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.

Key Takeaways

1. The “Leadership Lie” is that there's no time for 1:1s.
Jeff calls out the myth that leaders are too busy to coach; if you're too busy for your people, you're too busy to lead.

2. One-on-ones should be structured, consistent, and focused on development, not deals.
Effective 1:1s follow a repeatable process that goes beyond pipeline reviews to drive skill growth and accountability.

3. Coaching should start with reflection by the rep.
Asking “what went well?” first gives the rep ownership and builds a coaching culture grounded in self-awareness.

4. Top performers need coaching, too, especially around behavior and professionalism.
Being a high producer doesn’t exempt someone from expectations; true leaders help reps round out their game.

5. Managers must separate being in the action from building the team that drives the action.
If you're still acting like a super rep, you're not creating leverage, and you're stunting team growth.

6. Missed 1:1s should be rescheduled immediately, not skipped.
Treat coaching like a customer meeting; canceling without rescheduling signals that people aren’t the priority.

7. AI can be used to scale coaching, not replace it.
Jeff uses AI to track commitments, organize feedback, and personalize development, but the human connection stays central.

8. Be fully present, no Slack, no inbox, no distractions.
Undivided attention during coaching moments signals to reps that their development matters.

9. Coaching isn’t a task; it’s a leadership mindset.
Great leaders don’t wait for permission to coach or train; they take ownership of their team’s growth trajectory.

10. Pay mentorship forward, build a legacy through people.
Jeff credits his early mentors and reinforces that the best ROI in leadership comes from investing in others and teaching them to do the same.

LinkedIn profile: https://www.linkedin.com/in/jeffcummings/