I hate scheduling interviews.

The endless email chains. "Are you available Tuesday at 2?" "No, but Wednesday at 3 works." "Wednesday is bad for the hiring manager. How about Thursday at 1?" "I have a conflict. Can we do Friday?"

It takes DAYS to schedule ONE interview.

So I bought an AI scheduling assistant.

The promise: "Automate interview scheduling. The AI finds times that work for everyone and books them automatically. No more back-and-forth."

What actually happened: The AI triple-booked every time slot, scheduled interviews on weekends, put candidates in the wrong time zones, and created a scheduling apocalypse involving 47 very angry people.

How It Was Supposed To Work

The AI scheduling tool integrates with my calendar.

The process:

1. I add a candidate to the system
2. The AI scans my calendar for available times
3. The AI sends the candidate a scheduling link
4. The candidate picks a time
5. The AI books it automatically

Simple. Elegant. No human intervention required.

What Actually Happened

Week One: Everything Seemed Fine

I added 12 candidates to the system.

The AI sent them all scheduling links.

They picked times.

Interviews got booked.

I thought: "This is amazing. Why didn't I do this sooner?"

Week Two: The Triple-Booking Incident

Monday morning, I checked my calendar.

9:00 AM: Interview with Sarah Martinez 9:00 AM: Interview with James Chen 9:00 AM: Interview with Patricia Williams

Three people. Same time slot.

"Okay," I thought. "The AI made a mistake. I'll fix it."

I checked the rest of my week.

Tuesday 10:00 AM: 4 interviews booked Tuesday 2:00 PM: 3 interviews booked Wednesday 11:00 AM: 5 interviews booked Thursday 3:00 PM: 2 interviews booked

Every. Single. Time. Slot. Was. Double or triple-booked.

The AI had interpreted "find available times" as "book everyone during every available slot."

The Apology Tour Begins

I had to email 23 candidates explaining that their interviews were canceled and we needed to reschedule.

Email I sent:

Hi [Name],

I'm very sorry, but due to a scheduling error, your interview on [Date] at [Time] has been canceled. Our scheduling system double-booked several time slots.

I apologize for the inconvenience. Please use this link to reschedule at your convenience.

Thank you for your understanding.

Responses I got:

Candidate 1: "I took time off work for this interview. This is unprofessional."

Candidate 2: "I rearranged my entire day. Can you not manage a calendar?"

Candidate 3: "I'm withdrawing my application. If you can't schedule an interview properly, I don't trust your company to function."

Fair.

Week Three: The AI Schedules A Weekend Interview (That I Miss)

I thought I'd fixed the problem by manually reviewing the AI's bookings before they were confirmed.

But the AI had a "auto-confirm" setting I didn't know existed.

Saturday, 10:00 AM:

My phone started ringing.

I was at a farmer's market. I ignored it.

It rang again. And again.

I checked. Unknown number.

Then I got an email.

Subject: "Where are you???"

From: A candidate I was supposed to interview.

Body:

I'm on the Zoom call for my interview. You're not here. Did I get the time wrong?

I checked my calendar.

Saturday, 10:00 AM: Interview with Marcus Johnson

THE AI SCHEDULED AN INTERVIEW ON A SATURDAY.

I called Marcus immediately.

Me: "Marcus, I am SO sorry. The scheduling system made an error. I didn't realize an interview was booked for Saturday."

Marcus: "I cleared my Saturday morning for this."

Me: "I know. This is entirely my fault. Can we reschedule for Monday?"

Marcus: "Honestly, this has been such a mess. I'm going to pass on this opportunity."

Me: "I completely understand."

And that's how an AI cost us a great candidate.

Week Four: The 3 AM Interview Invitation

Subject: "Interview Invitation - 3:00 AM EST"

I stared at my email in disbelief.

The AI had sent a candidate an interview invitation for 3:00 AM on a Tuesday.

I immediately emailed the candidate.

Me: "Please disregard that interview invitation. There was a system error. Obviously we're not interviewing anyone at 3 AM."

Candidate: "I was very confused."

Me: "So am I."

I checked the AI logs.

Apparently, the candidate was in California (PST). I'm in New York (EST).

The AI tried to find a time that worked for both of us.

It found 12:00 AM PST (my time zone) = 3:00 AM EST.

The AI thought midnight was a reasonable interview time.

Technically, my calendar was "available" at midnight. Because I was asleep.

The AI didn't understand that "available" meant "awake and working," not just "no calendar conflicts."

Week Five: The Email Flood

One candidate received 14 interview invitations for the same role.

All different times. All from the AI. All within 24 hours.

She forwarded them all to me with one line:

"What is happening?"

I had no answer.

The AI had gotten stuck in a loop. Every time she didn't respond to an invitation within 2 hours, it assumed she wasn't interested in that time and sent a new invitation.

14 invitations later, she thought we were either incompetent or insane.

Why The AI Failed So Spectacularly

I called the AI scheduling tool's support team.

Me: "Your AI is scheduling interviews at 3 AM, triple-booking time slots, and spamming candidates with duplicate invitations."

Support: "Let me check your settings."

10 minutes of hold music

Support: "Okay, I see the problem."

Me: "What is it?"

Support: "You didn't set working hours."

Me: "What?"

Support: "The AI defaults to 'all hours are available unless blocked.' You need to manually set your working hours in the settings."

Me: "Why would ANYONE want interviews scheduled at 3 AM?"

Support: "Some users work internationally across time zones."

Me: "But I'm not one of them."

Support: "Right. You need to set that manually."

Me: "And the triple-booking?"

Support: "You enabled 'maximize scheduling efficiency mode.'"

Me: "What does that mean?"

Support: "The AI tries to book as many interviews as possible in the shortest time frame."

Me: "By booking three people at the same time?"

Support: "The AI assumes you can handle multiple interviews simultaneously if they're short."

Me: "They're 45-minute interviews."

Support: "Oh. That won't work then."

Me: "No. It did not."

The Settings I Didn't Know Existed

Apparently, the AI had dozens of settings buried in a "preferences" menu I never opened.

Settings I should have configured but didn't:

• Working hours (default: 24/7)
• Maximum interviews per day (default: unlimited)
• Buffer time between interviews (default: 0 minutes)
• Time zone handling (default: "auto-detect" which didn't actually work)
• Auto-confirm (default: ON)
• Candidate follow-up (default: send reminders every 2 hours until they respond)

I had activated an AI with zero guardrails.

It was like giving a toddler a flamethrower and being surprised when things caught fire.

I Turned Off The AI

I disabled the AI scheduling assistant.

Back to manual scheduling.

Yes, it takes longer.

Yes, it's annoying.

But at least I'm not scheduling interviews at 3 AM or triple-booking time slots.

The Fallout

Out of 47 candidates I tried to schedule with the AI:

• 12 withdrew their applications (citing unprofessionalism)
• 18 rescheduled manually (after I apologized profusely)
• 9 never responded again (presumably moved on)
• 8 completed interviews (despite the chaos)

We hired 2 people from that disaster of a cohort.

Both of them joked about it in their interviews.

Candidate: "I heard your scheduling system is... interesting."

Me: "We've since returned to doing things manually like it's 2015."

Candidate: "Good choice."

The Lesson

AI scheduling tools can work—but only if you:

1. Set working hours explicitly (don't assume the AI knows you sleep)
2. Disable auto-confirm (review bookings before they go out)
3. Set buffer times (humans need breaks between interviews)
4. Test it with ONE candidate before unleashing it on 50 people
5. Monitor it constantly (AI doesn't know when it's screwing up)

Or—and hear me out—just schedule interviews manually.

It takes 5 extra minutes per interview.

But you won't triple-book time slots, schedule weekend interviews, or send candidates 14 duplicate invitations.

Sometimes the old way is the better way.

(And if you're one of the 47 candidates I traumatized with AI scheduling chaos: I'm sorry. We're better now. Probably.)