How-To Guide2026-01-24

Coaching Underperforming Sales Teams: A Manager's Guide

AM

Alex Mirzaian

Modern Voice AI

Coaching underperforming sales reps is essential for insurance agents looking to close more policies and build successful careers. Learn how to coach underperforming sales reps effectively. Discover frameworks, improvement plans, and techniques to improve sales team performance.

In this comprehensive guide, we cover everything you need to know about coaching underperforming sales reps, from foundational concepts to advanced strategies. Whether you are new to insurance sales or looking to sharpen your skills, this article provides actionable insights you can apply immediately.

TL;DR - Quick Summary

  • Coaching underperforming sales reps starts with diagnosing root causes: skill, will, or circumstance
  • A sales coaching framework provides consistent structure for development conversations
  • Sales performance improvement plans document expectations, support, and consequences
  • Effective coaching combines observation, feedback, practice, and accountability
  • Prevention through better hiring, onboarding, and ongoing development reduces underperformance

Key Takeaway

Coaching underperforming sales reps requires understanding why performance lags before attempting solutions. Diagnose accurately, coach consistently, document thoroughly, and act decisively when coaching fails.

Diagnosing Performance Problems

Coaching underperforming sales reps effectively requires understanding why they are underperforming. Different causes require different interventions.

Skill Issues: The rep does not know how to do something. They lack techniques for discovery, objection handling, or closing. Training and practice address skill gaps. How to coach low performing salespeople often starts with identifying specific skill deficiencies.

Will Issues: The rep can perform but chooses not to. Motivation problems, attitude issues, or misaligned incentives undermine effort. Addressing will requires different approaches than addressing skill. For more information, see our guide on roleplay for skill development.

Circumstance Issues: External factors affect performance. Territory quality, lead flow, product problems, or personal situations impact results. Circumstances may require accommodation rather than coaching.

Diagnosis Approach:

  • Review data: What do metrics reveal? Where does the rep diverge from successful peers?
  • Observe directly: Listen to calls. Watch interactions. Identify specific behaviors.
  • Ask questions: What does the rep think is happening? What have they tried? What support do they need?
  • Consider context: What else is going on? Are circumstances contributing?

Misdiagnosis leads to wasted effort. Coaching skills when the problem is will frustrates everyone. Demanding more effort when circumstances prevent success damages trust. For more information, see our guide on enablement training approaches.

The Coaching Framework

A sales coaching framework provides structure for development conversations. Consistency helps both coach and rep know what to expect.

Observe: Watch the rep in action. Listen to recorded calls. Review deals in pipeline. Gather concrete examples of behavior.

Prepare: Before coaching conversations, identify specific points to address. Have examples ready. Plan how to frame feedback constructively. For more information, see our guide on training investment value.

Discuss: Start with the rep's self-assessment. What did they think went well? What would they do differently? Self-awareness often surfaces issues without confrontation.

Feedback: Share observations specifically. "I noticed you moved to presentation before understanding their current coverage" is more useful than "Your discovery needs work."

Practice: Address skills through practice immediately when possible. Roleplay the scenario differently. Roleplay for skill development accelerates improvement when integrated with coaching. For more information, see our guide on agency growth strategies.

Commit: End with clear action items. What will the rep do differently? When will you follow up? Specificity creates accountability.

Follow Up: Check on committed actions. Recognize improvements. Address continued gaps. Consistent follow-up signals importance.

This framework applies whether coaching formally scheduled or opportunistically after a specific observation.

Performance Improvement Plans

A sales performance improvement plan formalizes expectations when informal coaching has not worked. PIPs serve multiple purposes:

Documentation: Creates a record of expectations, support provided, and outcomes. Important if employment decisions follow.

Clarity: Eliminates ambiguity about what must improve and by when. Both manager and rep know the stakes.

Support Structure: Specifies resources and assistance available. Demonstrates organizational investment in success.

PIP Components:

Current State: Document current performance with specific metrics. Compare to expectations and peers.

Expectations: Define what success looks like. Use measurable criteria where possible. "Improve close rate from 15% to 25%" is clearer than "close more deals."

Timeline: Specify the improvement period. Common timeframes are 30, 60, or 90 days depending on sales cycle length and gap severity.

Support Plan: List resources available—training, coaching, tools, adjusted targets. Demonstrate investment in success.

Check-In Schedule: Define when progress will be reviewed. Weekly check-ins maintain momentum.

Consequences: State clearly what happens if improvement does not occur. Ambiguity undermines seriousness.

PIPs should be genuine development tools, not documentation for predetermined exits. If the decision is already made, proceed to separation rather than conducting theater.

Effective Coaching Techniques

Improve sales team performance through techniques that address specific development needs.

Call Coaching: Review recorded calls together. Pause at key moments. Ask what the rep was thinking. Discuss alternatives. This technique addresses skills in context.

Joint Calls: Accompany reps on calls. Demonstrate techniques live. Provide immediate feedback afterward. Reserve this for specific learning objectives rather than surveillance.

Role Reversal: Have the rep coach you through a scenario. Playing teacher reveals understanding gaps and builds ownership of techniques.

Micro-Commitments: Break improvement into small steps. Commit to one behavior change at a time. Small wins build momentum for larger improvements.

Peer Observation: Pair struggling reps with high performers. Learning from peers sometimes works better than learning from managers.

Self-Recording Review: Have reps review their own calls before coaching. Self-observation often surfaces issues before managers raise them.

Accountability Partners: Pair reps for mutual accountability. Regular check-ins with peers create social pressure that supplements manager oversight.

Sales rep ramp plans for new hires should incorporate these techniques proactively rather than waiting for underperformance to emerge.

Enablement training approaches complement individual coaching. Group training addresses common gaps while coaching addresses individual needs.

When to Exit Someone

Not every underperformer can be coached to success. Knowing when to make exit decisions protects team culture and resources.

Signs Coaching Is Not Working:

  • Improvement plan goals consistently missed
  • Same issues recur despite intervention
  • Rep disputes feedback or denies problems
  • Effort to improve is absent
  • Other team members express frustration

Exit Decision Factors:

  • How long has underperformance continued?
  • What investment has been made in development?
  • Has the rep shown genuine effort and progress?
  • What is the impact on team morale?
  • What is the opportunity cost of continued investment?

Executing Exits:

  • Document thoroughly before proceeding
  • Consult HR and follow organizational procedures
  • Be direct and humane in separation conversations
  • Avoid surprises—improvement plans should make stakes clear
  • Maintain professionalism regardless of rep reaction

After Exits:

  • Communicate appropriately with remaining team
  • Review what might have been done differently
  • Improve hiring and onboarding to prevent recurrence

Difficult exits handled well preserve team culture. Tolerating persistent underperformance damages high performers' morale.

Preventing Underperformance

The best coaching is preventive. Reducing underperformance through better systems serves everyone.

Hiring: Define success profiles based on actual top performer characteristics. Validate candidates against profiles. Poor hires become coaching challenges regardless of effort.

Onboarding: Structured onboarding accelerates time-to-competence. Clear expectations from day one prevent confusion. Regular check-ins catch problems early.

Ongoing Development: Continuous training maintains skills and adapts to changes. Training investment value compounds over careers. Wait until problems emerge and intervention costs more.

Performance Monitoring: Track leading indicators, not just outcomes. Activity metrics reveal problems before results decline. Early intervention is easier than remediation.

Culture: Create environments where feedback is normal. High performers seek coaching. Struggling performers ask for help. Cultures that normalize development reduce stigma around improvement needs.

Compensation Alignment: Ensure incentives drive desired behaviors. Misaligned compensation creates performance problems no coaching can fix.

Manager Development: Invest in coaching skills for managers. Many managers were promoted for sales performance, not management ability. Manager capability determines coaching quality.

Agency growth strategies depend on team performance, which depends on effective coaching. Organizations that build coaching capability compound advantages over competitors that do not.

Prevention requires investment but produces returns. Every underperformer who becomes a performer through early intervention saves the cost and disruption of replacement.

Frequently Asked Questions

How do you coach underperforming sales reps?

Start by diagnosing root causes (skill, will, or circumstance), then apply consistent coaching frameworks that include observation, feedback, practice, and accountability. Document expectations and provide genuine support for improvement.

What is a sales performance improvement plan?

A sales performance improvement plan (PIP) formalizes expectations when informal coaching has not worked. It documents current performance, specific expectations, timeline, support provided, check-in schedule, and consequences of non-improvement.

What is an effective sales coaching framework?

An effective framework includes observing behavior, preparing specific feedback, discussing with rep self-assessment, providing concrete feedback, practicing skills, committing to action items, and following up consistently.

How do you improve sales team performance?

Improve performance through call coaching, joint calls, peer observation, micro-commitments, accountability partners, and structured practice. Combine individual coaching with team training for comprehensive development.

When should you exit an underperforming sales rep?

Consider exits when improvement plan goals are consistently missed, same issues recur despite intervention, genuine effort is absent, and team morale is affected. Document thoroughly and follow organizational procedures.

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