Monthly Webinar
How To Navigate Onboarding in the AI Age
Nadia Vatalidis & Raf Guper · Doist & UJJI AI
In this session Adam was joined by Nadia Vatalidis (Doist) and Rafael Guper (UJJI AI) to discuss how to build better onboarding experiences in the age of AI.
🧭 Onboarding Horror Stories: Why the Basics Still Break
Even great companies get onboarding wrong. Automated welcome emails fail, laptops arrive late, or managers forget to check in, and the entire first impression disappears.
“When a new hire accepts a job and then nothing happens… that’s an utter horror story.” – Nadia Vatalidis
💡 What you could do next
- Map the first 48 hours from the new hire’s perspective.
- Run your onboarding flow manually before automating.
- Make sure every new hire gets a manager touchpoint on day one.
⚙️ Knowledge Transfer Is the Foundation
Raf framed onboarding as a knowledge transfer problem. Without the right information early on, people cannot perform and the ramp time becomes painful.
“Anything related to knowledge transfer starts with documentation. It doesn’t have to be perfect. You just need to start. AI will help you fill in the gaps.” – Raf Guper
💡 What you could do next
- Identify what knowledge lives only in people’s heads.
- Use AI to turn raw notes into clear guides or FAQs.
- Track time to value as a core onboarding metric.
🧩 Documentation Is Everyone’s Job
Nadia made the point that documentation is not a remote thing. Every company needs accessible, asynchronous onboarding that new hires can rely on without chasing people.
“Asynchronous documentation and accessible onboarding should be the bare minimum.” – Nadia Vatalidis
💡 What you could do next
- Create a single source of truth for onboarding.
- Make it easy to find, easy to search, and easy to update.
- Encourage teams to document as they go rather than after the fact.
🤖 The Real Role of AI in Onboarding
AI is not about replacing human connection. It is about reducing human error by catching the things people forget or do inconsistently.
“What if you can be so great at what you’re doing that you can leverage other things to not have these horror stories over and over again.” – Nadia Vatalidis
“It is so easy to do now. It is just a matter of doing a brain dump and having AI do the magic for you.” – Raf Guper
💡 What you could do next
- Integrate your ATS, HRIS and comms tools so no steps fall through the cracks.
- Automate repetitive admin like welcome emails or access setup.
- Use AI to fill documentation gaps and surface answers for new hires.
💬 Continuous Feedback Beats Quarterly Reviews
Nadia prefers fast, early feedback in onboarding because new hires forget quickly and problems compound if you wait.
“I love doing an onboarding check at two weeks because if I don’t have early feedback, I can’t iterate.” – Nadia Vatalidis
💡 What you could do next
- Run a two week pulse with new hires.
- Ask one simple question: “What confused you the most so far?”
- Treat onboarding like a product and improve every version.
🪞 The Culture of Documentation
Both speakers were clear that documentation is cultural. It cannot sit only with HR or operations. It has to become part of how work gets done.
“If it is not in the handbook, it does not exist.” – Nadia Vatalidis
💡 What you could do next
- Make documentation quality part of performance.
- Create a rule that if someone has to explain it twice, it gets written down.
- Archive outdated content so new hires trust what they see.
💡 Onboarding as a Commercial Advantage
Great onboarding shortens ramp time, reduces confusion, and strengthens trust. It is not just a people experience. It is a lever for performance.
“Onboarding is a commercial opportunity for the business, not just a people experience.” – Adam Horne
💡 What you could do next
- Track the return on onboarding through productivity, readiness and retention.
- Treat onboarding like customer activation by removing friction.
- Position onboarding as a revenue and efficiency driver, not an HR task.
Related playbooks
Useful resources
- Remote Onboarding PlaybookThis document is intended to be a helpful + practical guide for your growing business as you keep scaling. A lack of in-person communication makes it far harder to onboard people, to get to know them + for them to get to know their teammates + this is especially the case when you're not well-practi
- Open Org Onboarding CookbookThis is a curated buffet of onboarding ingredients (and some full recipes!) for you to remix into your own onboarding experience design. Includes recipes from: Buffer, Gitlab, Posthog, Candor, Unleashed, Switchee, Cal.com, Sourcegraph, Juro, Checkly, Accurx, Nexhealth, Loom, Atlassian, Monzo, Lev
- Onboarding - The Ultimate GuideA blueprint for building an onboarding experience you’re proud of, from pre-boarding to the first 6 months. Learn about new development, get examples, and look at a template moment -by-moment experience.
- How To Leverage AI For Your Team, Yourself And Your OrgA simple but powerful framework for spotting AI use cases, building your first GPT agents, and scaling AI confidence across your organization
- The 6 C's of Employee Onboarding
- Open Org's Slack CommunityCapped at just 500 startup People & Talent folks globally this is one of the most generous communities out there; blending virtual and in-person meetups throughout the year with day-to-day help from relevant peers on your toughest questions