Let’s be honest; most managers are still getting coaching wrong. It’s not their fault. They were never taught how to do it in the first place. And when your calendar’s packed, your team is behind quota, and you’re reporting up to the board, it’s easy to default to pipeline triage and performance pressure.
But if we’re serious about consistent quota attainment, we need to examine how frontline managers spend their time and what they think “coaching” actually means.
That’s why this conversation with Mike Montague, sales and marketing expert at Avenue9 and host of the Human-First AI Marketing podcast, hit home. Mike has spent decades in the sales performance world, from hosting Sandler’s How to Succeed podcast to leading their community of over 400 sales coaches and trainers for years. He’s coached sales teams, trained managers, and seen firsthand where the breakdown happens between enablement and execution.
Here are a few takeaways from our conversation that every CRO should be thinking about right now.
Managers Don’t Need All the Answers; They Need Better Questions
Mike said it best: “Coaching isn’t telling. It’s helping someone change their own mind.” If your managers are jumping into every 1:1 with a solution or a to-do list, they’re not coaching. They’re managing, and it’s creating dependence. Your best reps don’t need answers spoon-fed. They need to be challenged to think through their deals, behaviors, and gaps. The real value of coaching is in how it teaches people to solve problems without you in the room.
The Best Leaders Make Themselves Irrelevant
This one might sting, especially for high-performing FLMs who were promoted for being “closers.” But if your team needs the manager in every deal to win, you don’t have a sales team. You have a dependency loop. Mike draws the parallel to great sports coaches. Phil Jackson doesn’t go play shooting guard. The goal isn’t to be in the spotlight. It’s to build a team that executes when you’re not around.
AI Should Make Your People Better
Mike shared a useful analogy that we’re borrowing: Ironman vs. Terminator. Some companies are chasing Terminator-style AI, fully autonomous, cold-calling robots doing the work. That’s just not scalable or sustainable. The smarter move is Iron Man. Keep the human at the center, and wrap them in tools that surface insights, flag patterns, protect the humanity of your brand, and augment their decision-making. Think AI that helps your team do their job better, not just log more calls or analyze transcripts.
Qualification is the Skill Most Reps Avoid and Most Managers Don’t Coach
Mike hit on something we see constantly: Reps love “activity,” but not always the kind that drives deals forward. And too many managers reinforce this by skipping the harder coaching conversations around qualification, discovery, and deal progression. “Selling people what they need, who have budget and authority, isn’t cheating,” Mike said. “That’s the job.” But too often, reps chase deals they’ll never win, and managers let them because they don’t want to micromanage.
Most 1:1s Are Just Forecast Meetings Wearing a Coaching Mask
We asked Mike, “What’s really happening in manager-rep meetings?” His answer was, “Deal reviews. Not skill development.” That’s a problem. You don’t build a pipeline by just talking about it. You build it by helping reps improve the behaviors that create and close opportunities. If there’s no skill focus, no action items, and no accountability, you’re not coaching. You’re checking the box.
Frontline Sales Manager Is Still the Hardest Job in the Company
Every CRO knows this intuitively, but many still expect FLMs to be super-reps, analysts, recruiters, therapists, and coaches without giving them the training or tools to succeed. Mike calls out the burnout cycle: “They’re drowning. And if we don’t fix this, we’re going to keep losing good people and propping up our teams on the backs of the same top performers.”
He’s right. If we want scalable sales performance, we can’t keep burning out our frontline.
Behavior Change Requires Tough Love—and More Reps (of the Right Kind)
One of the most important insights from Mike was around discomfort. Most managers avoid tough conversations. They want to be liked. They want to stay in their comfort zone, but that’s where performance problems live. The only way to get better at difficult conversations is through exposure. Mike calls it “exposure therapy”; you’ve got to get the reps in. Skill development, like sales itself, doesn’t happen in theory. It happens in practice.
Why This Matters for CROs
If your team is missing targets, don’t just look at your tech stack or comp plan. Look at your managers. Are they coaching or just managing? Are they growing your reps or rescuing them? Are they asking great questions or filling dead air?
At CoachEm, we built our platform to help frontline managers coach better. When coaching improves, everything else follows: quota attainment, rep retention, pipeline velocity, and more.
This episode with Mike reminds us that leadership isn’t about having all the answers. It’s about helping your team find them. If you want consistent performance, you need consistent coaching and the tools to make it happen.
