How to Address Challenges in Remote Onboarding

My remote hires (probably) ramp faster than yours. Here's why: Most remote onboarding means a calendar packed with Zoom meetings and endless Slacks from strangers. No real connection. No clear priorities. No clue how tall anyone actually is. It can feel isolating, especially when you’re new and eager to prove yourself. That’s why I take a different approach at UserEvidence. I meet every new hire in person during their first week. Wherever they live, on their home turf. Every time, it leads to the same outcome: faster ramp-up, stronger confidence, and immediate momentum. I’ve improved this process three times now, cutting out fluff and getting feedback from every person to make it even better for the next hire. They each get a beast of a Notion page that covers: - Key people to meet (and why those meetings matter) - Important docs and links to review right away - A roadmap for their first 30, 60, and 90 days, clearly outlining expectations and where I need them to take ownership From day one, new hires have full visibility into what's working, what's not, and where our biggest opportunities lie. They don't have to hunt for information, either. It’s all there for them: board decks, old marketing roadmaps, past OKRs, and a clear breakdown of the agencies and freelancers we partner with (plus their “superpowers” and how to best work with them). By the end of week one, we’ve already had honest and vulnerable conversations about: - How we can best work together  - Our working styles and weird work quirks to be aware of (we all have them) - What success looks like in their role - Where they want to grow and how I can help We also make time for fun and get to know each other outside of work. Like our upbringing, favorite life stories, and who we are as humans. Work matters, but who you work with matters even more. Building trust right out of the gate makes everything easier.

Every struggling new hire carries “baggage” from their last job. They just need a reset, not a rejection. A new hire once froze in a meeting when I asked for their thoughts. Later, he admitted, "In my last job, only managers spoke. I wasn’t sure if I should." That’s when I realized you’re not just hiring a person. You’re hiring their past workplace norms too. I now use a 3-phase framework to spot, reset, and reinforce workplace norms early. Phase 1: Surface the hidden sensitivities New hires won’t tell you what’s confusing. They’ll just hesitate. I try to uncover what they assume is “normal.” I look for clues: 🔍 Do they wait for permission instead of taking initiative? 🔍 Do they avoid pushing back in discussions? 🔍 Are they hesitant to ask for feedback? You can do this with an easy expectation reset exercise in onboarding: 1. "At your last job, how did decisions get made?" 2. "How was feedback typically given?" 3. "What was considered ‘overstepping’?" Their answers reveal hidden mismatches between their old playbook and your culture. Phase 2: Reset & align Don’t assume new hires will "figure it out". Make things explicit. I set clear norms: 1. Here, we challenge ideas openly, regardless of role. 2. We give real-time feedback—don’t wait for formal reviews. 3. Speed matters more than waiting for perfection. For this, use “Culture in Action” moments. → Instead of just telling them, model it in real time. → If they hesitate to push back, directly invite them to challenge something. → If they overthink feedback, normalize quick iteration—not perfection. Phase 3: Reinforce through real work Old habits don’t vanish. They resurface under stress. The real test is how they act when things get tough. Create intentional pressure moments: 1. Put them in decision-making roles early. 2. Assign them a project where feedback loops are fast. 3. Push them to own a meeting or initiative. Post-action debriefs help here: “I noticed you held back in that discussion—what was going through your mind?” This helps them reflect & adjust quickly, instead of carrying misaligned habits forward. Most onboarding processes focus on training skills. But resetting unspoken norms is just as critical (if not more). A struggling new hire isn’t always a bad fit. Sometimes, they’re just following the wrong playbook. What’s a past habit you had to unlearn in a new job?

I’ve onboarded remote hires across time zones, continents, and cultures. And here’s what I’ve learned: Remote onboarding doesn’t ⭐fail⭐ because of location. It fails because of assumptions. Assuming someone will “just speak up.” Assuming they’ll know what success looks like. Assuming they feel like they belong. Without hallway chats or shadowing, remote employees miss all the informal context that makes onboarding feel human—not just functional. Here’s how I’ve made it work: 💬 Over-communicate expectations and priorities 🎥 Use video, even for 15-minute check-ins 📅 Create a rhythm of connection—1:1s, team intros, buddy syncs ☕ Encourage informal conversations (yes, even virtual coffee chats) Remote doesn’t have to mean disconnected. In fact, with the right systems, it can feel even more inclusive. It took me many years of learning the hard way to build this out. And I’d like to share it with you, no strings attached. (see link in comments) That’s why I built these practices right in our Manager Onboarding Kit—to help leaders support their teams with intention, no matter where they are.