Navigating Tough Conversations in Business

We all need to move to difficult conversations faster.

Leading a team isn’t just about numbers—it’s about alignment, accountability, and ensuring everyone is rowing in the same direction. Here’s a real-world example (anonymized) of how I help financial advisors lead with clarity and confidence.

1. Set the Stage with Openness

"I want to have an open and direct conversation. You’ve been with this firm for a while, and I value the expertise and effort you bring. Your ability to build strong client relationships is a real asset, and I appreciate the work you’ve done to bring in new business.

But we’ve reached a point where we need to talk about accountability and structure. Right now, I’m stepping in too often to catch issues, and that’s not how this should work. We need to have a serious conversation about roles, expectations, and what’s required for us to succeed as a team."

2. Focus on Indisputable Facts

"Let’s talk about some specific issues that have surfaced recently:

A key client review was missed, and I only found out when they reached out directly.

• Important portfolio updates weren’t entered into the system, which caused delays in decision-making.
• Compliance paperwork for a new client wasn’t submitted on time, putting us at risk.
• Team meetings are happening, but follow-through on key actions has been inconsistent.

When these things happen, I end up stepping in to fix them—and that’s not how this team should be running."

3. Share Feelings & Business Reality

"I’ve always wanted to create opportunities for team members to grow into leadership roles, including revenue-sharing and partnership tracks. But that only works when the team operates at a high level of ownership and accountability.

Right now, I’m still overseeing too many day-to-day operations instead of focusing on strategy and growth. Leadership roles—and the financial upside that comes with them—are for people who take full ownership of their work so I can focus on scaling the firm.

This isn’t about replacing anyone—it’s about making sure we have a team I can rely on without micromanaging every detail."

4. State Needs Clearly (What Full Ownership Looks Like)

"Here’s what I need moving forward:

• Client follow-ups and meetings need to happen consistently—without reminders.
• All client interactions and portfolio updates must be logged in the system in real-time.
• Compliance and paperwork deadlines must be met without me chasing them.
• Team meetings should end with clear action items—and those actions need to happen.
• If something is off track, I need to hear about it early, not when it’s already a problem.”

5. Set a Timeline and Define the Path Forward

"Here’s what I’d like to do moving forward:

If we’re still dealing with the same issues, we’ll need to reassess how roles are structured so the business can continue moving forward.”

Leadership is about tough but necessary conversations. If you’re leading a team, how do you approach conversations around accountability and performance?

We’re circling through our webinar series again

Register here to reserve your spot for the second of our three part series

Moving From Strategy To Action

May 21st 2025

In all that we do, let us seek wisdom, discipline, courage & justice.