Onboarding is the most crucial part of a new employee's journey. It's also the easiest to fumble. According to some estimates, organizations have just 44 days to convince employees to stick around for the long haul.
Yet too many companies still treat onboarding like a glorified information dump: hand over a laptop, point to the wiki, schedule a welcome lunch -- and hope the new hire somehow reverse-engineers how the place works.
Onboarding usually doesn't fail because of a lack of information. It fails because the make-or-break stuff doesn't live in the handbook. It lives in the tacit knowledge: the unspoken norms, the shadow org charts, and invisible rules that actually govern a company.
I recently started a new role at the work AI platform, Glean. While the formal onboarding has been stellar, I still leaned on AI to fill in the blanks (and was encouraged to do so).
These five non-obvious prompts helped me ramp up faster. They're the kinds of questions every new hire should be able to ask, and every leader should make easy to answer by investing in AI tools capable of understanding broader organizational context, and designed to respect access permissions, surfacing only the information employees are authorized to see.
Prompt 1: How does my new role and work connect to my organization's top-line objectives?
New hires are often handed a half-baked outline of what to deliver, a graveyard of old Google Docs, and a looming deadline, and then expected to hit the ground running. What they don't get is the "why." That's the critical context that gives their work purpose.
It's no wonder only 42 percent of employees say they understand how their work connects to company goals. The rest are stuck slogging through the motions and, in some cases, polishing their resumes.
AI can help, but only if it's embedded in the tools people use every day, like Slack, Google Docs, and project trackers -- where the messy, real-world context of work lives. AI can then follow the digital breadcrumbs from task to strategy, explaining not just what needs to be done, but why it's worth doing.
Because when people can't see the value of their work, they stop believing it has any.
Prompt 2: What do the highest performers here do differently?
Every company has star performers. But ask why they shine, and you'll usually get a cocktail of buzzwords and shrugs.
It's rarely just raw talent. The real differentiators are often subtle and undocumented. AI can help surface those patterns by analyzing feedback, shoutouts, and the quiet applause buried in Slack threads and Google Docs. It can show what actually gets noticed and rewarded.
When I asked Glean's Assistant this question, it gave me a one-word answer: "coachable." That insight rewired my approach. Instead of spending my first weeks trying to prove myself, I focused on chasing feedback and treating every conversation as a chance to level up.
Prompt 3: What's the company lingo, buzzwords, and acronyms -- and what does it mean?
Every company is wrapped in a thick smog of acronyms and insider-speak. And it builds up quickly. By week two, new hires start nodding along to terms they don't understand. It's what Stanford Professor Bob Sutton calls "jargon monoxide" -- language that sounds important but slowly suffocates clarity.
AI can help clear the air. By scanning Slack threads, Google Docs, and internal wikis, it can decode the tribal tongue: what terms mean, how they're used, and which ones actually matter. When new hires don't have to waste energy decoding, they can spend that energy contributing.
Prompt 4: Who holds the real influence on projects and initiatives related to my role?
The org chart shows who's in charge. It doesn't show who actually gets things done, or who can kill your project with a well-timed "Let's circle back." AI can surface these hidden influencers by tracing decision patterns and showing who gets looped in when the stakes are high or when things start to wobble.
Miss these behind-the-scenes power brokers -- the quiet operators, eyebrow-raisers, and Slack-thread whisperers -- and new hires end up chasing ghost approvals while their project quietly bleeds out.
Prompt 5: Who at my company shares personal interests, experiences, or life stages with me?
Loneliness at work is rampant. And yet, having a best friend at work is a strong predictor of engagement, collaboration, and retention.
AI -- when built on a knowledge graph of your organization -- can help surface what researchers call multiplex relationships: connections that span both work and personal life. People who share your hometown, your kid's daycare drama, or your obsession with triathlons, or Taylor Swift.
New hires don't need a forced friendship with a randomly assigned "onboarding buddy." They need someone who shares real personal ground, so they have someone to turn to on the hard days and connect with beyond calendars, deadlines, and forced small talk.
AI can make onboarding radically better, but only if it's embedded where work happens and only if it's built with security-first principles: strict permissions and access only to what a new hire is supposed to see.
Miss that early window, and new hires will build their own mental model of how their new company works -- shaped by folklore, guesswork, and leftover bad habits from their last job. And once that model sets in, good luck prying it loose.
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.
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