Explaining The Onboarding Process To New Hires

In the 20+ recruiting audits I have completed of companies, I have found that more than 25% of recruits who sign offer letters never join. All that energy with nothing more than a finish-line disappointment. Yet if you ask a recruiting leader what their game plan is, once someone says yes, most have nothing. Recruiting doesn't stop when someone agrees to join your team—it’s just the beginning of solidifying their commitment. A formalized game plan ensures recruits feel welcomed, valued, and confident in their decision, reducing the risk of last-minute changes of heart. Here’s a step-by-step approach to create a game plan: 1) Immediate Engagement: Celebrate their decision with personalized outreach (e.g., a call or handwritten note). Have senior leadership send congratulatory messages to validate their choice. 2) Bridge the Gap with Continued Conversations: Schedule weekly check-ins to discuss their onboarding, answer questions, and keep excitement high. Involve current team members to introduce them to the culture and key connections inside the company. 3) Create a Sense of Belonging: Arrange a dinner or event involving their spouse or family to build deeper connections. Ship a personalized welcome kit with branded items and a personal note to their home. 4) Showcase the Culture: Invite them to attend a team meeting or shadow virtually so they can experience the culture firsthand. Provide access to training resources or tools to give them a head start. 5) Eliminate Doubt: Reiterate the unique value your organization offers that their current company cannot match. Role-play possible counter-offer scenarios and coach them on how to respond confidently. 6) Formalize the Onboarding Journey: Provide a clear timeline for their first 90 days, with milestones and support touchpoints. Assign a mentor or buddy to guide them through the transition. A structured plan ensures recruits transition smoothly, feel connected, and remain committed to your team. It transforms the "yes" into a day one success.

We spend months interviewing to find the “perfect” CSM… and then set them up to fail. Here’s the reality I see too often: ❗ New hires are thrown customers after 1–2 weeks. ❗ Product training is rushed or nonexistent. ❗ SOPs are thin, outdated, or missing. ❗ Leaders don’t invest the time to set expectations or coach. ❗ And then KPIs are handed down that even seasoned CSMs struggle to hit. The issue isn’t the talent, it’s the lack of enablement. But here’s the good news: you don’t need a dedicated L&D team or endless resources to onboard well. You need intention. A simple enablement plan for new CSMs (even with limited resources): 1️⃣ Onboarding Buddy - Pair new hires with an experienced CSM for shadowing, Q&A, and feedback. 2️⃣ 30-60-90 Plan - Outline clear goals and expectations for their first 3 months. (Focus on learning before doing.) 3️⃣ Product Deep Dives - Host weekly “lunch and learns” where Product, CS, or Support walks through one feature in detail. Have them shadow customer onboarding or watch recordings. 4️⃣ Playbook Starter Pack - Even if you don’t have full SOPs, document 3–5 repeatable workflows (renewals, QBR prep, escalation handling). 5️⃣ Mock Meetings – Run practice customer calls internally before they ever face a real customer. 6️⃣ Leader Time - Block weekly 1:1s focused not just on performance but on coaching, context, and confidence-building. These aren’t heavy lifts, they’re discipline and focus. If you want your CSMs to succeed (and your customers to stay), stop spending all your energy on hiring the “perfect” candidate and start spending more on enabling them once they walk through the door.

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?

A good onboarding plan conveys: People - Who do you need to know Personalities - How to collaborate well Process - How to do stuff Policies - What the rules are Politics - What the unwritten rules are Think about format. How should you best convey this information? How should it be referenced or reinforced? Self-paced resources? One-on-one convos? Group trainings? A combo? It's going to be different based on the role, what you need them to know, and when. And WHEN. What information must be conveyed immediately vs later? If later, how do you ensure "later" doesn't become "never?" When I was still leading teams, my go-to onboarding template was: 1️⃣ Pre-scheduling 1:1s with key stakeholders in the role, prioritized and spread out over the first 14-30 days. No agendas, just get to know you's. 2️⃣ Pre-scheduling 1:1 role-related chats with process/policy/outcome stakeholders. These stakeholders were strongly requested (required, if poss) to create a 1-2 guide for the new hire to have as a reference. The new hire was expected to read the reference BEFORE the meeting and come with questions. It's meant to be more of a conversation than a training. 3️⃣ Creating (if needed) a role wiki that tracks with the JD, naming stakeholders and linking to recommended tools/docs 4️⃣ Making sure the team has updated their "User Manuals," documents that explain their roles, a bit about their personalities, and working style. These manuals include the sections "When I'm At My Best" and "When I'm At My Worst" so preferences and quirks are explicit, instead of discovered slowly by accident. 5️⃣ Scheduling 2x weekly hour-long 1:1s for the first month, staggering down in frequency and duration as needed into the appropriate cadence for their role and growth trajectory. Sounds like a lot, but it's worth it to make sure you get the best out of someone. So many downstream problems and costs can be avoided with decent onboarding, and it doesn't have to be high-tech.

How to Create the Best Onboarding Experience Ever The last company I worked for completely nailed onboarding. Here's what they did: T-19 days: email from IT on when I should expect to receive my company swag, my computer, and other logistics T-18 days: email from my manager checking in and letting me know they were around if I had any questions T-3 days: email introducing me to my onboarding buddy (an employee that they paired me with) that helped me through my first few weeks T-2 days: email from manager with onboarding info and my schedule for Day 1 T-1 days: email from IT with info on how to login and configure my laptop All before I even started. — Day 1: * Logged into my computer and my calendar was pre-loaded with recurring team meetings, manager 1x1s, and meetups scheduled for the next 30 days * There was a company-wide welcome call where all the new hires were introduced. Each of us shared our favorite childhood movie * We had an IT setup call outlining everything we needed to complete * I had a meetup with my onboarding buddy * Someone from the HR team walked us through a “culture session” * I had my first manager 1x1 Days 2-9: a series of actually delightful meetings with important C-suite execs. The most memorable of which was with our CEO. He said: "Your 1st 30 days here, you have nothing to prove. You've already proven that you should be here because we have a very rigorous interview process. So for these first 30 days, try to meet as many people as possible, try to learn as much as you possibly can about the business, and don't worry about proving anything. And so that was just like the start of the onboarding." Day 10: "Graduation” in front of the entire company where managers showered new hires with compliments and accomplishments you’ve made in the first couple of weeks. You also get an email from your direct team and quotes from each of them thanking you for something that you've helped them with. — That was more than 2 years ago. But it stuck with me because it genuinely made me feel welcomed, supported, and excited to be part of the company. What great onboarding experiences have you gone through? For more HR tips, sign up for our newsletter in the comments.