Welcome to Episode 100 of the Coach2Scale Podcast! In this milestone edition, host Matt Benelli delivers a no-nonsense Q2 debrief packed with hard-earned lessons, powerful guest stories, and leadership truths that cut through the noise. From blind spots that sink careers to the non-negotiables of trust, culture, and coaching, this episode distills what it really takes to scale teams and drive meaningful results. Hear firsthand from Kevin McCarthy on self-inflicted downfall, from John Walston on building mental resilience, and from Neil Wood on solving, not selling, your way to a billion-dollar success.
This episode is more than a recap; it’s a call to action. Matt shares five brutally honest themes that every sales leader, coach, and executive needs to hear: coaching is about asking questions, not issuing commands; culture is defined by what you tolerate, not what you say; inconsistency erodes trust; and enablement isn’t optional; it’s your competitive edge. Whether you’re leading a team or trying to level up, this episode will challenge your assumptions and light a fire under your Q3 game plan. Let’s get after it, and as always, CoachEm if you want to keep ‘em.
Let me be straight with you.
This isn’t just a celebration of the Coach2Scale podcast hitting 100 episodes (though only 10% of podcasts ever do). This is your gut check. Your Q2 debrief. Your mirror. And it’s not always flattering.
Over the last quarter, we talked with leaders who’ve been through the fire and a few who started the blaze themselves. These aren’t feel-good stories wrapped in LinkedIn platitudes. They’re real, raw, and sometimes uncomfortable. But if you’re a CRO who’s serious about building a coaching culture that scales, then lean in because your competitors are listening. And learning. And investing.
Here are the five brutal truths we unpacked and why ignoring them might just cost you your best people and your next deal.
1. Blind Spots Will Sink You
Kevin McCarthy ran one of the biggest Century 21 franchises in the country until he didn’t. Prison followed. Why? Not because he was evil. Because he wasn’t aware, he didn’t see the iceberg underneath the water. And guess what? That’s leadership without self-awareness.
“If you don’t know your blind spot, that’s your blind spot.”
As a CRO, your job isn’t to be perfect. It’s to be honest with yourself, your leaders, and your team. When was the last time you invited feedback? When was the last time you looked in the mirror without flinching?
2. Coaching is a Skill;But Most Managers Suck at It
Let’s not sugarcoat it. Most front-line managers don’t know how to coach. Why? Because we never trained them. We promoted high performers and hoped they’d figure it out.
“It’s not your job to have all the answers. It’s your job to ask the right questions.” Mike Montague
If your managers are still rescuing reps, dictating playbooks, and calling it leadership, you’re not building a team; you’re building a dependency. Coaching is about empowerment, not control. Want a test? Ask your leaders what questions they asked in their last 1:1. If they can’t remember, you’ve got a coaching problem.
3. Stop Selling. Start Solving. Or Step Aside.
Neli Wood raised over a billion dollars. Not by selling. By listening. By solving. By staying curious.
Mike Muhlfelder tore the BANT framework to shreds and replaced it with something better: the 4Ws
- What happened?
- Why now?
- Who owns it?
- What’s the plan?
Buyers aren’t interested in features. They want clarity. Insight. Confidence. If your team is still pitching, they’re already behind.
“Prospects can smell commission breath through Zoom.”
And Tom Young nailed it: most buyers don’t even know what they need. It’s our job to help them figure that out.
4. Culture Is Not a Slogan; It’s What You Tolerate
You can print all the posters you want. Run all the all-hands you want. None of it matters if you’re tolerating mediocrity, drama, or inconsistency.
“People don’t quit jobs. They quit leaders who can’t be counted on.” – Dan Freund
We had an incredible debate between Mark Kosoglow and Kevin Gaither about whether leaders should be friends with their reps. Their conclusion? It’s not about friendship. It’s about trust. That comes first. That stays last.
Tony Burnside echoed it in hiring: good people first, skills second, work ethic third. If you’re leading with credentials instead of character, you’re playing the short game.
5. Enablement is Your Competitive Edge; Not a Side Project
Pam Dake said it best: enablement isn’t optional. It’s the lever most of your competitors are ignoring. And it’s the one that will separate the teams that survive from those that scale.
Ask yourself this: Are your reps equipped to win? Not just trained once and left alone, but continuously coached, challenged, and developed? If not, you’re not falling behind; you already are behind.
Final Gut Check: Q3 Is Here. What Are You Going to Do?
This episode isn’t a highlight reel. It’s a warning. Because Q3 isn’t waiting. And if you’re coasting on last quarter’s wins, you’re already vulnerable.
So ask yourself:
- What blind spot are you ignoring?
- What coaching behavior are you tolerating?
- What’s the one uncomfortable truth you’ve been avoiding?
Then act.
Because this is the game.
This is how you scale.
This is how you lead.
🎧 Catch Episode #100 of Coach2Scale wherever you get your podcasts. Share it with your team. Talk about it in your next leadership meeting. And remember, CoachEm, if you want to keep ‘Em.
