33 Questions Executives Ask About AI

Natalia Quintero, who leads Every’s consulting practice, has spoken with more than 100 companies about AI adoption, including the New York Times and the hedge fund Walleye Capital. In June, she and Mike Taylor—now Every’s head of evals practice—hosted a live webinar for 400 executives on how organizations can adopt and implement AI without stalling out. More questions came in than they could answer live, so afterward they wrote up 33 of them—covering strategy, winning over skeptics, tool selection, governance, and how to restructure a company for an AI-native future. We sent that document to the webinar’s attendees at the time and are making it public for the first time here.—Kate Lee

When you put a room full of executives in front of two AI consultants and let them ask anything, you learn about where organizations are stuck with this technology. Here are all the questions that came up on our live session on June 2—from how to get skeptics on board to keeping context fresh.

Every Consulting works with tech and finance teams to implement AI across their workflows, from strategy to training to building the actual tools.

Strategy and organizational transformation

Q: How do you get teams to think bigger about change? Not just getting the work done faster, but rethinking how the work is done?

A: Give your most AI-curious staff permission to build ambitious projects. It’s easier to raise the ceiling than the floor. It’s easier for one AI-fluent person to create 10 good skills and do 10 times the work than it is to get 10 people to each create one skill or double their output. Once that’s in place, set a vision, designate AI champions, prove out high-value skills, then scale.

Show it once, and it runs the process from then on

Walk a Bot through a workflow the way you’d walk a new hire through it: the steps, the exceptions, the part where you check the invoice against the PO. It remembers, then runs the whole thing on its own, in its own browser, on its own computer in the cloud. Onboarding, reconciliation, outbound, release notes: pick the process nobody on your team wants to own and hand it over. Grok Bot, from the team behind SpaceXAI.

Teach your first Bot

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