Too many frontline managers are promoted for hitting quota, then left to figure out leadership on their own. In this episode, Jeff Cummings, COO at LLC Attorney, shares a battle-tested coaching playbook built through 20+ years of leading high-growth teams. He challenges the “leadership lie” that there’s no time for 1:1s and lays out a structured, repeatable framework that transforms one-on-ones from status updates into high-impact coaching sessions.
Jeff walks through how to coach top performers without coddling them, how to use AI to scale personalized development, and why being a good manager has nothing to do with being in the deals. This episode is packed with practical guidance for CROs, RevOps, and enablement leaders looking to build durable revenue teams, starting with better coaching habits at the frontline.
When Jeff Cummings was first promoted into leadership, he wasn’t handed a management playbook. Like most new leaders, he had to figure it out through repetition, reflection, and mentorship. Today, as COO of LLC Attorney, he’s built a repeatable framework for coaching that scales performance without adding headcount.
In this episode of Coach to Scale, Jeff makes the case that if you’re a CRO chasing consistent performance and missing plan more often than you’d like to admit, the problem might not be your reps. It’s how your managers are or aren’t coaching them.
Here’s what every CRO should be watching for.
1. The Leadership Lie: “We Don’t Have Time to Coach”
When managers say they don’t have time for 1:1s, what they’re really saying is: “I don’t know how to run one that’s worth my time.”
Jeff calls this out as the leadership lie. The highest-leverage meeting in any sales org isn’t the pipeline review with your largest customer. It’s the 30-minute, no-distractions session between a manager and their rep that creates accountability, builds trust, and drives better inputs. Without that, your strategy doesn’t matter.
2. Don’t Let Super Reps Lead the Team
Too many managers are stuck in individual contributor mode. They’re still hopping into deals, handling the customer conversation, or fixing problems directly. That may work for short-term saves, but it stunts the long-term development of your reps and it burns out your managers.
CROs need to be explicit: if you’re still doing the work of the team instead of building the team that does the work, you’re not leading. You’re patching.
3. Coaching Needs a Cadence and a Structure
One-on-ones are not therapy sessions or loose check-ins. Jeff’s model gives every conversation structure:
- Start with the data
- Ask the rep what went well, and what didn’t
- Share your observations
- Coach around one specific behavior or skill
- Set commitments before the next meeting
- End by asking: “What do you need from me?”
This structure forces reps to reflect, helps managers inspect, and ensures that coaching isn’t generic. It’s targeted and accountable.
4. Coach Top Performers on Behavior, Not Just Results
Your best reps aren’t immune to coaching. They often need it the most, but not on how to close. Jeff shared a story about a top performer who started skirting the process because they assumed their results gave them a pass. He coached them not on numbers, but on the professional habits that would serve them once they moved into leadership themselves.
That’s real development. And it signals that excellence isn’t just about revenue, it’s about how you operate.
5. Use AI to Scale Attention, Not Replace Empathy
Jeff’s built a private GPT to help him prep, track, and follow through on coaching conversations. It reminds him of commitments reps made weeks ago. It flags behavioral patterns. It helps him personalize conversations across a growing team.
The key: he’s not automating empathy. He’s using AI to free up the mental bandwidth required to be present, thoughtful, and consistent.
For CROs managing distributed teams with overwhelmed FLMs, this is the model. Use tools to eliminate the noise so your people can focus on what matters.
6. Presence Is the Signal That Coaching Matters
During 1:1s, Jeff turns Slack off. He closes email. Phone facedown. No Apple Watch. When reps see that, they mirror it. That’s how cultures change.
If you want your frontline to coach like that, your managers need to see you model it. When was the last time you gave your revenue leadership team that kind of undivided attention?
7. Don’t Cancel 1:1s. Reschedule Them.
Missing a 1:1 is missing the only moment you might get that week to change how a rep thinks, operates, or improves. If your managers skip these meetings, hold them accountable. If you skip them yourself, be honest about the signal that sends.
Every time coaching gets bumped for “more important” priorities, you’re reinforcing the idea that pipeline matters more than people. Over time, that mindset kills performance.
Final Word: Don’t Just Coach to Close, Coach to Build
Jeff said something toward the end of our conversation that stuck with me: “People are the engine. We’re just the drivers. But if you want that engine to run well, you’ve got to take care of it.”
That’s what coaching is. Not motivational fluff. Not deal triage. It’s about building durable, scalable performance at the rep level so your revenue engine doesn’t stall every quarter.
If you’re a CRO frustrated by inconsistent performance, high attrition, or stagnant growth, start by asking: Are my managers actually coaching? And if not, what’s my role in changing that?
📩 Want Jeff’s coaching prompt for your own AI-powered 1:1s? DM him on LinkedIn.
💡 Subscribe to Coach to Scale and follow @CoachEmNow for more ways to operationalize coaching.
