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How do you coach the coaches — developing your sales managers?

Kory WhiteCurated by Kory White · Fractional CRO, CRO Syndicate
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Direct Answer

You coach the coaches by treating your sales managers as a coachable population with their own skill gaps — and the core move is to observe them coaching a live rep, then coach the manager on what you saw, not on the deal. Run a coach-the-coach cadence: sit in on (or review the recording of) each manager's 1:1s and call reviews, score *their* coaching behavior against a rubric, and hold a weekly skip-level rhythm where you develop them the same disciplined way you ask them to develop reps.

This is ongoing manager development, not onboarding — the manager already knows how to run a 1:1; your job in 2027 is to keep their coaching sharp, consistent, and AI-assisted. If a manager won't observe their own calls or refuses to be coached, that is a will problem you escalate, not a skill you keep teaching.

How do you coach the coaches — developing your sales managers?

Why This Happens — Diagnose Before You Coach

Most second-line leaders default to coaching managers on *numbers* ("your team's pipeline is light") instead of on the *coaching behavior* that produces those numbers. That is coaching the lagging indicator. Before you correct a manager, separate four root causes, exactly as you'd ask them to do with a rep:

A manager whose team is missing quota because the manager personally carries three deals every quarter has a will/identity problem (still selling, not leading). A manager who *wants* to coach but gives vague "great call, keep it up" feedback has a skill gap. Those need opposite interventions. Diagnose first.

flowchart TD A[Manager's team is underperforming] --> B{Did you observe the manager actually coaching?} B -->|No| C[Sit in on a 1:1 and a call review first] B -->|Yes| D{Is the coaching specific and behavior-focused?} D -->|No, vague praise| E[SKILL: teach feedback + GROW] D -->|Yes, but rep ignores it| F{Does manager follow up next week?} F -->|No| G[WILL: accountability on follow-through] F -->|Yes| H{Does manager have time + tools?} H -->|No| I[SYSTEM: fix span of control / Gong access] H -->|Yes| J{Does manager still close deals themselves?} J -->|Yes| K[IDENTITY: shift from player to coach] J -->|No| L[KNOWLEDGE: deepen MEDDPICC / product fluency]

The Coaching Conversation

Coach the manager on a *specific observed moment*, never in the abstract. Use the GROW model (Goal, Reality, Options, Will) so the manager experiences the exact framework you want them using with reps. Here is a verbatim skip-level coaching script after you've watched one of their 1:1s:

Goal — "What were you trying to get your rep to change in that 1:1, specifically?" Make them name one behavior. If they say "I wanted to motivate her," push: *"Motivate her to do what differently on Monday?"*

Reality — "Here's what I observed. You spent eleven of the fifteen minutes talking, and you gave her the answer to the objection instead of asking how she'd handle it. What's your read on that?" State the data, then hand the diagnosis to them. Silence is your tool — let them sit in it.

Options — "If you ran that again, what are two things you could do to make her solve it herself?" Do not supply the answer. If they stall, offer one: *"One option is the 80/20 rule — they talk 80% of a coaching 1:1. What else?"*

Will — "Which of those will you try in your next 1:1 with her, and how will I know you did?" Lock a commitment with a verification mechanism — a recording, a follow-up note, a metric.

For a manager who is still selling instead of coaching, the script is sharper:

*"You closed the Henderson deal yourself last week, and I get why — it felt faster. But your team's win rate dropped to 19% because nobody else is getting reps at that table. I'm changing the deal: your number is now how many of your reps run a clean MEDDPICC deal review without you taking the wheel. What gets in the way of you stepping back?"*

For a manager avoiding a hard conversation with a low performer, name it directly:

*"You've coached Marcus on prospecting for three months and the activity hasn't moved. That's no longer a coaching problem — it's a performance-management decision. I'll help you build the PIP and run the conversation. When are we doing it?"*

Bold the move every time: you are modeling the coaching behavior you want them to copy. Managers learn coaching the same way reps learn selling — by being coached well themselves.

The Coaching Plan / Cadence

Run a repeatable coach-the-coach loop, not ad-hoc check-ins. A practical weekly + 30/60/90 rhythm:

flowchart LR A[Observe manager coaching a rep] --> B[Diagnose: skill/will/knowledge/system] B --> C[Coach the manager via GROW] C --> D[Manager practices in next 1:1] D --> E[Measure downstream rep behavior change] E --> F[Skip-level to verify it landed] F --> A

Drills & Role-Play

Build manager coaching skill with reps, not lectures:

What to Measure

Lagging quota tells you nothing about coaching quality until it's too late. Track the leading indicators that prove your manager development is working:

Common Mistakes Managers Make

FAQ

How is coaching managers different from coaching reps? The framework (GROW, observe-diagnose-coach-measure) is identical, but the *unit of behavior* changes. With a rep you coach selling behavior; with a manager you coach coaching behavior — how they run 1:1s, give feedback, and develop people.

The hardest shift is getting managers to stop selling and start building sellers.

How often should I sit in on my managers' coaching sessions? At least one recorded session per manager per week to start, dropping to bi-weekly once the coaching rubric scores stabilize. Use AI call-coaching (Gong, Chorus) to scale your visibility so you're not personally attending everything.

What if a manager resists being coached? First diagnose: is it skill embarrassment (fix with a low-stakes recording review) or genuine will/ego? Persistent refusal to be observed or developed is a leadership red flag, not a coaching project — escalate it as a performance conversation.

Should I skip-level with my managers' reps? Yes, carefully and transparently. Tell the manager you're doing it to hear how coaching lands downstream, not to undermine them. Skip-levels are your best source of truth on whether the coaching is actually changing rep behavior.

Can AI replace the second-line coaching loop? No. Gong and Chorus scorecards scale *observation* and surface patterns, but the GROW conversation, the accountability, and the identity shift from player to coach still require a human leader. AI is the telescope, not the coach.

When is more coaching the wrong answer for a manager? When the data shows a wrong-fit hire, a comp or territory problem, or a manager three months into unchanged behavior despite specific feedback. At that point it's a performance-management decision, not more reps.

Bottom Line

The one move that matters: observe your managers coaching, then coach them on what you saw using GROW — develop the coaching behavior, not the number. Build a weekly skip-level loop, measure downstream rep behavior change, and be honest about when it's a will or hiring problem rather than a skill gap.

Coach your managers exactly as disciplined as you ask them to coach their reps.

Sources

*Sales coaching for developing your sales managers — how to coach the coaches, sales manager coaching guide, second-line leader coaching framework, skip-level coaching playbook, and a coach-the-coach development plan for 2027.*

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