Coaching to Values & Navigating Difficult Conversations
As we near the close of our time together in the Transformative Coaching Essentials program, each weekend feels both deeper and more essential. Weekend 11 was no exception. It was all about getting to the heart of coaching: values — what matters most — and learning how to navigate the conversations that aren’t easy, but are often the most necessary.
These two themes — coaching to values and coaching through difficult conversations — go hand in hand. When we help clients clarify what they truly care about, they gain the clarity and courage to face challenges with integrity. And when we hold space for the tough stuff — the stuck places, the tension, the vulnerability — real transformation happens.
Coaching to Values: What Drives Us?
We began the weekend exploring values — not in the abstract, but in the deeply personal, lived sense. As coaches, we don’t define values for our clients. Instead, we help them discover and articulate the principles that matter most to them, so they can make aligned and powerful choices.
Through our process we helped our coaches:
- Identify their core values through looking back at their lives and where they felt out of sync or like something “was not right”; and where they felt like they were standing up for something important to them;
- Recognize when they were living in alignment — or out of alignment — with those values; and
- Use values as a compass for decision-making and goal-setting.
All in service of them coaching their clients around values and values-based decision-making.
When clients connect with their values, they get clearer. Their energy shifts. They become more committed — and more confident. This helps them to live in more honest, fulfilling and meaningful ways.
Coaching Difficult Conversations: Holding Space for Discomfort
Then we turned our attention to a skill every coach needs: how to coach a client through a difficult conversation — whether it’s one they have been avoiding, one they are dreading, or one they are not sure how to approach.
We learned frameworks for:
- Understanding what makes a conversation “difficult” for a client;
- Helping the client clarify what outcome they want — and what’s getting in the way;
- Exploring emotions and how to manage them before having the conversation;
- The difference between expressing a position and a point of view and how important this is to having a productive conversation when the topic feels challenging; and
- Role-playing and preparing the client to speak with courage and compassion.
We also talked honestly about what it takes to be the coach in a hard moment — when emotions are strong, when stakes feel high, or when the client is sitting in uncertainty. This part of the work isn’t about fixing. It’s about staying present. Holding the space. Trusting the process.
Practice, Feedback, Growth
As always, we practiced — a lot. We gave and received feedback. We stretched. We made mistakes and learned from them. We witnessed how values can illuminate a client’s path — and how just naming a hard conversation out loud can shift the energy completely.
There were moments of laughter, tears, insight, and connection. One of the beautiful things about this group is how safe and real the space has become. It’s not just a classroom — it’s a community of practitioners learning to live and lead with presence, courage, and heart, all in service of their clients living the way they want to live!
Looking Ahead
Weekend 11 reminded us that being a coach isn’t about having all the answers — it’s about helping people find their truth and walk toward it. It’s about sitting with someone as they uncover what really matters to them and then supporting them to live it out — even when it’s uncomfortable.
We’re almost at the end of our training, and it’s clear: this group is ready.
Ready to coach with integrity.
Ready to face the tough stuff.
Ready to help others live in alignment with what matters most.
On to Weekend 12…
