How to Coach Your Sellers

Turning Sales Managers into Growth Multipliers Post #20

Mort Greenberg
October 19, 2025

Hi,

Sales coaching isn’t about delivering pep talks or micromanaging deals, it’s about unlocking performance in ways that last.

When done right, coaching creates sellers who think strategically, execute consistently, and adapt to changing market conditions.

Without coaching, teams plateau, burnout rises, and organizations miss out on growth they could have captured.

This workshop equips leaders with frameworks, real-world tools, and best practices to coach sellers effectively, ensuring better results for individuals and the business as a whole.

Why does this matter? Because the best sellers are rarely “born”, they’re developed. Coaching bridges the gap between raw talent and repeatable success.

Coaching is the lever that turns average sellers into top performers, and top performers into leaders. In an environment where competitors are always innovating, great coaching keeps your team sharp, engaged, and ahead of the curve.

Turn to Best View Tables Below

ACTIONS YOU GAIN FROM THIS WORKSHOP

Run structured, high-impact coaching sessions every week.
Diagnose seller needs with a clear, repeatable framework.
Measure coaching ROI through performance and skill growth.

DO’S & DON’TS

WHAT TO DO	WHAT NOT TO DO
Do create structured coaching rhythms (weekly/bi-weekly).	Don’t confuse coaching with performance reviews.
Do focus on both skill development and deal strategy.	Don’t use coaching time to simply check the pipeline.
Do personalize coaching for each seller’s style and goals.	Don’t try to “c l o n e” yourself, let sellers grow their own strengths.
Do measure impact through performance and engagement.	Don’t overcomplicate it, simple frameworks are more effective.

KEYS TO SUCCESS

Consistency – Make coaching a habit, not a one-off.
Empathy + Data – Balance human understanding with hard numbers.
Future-Focus – Coaching should prepare sellers for tomorrow, not just critique yesterday.

THREE WORKSHOP STEPS

STEP 1: DIAGNOSE SELLER NEEDS

Action: Assess each seller’s strengths, gaps, and motivations.
Execution: Use a simple skills vs. willpower matrix.
Tip: Don’t assume performance = potential.

Seller	Strengths	Gaps	Motivation Level	Coaching Focus
Alex	Prospecting, Energy	Closing deals	High	Objection handling
Jordan	Relationship building	Pipeline hygiene	Medium	Discipline & tracking
Casey	Analytical	Confidence in pitching	High	Storytelling & presentation

STEP 2: STRUCTURE THE COACHING CONVERSATION

Action: Use a repeatable framework: Ask > Listen > Guide > Commit.
Execution: Role-play with sellers on current deals or skills.
Tip: Spend 70% of the session listening.

Example Framework:

Ask: “What’s the biggest barrier in your deals right now?”
Listen: Capture themes, don’t interrupt.
Guide: Offer frameworks (e.g., Challenger questioning).
Commit: Agree on 1–2 actions by next session.

STEP 3: REINFORCE AND MEASURE

Action: Track coaching commitments in a shared system (CRM notes or coaching log).
Execution: Review progress in each session, celebrate wins and recalibrate misses.
Tip: Link coaching outcomes to business metrics (pipeline velocity, close rates).

Real-World Example:
At a SaaS company, managers began logging every coaching action plan in Salesforce. Within two quarters, SDR productivity rose 18% because reps were accountable to goals that were clear, documented, and tracked.

THREE UNIQUE FOCUS AREAS

Coach the Person, Not Just the Numbers
- Tip: Get curious about what drives each seller.
- Example: A rep missing quota improved dramatically when the manager reframed coaching around confidence in client conversations rather than raw dials.
Make Coaching Collaborative
- Tip: Co-create action steps instead of dictating them.
- Example: In one manufacturing firm, reps committed to peer-led practice sessions that grew out of coaching conversations.
Celebrate Growth, Not Just Wins
- Tip: Recognize progress in skills, not only closed deals.
- Example: A financial services company tied bonuses partly to skill improvement, rewarding reps who grew in presentation ability even if the quarter was tough.

What Workshop(s) Would You Like to See Next? Click Image Above… (Thank you!)