For more than 20 years, I’ve supported B2B sales teams, first as a product manager, then as a sales effectiveness manager, and now as a marketing executive.
For too many of those years, I delivered everything I was asked to do. Beautiful collateral? Yup, I created reams of it. Killer demos? I’m your guy. I fired emails to my sales team announcing new materials, and was constantly frustrated, because no one read the emails or used the materials.
Then one day, I had a life-changing experience. One of my sales reps—let’s call him Tom-lost an important deal that had been forecasted to close. When I asked him what happened, Tom seemed genuinely puzzled: He said he had really “hit it off” with the decision-maker—they were both into cycling and had gone to a Bulls game together. According to Tom, the client team “really liked the product” and had made positive comments during the demos. “Every call went really well,” Tom said.
But when I called the decision-maker who shot us down, I got a very different story.
Yes, Tom had given “very slick presentations,” the prospect said, “but he didn’t know enough about our business.” Further, Tom “did little to help me understand how our product would solve his company’s problems.” When pressed with questions, Tom “took a long time getting back with answers” and when he did, some of the information was just plain wrong.
But it got worse. When I reviewed some of the information Tom had shared with the prospect, I found he had used a four-year-old slide deck with outdated messaging and branding, and a poorly written, inaccurate data sheet that he had “borrowed” from another rep. I can only imagine what his conversations sounded like.
That's when it hit me. Tom hadn't failed, the company had failed Tom. I realized we weren't doing anything to help Tom have the conversations he needs to have to give buyers to move to the next step in their buying process. And the things we were doing were actually causing more harm than good.
I set out that day to reinvent sales enablement, and this blog contains lessons I've learned in the trenches, and provocative ideas that I hope will get people to consider a new mindset towards how they enable sales.




