ICYMI: Challenge Accepted #2 - Scaling Onboarding and Enablement Programs

Scaling Onboarding and Enablement Programs with Brandon Iljas

Our latest Challenge Accepted session featured Brandon Iljas — L&D and Enablement leader, community favorite, and all-around straight-shooter. This wasn’t your average webinar. It was a real-time exchange of questions, stories, and insights from people in the trenches of onboarding — figuring out how to make new hires successful without burning out the teams who support them.

Setting the Stage

Brandon kicked things off by naming the challenge head-on:

“Most companies don’t struggle with getting content out. They struggle with making it stick at scale.”

The chat came alive quickly, with participants sharing their experiences, frustrations, and experiments.

The Big Reframe

One of the most important insights that surfaced: scaling onboarding isn’t about creating more. It’s about building the right frameworks so managers, peers, and systems all play their part. Brandon highlighted a few common pitfalls:

• Overloading new hires with too much information in week one.
• Treating onboarding as an “L&D project” instead of a shared company responsibility.
• Failing to track whether onboarding connects to actual business outcomes.

The Real Questions Leaders Are Asking

The best part of this session? The questions that surfaced from the group. Here are just a few we explored together:

• “I’m leading my company’s first L&D program. How do we create something engaging and relevant when company goals are so vague?”
• “What are new onboarding approaches that go beyond the standard playbook — and actually work?”
• “How do you equip managers (who aren’t used to it) to take real ownership of onboarding their people?”

These weren’t hypothetical — they’re the day-to-day fires L&D and Enablement pros are trying to put out.

From Theory to Application

Brandon and the community shared practical approaches for tackling these questions:

• Anchor onboarding in outcomes: define what “success at 30/60/90 days” looks like and build around it.
• Involve managers early: onboarding isn’t a handoff; it’s a partnership. Give managers clear tools and accountability.
• Create repeatable frameworks: instead of reinventing the wheel, build playbooks that can flex by role or department.
• Layer learning: spread knowledge over time, instead of front-loading everything into week one.

Closing with Curiosity

Brandon left us with a powerful reminder:

“Onboarding never really ends — it just evolves into enablement. The best programs think about how to support people continuously, not just in their first 30 days.”

Scaling onboarding is just one of many challenges our community is wrestling with. That’s why Challenge Accepted exists: to bring smart, curious people together, share what’s working (and what isn’t), and learn from each other. Stay tuned for our next session — and if you missed this one, keep an eye out for the recording. Trust me, you’ll want to catch it.