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How to Have Better Sales Conversations w/ Chris Orlob [Episode 290]

Among the many topics Chris and I discuss are how having visibility into sales calls (conversations) is essential for sales leaders today, how listening to actual calls services as a great sales coaching and auto-correcting mechanism and why sales leaders need to understand the important difference between skills and habits/behaviors in the context of sales coaching.

Joining me on this episode of Accelerate! is Chris Orlob, Founder and CEO of Conversature, a conversation coaching platform for sales teams.


Chris explains how the Conversature software helps sales teams by functioning as an “x-ray vision into a sales organization’s conversations”.

Questions to ask if you’re concerned about the effectiveness of your outbound calling:

  1. Are your sales reps having low quality conversations?
  2. Do you know the quality of your sales reps’ conversations?
  3. Have you tried very hard to improve the quality and effectiveness of your sales reps’ conversations but to unpredictable ends?

Having visibility into sales calls/sales conversations acts as an auto-correcting mechanism, because when reps know their calls are being reviewed they employ the right behaviors and refrain from destructive behaviors a lot more often.

Chris believes conversations are the part of being a professional salesperson that require most preparation, skill, coaching, training, education, etc.

Chris shares his belief that sales success often comes down to judgment and there’s no formula for sales success.

Chris makes the point that leverage in sales coaching comes from strengthening strengths rather than focusing on correcting weaknesses, and Andy suggests it’s beneficial to focus on strengthening one good behavior (or habit) at a time.

Andy clarifies there’s an important difference between skills and habits/behaviors because the two are often times conflated.

Chris explains why he wrote in a blog post that strong sales managers or strong sales leaders should not distribute leads equitably — a point I strongly disagree with.


What’s your most powerful sales attribute?

The ability to deliver insights that make people think differently.

Who is your sales role model?

Mark Cuban.

What’s one book that every salesperson should read?

Amp Up Your Sales, by Andy Paul.

The Challenger Sale, by Brent Adamson

What music is on your playlist right now?

Blink 182 and A Day to Remember.