From Checklist to Connection: Why Most Onboarding Fails—and How AI Can Fix It
May 21, 2025Part 2 of our AI + Onboarding series
Read Part 1: AI in Adult Learning – Rethinking the First Steps From Classroom to Onboarding
“If engagement doesn’t happen early in the process, you can’t get quick wins and you will lose their attention immediately.”
— Amy Tan, Temasek Polytechnic
Let’s be honest: most onboarding programs feel like a checklist. Whether you’re entering a new company or a new course, the process is often rushed, compliance-heavy, and lacking in real connection.
In this second part of our AI + Onboarding series, Noodle Factory Co-founder Jim Wagstaff and educator Amy Tan explore why traditional onboarding struggles to stick and how AI is helping organizations reimagine it as a personalized, scalable, and emotionally intelligent journey.
🔎 Why Traditional Onboarding Falls Short
Jim opened the session with a familiar reality: onboarding is often treated as a formality—transactional and top-heavy with compliance.
“It’s make or break, as you know.”
— Jim Wagstaff
Amy echoed this, drawing from her experience in a former organization with over 100,000 employees:
“I was already 10th year in my job and I have to be trained as a foundation engagement trainer for that. I was skeptical at first… but they really trained me to get to the engagement first—connect with the employee first.”
— Amy Tan
The challenge? Most new hires feel disconnected before they even begin. The solution? Start by building emotional connection—not just checking boxes.
🤖 How AI Makes Onboarding Personal (and Powerful)
Amy shared how she redesigned the onboarding experience using Noodle Factory’s AI assistant—no coding required.
“It is much easier than I thought… I didn’t really need technical skills.”
— Amy Tan
Here’s what worked in her AI onboarding design:
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80/20 balance: AI handles delivery and support (80%), while educators and managers add human moments (20%).
“You can make it 80% AI, but 20% that you build in the personalized touches is important.”
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Real-time engagement: Adult learners engaged with the chatbot at 3AM—asking questions they’d otherwise keep to themselves.
“Sometimes they can’t sleep, they’ll ask questions.”
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Gamification and roleplay: Noodle Factory’s onboarding flow included knowledge checks, roleplay scenarios, and even fun quizzes.
“We’ve interspersed things like quizzes and knowledge checks. There’s a little bit of gamification with this—with badges that new hires can earn. There are role plays…"
– Jim Wagstaff -
Companion-like experience: It felt more like a friendly colleague than a robot.
“They really don’t feel like they are talking to a robot.”
– Amy Tan
🙋♀️ Key Questions Answered in the Session
The livestream also tackled common concerns from HR teams and L&D leads exploring AI onboarding systems:
❓Do you need a tech team to implement this?
Nope. Amy built the entire onboarding flow herself.
“Most of the heavy lifting is actually in designing the right journey.”
— Amy Tan
❓Will it feel robotic or impersonal?
Not if it’s designed well.
“I like the way [the chatbot] responds… it’s like my companion buddy.”
— Amy Tan
❓Does it support multilingual or remote learners?
Yes. Amy’s learners tested it in Mandarin and Malay using both text and voice—fully supported.
❓Can it be tailored across job roles or departments?
Absolutely.
“You can make it modular… tailor flows for different job roles, departments, even experience levels—without even building a program from scratch.”
— Amy Tan
🧠 What Makes AI Onboarding Actually Work
Amy laid out three must-haves for designing effective onboarding with AI:
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Design with emotional connection in mind
“Once you can get to the new hire in a pretty emotional manner, you sort of make them feel that they’re part of something bigger.— Amy Tan
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Start with key engagement goals
“You really got to know what are the key engagement goals… especially for the new hires in the whole journey.”— Amy Tan
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Anticipate “silly” questions
“They know that it’s a non-judgmental area where they can ask maybe what you call silly questions that everyone seems to know and I do not know.”
— Amy Tan
When new hires feel safe asking questions, they’re more likely to stay curious, learn deeply, and build confidence quickly.
🧭 The Brand Ambassador Mindset
Amy shared one of the most powerful ideas of the session:
“A new hire that comes into the organization is actually your brand ambassador… It is important then for your AI onboarding to shape the kind of brand ambassador that you want them to be.”
— Amy Tan
“You sort of make them feel that they’re part of something bigger… not just another headcount.”
— Amy Tan
The onboarding journey isn’t just functional—it’s foundational. Done right, it helps new hires internalize your values and represent your brand authentically from day one.
🚀 AI Onboarding Isn’t Just Scalable—It’s Transformational
With AI-powered onboarding:
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Culture is reinforced early
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Emotional connection is built quickly
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Support is available 24/7
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You deliver consistent experiences—without starting from scratch
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HR and L&D teams get time back to focus on deeper, human conversations
“It’s not just about compliance. It’s about giving people a sense of presence—even when they’re remote.”
— Jim Wagstaff
📥 Free Download: AI Onboarding Journey Template
Want to design your own onboarding flow—quickly and without the guesswork?
We’ve created a free AI Onboarding Journey Template to help you get started. Whether you’re just mapping your first three stages or building a full 4-week plan, this plug-and-play resource is here to guide you.
What’s inside:
- ✅ Quick-start planner (fill in just 3 onboarding moments)
- ✅ Full journey canvas (from Pre-Day 1 to Week 4)
- ✅ Real examples and prompts
- ✅ Optional support from our team to turn your plan into a live experience
👉 Fill out the form below to get your free copy instantly.
After submitting, we’ll email you the template and a short walkthrough on how to use it effectively—no tech skills required.
Ready to Build Your Own AI Onboarding Flow?
Start today at noodlefactory.ai
