I just wrapped up several hours of difficult conversations stacked back-to-back, and I want to share something that changed my entire management career: the conversations that are going to have the biggest impact on your business are the ones that are really fucking hard. There's almost a direct correlation between how difficult a conversation is and how much impact it has. Yet we avoid them—for days, weeks, months, sometimes years. I've talked to business owners who've let problems fester for years because they don't want the discomfort of a 30-minute conversation. Here's what helped me: reframing these conversations entirely. When you avoid the hard talk, you're not actually avoiding discomfort—you're just reducing its intensity and spreading it out over time, sometimes forever. That nagging voice in your head saying "you know you should be doing that" never goes away until you do it. But after you have that conversation? You feel stronger, empowered, and you immediately wonder who else you need to talk to. This episode breaks down why avoiding these conversations is negligence, how to reframe the temporary discomfort versus permanent relief, and why this muscle becomes addictive once you experience the benefits. If there's a conversation you're avoiding right now, consider this your sign.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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