How To Handle Miscommunication In Onboarding

When onboarding a new team member, a recent experience with asynchronous collaboration brought a humbling revelation. As I was onboarding her to our tech stack, I uncovered a blind spot in communications within our project management software, Asana. 📝 In the meticulous notes I left for myself a while ago in one of the Asana projects, I had cut and pasted some language from an email to a client that included the word "YOU". 🤔 I failed to consider the potential confusion for my new team member. It hadn't occurred to me that she would interpret that "YOU" to be referencing her. ⚠️ What I had put in Asana as notes became unintended directives for the new Virtual Work Insider team member! The result? 📉 A cascade of actions on her end, each based on a misinterpretation of my notes. ⏳ This was an inefficient use of her time and effort that were invested in tasks that weren't needed or intended. The fix? 🔄 Once I realized what had happened we had a great discussion about how I would change my note-taking behavior in shared Asana projects to make the async communication clearer and we refined on our norms for how new requests would come through to her. My aha moment made we want to share some actionable insights for seamless onboarding in asynchronous settings. ✅ Precision in Messaging: Avoid vague language and ensure that your notes are explicitly for personal use and directives to others are clearly marked as tasks. ✅ Establish Communication Norms: Kickstart the collaboration by setting expectations on how tools like Asana are used. Establish a shared understanding of communication conventions to avoid misinterpretations. ✅ Feedback Loop: Create an open channel for feedback. Encourage your team to seek clarification if something seems ambiguous. This proactive approach can avoid potential misunderstandings. What would you add to this list? 👇 #virtualleadership #hybridleadership #hybridwork #async

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?

Leadership mishaps happen. Here’s how I owned it and made sure it wouldn’t happen again. One of my biggest leadership misses happened during a Holiday launch. Not because something broke, but because no one knew what to do when it did. We were launching a new offer. Two of my leads, the ones closest to the launch, were out on PTO. So newer team members stepped in to run point. → QA looked good. → Tech gave the green light. → Marketing launched. A day later, one of the newer folks noticed that clicking through the campaign led to a blank page. They didn’t escalate it. They just quietly turned the campaign off for the weekend. No one knew until Monday, when I asked a question and the story unraveled. There were breakdowns between QA, tech, and marketing, but I’ll save that part for another day. This one’s about how I handled a revenue loss. We’d launched a campaign that didn’t drive revenue because it wasn’t live. → And I didn’t yell. → I didn’t panic. → I didn’t point fingers. → We talked through it as a team. The newer folks did what they thought was best. The onus was on me and my leads. We’d been there for years. We knew the protocols, and we just hadn’t shared them. That was the real miss. So we fixed it. → We updated onboarding to include failure scenarios. → We built in escalation flows. → We practiced what to do when things go off-script. Yes, this was a learning moment for the newer team members. But more importantly, it was a reflection moment for me, and a turning point for our process. We took what happened and built it into onboarding. → Not just the steps.  → The judgment calls.  → The escalation paths. → The parts no one remembers to train for until it’s too late. What’s one scenario you’ve now built into onboarding because of a past miss? 📌 Save this if you're building onboarding docs or team training 💬 Drop your own lesson below. I’d love to learn from it ♻️ Share with a leader who cares about team readiness