How We Taught Our AI Bot Shakespeare (And Why Customers Didn’t Get It)
Week 2, and I’m starting to crack.
Not visibly, of course. On the outside, I’m still Kate: composed, professional, the woman who has it all together. But inside? Inside, I’m screaming for help.
Sprint 2: “Let’s Make It Smart!”
Ahi the joys of Agile Project Management! After Sprint 1’s spectacular achievement of creating a bot that only says “Hello,” Richard (our CTO) had notes.
“Kate, we need this thing to actually DO something. Can we get it answering questions by end of sprint?”
What I said: “Absolutely! We’ll start training it this week.”
What I thought: How? HOW? I had zero idea, so I Googled it at 2 am last night, and now I’m more confused.
Week 1: The Data Disaster
Carlos (our dev) suggests we feed the bot training data. Great idea! What data? Well… we need customer service conversations, right?
Brilliant plan: Let’s use our company Slack history! Thousands of conversations, real language, perfect!
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Actual result: The bot now responds to customer inquiries with inside jokes, “meeting cancelled” notifications, and an alarming amount of coffee emoji.
Customer: “Where is my order?”
Bot: “Sorry, that meeting got moved to Tuesday. What about some coffee? ☕️☕️☕️”
Emergency pivot required.
Meanwhile: Kate’s Internal State
Monday: My idea got cut off in the standup. Third time this week. Started my sentence with “Actually…” and hated myself for it. Why do I have to prove my expertise?
Tuesday: Richard asked, “Do you actually understand how this works?” I do. I absolutely do. But now I’m questioning everything I know. Spent lunch Googling “neural networks for dummies” even though I have a Computer Science degree with a masters on top.
Wednesday: Worked until 1 am fixing the Slack data disaster. Male colleagues left at 6 pm. I stayed because I need to prove I’m “dedicated enough.” Woke up with a migraine. Took an aspirin, did my makeup, went to work. No one can see my weakness.
Thursday: Almost cried in a meeting. Had to excuse myself to the bathroom. Splashed water on my face. Looked in the mirror and whispered “You got this girl”. Mei from the team walked in 😱. Pretended I was doing “breathing exercises for focus.” She nodded and left. I died inside.
Friday: Completely exhausted. But it’s demo day. Time to smile and pretend everything is under control.
Week 2: The Shakespeare Incident
After the Slack disaster, we need “quality training data.” Carlos suggests classic literature – it’s well-written, grammatically correct, and publicly available.
I’m too tired to argue. “Of course!” I say. Mistake, BIG mistake.
Carlos downloads Shakespeare’s complete works. All of them. And feeds them to our customer service chatbot.
Can you see where this is going?
The Demo That Broke Me
Friday afternoon. Demo to stakeholders. Richard, the product team, senior leadership. I’m running on 4 hours of sleep and pure anxiety.
Demo conversation:
Test User: “What’s your refund policy?”
Bot: “To be or not to be, that is thy refund policy. All the world’s a stage, and your purchase merely a transaction upon it.”
Silence.
Richard: “Kate. What is this?”
Me (professional smile intact): “We’re testing different training datasets. This is the literary approach—”
Richard: “It’s quoting Hamlet to customers about refunds.”
Me: “…yes.”
More silence. The kind where you can hear your career dying.
Richard: “Can you fix this by Monday?”
Me: “Absolutely.”
(I have no idea how. But I’ll figure it out. I always do. Even if it kills me.)
The Aftermath
That night, I’m still at the office. It’s 10pm. Carlos left at 6. Mei left at 7. I’m alone with my laptop and the crushing under the weight of my imposter syndrome.
My brain: “You’re a fraud. A real PM would have caught this. You should have reviewed the training data. You’re going to get fired. Everyone knows you don’t know what you’re doing.”
I Google: “Can you get fired for AI bot quoting Shakespeare?” (Surprisingly, no direct results.)
Then I do what I’ve been doing for weeks: I open LinkedIn and look at job postings. Just in case.
At 11:47pm, I’m still spiraling. I open our Whatsapp group. Maybe someone else is awake. Maybe someone else understands.
Me: “Demo disaster today. Bot quoted Shakespeare to stakeholders. Richard asked if I understand how this works. I do, but now I don’t trust myself. Is this imposter syndrome or am I actually incompetent?”
3 minutes later:
Sarah (VP of Eng somewhere): “Kate. Breathe. First: Shakespeare bot is hilarious and we’ve ALL been there. Second: Richard asking ‘do you understand this’ is HIS problem, not yours. Would he ask a male PM that? Probably not.”
Priya (Product Lead): “Last year my bot told customers to ‘have a blessed day’ because I trained it on customer service emails from the Bible Belt. Shipped to production. We all survive our bot disasters. You will too. 💜”
Me: “…I needed this. Thank you.”
Sunday Night: The Unraveling
It’s Sunday, 2:47 am. I’m in bed with my laptop researching AI training methods for the hundredth time.
My search history:
• “How to fix AI bot Shakespeare problem”
• “Best training data for customer service bot”
• “Am I having a breakdown or is this burnout”
• “Signs of imposter syndrome female leaders”
• “How much sleep is too little sleep”
• “Is 4 hours enough” (spoiler: it’s not)
Monday Morning: Masks On
Monday, 9am standup. I slept 2 hours. I’m wearing extra concealer to hide the bags under my eyes. Professional smile: activated.
Richard: “Kate, update on the bot?”
Me: “We’re pivoting to curated customer service data. Should have a clean training set by Wednesday.”
Richard: “Good. Keep me posted.”
He doesn’t ask how I’m doing. He doesn’t see the exhaustion. Why would he? I have my mask on.
After the meeting, Mei approaches me quietly:
Mei: “Kate… are you okay? You seem tired.”
My first instinct: Deny. Deflect. Perform strength.
Me: “I’m fine! Just busy. You know how it is.”
Mei: “…okay. Let me know if you need help.”
She walks away. I almost called her back. Almost said “Actually, I’m drowning.” But I didn’t. Because admitting struggle feels like admitting failure.
The Pattern I Didn’t See Yet
Looking back (because I’m writing this after everything that happened), I can see it now:
→ Work problem happens
→ I internalize it as personal failure
→ Work harder to prove I’m not a failure
→ Get more exhausted
→ Make more mistakes because exhausted
→ Repeat
But no, not yet, I didn’t see it yet after Sprint 2. I just kept running on the hamster wheel, convinced that if I ran fast enough, I’d finally be “enough.”
What I Didn’t Know
What I didn’t know in then was that this was just the beginning. The Shakespeare bot was embarrassing. The late nights were exhausting. The imposter syndrome was crushing.
But Sprint 3? That was when I broke.
Actually broke. Not figuratively. Not “I’m so tired” broke. But couldn’t-get-out-of-bed, everything-is-too-much, I-can’t-do-this-anymore broke.
And that’s when everything changed.
For You
Have you ever had a “Shakespeare bot” moment?
That project that went hilariously wrong, but instead of laughing, you internalized it as proof that you’re not good enough?
That moment when someone asked “do you understand this?” and instead of confidently saying yes, you went home and Googled everything to make sure you really did know?
That pattern of working late while your male colleagues went home at 6, convinced that you needed to be “twice as good” to be seen as equal?
Share your story in the comments. Because I promise you: you’re not alone. And your Shakespeare bot moment doesn’t define you.
It’s just part of the journey. And sometimes, the caravan does get sorted on the road.
(Even if it doesn’t feel like it yet.)
Next week: The breaking point, the bathroom floor, and the phone call that changed everything.