In this episode of Coach to Scale, sales trainer and former Olympic trials athlete Neil Wood joins Matt Bonelli to challenge one of the most pervasive mistakes CROs and sales leaders make: reserving coaching only for the bottom performers. Drawing from decades of real-world experience and high-performance athletics, Neil makes the case for why top sales reps need consistent, skill-based coaching just as much as, if not more than, struggling reps.
From tactical strategies to improve frontline manager execution to the psychological traps that stall rep development, Neil and Matt explore why most sales training fails to stick, what a real coaching culture looks like, and how reinforcement (not rah-rah) builds consistent revenue teams. If you’re serious about sales performance, this episode breaks down what separates good teams from elite ones and why your top talent should be the first to get coached.
A lot of sales leaders nod their heads when you talk about coaching, but if we’re being honest, most are still getting it wrong. They treat coaching like a remedial plan instead of a performance driver. That’s why I asked Neil Wood to join me on the Coach to Scale podcast. Few people have spent more time helping good reps become great and, more importantly, helping leaders stop spinning their wheels on reps who aren’t going to move the needle.
Neil has coached reps, built teams, and even trained for the Olympic marathon trials. He’s not just a motivational speaker; he’s someone who has put the reps in, literally and figuratively. Our conversation was packed with insight, and if you’re a CRO trying to build consistency, develop your managers, and scale performance without adding more headcount, this one’s worth a listen.
Here’s what stood out.
Training Without Reinforcement Is a Budget Drain
Neil didn’t mince words: Sales training without follow-up is mostly a feel-good event. We’ve all seen it: the national sales meeting, the inspiring keynote, the breakout session that sounds great in the moment… then everyone goes back to their inboxes. There’s no plan, no reinforcement, and no behavior change. Neil insists on mandatory coaching for months after any training engagement, and he’s right. If you’re not reinforcing, you’re not transforming.
Your Top Performers Should Be Your First Coaching Priority
Here’s where Neil drops the hammer: if you only coach your bottom performers, you’re allocating resources where they’ll make the least impact. A 5% lift from your best reps often yields more revenue than a 30% lift from the bottom tier. But too many leaders feel like they’re “being fair” by focusing on those who struggle. That’s not fair, that’s bad math. Start with the people who are most coachable and already driving your number
The Frontline Manager Execution Gap Is Still Real
Neil and I both agreed: the FLM role is the hardest job in sales. They’re stretched thin, undertrained, and often left to figure it out alone. Most were top reps promoted into leadership without a playbook, and now they’re expected to coach others with no framework. The result? One-on-ones that turn into therapy sessions, deal inspections, or generic pep talks, not skill-building conversations.
If your managers lack time, tools, or training, they’ll default to what they know: pipeline reviews, and reps will stagnate.
Managers Avoid Tough Conversations Because They’ve Never Been Taught How to Have Them
Coaching isn’t just about what to say, it’s about how to say it. Neil shared story after story of managers who delay giving feedback or avoid confrontation because they don’t know how to deliver it constructively. The skill gap here has a massive downstream cost: poor performers stay too long, accountability erodes, and your culture takes the hit.
Want a high-leverage move? Equip your FLMs with coaching language and structure. Give them a way to have the hard conversations without feeling like they’re throwing a grenade.
The Real Opportunity is Coaching Moments, Not Just One-on-Ones
This one hit home. We’ve turned “one-on-one” into a calendar item when we really need coaching moments and conversations where the rep gets clarity, guidance, and challenge. Neil calls this out clearly: If your one-on-ones feel like status updates or check-ins, you’re missing the moment to uplevel your team.
Your managers need a system that distills the noise and tells them what to coach and why it matters. That’s why we built CoachEm to surface those moments, at scale, for every manager, every week.
You Don’t Win or Lose by a Lot — It’s the Small Stuff That Matters
Neil brought his athlete’s mindset to this conversation, and it’s worth repeating. The difference between first and fourth in marathons, golf, or Olympic skiing can come down to fractions. Sales is no different. That rep who finishes at 98% of the quota? One more deal could’ve put her over. The key is consistent, focused improvement, which starts with coaching the reps who want to improve.
Stop Coaching for Compliance. Start Coaching for Confidence.
Reps, even the seasoned ones, want guidance. The good ones are asking for it. They don’t want another rigid process or “check-the-box” coaching template. They want real feedback. They want to know what they’re doing well, where they can grow, and how to sharpen their edge.
Coaching isn’t a performance management tool. It’s a competitive advantage. The question is, are your managers using it that way?
Final Word
If you’re still thinking of coaching as something you “roll out” once a year or something that only matters for new reps, you’re leaving serious performance on the table. Your top reps want to be coached, and your managers want to coach; they just need the right structure and support.
Neil put it simply: “If you’re willing to learn, nothing will stop you. If you’re not, nothing will help you.” That applies to reps, managers, and leaders alike.
Let’s talk: www.coachem.io
