The Leadership Blind Spot Most Business Owners Never See Until It’s Too Late episode artwork

EPISODE · Sep 10, 2026 · 54 MIN

The Leadership Blind Spot Most Business Owners Never See Until It’s Too Late

from The Modern Insurance Agent · host Jumpstart Go

Send us Fan MailWhat if your employees aren't the problem… but your leadership is?When Ken asked his team whether they always knew when they were doing a good job, only 20% said yes.But when he asked whether they knew when they were in trouble?80% said yes.That realization changed the way Ken led.Instead of only pointing out what went wrong, he became intentional about recognizing what his team was doing right.And when mistakes happened, he stopped asking:"Who messed up?"He started asking:"Is this a one-time mistake or is there a systemic problem we need to fix?"That shift helped create a culture of accountability without turning every mistake into a personal attack.But Ken learned another powerful lesson:Sometimes you don't have the wrong employee. You have the right employee in the wrong seat.Two employees weren't thriving in their roles. One was introverted but answering the phones. The other was outgoing and magnetic but stuck typing contracts.So Ken switched their positions.Both became happier.The team performed better.And the business benefited.That same philosophy of listening extends to Ken's clients.Today, roughly 75–80% of FUN Enterprises' business comes from repeat business and referrals.His philosophy is simple:Customers are transactional. Clients are people under your care.That mindset became even more important when COVID hit.Ken remembers approximately $350,000 in cancellations in a single week, with total cancellations eventually reaching between half a million and three-quarters of a million dollars.Instead of waiting for things to return to normal, his company adapted—turning in-person experiences into virtual events and eventually rebuilding its live-event business.After more than three decades as an entrepreneur, Ken's advice to anyone building a business today is surprisingly simple:Check your ego at the door.Being vulnerable isn't weakness.Asking for help isn't weakness.Changing direction isn't failure.And admitting you don't have all the answers can be the thing that helps you find better ones.Inside this episode, you'll discover:• How to recognize and reinforce the right behaviors on your team• Why accountability doesn't have to mean blame• How putting the right people in the right roles can transform performance• Why listening is one of the most powerful leadership skills• How repeat business and referrals create long-term growth• How to lead through massive business disruption• Why adaptability matters more than having a perfect plan• The leadership mindset every growing agency owner needsIf you're an insurance agency owner, entrepreneur, sales leader, or business owner trying to build a stronger team, improve leadership, create lasting client relationships, and build a business that can survive change, this conversation is packed with lessons you can put into practice.Connect with Us:🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcastJoin the Movement of Modern Insurance Agents!Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

Episode metadata supplied by the publisher feed · Published Sep 10, 2026

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Send us Fan Mail What if your employees aren't the problem… but your leadership is? When Ken asked his team whether they always knew when they were doing a good job, only 20% said yes. But when he asked whether they knew when they were in trouble? 80% said yes. That realization changed the way Ken led. Instead of only pointing out what went wrong, he became intentional about recognizing what his team was doing right. And when mistakes happened, he stopped asking: "Who messed up?" He s...

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The Leadership Blind Spot Most Business Owners Never See Until It’s Too Late

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This episode was published on September 10, 2026.

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