Online Workshop

Difficult Conversations Series

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About this Online Workshop Series

OMSSA is pleased to offer workshops that assist with making difficult conversations easier, and that enhance your communication and listening skills. 

Workshop 1: Making Difficult Conversations Easier

The basic building block of all communication is the conversation. What, when, how and why we hold a conversation can have a profound impact on achieving our desired results.

But when the stakes are high, emotions run strong, or opinions conflict, we label these conversations as difficult. Whether we face difficult conversations with coworkers, clients, friends or family, invariably the same fear and apprehension comes over us the fear of failure or making matters worse.

During this workshop, we will explore the construct, traps and pitfalls of difficult conversations, why they may go wrong and how to approach, plan and execute them in a more successful manner, using practical tips, tools and real-world examples.

By the conclusion, fear and apprehension of that difficult conversation will transform into confidence and encouragement.

Learning Objectives

  • Overcome barriers and turn conversations from difficult to collaborative
  • Explore the structure of conversations and how they can either snare you or release you from "conflict traps"
  • Become aware of conflict styles, personalities and emotions, and how each hinders or help conversations
  • Learn effective and practical communication tools, including:
  • Avoiding communication "blockers"
  • First words to use
  • Agreeing vs. acknowledging
  • Framing and asking good questions
  • When to be empathetic, and when to be assertive
  • Learn a simple yet powerful four-step technique to aid in having better and more collaborative conversations

Workshop 2: Improve Your Listening with the 4-Step Empathy Loop

One secret about making difficult conversations easier is being able to gain insight into the perceptions, perspective and interests of the other person.  To do this it is essential to ask good questions and be an effective listener.

During the foundational workshop Making Difficult Conversations Easier participants were introduced to a simple yet effective 4-step Empathy Loop that can make anyone an expert listener.  Armed with this specific skill one can more effectively build better human connections and collaborative relationships.

While learning about the skill is one thing.  Having the opportunity to practice it and gain expert feedback is something more.

Learning Objectives

  • Repeatedly practice the 4-step listening loop of understanding in a safe, confidential and controlled environment
  • Get guided feedback directly from the workshop’s instructor for improvement
  • Test variations to determine what works and what doesn’t based on the participant’s own personal style
  • Experiment with how looping might be useful across a variety of real-world situations

Workshop 3: Resolving Difficult Conversations

During the foundational workshop, we examined what makes conversations difficult, why they occur and how to manage them. We outlined and practiced the key skills of de-escalating angry emotions, empathetic listening and asking good questions to unpack and focus on interests instead of positions. In addition, we explored the proper sequencing of the conversation along with how best to be both empathetic and assertive.

Now, in this advanced workshop, we will pick up where we left off and discover:

  • How best to prepare for a difficult conversation,
  • Additional conversation tools that can be used to move the conversation to positive results
  • A multi-faceted questioning technique that zeroes in on the core areas where the causes of the conflict and impasse lie
  • Participants will also walk along the Resolution Pathway, a robust and comprehensive step-based process that ties everything together from start to finish and, if followed, is guaranteed to lead to a positive conclusion and relationship.

Learning Objectives

  • Properly prepare for a difficult conversation
  • Develop greater questioning skills by examining the root causes of behavior (including broken promises) using a model that contains six sources of influence
    • Learn more advanced, effective and practical communication tools, including:
    • Managing the angry person
    • Delivering bad news
    • Making it safe to talk
    • Understanding unconscious bias
    • Tone, volume and cadence
    • Unpacking the importance of the Best Alternative to a Negotiated Agreement (BATNA)
    • Summarizing and Paraphrasing
    • Futurizing
    • Reframing
    • Reality testing
  • Learn a comprehensive step-based process known as the Resolution Pathway that ties everything together from the foundational and advanced workshops
  • Practice skills using real-world case scenarios

NOTE: This is an interactive, virtual workshop, which is different from a webinar. Participants will be expected to participate through voice and video, and to engage with each other and the facilitator in large and small group discussions, to learn from each other and practice skill development.

Workshop Dates and Registration

All sessions in Eastern Standard Time.

This series is a bundle that includes the following three workshops: Making Difficult Conversations Easier, Improve Your Listening with the 4-Step Empathy Loop, and Resolving Difficult Conversations. Please ensure you are able to attend all three workshops when registering for a session.

If you wish to register for just one course in the series, please reach out to Please note that Making Difficult Conversations Easier is a mandatory prerequisite for the 4-Step Empathy Loop, and Resolving Difficult Conversations.

Difficult Conversations Series 2: May 23 - 24, June 5, & June 19 - 20, 2024

Making Difficult Conversations Easier 

  • Part 1: Thursday, May 23 | 10:00 – 12:00

  • Part 2: Friday, May 24 | 10:00 – 12:00

Improve Your Listening with the 4-Step Empathy Loop

  • Wednesday, June 5 | 10:00 – 12:00

Resolving Difficult Conversations

  • Part 1: Wednesday, June 19 | 10:00 – 12:00

  • Part 2: Thursday, June 20 | 10:00 – 12:00

Registration is closed for these sessions.

Difficult Conversations Series 3: October 8 - 9, October 22, & November 5 - 6, 2024

Series Registration Cut Off: Friday, October 4

Making Difficult Conversations Easier 

  • Part 1: Tuesday, October 8 | 10:00 – 12:00

  • Part 2: Wednesday, October 9 | 10:00 – 12:00

Improve Your Listening with the 4-Step Empathy Loop

  • Tuesday, October 22 | 10:00 – 12:00

Resolving Difficult Conversations

  • Part 1: Tuesday, November 5 | 10:00 – 12:00

  • Part 2: Wednesday, November 6 | 10:00 – 12:00

Register Today


  • Members: $270 + HST

  • Non-Members: $351 + HST

  • Non-Member Education Level 1 & 2: $281 + HST

Bring This Workshop to Your Staff

OMSSA can work with you to deliver this workshop to you and your team in an in-person format at a time that works for you. We can also customize the content of each workshop to meet your specific needs. Contact OMSSA's Director, Education Christie Herrington to learn more about bringing this workshop to your staff. 


Here are what some attendees had to say about this workshop:

I really appreciated the clearly laid-out slides and the use of relevant media clips to generate conversation and thinking about the topics being presented. The instructor [Sharad] was clearly passionate about the topic and worked hard to engage his participants.

I enjoyed the instructor's positive manner, humour and opportunity to provide feedback in the session.

Learning how emotions play a part. I am a very emotional person and have now learned how to take a breath and to prepare for these conversations.

Who Should Attend?

All three workshop are well-suited for any human services professional. In order to attend the series of workshops, participants must complete all three workshops in this order: Making Difficult Conversations Easier, Improve Your Listening Skills with the 4-Step Empathy Loop, and finally, Resolving Difficult Conversations.

Format and Duration

  • Making Difficult Conversations Easier 
    • Two, two-hour online workshops over two back-to-back days
  • Improve Your Listening Skills with the 4 Step Empathy Loop
    • One, two-hour online workshop 
  • Resolving Difficult Conversations 
    • Two, two-hour workshops over two back-to-back days

Technical Requirements

OMSSA will be hosting this virtual workshop using Zoom, an online, interactive platform that you can join straight from your web browser, or by downloading 'Zoom Client for Meetings' on your computer or tablet

Participants will be expected to join the workshop via both video and audio. Participants should therefore have access to a desktop computer, laptop computer or tablet with:

  • a webcam or built-in camera

  • a built-in microphone or a headphone jack where you can plug in a headset or earphones

We strongly recommend that participants use a headset or earphones with a built-in microphone in order to limit background noise. 

System requirements: Click here for more detailed information on system requirements from Zoom.

About the Facilitator

Sharad Kerur has a Bachelor of Commerce (Honours) and Master of Industrial Relations from Queen's University, with a focus on negotiation theory and alternative dispute resolution methods.   

For over 30 years, Sharad held senior level positions in the union and association sectors. His most recent position was Executive Director of the Ontario Non-Profit Housing Association (ONPHA), Canada's largest non-profit housing association. As a result, he has a strong grasp on the business of non-profit organizations and associations, and real-world experience in negotiation and mediation.

Sharad is Harvard-trained, having obtained a Certificate in Mediating Disputes and a Certificate in Negotiating Difficult Conversations from the Harvard Negotiation Institute (Harvard Law School) and also holds a Certificate in Dispute Resolution and an Advanced Certificate in Dispute Resolution, both from the York University in Toronto.

Amongst his credentials, Sharad is:

  • a Qualified Mediator through the ADR Institute of Canada, 
  • an accredited Chartered Community Mediator through the Ontario Community Mediation Coalition, 
  • a Certified Conflict Management Coach, coach-mentor and trainer with CINERGY®
  • an Associate Certified Coach through the International Coaching Federation, 
  • a certified Personal and Business Coach through the Coach Academy (Canada)
  • a certified Conflict Dynamics Profile practitioner through Eckerd College in Florida, and
  • a certified Senior Workplace Fairness Analyst accredited by the Workplace Fairness International.  

Sharad also leads his own consultancy firm known as Resolution Pathways, which assists people and organizations to transform conflicts into collaboration.  With his knowledge, expertise, and experience, he currently provides services in:

  • 1-to-1 conflict management coaching
  • "understanding-based" mediation services
  • training on managing difficult conversations and navigating conflict relationships
  • assistance in the development of high-performing teams
  • workplace conflict assessments and fairness restoration strategies