How to Train Your Sales Team to Actually Win Deals
How to Train Your Sales Team to Actually Win Deals
Your sales team isn't hitting quota.
You hired smart people. They have experience. But deals aren't closing.
The problem? They don't have a repeatable system.
Here's how to train your team to win consistently.
The Problem with Most Sales Training
Most companies do sales training wrong:
❌ One-time workshop → everyone forgets in 2 weeks
❌ Generic training that doesn't fit their product
❌ No follow-up or reinforcement
✅ Ongoing coaching
✅ Product-specific playbooks
✅ Role-play + real-world practice
The 4-Phase Sales Training Framework
Phase 1: Product & Market Mastery (Week 1)
Your team can't sell what they don't understand.
Outcome: Every rep can articulate your value prop in 30 seconds.
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Phase 2: Sales Process Training (Week 2–3)
Teach your exact sales process.
1. Prospecting: How to identify and reach ICP
2. Qualification: How to use BANT framework
3. Discovery: What questions to ask (and why)
4. Demo/Presentation: How to tailor your pitch
5. Objection Handling: Common objections + responses
6. Closing: How to ask for the deal
Outcome: Every rep knows the playbook step-by-step.
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Phase 3: Role-Play & Practice (Week 3–4)
Learning ≠ doing.
1. Manager plays the prospect
2. Rep runs the call
3. Debrief: What went well? What to improve?
4. Repeat until smooth
Outcome: Reps build muscle memory before real calls.
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Phase 4: Live Coaching (Ongoing)
Training doesn't end after onboarding.
1. Call review (20 min): Listen to a recorded call together
2. Feedback (10 min): Identify 1–2 areas to improve
3. Role-play (20 min): Practice the fix
Outcome: Continuous improvement, week after week.
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What to Include in Your Sales Playbook
A playbook is your team's operating manual.
1. ICP Definition
2. Value Proposition
3. Discovery Questions
4. Common Objections + Responses
Objection: "We're happy with our current solution."
Response: "That's great to hear! What's working well? And if there's one thing you could improve, what would it be?"
5. Demo Script
Step-by-step guide to running a product demo.
6. Closing Techniques
How to ask for the business without being pushy.
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How to Coach Your Team (Weekly)
Step 1: Review the Numbers
If activity is low → fix that first.
Step 2: Call/Email Review
Pick one call or email to review together.
Step 3: Role-Play the Fix
Don't just give feedback. PRACTICE the improvement.
"Let's role-play that objection again. This time, try asking a follow-up question instead of jumping to features."
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Common Training Mistakes
Mistake 1: Info Dump
Don't try to teach everything in Week 1.
Spread it out. Reinforce over time.
Mistake 2: No Accountability
Training without follow-up = wasted time.
Check in weekly. Track improvement.
Mistake 3: Not Customizing to Your Product
Generic sales training doesn't work.
Your playbook should be specific to YOUR product and YOUR market.
Mistake 4: Only Training New Hires
Even experienced reps need ongoing coaching.
Top performers practice constantly.
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Sales Training Checklist
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The Bottom Line
Great sales teams aren't born. They're trained.
Invest in:
Do this consistently, and your team will start winning more deals.
Need help building a sales training program? Let's talk.