Is your company behind in the AI race?
Cisco surveyed 2,500 CEOs and found 65% fear they're underinvesting in AI. Another study found 80% believe their job is at risk if their AI strategy fails. Thirty-eight percent report "high or crippling" stress about it.
Quick AI Survey - Participate and I'll show you the results!
I built SurveyPlaybook.ai — an AI that interviews you instead of handing you a form. I've set it up with these five questions, and it will dig into your answers the way a good analyst would.
Take a couple minutes and chat with the survey. I'm closing it at the end of September, and every participant gets the full report: how executives across the Playbook audience answered, where you rank on each of the five questions, and where the race is real versus theater. Your answers stay anonymous in the report.
Chances are you are not behind. The race you're measuring yourself against mostly doesn't exist. I believe we are being told a lie.
Here are seven signs the AI Race is a Lie
1. The real frontier is dumber than you think
I was on a leadership call at my company today. One of the problems that came up: account executives go on vacation and forget to turn on their out-of-office in Outlook. Teammates email them for days, wondering why they're being ignored, and eventually find out the person was on a beach.
Sit with that. In 2026, with all this intelligence available, a human still has to remember to open Outlook, find a screen, and click a button to tell the world they're gone. And that was one of about fifteen ticky-tacky little things on our list — none of them hard, all of them still eating human attention.
That's the actual AI frontier at most companies. Not AGI. Not the billion-dollar platform your competitor announced. Fifteen dumb frictions nobody should have to think about anymore. (This is exactly the class of problem I'm building TextMyAgent around — your agent can see the calendar says vacation and handle it.)
While you're anxious about the race, the winnable ground is lying there untouched.
2. The "winners" can't tell you what they won
MIT looked at 300 enterprise AI deployments: 95% of GenAI pilots produced zero measurable P&L impact. IBM puts the share of projects hitting expected ROI near 25%. S&P Global found 42% of companies abandoned most of their AI projects last year.
If the leaders were actually winning, someone could point at the scoreboard. Nobody can.
3. The teams "ahead" are the most anxious
My favorite stat of the year: AlixPartners found that executives at companies leading in AI adoption report MORE anxiety than their peers, not less.
If being ahead brought clarity, the leaders would be calm. They're not — because they're ahead in spending, not outcomes, and when your job feels at stake you keep buying visible things: the big platform, the splashy pilot, the demo for the board. Fear optimizes for looking busy. It has never once optimized for the boring fix that pays.
4. FOMO is doing the purchasing
Ask what's driving AI adoption and the top answer isn't a bottleneck or a business case. It's competitor moves. Companies are buying because the company next door bought.
Gartner said it better than I can: "FOMO is not a strategy. And in the agentic era, it is an expensive mistake." They predict a third of companies will actively damage customer experience this year by deploying AI prematurely.
5. Half of what you're chasing is fake
Gartner calls it "agent washing" — vendors relabeling old chatbots and automation as autonomous agents. Of the thousands of vendors claiming agentic AI, Gartner estimates only about 130 are selling the real thing.
You cannot be behind competitors whose capabilities are marketing copy.
6. The race already has a refund line
Nearly 70% of executives say they'll cut AI budgets if ROI targets are missed. Uber capped agentic coding tools at $1,500 per employee per month after burning its annual AI budget in four months. Gartner expects over 40% of agentic AI projects canceled by end of 2027.
The frantic spending you're comparing yourself to is already being walked back. You're not behind the pack — the pack is turning around.
7. "Behind" is measured in demos, not deletions
A second story from my own shop. I have a developer on my team — ambitious, talented — who used Claude Code to build a large application inside the console that runs our company. It's big. It's genuinely pretty. And I've been trying to figure out how to tell him it's way too much: too large, and built on a stack of assumptions that people will actually use it.
AI made building so cheap that he skipped the only test that matters — putting something small in front of real users who will tell you the truth. Whether it's a game changer or whether it sucks. Cool and pretty doesn't survive contact with a user who didn't ask for it.
Last issue I called this the 95% problem: the AI projects that work share one trait — they remove work. The ones that fail generate surface area: more dashboards, more reports, more places to check. The "race" measures demos shipped. It should measure work deleted. By that measure, almost everyone is standing at the starting line, including the companies you envy.
So what does "ahead" actually look like?
Here's the exercise from our leadership call, and I'd put it against any AI strategy deck: ask your team to list the fifteen dumbest recurring things they still have to remember to do. Out-of-office buttons. Forwarding the same confirmation. Chasing a reply that already came in.
That list is your AI roadmap. Pick one, delete it, measure the time that comes back, then take the next one. It's not glamorous and it doesn't demo well — and it's the only version of this race with a finish line.
The 5-question reality check
Before your next AI purchase, answer these honestly:
- Name one AI deployment at your company that removed work from someone's day. Can you?
- What percentage of your AI spend can you tie to a specific P&L line?
- Who owns AI outcomes at your company — a name, not a committee?
- If every AI pilot you're running vanished tonight, who would notice first: your customers or your vendors?
- What's actually driving your next AI purchase — a measured bottleneck, or a board meeting?
The bottom line
The anxiety is real. The race is not. The companies "winning" are burning money on things they're about to cancel, while fifteen dumb frictions sit on every team's desk, free to delete.
At that point, you are not behind in a race. You are the only one actually running.
Hit reply and tell me where I'm wrong — the best conversations in this newsletter's history started as replies.
— Keith