Conversations That Count: How to Build Confidence and Clarity in Difficult Conversations (Series Begins Jan. 14, 2025)

For this webinar series, participants will automatically be enrolled in all 5 sessions.

Speaker

Lisa MacDonald, M.Ed., Founder, Lisa MacDonald Consulting, LLC

Description

This five-part webinar series is designed to help participants develop the confidence and clarity needed to navigate difficult conversations in their professional roles. Each session blends real-world examples with actionable strategies to address emotionally charged, high-stakes, or sensitive topics. Participants are encouraged ahead of time and throughout the five-part series to submit their own questions and scenarios (anonymously) to ensure the series remains grounded in their lived experiences. You’ll leave each session with clear, practical tools to use right away, and a stronger sense of self when facing tough moments.

Note: While many participants choose to watch recorded sessions later, this series works best for those who are able to attend and engage on camera as all sessions are highly interactive and discussion based. Participants are the drivers of these sessions—meaning, while there are planned activities and content for each session, the specific topics we get into are determined by participants who are able to share (anonymously if preferred) their current experiences to the table and gain insight and perspective from others! 

To receive PDPs and CEUs, participants must attend all 5 sessions and successfully pass a quiz following Session 5. Within 24 hours of the live webinar, registrants will be emailed a link to view the recorded webinar. The recording will be made available for 7 days after each session.

We begin by helping participants explore how their values, roles, and internal narratives shape their approach to difficult conversations. This session builds self-awareness and encourages participants to reflect on why certain interactions feel particularly hard. You’ll gain clarity about your communication style and how to stay grounded when the stakes are high.

This session helps participants understand how bias, assumptions, and past experiences influence their perception of difficult people and situations. We’ll explore tools to move from frustration to curiosity and shift from reaction to reflection. The goal is to increase clarity in how we interpret others, and ourselves, when tensions rise.

In this session, we’ll focus on language and strategies to communicate clearly, respectfully, and confidently, even when we’re unsure how it’ll be received. We’ll explore how to respond to uncomfortable comments, set boundaries, and handle pushback. Tools like bystander intervention, email tone management, and intent vs. impact are featured.

Individuals often navigate conversations complicated by power dynamics, egos, or unclear expectations. This session offers strategies for staying composed and confident when dealing with authority figures, colleagues, or tense team dynamics. You’ll learn how to assess risk, name your concerns, and speak up without losing your voice.

Our final session helps participants sustain their confidence and keep showing up with clarity, even when conversations feel polarizing or unresolved. We’ll explore how to say no without guilt, hold boundaries with care, and stay motivated when things don’t change overnight. This is also a space to revisit participant-submitted scenarios and build personalized takeaways.

About the Speaker
Lisa MacDonald, M.Ed.

Lisa MacDonald (she/her) is the Director of Equity Compliance at MassBay Community College where she serves as the institution’s Title IX Coordinator and Affirmative Action Officer. As a member of the College’s equity leadership team, she provides ongoing education on harassment and discrimination prevention, serves as an investigator for harassment and discrimination complaints, and is currently co-chairing the College’s Review of Policies and Procedures for Systemic Racism. Before arriving at MassBay, Lisa was primarily in Student Affairs at small private institutions where she served as the Director of Residence Life at Babson College (2006-2012) and Assistant Vice President for Student Affairs/Director of Student Conduct at Curry College (2012-2018). Passionate about creating positive relationships and fostering confidence in others, Lisa has her own consulting business, Lisa MacDonald Consulting where she provides businesses and organizations with training, coaching, and best practices on how to engage in difficult conversations and have confidence in conflict. She resides in Natick, Mass., with her husband and daughter.

Membership Information

Most MPY webinars are available ONLY to current staff from member districts and organizations. Public school memberships include police and fire personnel. Former and retired employees and members of committees, including but not limited to, PTO/PTA, PAC, School Improvement Councils, Health Councils, Drug/Alcohol Councils, and school volunteers, are not considered MPY members.

PDPs and CEUs

MPY is an approved Professional Development Provider through the Massachusetts Department of Elementary & Secondary Education (Provider No. F20180079). Professional Development Points (PDPs) are offered for most MPY professional development webinars. PDPs are issued in 10 hour increments, per DESE requirements.

Continuing Education Units (CEUs) are available for clinical staff through the National Association of Social Workers (NASW) and the Massachusetts Mental Health Counselors Association, Inc. (MaMHCA). The NASW and the MaMHCA approve each event individually. CEUs may be given in hourly increments.

To receive PDPs and CEUs, participants must pass the quiz.

Event Cancellation Policy

If you are unable to attend a MPY webinar you must cancel, through Bonnie Mullen at bonnie@mpyinc.org, one business day before the webinar.

For MPY hybrid conferences, the date in-person registration closes will be posted on MPY’s website. Virtual conference registration will close one business day before the hybrid conference. You cannot cancel or switch your registration from in-person to virtual after in-person registration closes. Please email Bonnie Mullen at bonnie@mpyinc.org with any questions regarding registration.

 

Register

FREE
MEMBER PRICING
Register Now

If you are seeking to receive CEUs and/or PDPs, please click Register Now. Once you complete the webinar series, you will be able to take quizzes for CEUs and/or PDPs. Upon completion of each quiz, you will receive a certificate.

All sessions are 9:30 am – 11:30 am.

  • Session 1: January 14, 2026, Who Am I In This Conversation?
  • Session 2: January 28, 2026, Why Do I See It That Way?
  • Session 3: February 11, 2026, How Do I Say It? 
  • Session 4: February 25, 2026, What’s Mine, What’s Theirs, and What Gets In the Way?
  • Session 5: March 11, 2026, What’s Left?