Leading Advisor Simon Reilly

One Bad Hire Can Quietly Derail Your Whole Firm

Simon Reilly — Wed, 24 Jun 2026 14:00:00 +0000

Every leader knows the financial cost of a bad hire. The lost time. The training. The rework. The missed opportunities. The eventual replacement. But the real cost of a bad hire isn’t financial. It’s emotional. It’s cultural. It’s structural. It’s energetic. And it often takes months — sometimes years — for founders to see the full impact. Because a bad hire rarely…

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The AI Age Will Reward the Most Human Leaders

Simon Reilly — Wed, 17 Jun 2026 14:00:00 +0000

This article was inspired by Fareed Zakaria’s May 23, 2026 commencement address to Bard College graduates, in which he reflected on artificial intelligence, human intelligence, and the enduring value of our imperfect humanity. Fareed Zakaria’s commencement speech to Bard College’s class of 2026 offered a timely and powerful reminder for this moment in history: artificial intelligence may be…

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Stop Plugging Holes — Hire for the Firm You’re Becoming

Simon Reilly — Wed, 10 Jun 2026 14:00:00 +0000

Most advisory firms don’t make hiring mistakes because they hired the wrong person. They make hiring mistakes because they hired for the wrong reason. Usually, it starts the same way: Someone resigns. A team member hits capacity. A new initiative demands extra support. Client volume spikes. Deadlines stack up. The founder feels the pressure rising. And in that moment…

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When a High Performer Becomes the Bottleneck

Simon Reilly — Wed, 03 Jun 2026 14:00:00 +0000

One of the hardest leadership conversations an agency owner will ever have is not with a poor performer. It’s with a high performer. Someone who helped build the business. Someone who was there early. Someone who contributed meaningfully to the firm’s growth. Someone who, at one point, was exactly the right person for the role. And yet, despite their contributions…

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The Hidden Emotional Cost of Growing a Team

Simon Reilly — Wed, 27 May 2026 14:00:00 +0000

Most leaders expect that scaling their team will make life easier. More hands. More support. More capacity. More relief. But almost every founder eventually discovers a truth no one warned them about: Growing a team doesn’t immediately reduce pressure — it changes the kind of pressure you feel. And that emotional shift can catch even the strongest leaders off guard.

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The Leaders Who Win Long-Term Aren’t Takers—They’re Structured Givers

Simon Reilly — Wed, 20 May 2026 14:00:00 +0000

There’s a quiet belief running through many financial advisory firms and insurance agencies—especially those led by high-performing, growth-driven owners. It sounds something like this: “If I don’t push hard, drive results, and stay on top of everything… it all falls apart.” And so the leader leans in. They take control. They make the decisions. They carry the weight.

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Is Your Leadership Style Quietly Slowing Your Team?

Simon Reilly — Wed, 13 May 2026 14:00:00 +0000

There’s a difficult truth that every founder eventually has to face: Sometimes the bottleneck isn’t the team. Sometimes the bottleneck is the leader. Not because you’re doing anything “wrong.” Not because you aren’t committed. And certainly not because you don’t care. It happens because as the business grows, the leadership style that once worked beautifully…

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What Outdated Leadership Habits Are Sabotaging Your Business & Team?

Simon Reilly — Wed, 06 May 2026 14:00:00 +0000

There’s a quiet problem inside most successful advisory firms—and it doesn’t show up on your financial statements. It shows up in how you think. It shows up in how you decide. And most importantly, it shows up in what you feel responsible for. Because the truth is this: Many high-performing leaders are still operating from outdated leadership habits that quietly create…

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How to Grow the Firm While You Let Go of the Work

Simon Reilly — Wed, 29 Apr 2026 14:00:00 +0000

There’s a stage in every founder’s journey when the business’s growth depends on something far more difficult than strategy, systems, or staffing. It depends on letting go. Not in a dramatic way. Not in a “step back and disappear” way. But in a deliberate, uncomfortable, deeply personal way. Letting go of tasks you can do faster. Letting go of responsibilities you’ve carried for…

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Care Without Collapse: The Leadership Trap That’s Quietly Draining Agency Owners

Simon Reilly — Wed, 22 Apr 2026 14:00:00 +0000

There is a silent pattern I see repeatedly with financial agency owners. It doesn’t come from a lack of capability. It doesn’t come from a lack of work ethic. And it certainly doesn’t come from a lack of care. It comes from too much of the wrong kind of care—combined with a mind that never fully shuts off. The result? You carry too much. You think too much. You step in too…

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