Challenging Conversations for Leaders

Do you want to take the angst out of preparing for uncomfortable conversations? We worry that failed conversations will impact negatively on everyone involved, or even make things worse. However, when handled well a challenging conversation allows you to broach a difficult topic before it becomes a bigger issue, provides an opportunity to increase trust, and can improve the relationship.

"An excellent workshop that really gave me the tools to manage challenging conversations." ... “All new leaders need to know how to effectively address these situations.”

Option A

Workshop Only

In this full-day workshop we will look at challenging conversations: what they are, what stops us having them, and the factors that influence successful delivery.

In the Full Day Workshop you will:

  • Learn how to prepare for an uncomfortable conversation.
  • Understand why it is unkind (and unfair) to tell half-truths and set vague expectations.
  • Know what is required to create psychological safety – and recreate it if lost.
  • Understand when different types of conversations are needed.
  • Evaluate the impact of avoiding challenging conversations.

We will also experiment with preparing for an actual challenging conversation you need to have, so you can practice in a safe and supportive learning environment.

Option B

Tailored Program

Incorporating a Workshop & embedding learning through coaching, the Program will normally run over a period of 6-9 months. A 'Sample Program Structure' below is provided below.

  • Full Day Workshop
  • + Small Group Coaching – Working with an ICF Credentialed Coach, these sessions focus on the real-life application of your new skills. The opportunity to learn from peers and the collective wisdom of the group is often what people find valuable about group coaching. A smaller group size of 6 guarantees participants a high degree of interaction, and individual attention.  Small group coaching sessions can be delivered virtually (via Zoom) or face-to-face.
  • + 1:1 Mentor Coaching – you will work 1:1 with an ICF-Accredited Mentor Coach, to develop skill, celebrate success, and explore challenges. Your mentor coach will help you sharpen your skills and develop your capability. Sessions are conducted virtually (via Zoom). 
  • Pre-work and other supporting resources will be provided throughout the program.

If you are organising development for a group/team: workshops can be delivered face-to-face or virtually for a date that suits your group. Get in touch to find out more!

If you are organising development for a group/team: the Workhop and Tailored Prorgram can be scheduled for dates that suit your group. 

BOOK a time TO DISCUSS YOUR team's LEADERSHIP DEVELOPMENT NEEDS

Sample Structure for Tailored Program

Full-Day Workshop

February

Full day face-to-face workshop for up to 18 people.

+ Small Group Coaching

Apr/Jun/Aug/Oct

60-minute group coaching sessions, in small groups of 6.

+ 1:1 Coaching

Mar/May/Jul

30-minute 1:1 virtual mentor coaching sessions.

Accountability Buddy

Ongoing

Self-paced practice with a peer.

Workshop - open enrolment

If you are an individual, funding your own development: these virtual workshops have been scheduled for ‘open’ enrolment. Delivered virtually, the registration fee is $450+GST per person, which includes pre and post work, and workshop participation. A 10% deposit is payable on registration, with the balance payable one month prior to the workshop.

Next Offering

Wednesday 17 September, 2025

Full Day
8.30am-4.30pm (Adelaide time)

REGISTER NOW!

2026 - TBA

What workshop participants said in their feedback...

Feedback from Challenging Conversations workshops:
“An excellent workshop that really gave me the tools to manage challenging conversations.”
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Feedback from Challenging Conversations workshops:
“So good to be able to collaborate and hear from others,getting ideas and feedback. Learning about my own triggers and use this to be able to build my confidence in my ability to have compassionate conversations going forward."
Click Here
Feedback from Challenging Conversations workshops:
“The structure of the day. Breaking down key factors surrounding these conversations. Listening to others and hearing them share the same triggers and emotions they experience.”
Click Here
Feedback from Challenging Conversations workshops:
“All new leaders need to know how to effectively address these situations.”
Click Here
Feedback from Challenging Conversations workshops:
"An excellent workshop that really gave me the tools to manage challenging conversations."
Click Here
Feedback from Challenging Conversations workshops:
“So good to be able to collaborate and hear from others, getting ideas and feedback. Learning about my own triggers and use this to be able to build my confidence in my ability to have compassionate conversations going forward."
Click Here
Feedback from Challenging Conversations workshops:
"The structure of the day. Breaking down key factors surrounding these conversations. Listening to others and hearing them share the same triggers and emotions they experience."
Click Here
Feedback from Challenging Conversations workshops:
"I was a little concerned about the day and how formal it would be. I appreciate the approach taken and look forward to future sessions."
Click Here
Feedback from Challenging Conversations workshops:
“There is so much I took away. The FOCUS template to prepare for conversation was helpful. It was also helpful to shift the thinking from a negative conversation to a positive thought process and being open to learning."
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Feedback from Challenging Conversations workshops:
"It was honest and supportive of what we can achieve."
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Feedback from Challenging Conversations workshops:
"Shared learning with research is the best learning."
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Feedback from Challenging Conversations workshops:
"I think anyone can learn, no matter their experience level."
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Feedback from Challenging Conversations workshops:
"All new leaders need to know how to effectively address these situations.”
Click Here
Feedback from Challenging Conversations workshops:
"Very interesting, insightful and will leave with some immediate actions in toolkit.”
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My aim is to provide a supportive and collaborative environment for leaders to undertake professional development that generates a lasting impact on both the individuals involved and the organisations they lead, in terms of skill enhancement and the creation of sustainable learning communities. 

Shifting Mindset

As a leader, you have a responsibility to deliver difficult messages. We will explore the shift from “difficult conversation” to “compassionate conversation”.  

Tools to Help You

We will introduce a structure to help you prepare – to say what needs to be said, with a focus on shared understanding and co-creation. 

Skills to Help You

Developing fundamental skills for compassionate communication (listening to understand, overcoming assumptions and managing your emotions).