Leading Advisor Simon Reilly

The Leadership Test Most Agency Owners Fail Before Vacation

Simon Reilly — Wed, 11 Nov 2026 14:00:00 +0000

For many agency owners, vacation doesn’t feel like rest. It feels like risk. Even after booking the trip… Even after stepping away from the office… Even while sitting beside the ocean or walking through an airport… Part of their mind remains attached to the business. Checking messages. Monitoring problems. Thinking about the team. Wondering what’s being missed.

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Are You Leading Your Team—or Rescuing Them?

Simon Reilly — Wed, 04 Nov 2026 14:00:00 +0000

There is a leadership habit that looks like caring, feels like helping, and can quietly undermine the very team you’re trying to build. It’s rescuing. And I’ve seen it happen with some of the most committed financial advisory firm owners and insurance agency leaders. An employee encounters a problem. They come to you for help. You provide the answer.

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Your Open-Door Policy May Be Costing Your Agency More Than You Think

Simon Reilly — Wed, 28 Oct 2026 14:00:00 +0000

One of the most expensive habits inside a growing financial advisory or insurance agency often begins with four well-intentioned words: “My door is always open.” It sounds like good leadership. You want your team to feel comfortable approaching you. You want questions answered quickly. You want clients looked after and problems resolved before they escalate.

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The Leadership Problem That Isn’t in Your Calendar — It’s in Your Head

Simon Reilly — Wed, 21 Oct 2026 14:00:00 +0000

Most agency owners believe their biggest challenge is workload. Too many meetings. Too many clients. Too many moving parts. Too many decisions. And at first glance, that seems true. The business grows. The team expands. Responsibilities multiply. So naturally, the solution appears obvious: Work harder. Push more. Stay later. Carry more. But after working with growing…

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The Best Business Lesson I’ve Learned Was Never About Sales

Simon Reilly — Wed, 14 Oct 2026 14:00:00 +0000

Over the past thirty-five years, I have worked with hundreds of financial advisors, agency owners, and leadership teams across North America. People often ask me what I do. The answer has changed over the years. I’ve been an executive coach, a leadership consultant, a hiring specialist, a speaker, and today I serve many organizations as a Fractional Chief Operating Officer.

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Will You Carry The News To “All The Young Advisor Dudes”?

Simon Reilly — Wed, 23 Sep 2026 14:00:00 +0000

David Bowie wrote All the Young Dudes more than 50 years ago, and Mott the Hoople turned it into one of the defining songs of the glam-rock era. Lately, that title has been running through my head for an entirely different reason. A surprising number of my recent coaching conversations with agency owners have involved young men entering or developing within the financial-services…

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Tomorrow: Why Do the Same Agency Problems Keep Coming Back?

Simon Reilly — Tue, 15 Sep 2026 14:25:47 +0000

A quick reminder that my complimentary webinar is tomorrow, September 16: Why Do Leadership, Team, and Hiring Problems Keep Reappearing in Your Agency? How to Diagnose and Strengthen the Human Operating System Behind Agency Performance Over the past two weeks, I have shared two practical resources: The Leadership Operating System Diagnostic — to help identify where recurring…

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A Practical Tool to Strengthen Leadership and Accountability in Your Agency

Simon Reilly — Wed, 09 Sep 2026 14:00:00 +0000

Last week, I shared our Leadership Operating System Diagnostic to help you identify where recurring leadership, team, accountability or hiring problems may actually be coming from. Today, I want to give you something equally practical. Our complimentary: Agency Leadership Clarity & Accountability Tool GET THE COMPLIMENTARY TOOL The purpose of the Tool is simple…

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What Is Really Causing the Same Problems to Keep Reappearing in Your Agency?

Simon Reilly — Wed, 02 Sep 2026 14:00:00 +0000

When the same leadership, team, accountability or hiring problem keeps coming back, it is tempting to keep treating the symptom. But recurring problems are often telling you something deeper. The real issue may be within the Human Operating System behind your agency — how leadership, people, roles, accountability and decision-making work together. To help you take a closer look…

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Would You Like a Practical Tool to Resolve Recurring Agency Problems?

Simon Reilly — Wed, 26 Aug 2026 14:00:00 +0000

Many agency owners can identify the problems occurring inside their business. The more difficult question is what to do about them. Would you like to receive my complimentary Agency Leadership Clarity and Accountability Tool to help you uncover the deeper issue, clarify ownership, and determine the appropriate leadership action? When you register for my upcoming complimentary…

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