AI. LinkedIn video selling. Complex ROI calculators. Buyer committees. Oh—and still hit your number.
Sales reps in 2025 are expected to learn a lot. Fast.
But learning doesn’t happen in a vacuum. And your team is likely already stretched thin.
This article shows how Chicago and Northbrook sales managers can reskill their teams without burnout, using Sandler’s proven tools of behavior tracking, bite-sized reinforcement, and practical coaching.
The Reskilling Dilemma
You’re being told:
“Make your reps storytellers, consultants, technologists.”
“Train them on 5 new tools.”
“Fix pipeline conversion.”
Meanwhile, your reps feel:
Overwhelmed
Disconnected
Resentful of “flavor of the month” changes
Sandler Insight: Small Wins > Massive Shifts
Learning sticks when it’s:
Behavior-based
Actionable in the field
Supported over time, not just once
Step 1: Use a Reskilling Cookbook
Create a “reskilling plan” just like a sales activity plan. Weekly behavioral goals might include:
Watch 1 training video
Use a new talk track 3x
Run a practice ROI conversation with peer
Track just like prospecting.
Step 2: Coach One Thing at a Time
Managers often overload reps with 3-5 new behaviors per coaching session. That leads to overwhelm.
Instead:
Pick one skill to reinforce for 2–3 weeks
Use role-plays and call reviews
Acknowledge effort, not just mastery
Step 3: Let Reps Co-Design Their Learning Path
Use the Sandler “equal business stature” principle:
“Here’s what HQ wants us to learn. What’s one area you want to level up in? Let’s build your plan together.”
Reskilling doesn’t require massive disruption. With Sandler tools, you can create a culture of steady, supported growth.
