Why change management fails (and how to fix it)

Change is everywhere in RevOps. We're constantly pivoting with new products, adapting to market shifts, and orchestrating transformations across our organizations. Yet despite being the architects of change, we still struggle to make it stick.

I recently experienced this firsthand at Affirm when we tried to get our sales teams to actually use Salesforce. You know the story: sellers who'd rather do anything than update their opportunities, missing data that makes forecasting a nightmare, and leadership wondering why they can't get basic visibility into the pipeline.

This summer, we decided enough was enough. We had everything going for us: buy-in from our SVP of Revenue, a clear vision of AI-powered risk reporting, and all the standard change management tactics.

Training sessions? Check. Manager engagement? Check. Executive communications? Check.

The results? Well, let me show you what "success" looked like.

The 20% problem nobody talks about

After months of effort, we celebrated hitting 20% adoption across the board. Leadership was cautiously optimistic. The project team was exhausted but hopeful. Everyone agreed we just needed to push harder; more training, more communications, more executive pressure.

But here's what the celebration missed: 80% of our opportunities still weren't being updated. Eight out of ten deals were flying under the radar. That's not a success story; that's a massive blind spot in our revenue operations.

When you dig deeper into the data, the picture gets even more interesting. Our direct sales team had actually jumped from 10% weekly updates to 45%. Not perfect, but real progress. Meanwhile, our customer success team? They went from 2% to... 2%.

Zero movement. Complete failure.

This raised an uncomfortable question: why would the same change initiative produce such wildly different results across teams? CSMs and sellers face similar operational challenges. They both juggle competing priorities. Neither group particularly loves updating Salesforce. So what was really happening here?

Understanding the psychology of change

To figure this out, I turned to one of my favorite change management frameworks from Chip and Dan Heath's book "Switch." They break down successful change into three core elements that perfectly explain what we were seeing at Affirm.

First, there's the Rider. The rational, analytical part of our brain that processes information and makes logical decisions. The Rider loves clarity, step-by-step instructions, and knowing exactly what success looks like.

Then there's the Elephant. The emotional, instinctive side that actually powers our behavior. The Elephant needs to feel the change, not just understand it. It needs motivation, inspiration, and a compelling reason to move.

Finally, there's the Path. The environment and systems that either facilitate or hinder the change. Even with a motivated Elephant and a clear-thinking Rider, a rocky path will stop progress in its tracks.

Looking at our Salesforce adoption through this lens, everything started making sense.