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:
- your equipment was designed and checked to withstand storms even worse than the one you’re in
- you know exactly how to engage with your crew to steer all of you safely through the storm
- you and your crew will emerge from the storm in calmer waters, able to see the horizon
- you have an anchor you can drop that will make all of your crew feel safe and protected.


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:

- Develop strategies for handling your discomfort and being present
- Understand yourself better so that you can show up more authentically as a leader
- Build your confidence to tackle that issue directly
- Maintain rapport, trust and connection when disagreeing
- Get clarity on what’s going on for you and the other person/ people involved
- Make clear and grounded requests of others
- Understand the often missed link between your physical health and your success at having challenging conversations

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.

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
Worksheets and handouts
Transcripts
Full transcripts
Downloadable Content
Downloadable audio
Participants
Small group, interactive participation
Investment
US$ 2,700
PART 1
LEARNING THE FOUNDATIONS
8.30AM US PT / 3.30PM UK
- Mar 15: Orientation week
- Mar 22: Live Coaching Workshop. Understanding yourself better in conflict.
7.30AM US PT / 3.30PM UK
*Note change in US times
- Mar 29: Live Coaching Workshop. How to handle your discomfort.
- April 5: Live Coaching Workshop. Building confidence to talk about challenging topics.
-
April 12: Live Coaching Workshop. Maintaining rapport, trust and connection when disagreeing.
- April 19: BREAK WEEK
PART 2
DEVELOPING YOUR PRACTICE
Time: 7.30AM US PT / 3.30PM UK
- April 26: Small group practice
- May 3: Live Coaching Workshop. Dispelling the confusion and getting clear.
- May 10: Small group practice
- May 17: Live Coaching Workshop. Saying what you mean by making clear requests.
- May 24: Small group practice
- May 31: BREAK WEEK
- June 7: Live Coaching Workshop. How to give difficult feedback.
- June 14: Small group practice
- June 21: Live Coaching Workshop. What’s next for you as a leader?
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.

JOIN:
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).