Episode Details

SaaS tools promise to be intuitive. And for a single user, they often are. But add a team, skip the requirements conversation, and you've got a box of 300,000 Legos with no instructions and a deadline.

In this episode, Toby and Chris dig into why technology implementations go sideways — and why the problem is almost never the software. Drawing on their work at Magic Button Labs, they cover:

• Why requirements anchored to your old system will recreate all your old problems in a new environment
• The difference between a Salesforce F1 crew and a ClickUp free-for-all — and why each demands a different approach
• Chris's month-long Zoom waiting room nightmare (and what it reveals about SaaS complexity)
• Why pushing people into the tool before locking in requirements is actually the right move
• The three non-negotiables for any team tool adoption: right people, clear process, executive sponsor

They close with a challenge: if your tool isn't helping, it's because you haven't defined what you're trying to do clearly enough to build it in. The fix isn't a new tool. It's a better conversation.