Matt Benelli sits down with Mike Montague, sales and marketing expert at Avenue9 and host of the Human-First AI Marketing podcast, for a candid conversation about what sales managers are still getting wrong about coaching. From the myth that leaders need to have all the answers to the burnout caused by "super reps" turned managers, Mike breaks down why most 1:1s fail and how asking better questions can flip the script on team performance. If you're still equating pipeline reviews with coaching, this one’s for you.

They also unpack the critical gap between coaching and execution and why online learning and conversation intelligence tools fall short without behavior change. Mike shares his "Iron Man vs. Terminator" analogy to help sales leaders reframe their use of AI and makes the case for exposure therapy and tough love as the missing ingredients in most sales organizations. Whether you’re trying to scale performance or stop regrettable attrition, this episode gives frontline and senior leaders a roadmap for more effective, accountable teams.

Top Takeaways:

• Coaching is about asking questions, not giving answers. Managers who try to “know it all” become bottlenecks; real coaching empowers reps to think for themselves.
• The best leaders make themselves irrelevant. Like elite sports coaches, great sales leaders build systems and skills so teams can operate independently.
• AI won’t replace salespeople, but it will replace those who don’t use it. Sales leaders need to think like Ironman, using AI as an enhancement tool to increase awareness and execution, not as a replacement for human strategy.
• The frontline sales manager (FLM) role is the hardest in the company. FLMs are overwhelmed by tasks, undertrained in coaching, and lack the time or tools to develop their teams effectively.
• Selling someone what they need and can afford isn’t cheating—it’s your job. Sales should focus on qualified buyers with budget, authority, and urgency, not on convincing disinterested prospects.
• Coaching fails when it focuses only on deals, not skills. Most coaching sessions are just pipeline reviews; they don’t address the behaviors that improve performance in the long term.
• Exposure therapy is essential for growth. Managers need more reps, not more theory, to improve at hard conversations or high-stakes moments.
• Online learning is helpful but only if it’s paired with feedback and behavior change. Asynchronous learning tools often reinforce what reps already know; without coaching moments, they don’t close performance gaps.
• Managers who need approval frequently avoid necessary conversations. Leadership requires discomfort, and effective managers must overcome the urge to be liked to hold reps accountable.
• Coaching is different from managing—and most people don’t know how to do it. There's a widespread misunderstanding of coaching; most FLMs were never taught how to develop others, and it shows.

Ways to Tune In:

• Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A
• Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434
• Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU
• Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77
• Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703
• YouTube: https://www.youtube.com/@Coach2Scale

CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward. These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

Learn more at coachem.io