52. Sales Without the Hard Sell: Coaching for Authentic Wins

In this episode of Thoughts on Selling, I sit down with sales coach and former VP of Sales, Shane Jamison, to talk about the real work behind sustainable sales—coaching to the numbers, managing pipeline pressure without compromising relationships, and becoming the guide your customer needs.

We dive into what it means to stay authentic when management wants pull-ins, how to balance urgency with trust, and why pressuring a customer to act early can create more harm than good.

Shane shares lessons from his time building and leading teams, and how his passion for coaching emerged from a love of helping people do more than just hit quota—helping them discover where they thrive.

👉 Key Takeaways:

• Align deal timing to customer priorities, not fiscal quarter deadlines.

• Pressure testing a deal timeline isn’t pushy—it’s collaborative.

• Discounts rarely drive true urgency in B2B—clarity does.

• Coaching is about surfacing what reps already know and helping them apply it with confidence.

• Sometimes the best coaching outcome isn’t closing a deal—it’s helping someone realize they’re in the wrong role.

✅ Action Items:

• Revisit your pipeline: Are close dates based on your internal quarter or the customer's implementation needs?

• When coaching reps, shift the conversation from "what can you close?" to "where can we create value now?"

• For managers and sellers alike: take 30 minutes to map the actual steps it takes from verbal commit to closed-won—then build backward.

If you're coaching or mentoring, ask: "What kind of sale—and sales environment—helps you do your best work?"

Thank you for listening to this episode. I look forward to hearing how you incorporate these strategies into your sales approach.

— Lee