agencies including the Transportation Security Administration (TSA), Federal Reserve Board (FRB), and U.S. Secret Service (USSS), often in high-stakes environments involving union representation and formal grievance processes. He played a key role in piloting TSA’s agency-wide mediation program, providing advanced skills training, mentorship, and performance evaluation to mediators who now support more than 1,300 cases annually. His mediation work has contributed to improved relationships, reduced grievance filings, and strengthened workplace trust. In addition to his mediation practice, Rick designs and facilitates cultural and climate assessments, leadership development programs, executive retreats, and enterprise-wide transformation efforts. His recent work includes leading large-scale organizational redesign initiatives, facilitating executive alignment sessions, and delivering advanced training to thousands of federal employees. He has also served as an adjunct instructor at American University, mentoring graduate students in applied organizational consulting. Rick holds an M.S. in Organizational Development from American University. He is a certified conflict coach and mediator, and a member of the Advisory Board for the NTL Institute for Applied Behavioral Science. Rick brings both human insight and disciplined methodology to his work, helping organizations resolve conflict, build resilience, and lead change with clarity and purpose. ### Nike Carstarphen — Instructor Nike Carstarphen, Ph.D., is an organizational development consultant with more than three decades of experience advancing peacebuilding, civil society development, and conflict management. A specialist in monitoring and evaluation, conflict analysis, and organizational resilience, Nike partners with government agencies, civil society organizations, and multi-stakeholder groups to design processes that strengthen collaboration, improve performance, and support sustainable change. She is a senior practitioner with ADR Vantage and develops and delivers curriculum on conflict assessment, mediation, peacebuilding, dialogue facilitation, and cross-cultural engagement, helping leaders and practitioners translate theory into practical skills. Her work includes conflict resolution training and training-of-trainers programs, as well as facilitating staff retreats, work groups, task forces, and action-planning initiatives focused on visioning, organizational alignment, and problem solving. Nike has also designed and facilitated engagements ranging from small executive teams to multi-stakeholder convenings of more than 300 participants. She is particularly skilled at structuring dialogues and cooperative problem-solving processes that address complex interpersonal, group, and cross-cultural dynamics. For more than a decade, Nike has worked extensively with U.S. federal and quasi-federal agencies, including the U.S. Department of the Interior (USDOI), Transportation Security Administration (TSA), U.S. Agency for International Development (USAID), U.S. Department of Defense (USDOD), U.S. Department of State (USDOS), and the U.S. Institute of Peace (USIP). In these environments, she has facilitated formal and informal mediations, led multi-stakeholder dialogues, and supported the design and evaluation of conflict management systems that strengthen organizational capacity and mission effectiveness. In addition, Nike has conducted research, developed evaluation frameworks, and designed metrics to assess the impact of conflict resolution and organizational development initiatives. She holds a Ph.D. in Conflict Analysis and Resolution from George Mason University, along with advanced degrees in International Affairs and Business Administration. She is known for her analytical rigor, inclusive facilitation style, and ability to guide diverse stakeholders toward shared understanding and constructive action. ### David Clark — Instructor David Clark, Esq., is an accomplished mediator, arbitrator, administrative judge, and facilitator with more than 25 years of experience helping public and private sector organizations navigate complex workplace challenges. With a career grounded in both law and alternative dispute resolution (ADR), David brings analytical rigor, balanced judgment, and practical insight to every engagement—supporting leaders and teams in preventing conflict, resolving disputes, and strengthening organizational performance. David is a senior practitioner with ADR Vantage. He began his career as an attorney-adviser at the Federal Labor Relations Authority, where he oversaw appeals involving federal sector labor-management relations and managed the agency’s ADR office. This foundation shaped his deep understanding of workplace systems, collective bargaining, and the legal frameworks that govern employment relationships. Since 2002, he has served as an Arbitrator and Administrative Judge, presiding over matters involving collective bargaining disputes, discrimination claims, and other employment-related issues with efficiency and fairness. In addition to his adjudicative work, David has mediated and facilitated hundreds of workplace conflicts and strategic organizational discussions for federal agencies, local governments, and private organizations. His experience includes assisting with contract negotiations, board deliberations, and leadership-level problem-solving initiatives. As a trusted neutral for the American Arbitration Association and the U.S. Congress Office of Congressional Workplace Rights, he is frequently called upon to manage high-stakes matters requiring discretion, clarity, and sound decision-making. David also advises organizations on the design and effectiveness of conflict management systems and related programs, helping leaders build internal capacity for constructive dialogue and early dispute resolution. From 2008-2021, he served as an Adjunct Professor of ADR at American University’s Washington College of Law, where he shared his practical experience with the next generation of dispute resolution professionals. He holds a J.D. and M.A. from American University and is a certified mediator with the Supreme Court of Virginia. Known for his measured presence and strategic approach, David helps organizations resolve conflict with integrity while enhancing communication, accountability, and long-term effectiveness. ### Toby Guerin — Instructor Toby Guerin, JD, is a highly respected dispute resolution practitioner, trainer, and facilitator with more than 20 years of experience helping individuals and organizations navigate complex conflict with clarity and professionalism. Drawing on her extensive background in mediation, conflict management, and academia, Toby designs and delivers practical, skill-based training that equips professionals to manage workplace challenges with confidence and integrity. Through her role as Executive Director of the Center for Dispute Resolution at the University of Maryland Francis King Carey School of Law, Toby integrates academic rigor with real-world application. She oversees program development, supervises law students in small claims and workplace mediations, and launched the university’s first workplace mediation program, building sustainable systems that promote a positive workplace climate. Her teaching and supervision emphasize self-reflection, ethical practice, and intentional application of communication skills. Toby is a senior practitioner with ADR Vantage, and she has maintained a continuous mediation practice since 1999. She has served as a contract neutral for the National Archives and Records Administration, providing mediation, facilitation, and consultation on workplace and communication issues. She also serves as a roster mediator for the Maryland Department of Agriculture and the District Court of Maryland ADR Office and volunteers as a community mediator, where she provides mediation, facilitation, conflict management, and coaching. A sought-after national trainer and speaker, Toby has trained hundreds of professionals, from federal agencies and courts to private sector organizations and institutes of higher education, in strategic negotiation, workplace conflict management, conflict styles, advanced mediation skills and ethics, agreement writing, de-escalation, restorative practices, and elicitive feedback. Toby’s contributions to the field have been widely recognized, including receiving the Robert M. Bell Award for Outstanding Contribution to Alternative Dispute Resolution (ADR) in Maryland. Grounded in her J.D. from the University of Maryland Francis King Carey School of Law, she brings intellectual rigor, practical wisdom, and steady professionalism to every engagement, helping organizations and individuals build internal capacity to navigate conflict and promote communication. ### Cheryl Jamison — Instructor Cheryl Jamison, JD, is a respected conflict resolution leader, mediator, and educator with more than 17 years of experience advancing excellence in mediation practice and professional standards. Blending deep practical experience with thoughtful scholarship, Cheryl is known for her reflective approach, strong facilitation skills, and commitment to fostering inclusive, constructive dialogue in complex environments. Cheryl is a senior ADR Vantage practitioner, and she previously served as President and Executive Director of the Association for Conflict Resolution (ACR), providing national leadership to the field and advancing professional standards for mediators and conflict resolution practitioners. Prior to that, she led the Maryland Program for Mediator Excellence (MPME) within the Maryland Judiciary’s Mediation and Conflict Resolution Office, where she established statewide training, mentoring, assessment, and certification programs that standardized mediation practice across court-connected and community programs. Throughout her career, Cheryl has mediated a variety of disputes, and in addition to mediation, she conducts facilitated dialogues and conflict coaching engagements, helping individuals and organizations navigate sensitive issues with clarity and mutual respect. Trained as both a conflict coach and ombudsman, Cheryl brings a systems perspective and a strong ethical foundation to her work. An accomplished trainer and educator, Cheryl designs and delivers programs on mediation skills, listening skills, mediator ethics, team building, interest-based negotiation, and facilitating race-based conversations. She serves as an adjunct professor at the University of Maryland, the University of Baltimore, and Anne Arundel Community College. Cheryl holds a J.D. from the University of Baltimore and has completed advanced training in transformative mediation, conflict coaching, ombuds practice, and diversity and inclusion. A sought-after speaker, she has delivered keynote addresses and appeared on professional podcasts addressing contemporary conflict challenges. Cheryl is widely recognized for her ability to integrate mediation expertise with inclusion principles, helping organizations build cultures of accountability, equity, and meaningful dialogue. ### Gururaj Kumar — Instructor Gururaj Kumar, MA, is an accomplished mediator, facilitator, and educator with more than two decades of experience resolving workplace and cross-cultural conflicts in high-stakes environments. He is a senior practitioner with ADR Vantage, and he has mediated more than 200 cases domestically and internationally, serving a wide range of federal clients including the Transportation Security Administration (TSA), Social Security Administration, Federal Reserve Board, USAID, and FEMA. Known for his cultural fluency and steady presence, Gururaj helps leaders and teams navigate sensitive disputes with professionalism, respect, and strategic focus. A sought-after lecturer and executive educator, Gururaj has trained thousands of senior managers, executives, diplomats, and ambassadors in negotiation, conflict management, and cross-cultural engagement. He has delivered programs for the Office of Personnel Management’s Center for Leadership Development and the Federal Executive Institute. Gururaj has been adjunct faculty at Champlain College’s M.S. in Mediation and Applied Conflict Studies Program, at American University’s School of International Service, and at Northwestern University, where he taught graduate-level courses in mediation, conflict resolution, negotiation, and cross-cultural dynamics. His training style combines practical skill-building with global awareness, equipping participants to manage both interpersonal and systemic challenges. Gururaj is a trusted practitioner across multiple federal agencies, where he provides a full spectrum of conflict management services, including mediation, group facilitation, dialogue design, and conflict coaching. His work frequently involves complex EEO matters, cross-cultural misunderstandings, and organizational communication breakdowns, where his ability to balance accountability with understanding is especially valued. He holds a master’s degree in International Peace and Conflict Resolution and a Graduate Certificate in Managing Organizational Change from American University. A certified mediator in Washington, DC, and Chicago, and a member of the Association for Conflict Resolution (ACR), he brings federal workforce perspective, academic rigor, and deep practical experience to his work, helping organizations build durable skills for managing conflict across cultures, hierarchies, and missions. ### Dawn Martin — Instructor Dawn Martin, JD, is a senior practitioner with ADR Vantage and a seasoned mediator, trainer, coach, and dispute resolution systems designer with more than four decades of experience advancing constructive conflict engagement in complex organizations. Dawn has built a distinguished career helping public, private, and international institutions resolve high-stakes disputes, design sustainable conflict management systems, and strengthen leadership effectiveness. Dawn served for many years as a mediator, mediator trainer, and supervisor with the District of Columbia’s Mediation Service, where she also mentored interns in pioneering university-based dispute resolution programs. Over the course of her career, she has supported the development of hundreds of mediators through hands-on training, coaching, and supervision, helping practitioners build technical skill and professional judgment both in the United States and for justice systems and multilateral organizations around the globe. She facilitates system design processes that engage public sector agencies, corporations, NGOs, and academic institutions in building tailored approaches to managing conflict. Her client portfolio includes the United States Agency for International Development, Federal Reserve Board, Department of the Interior, Transportation Security Administration, American Bar Association, CARE, Chemonics, International Food Policy Research Institute, Abt Associates, DAI Global, International Monetary Fund, World Bank, and the Inter-American Development Bank. Building on her early experience as an attorney, Dawn brings both legal acumen and systems thinking to her work. In recent years, she has expanded her focus to leadership and team coaching, organizational resilience, and strengthening relationships within executive teams, between supervisors and staff, and among peers. Her approach integrates mediation expertise with advanced coaching methodologies, supporting leaders in addressing not only interpersonal disputes but also the systemic dynamics that drive them. Dawn holds a J.D. from The Catholic University of America, Columbus School of Law. She is a professionally certified coach and holds numerous certifications in leadership and organizational development tools. Dawn is recognized for her depth of experience, thoughtful presence, and ability to translate complex conflict dynamics into practical, sustainable solutions. ### Brian Schwartz — Instructor Brian Schwartz, MA, is a respected leader in facilitative mediation and community development mediation, with over two decades of experience helping individuals, teams, and organizations make sound decisions in complex environments. An expert in collective decision-making and consensus-building, Brian equips professionals with the communication and relational skills necessary to navigate difficult conversations, bridge differences, and build durable agreements. Brian is a senior practitioner with ADR Vantage, and he has mediated cases across a wide range of settings, including small-claims courts, workplaces, community forums, and federal agencies. He has served as a mediator through the Federal Government’s Shared Neutrals Program and has conducted numerous virtual federal mediations, supporting parties in resolving high-stakes workplace disputes. Brian focuses on helping people understand one another, and themselves, more deeply. As a community development mediator with Justice and Sustainability Associates, he designed and facilitated consensus-building processes for clients in nonprofit organizations, higher education, government, and the private sector. His work often involves guiding diverse stakeholders toward shared solutions in environments marked by competing priorities and limited resources. Brian is certified through the Harvard Mediation Program, where he has also trained new mediators, including Harvard Law students. He integrates mediation expertise with executive and leadership coaching, holding credentials as an Associate Certified Coach (ACC) with the International Coach Federation and as a Certified Integral Coach. He is also certified in emotional intelligence assessments, strengthening his ability to support leaders in building self-awareness and interpersonal effectiveness. Brian holds a master’s degree in Intercultural Relations from Lesley University. An active member of multiple professional associations, he is recognized for his thoughtful facilitation style, cross-cultural sensitivity, and ability to guide groups toward clarity, collaboration, and shared purpose. ### Danette Ross Watson — Instructor Danette Ross Watson, MA, is a highly experienced mediator, facilitator, consultant, and trainer with over 30 years of practice across federal, community, and public policy settings. She is a senior practitioner with ADR Vantage and has mediated more than a thousand cases spanning workplace and labor disputes, EEO matters, family and domestic conflicts, divorce, public policy, civil and personal injury cases, and mental health care conflict management. Known for her steady presence and disciplined approach, Danette helps organizations and individuals resolve complex disputes while strengthening long-term conflict competency. Danette’s federal experience is extensive. She has served as a mediator for the United States Postal Service REDRESS Program, Department of Veterans Affairs, National Archives and Records Administration, Department of the Air Force, and the Social Security Administration, and has facilitated departmental conflict resolution processes. Her work reflects deep familiarity with the dynamics of federal workplace systems and high-stakes employment disputes. In addition to mediation, Danette has served in roles requiring advanced communication and negotiation skills, including as a member of a Hostage Negotiation Team. She has also supported conflict resolution initiatives in mental health systems and correctional settings, and she is a certified family mediator for the West Virginia Supreme Court, demonstrating versatility across diverse and challenging environments. A committed leader in the field of Alternative Dispute Resolution (ADR), Danette has held board and leadership roles with the Texas Association of Mediators; is an active presenter and member of the Association for Conflict Resolution (ACR) and the National Association for Community Mediation; is a certified mediator/assessor, Membership Chair, and Cochair of the Certification Committee for the Maryland Council for Dispute Resolution; and is the current Executive Director and Founder of the West Texas Community Mediation Center. She has received several awards for innovation and leadership in the field. Danette holds a master’s degree in Conflict Resolution and has completed extensive advanced training in transformative mediation, public policy facilitation, motivational interviewing, peacemaking circles, and arbitration. Her work is distinguished by professionalism, cultural awareness, and a deep commitment to equitable and durable resolutions, helping organizations and communities move forward with clarity, accountability, and strengthened relationships. ## Pricing **Tuition:** $899