Every sales team has at least one underperformer. The question isn’t whether you have them—it’s how you coach them. In 2025, where retention and morale are just as important as performance, sales managers in Chicago are walking a fine line: how do you help a struggling rep without damaging the relationship?
The answer lies in structured, respectful, behavior-driven coaching—not micromanagement or shame.
Why Traditional Coaching Fails
Underperformance is often met with reactionary fixes:
“You just need to make more calls.”
“Let me sit in on your demos.”
“You need to want it more.”
These create resistance, not improvement. The real fix isn’t telling—it’s collaborating.
Sandler Rule: No Mutual Mystification
Sandler teaches that both coach and rep must be on the same page. If expectations are fuzzy, progress stalls. Coaching must be built on clear agreements and shared accountability.
Step-by-Step: Coaching a Struggling Rep
1. Diagnose the Root Cause
Use these lenses:
Behavioral: Are they doing enough of the right activities?
Skill: Are they competent in discovery, qualification, closing?
Attitude: Are they mentally bought in, or disengaged?
2. Use a Coaching Up-Front Contract
“Can we agree to meet weekly for 20 minutes to focus on one area at a time? I’ll bring feedback and ideas, and you bring specific deals or challenges. If something feels off, we commit to saying so.”
3. Set Behavior-Based Micro Goals
Instead of “hit $50K this quarter,” aim for:
5 new discovery meetings
10 quality follow-ups
3 strong referral asks
Progress breeds confidence.
4. Reinforce Small Wins
Celebrate effort and learning. “That call didn’t close a deal, but your budget question was spot on. Let’s keep building that muscle.”
5. Know When to Reset or Reassign
If behavior, skill, and attitude aren’t improving after 60-90 days of support, it’s time for a deeper career conversation. That too can be done with empathy.
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A Northbrook-based financial services firm had a rep who hadn’t closed a deal in 4 months. After switching from quota pressure to a Sandler-based coaching rhythm (weekly behavioral tracking, role-plays, accountability contracts), the rep closed two deals in the next 6 weeks. Confidence returned, and so did results.
Coaching underperformers isn’t about being tough. It’s about being clear, consistent, and compassionate. With the right tools and mindset, any rep can turn things around—and so can your team dynamic.
