In this episode of Corporate Underpants, I sit down with Adam to dig into the messy world of early-stage alignment in higher ed and non-tech-first organizations. Spoiler: It’s nothing like working at a tech company. Adam shares war stories from two major web strategy projects—one that went off the rails thanks to (surprise, surprise) misalignment, and another that actually worked (because alignment wasn’t an afterthought). We talk about why clarity on business goals is everything, how to get stakeholders on board early, and why adaptability is your secret weapon when dealing with large, bureaucratic orgs. If you’ve ever been stuck in a project with 40 stakeholders, changing priorities, and no clear direction—this one's for you. Timestamps: 00:00 Corporate Underpants Live S1E4 – Managing 40 Stakeholders01:45 Welcome!04:27 Starting the next project with alignment06:35 Asking for four days, getting four hours07:53 What’s the actual goal here?09:07 Overview of The Five Conversations10:13 Adam’s zero-resistance feedback hack12:47 Yes, you CAN meet hundreds of user needs16:33 “Doing personas” whether they think they are or not17:13 Why personas have a bad rap18:56 Higher ed stakeholders actually talk to users—so their assumptions aren’t just “assumptions”19:45 What about bias?21:08 Proto personas, presumptive personas, alignment personas, archetypes… what’s the difference?22:26 If your team hates personas, just don’t call them personas23:03 HYPOTHESIS!27:32 Everyone freaks out about stereotypes…29:28  People have a hard time working together—this helps fix that30:35 Four hours later, we had clear goals!32:53 The result? Three months, under budget… and thank-you notes.34:46 "Where’s the big red button?"36:12 The Lifeboat37:14 This work requires political capital39:24 Start small!41:11 The politics are always the hard part51:47 Why agencies should bake alignment into their projects52:08 Word choice makes a difference53:37 Why goals never exist58:22 Tech people need to adjust when working with nonprofits59:43 Not everything can be fixed01:05:07 Final thoughts