Not Everything With “AI” In the Name Is Useful (Or Even Real)
If you’re a CEO right now, chances are someone on your team has already pitched you an AI tool that promises to “revolutionize everything.”
Some of them are brilliant.
Some are… basically Google Sheets with a cooler name and more confidence.
One tool we reviewed claimed to boost morale by sending emoji reactions based on email tone.
It sent a 🎉(party popper) when someone submitted their resignation.
So yes—this list exists for a reason.
Here are 10 questions I now ask before we approve any AI tool.
They’ve saved us money, sanity, and the need to issue apology emails to clients we “auto-tagged” incorrectly.
1. Is it solving a real problem—or just automating a minor inconvenience?
Not everything needs to be “optimized.” Sometimes, people just want to do their job, not talk to a chatbot about it.
2. Would we still use this tool if the word “AI” wasn’t attached to it?
If the answer is no—it’s a feature, not a product. Let’s not rebrand automation as innovation.
3. Does it help my team think better—or just think faster… and wronger?
Speed is great. But making bad decisions quickly isn’t innovation—it’s panic, just more efficient.
4. Who trained this thing—and what were they drinking?
One tool suggested we fire our top performer to “improve departmental symmetry.” Helpful.
5. Can we explain how it works to someone outside the tech team?
If your product manager can’t explain it to someone in Finance without sounding like they’re describing a Marvel villain, that’s a red flag.
6. What happens when something goes wrong?
There’s a difference between “the tool crashed” and “it deleted our vendor contracts because it thought they were spam.” Always test the fallback.
7. Is it quietly listening to everything—like a toddler with perfect memory?
One tool started auto-replying to my emails with “Sounds good 👍” — including a legal contract. Fired.
8. Does this reduce human effort—or remove human judgment?
Automation is great for repetitive tasks. But if it’s making decisions with ethical or emotional nuance—pause.
9. Can we break up with it easily? Or is this a lifetime SaaS marriage?
If uninstalling the tool requires a calendar invite, a contract review, and emotional closure… hard no.
10. Is my team excited about using it—or just afraid to say no?
The best tools create pull, not pressure. If your team is being “voluntold” to use something clunky, it’s time to rethink.
Bonus: Has someone already tried this tool in the company without telling me?
It happens. You’d be surprised how many “experimental” AI tools are already running quietly in the background because someone got excited at 11 p.m. and clicked “Connect to Google Workspace.”
So What’s the Real Job Here?
AI isn’t the problem.
Our judgment around it is.
Every new tool sounds impressive in the demo.
But great leadership isn’t about getting excited first. It’s about asking what happens after.
After the hype. After integration. After someone hits “send” and the AI replies with a dancing octopus.
As CEOs, our job isn’t to stop innovation.
It’s to slow it down just enough to make sure it’s useful, safe, and actually aligned with how we want our teams to work.
Because approving AI isn’t a tech decision anymore.
It’s a cultural one.
Regards,
Rupesh
P.S.
If you’ve ever said yes to a tool that auto-summarized your team’s strategy as “???,” you’re not alone.
We’re all learning. Let’s just laugh, review the fine print—and maybe ask better questions next time.
Cloverbites By Rupesh Sanghavi 
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