This article comes from Tjeerd Veninga’s talk, ‘Changing behavior – The good, the bad, the ugly… and a way that actually works’, at our 2023 Amsterdam Sales Enablement Summit, check out his full talk here.

Old habits die hard, especially when money is on the line. So how do you transform decades-old sales approaches across an organization?

In my 15+ years in sales enablement at companies like Microsoft and MessageBird, I've banged my head against the wall many times trying to get teams to embrace new skills. 

While I don't have all the answers, I've picked up some hard-won lessons on the good, the bad, and the downright frustrating parts of transforming behavior.

In this article, I want to share my key takeaways to help fellow enablement leaders and frontline managers drive real change. I'll take you through my failures and successes, organizing it into "the good, the bad, and the ugly.

My goal is to provide practical tips you can start applying now to motivate your teams. So, let’s dive right in!

The ugly: Why changing behavior is so hard

We all know driving real change is hard. As Mark Twain famously said, "I'm all in favor of progress; it's change I don't like." 

Customers initially get excited about new ideas and progress. But when it comes time to actually change entrenched habits and behaviors, resistance invariably crops up.

On the sales enablement side, we often see that simply providing training isn't enough to produce real changes in seller behavior with customers.

The metrics may look good on paper, but out in the field, reps quickly revert back to old habits.

On the business side, appeals for more training or feedback from customers frequently fall flat. Mandating actions doesn't work well either, as sellers resist top-down edicts.

So why is driving change so difficult? I've learned it comes down to three core challenges: