Hi {{first_name|there}},
Most AI transformations fail before a single tool gets purchased. Kanika Choudhary, Chief of Staff at People IX, makes the case that the real problem isn't the software -- it's that companies don't actually understand how they work.
There's a seductive logic to AI FOMO. Another company announces it's automating its ops stack, a new model drops, your inbox fills with case studies. The pressure to move is real. And it's producing a predictable pattern: organizations buy tools before they can describe the problem those tools are supposed to solve.
Kanika Choudhary ahas spent time at People IX interviewing full organizations to map how work actually flows, and what she found was striking. Leadership consistently comes in with a hypothesis about how the company operates, confident in what they think they know from a handful of department-head conversations. They're almost always wrong.
"So far we haven't met a single company where we confirm the hypothesis. They were always wrong."
This isn't a small calibration error. It's a systemic one. When leaders hear from four people and believe they understand a hundred, the entire AI strategy that follows is built on false premises. Automating those premises doesn't fix them -- it locks them in.
Her central thesis cuts straight to it: "You cannot automate what you can't see." Before any tool evaluation, a Chief of Staff needs to get on paper where time and money are actually leaking. Not where leadership thinks they're leaking. The map has to precede the purchase.
This puts the Chief of Staff in a position of unusual leverage -- and unusual risk. The temptation is to pick a low-stakes automation win, something visible and safe, and call it an AI initiative. Kanika is clear about where that leads: appearing to play it safe while delivering nothing meaningful is exactly how a Chief of Staff loses credibility with leadership.
"If you don't understand how your company works, no AI will save you."
The deeper organizational challenge underneath all of this is about inclusion, not just accuracy. Change imposed on people rather than built with them doesn't hold.
Which raises the harder question: if the mapping phase is unglamorous, slow, and politically uncomfortable, who in most companies actually has the standing and the access to do it? And what happens to organizations where nobody takes on that role?
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best,
Scott
Founder, Chief of Staff Network & BizOps Network
