15 March 2022 - 21 June 2022

🎙 Enrolment Open! 🎙

Challenging Conversations

Learn how to master challenging conversations

Do you know what needs to be said to your boss, colleagues, and team, but you’re afraid to say it?

Maybe you find it challenging to find the right words to say at the right time.

You know that you need to be able to communicate well with the people you work with, but sometimes the conversations don’t happen the way you want them to.

So, you avoid having the conversation, focus on other things, and the issue is left unaddressed.

EVEN worse, the people you aren’t connecting with feel unheard: and won’t tell you how they’re feeling.

We know how frustrating it can be when you struggle to find the words to say or how to say them. You’re certainly not alone if you  finish meetings not having fully addressed the difficult topic you planned to talk about.

The problem is that these conversations still happen elsewhere.  And, when the ‘real’ conversations happen without you–or even over text or email–you may not know what’s really going on, creating a chasm between you and others.

When you’re a leader who is trying to do better, it’s frustrating when people don’t get how hard you’re trying or how much you care. You really want this effort and care to come across, but for some reason it doesn’t seem to land, and you end up feeling misunderstood.

The willingness to have challenging conversations is a hallmark of great leadership. And you can master these conversations with the right skills.

We look forward to seeing you show up for your team and your colleagues feeling confident that you can create trust and connection no matter how difficult the conversation.

Feeling adrift?

Imagine scanning your diary and seeing a meeting, like “Performance Review with Project Team,” that fills you with dread and anxiety. 

That experience is like being on a boat in stormy weather. You might be ok, but it’s going to be a pretty unpleasant journey riding it out.

As the team leader, you’re the captain of this boat in the storm, but what if you knew that:

What You Gain From Challenging Conversations

As coaches we have a bit of a head start when it comes to handling tricky topics. Most leaders approach this problem by turning to the same tools and skills they’ve always used to solve problems: deductive reasoning, persuasion or charisma, delegation or wielding authority. 

The problem is that’s not where the effective solutions are.

At WELL Leaders, we support leaders to grow in self-awareness because we know that mastering challenging conversations starts with you. It begins by increasing your own awareness of how you handle conflict now and the impact of this approach on others. 

You’re not alone if you dread challenging conversations, or if you feel confused and angry after attempting to raise a particular topic and then not getting the response you’d hoped for. No-one wants to feel misunderstood or judged for their well-intentioned attempts.

We will show you how to ride safely through those stormy seas of challenging conversations by focusing on how you show up as a leader. Drawing on our training in nonviolent communication and mediation, we will equip you to:

As a leader, you really CAN do things differently when it comes to disagreement and challenging topics, you just need to commit to learning and practising the skills.

And that takes investment and the support of a community.

If this resonates with you, read on to learn more about our ‘Challenging Conversations’ programme coming up in Spring 2022.

Register and we’ll share with you  how you can create trust and  connection in your team.

Have a conversation with one of us to see if this programme is right for you.

3. Join

Join our Spring 2022 Online Leadership Coaching Programme

Leadership Coaching Programme Overview

🏁 Enrolment Open (up to 1 March 2022)🏁

Programme Duration: 15 March 2022 - 21 June 2022

Our highly interactive ‘Challenging Conversations’ Leadership Coaching Programme is created for leaders, like you, who are committed to building the knowledge, awareness and skills to handle challenging conversations with quiet confidence and ease.

This is a practice-based course, founded upon our core values of prioritising health and wellbeing, creating community and inspiring authentic leadership

Read more about our values here.

We have taken the very best experiences of all the online programmes we’ve participated in to create something unique: core content that you can watch or listen to in your own time with live workshops to integrate the learning and create a solid practice. 

The course is ‘front-loaded’ so that the time commitment is greater in part 1 over the first 5 weeks and less intense in part 2.

Challenging Conversations

Programme Overview

Live Coaching

1 Live Orientation Session + 12 Live Coaching Workshops via Zoom: 90 mins/session

Video Content

Weekly recorded video content - watch or listen in your own time

Group Practice

Small group practice sessions: 1 hour/session


Worksheets and handouts


Full transcripts

Downloadable Content

Downloadable audio


Small group, interactive participation


US$ 2,700



8.30AM US PT / 3.30PM UK

7.30AM US PT / 3.30PM UK
*Note change in US times



Time: 7.30AM US PT / 3.30PM UK

Ready to Embrace Challenging Conversations?

We love it when we see leaders embrace challenging conversations because they know  that they can say what they mean and create trust and connection. 

How do you know when you’ve done it?  A feeling of relief that says, “that was a really challenging conversation with a member of my team about their underperformance, and I know they left feeling heard, and knowing what they need to do”.

We need to be honest here. This stuff is not quick or easy. If you want a fast solution, our approach probably isn’t for you!

The skills we will share with you are simple. But learning about them is not enough. You need to create time and have the commitment to put your new skills into practice.

On the other hand, if you choose to say yes and go all in, this will be both a personal and a professional journey. You will learn awareness, knowledge and skills that will change your life, not just your work.

We’ll hold space for you to integrate those new skills. That’s your single biggest obstacle in you transforming your own behaviour. It’s not what you know about how to have difficult conversations, but it’s how you go about it. And like any skill, mastery takes practice until it becomes second nature.

In our webinars, our community and our group coaching sessions, you’ll have the time and space to practice with us and your fellow leaders so that you can go into every future conversation with more confidence than before.

Feeling confident and building mastery take time, but we’ll be here to keep you on track. And if you choose to, you can work with one of our team one-on-one to take your leadership to the next level.

When you leave uncomfortable conversations to linger and don’t say what you mean, your leadership suffers with a lack of trust, colleagues that don’t share, and a team that feels fragmented.

Create trust and connection with your team, no matter how difficult the conversation.

WELL Leaders Challenging Conversations Programme

Spring 2022 Leadership Cohort

Having challenging conversations with ease is a hallmark of great leadership. And it’s easier than you think with our simple method. 

Register and we’ll share with you  how you can create trust and  connection in your team (aka not be a jerk at work).