110. Difficult Conversations: Tough Talks That Build Trust

I used to lose sleep before coaching sessions where I knew I had to deliver tough news. If I saw someone's finances and they were way over budget every month, I felt like, oh my gosh, I'm going to have to be the messenger of terrible news. What are they going to think? How are they going to react?

Today we're talking about those conversations that make your stomach tighten—the ones many coaches want to avoid because they think their client will be unhappy or uncomfortable. But when we avoid these conversations, problems compound, resentment builds, and most importantly, we fail to serve our clients with the honesty they deserve.

We'll cover the specific language that transforms these dreaded moments into opportunities for deeper connection. Instead of saying “at this rate, it will take you 13 years to pay off your debt,” you'll learn how a simple reframe can shift everything. Plus, I'll share how asking clients to rate their financial health on a scale of one to ten changed my entire approach to difficult conversations.

Whether it's discussing negative cash flow, addressing spending habits that don't align with goals, or talking about business finances that aren't working, you'll get concrete phrases and questions that create openness instead of defensiveness. We'll also talk about what happens when clients get emotional (because money is emotional) and how to handle those vulnerable moments in ways that deepen trust rather than damage it.

If you've ever felt uncomfortable having to tell a client something they don't want to hear, this episode gives you the tools to approach these conversations with confidence. Because the truth is, delivering tough news with care is one of the most valuable services we provide as financial coaches.

Links & Resources:

• Ultimate Growth Guide
• Join the Facebook group
• Episode 27: The Stages of Learning for Financial Coaches

Key Takeaways:

• Preparation beats panic: Practice what you'll say before tough conversations, because delivering bad news with care is one of the most valuable services you provide as a coach.
• Questions starting with “why” create defensiveness, but “what” and “how” create openness. Choose your question words carefully to unlock client insights.
• “You should have” focuses on a past that can't be changed, while “Let's explore what's working” builds on strengths that already exist.
• Emotional moments aren't interruptions to coaching. They're opportunities to create profound trust by staying present without trying to fix or change the feelings.
• Ask clients to rate their financial health 1-10 before delivering tough news; often they already know something's wrong and just don't want to face it alone.
• Every problematic financial habit began as an attempt to meet a legitimate need. Acknowledge this and clients feel seen rather than judged.
• Your comfort with client emotions directly impacts your effectiveness as a coach; when you can hold space for tears without rushing to solutions, real transformation begins.