AI Flight Readiness Plan

Hype warrants both cautious optimism and careful evaluation of risks. In 2-3 weeks, you’ll have both—and the confidence to move forward on your terms.

You’re not reckless. You’re disciplined.

You’ve had valid reasons to hold off on AI. The risks are real, the hype is exhausting, and picking wrong costs money you don’t get back. But waiting has a cost you can no longer ignore—while you stay in place, your vendors, your competitors, and your own team are advancing the ball, without your input. Our AI Flight Readiness Plan helps you move forward on your terms.

YOU’VE HELD BACK FOR GOOD REASONS:

  • You have sensitive data you can’t risk feeding into the wrong tool.

  • AI can be confidently wrong—with no easy way to tell when.

  • With rapid change, tools could be gone or unrecognizable in a year.

  • You’ve seen hype cycles before: software bought, rolled out, and ignored.

  • Your team is split—some already experimenting on their own, some dead set against it—and you stuck in the middle.

IN 2–3 WEEKS, YOU’LL HAVE

  • A clear, prioritized plan: what to do first, what to skip, what it costs—before you commit.

  • Your whole team feeling heard, the eager and the wary both. (We run the interviews. It’s a craft we practice daily, and people are more honest with us than with the boss.)

  • AI decisions you can explain to anyone—your team, your board, yourself—without hand-waving.

  • A roadmap you can follow confidently (even when your competitor is bragging about their AI tools again).

How it works

This two-part workshop gets your key stakeholders ready and on-board, while leadership walks away with a clear plan and breakdown of your top 1-3 AI opportunities, with ROI vs. cost estimates.

Part 1:

  • We interview your stakeholders for you.

  • This is an easy process for your team. Our interviews are designed to tease out key information with no prep required from your team. They just show up and share their thoughts when asked. We do the rest.

  • Our clients tell us this is a hidden benefit: the teams find it fun, and by letting everyone be heard, you are set up for a smoother deployment if you do decide to implement AI.

Part 2:

  • After evaluating the feedback we heard from your team, we put together cost estimates for your top opportunities. We may find that AI is not to your advantage. We may find several worthwhile opportunities. Either way, we’ll give it to you straight.

  • We share both what we are recommending and what we aren’t along with the why — so everyone is clear on the priorities.

  • We give the team a chance to ask questions.

  • We conduct some quick AI education so everyone leaves more confident in their understanding of AI.

  • We share the deck as a deliverable you can keep.

AI risk, contained.

Every recommendation is weighed against real risk—security, privacy, accuracy—not just the upside. We won’t sell you on using AI just because it’s cool. We consider ourselves optimistic curmudgeons. A “go” from us is one you can stand behind.

Ask us about:

  • Environmental concerns

  • Token usage

  • Security

  • Privacy

  • Social risk such as layoffs

Our Credentials

We’ve spent years building software people use and love. Our team presents on AI at conferences regularly, and our leadership holds advanced AI credentials—including a Wharton certificate in AI for Business Decision-Making. You’re hiring an experienced team that does this for a living.

Let’s talk.

We love talking AI Flight Readiness Plans, and we respond to most inquiries within 1 business day or less.