Skill Development during Onboarding

A VP of Sales told me "Our new reps take 6 months to close their first deal." Six months of salary before any return. "We give them two weeks of intensive training. Why does it take so long?" Here's the problem: His onboarding was information dumping. Not skill building. New reps sat through two weeks of boot camp. Product features. CRM navigation. Company history. Sales process. Objection handling. Then they got thrown into the field. Zero real-world practice. Zero muscle memory. Zero confidence. So they flailed for months before closing anything. This is broken. Here's what I do instead. I structure onboarding around immediate application. Not information retention. Week one: Core messaging and persona training. CRM basics. They shadow senior reps on live calls. They're learning in context. Week two: They make calls. Book meetings for senior reps. While getting trained on discovery frameworks. They're applying what they learned. Building muscle memory. Week three: They run discovery calls with oversight. While learning the rest of the process. Real practice. Real feedback. Real improvement. Week four: They work their first deal through to close. My target: First deal within 30 days. Not because I rush them. Because I structure learning differently. BTW: One client had average 157 days to first deal. We rebuilt onboarding with this approach. New average: 28 days. (Not bad, huh?) — Here’s what I would do if I had to build a sales org in 2025 from Day 1: https://lnkd.in/er9X7ivP

Good news: Malaysia’s latest pulse data shows employers and markets still creating opportunities—and firms are investing in experience and skills alongside growth. That’s a rare, useful balance. Source: (link in comment) However, growth without skills is fragile. If companies scale without reskilling, onboarding and engagement suffer. So treat skills work as culture work. If you’re launching a growth push, pair it with an explicit skills path: who will teach, where the learning happens, and how progress is visible. Action plan (simple): when approving any new project or headcount, require a 1-page Skills & Onboarding plan: who mentors, first 30/60/90 milestones, and one metric to check after three months. Make those plans public within the team. When you name development responsibility and make progress visible, engagement follows. Good jobs are one thing. Good jobs where people grow and belong — that’s culture. Build both.

Most new hires don't fail because they can't do the job. They fail because we don't teach them how. We spend months recruiting the perfect candidate, then throw them into the deep end with a laptop and "good luck." But the best companies know something different. They understand that the first 90 days aren't just about orientation - they're about transformation. Here's the 30-60-90 framework that turns confused new hires into confident contributors: Days 1-30: Learn & Assimilate Focus on cultural integration and foundational knowledge. Give them small wins to build confidence while they absorb your mission, systems, and workflows. Days 31-60: Contribute & Collaborate Shift to independent contribution. Assign real projects with deliverables.  Expand their network through cross-team collaboration and establish regular feedback loops. Days 61-90: Lead & Innovate Full autonomy on core responsibilities. Encourage strategic thinking and fresh ideas. They should be mentoring newer hires or learning from senior team members. The magic happens when you combine three elements: → Structure: Clear expectations for each phase → Ownership: Let them shape their own learning journey → Support: Pair them with a buddy and celebrate small wins Most companies treat onboarding like a checklist to complete. The best companies treat it like an investment to maximize. A strong 30-60-90 plan doesn't just help new hires succeed - it transforms them from "just another seat" into high-impact contributors who stay, grow, and refer others. What's the biggest onboarding mistake you've seen companies make?

𝐅𝐫𝐨𝐦 𝐃𝐚𝐲 𝐎𝐧𝐞 𝐭𝐨 𝐓𝐡𝐫𝐢𝐯𝐢𝐧𝐠: 𝐇𝐨𝐰 𝐍𝐞𝐰 𝐇𝐢𝐫𝐞𝐬 𝐋𝐞𝐚𝐫𝐧 (𝐚𝐧𝐝 𝐖𝐡𝐲 𝐘𝐨𝐮𝐫 𝐎𝐧𝐛𝐨𝐚𝐫𝐝𝐢𝐧𝐠 𝐍𝐞𝐞𝐝𝐬 𝐭𝐨 𝐂𝐡𝐚𝐧𝐠𝐞) A recent study published in Frontiers in Organizational Psychology explored how newcomers learn during onboarding by looking at three key learning forms:  • 𝐅𝐨𝐫𝐦𝐚𝐥 𝐥𝐞𝐚𝐫𝐧𝐢𝐧𝐠 (structured training, onboarding plans)  • 𝐈𝐧𝐟𝐨𝐫𝐦𝐚𝐥 𝐥𝐞𝐚𝐫𝐧𝐢𝐧𝐠 (peer conversations, job shadowing)  • 𝐒𝐞𝐥𝐟-𝐫𝐞𝐠𝐮𝐥𝐚𝐭𝐞𝐝 𝐥𝐞𝐚𝐫𝐧𝐢𝐧𝐠(goal-setting, reflection, proactive follow-ups) The findings reveal something powerful: Onboarding is most effective when organizations move beyond rigid training programs and create opportunities for self-directed, informal, and interactive learning. New hires who actively shape their onboarding—asking questions, seeking feedback, reflecting on progress—adjust faster, feel more connected, and stay longer. So, 𝐰𝐡𝐲 𝐬𝐡𝐨𝐮𝐥𝐝 𝐨𝐫𝐠𝐚𝐧𝐢𝐳𝐚𝐭𝐢𝐨𝐧𝐬 𝐜𝐚𝐫𝐞?  • 𝐑𝐞𝐭𝐞𝐧𝐭𝐢𝐨𝐧 & 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭: Poor onboarding is one of the top reasons for early turnover.  • 𝐅𝐚𝐬𝐭𝐞𝐫 𝐫𝐚𝐦𝐩-𝐮𝐩: Structured and self-directed learning accelerates role clarity and confidence.  • 𝐂𝐮𝐥𝐭𝐮𝐫𝐞 & 𝐜𝐨𝐧𝐧𝐞𝐜𝐭𝐢𝐨𝐧: Informal learning helps newcomers integrate socially and culturally, which is often overlooked in formal training. What can I/O Psychology and L&D practitioners do?  • Design onboarding that blends 𝐟𝐨𝐫𝐦𝐚𝐥 𝐬𝐭𝐫𝐮𝐜𝐭𝐮𝐫𝐞 𝐰𝐢𝐭𝐡 𝐢𝐧𝐟𝐨𝐫𝐦𝐚𝐥 𝐢𝐧𝐭𝐞𝐫𝐚𝐜𝐭𝐢𝐨𝐧𝐬(e.g., mentorship, peer learning, shared breaks).  • Incorporate 𝐬𝐞𝐥𝐟-𝐫𝐞𝐠𝐮𝐥𝐚𝐭𝐞𝐝 𝐥𝐞𝐚𝐫𝐧𝐢𝐧𝐠 𝐭𝐨𝐨𝐥𝐬 like reflection prompts, learning goals, and follow-up checklists.  • Map onboarding activities to 𝐤𝐞𝐲 𝐜𝐨𝐧𝐭𝐞𝐧𝐭 𝐚𝐫𝐞𝐚𝐬—compliance, clarification, connection, and culture—so learning is intentional and complete.  • Use data to 𝐦𝐞𝐚𝐬𝐮𝐫𝐞 𝐧𝐞𝐰𝐜𝐨𝐦𝐞𝐫 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭 with both formal and informal learning pathways, not just training completion rates. Onboarding should be a co-created learning experience, not just a process to get through. When we empower new hires as active participants in their learning journey, everyone wins—newcomers, teams, and the entire organization. #WorkplaceEngineer #IOPsychology #LearningThatSticks #TrainingAndDevelopment #Onboarding #EmployeeExperience #LeadershipDevelopment

My two cents… I had an enablement colleague ask me a question about onboarding and how it’s changed, how we tailor it, what reps should know and when, how much selling vs. product vs. industry training should be done, and when they should start selling. My peers in the business know this line of questioning well. In my opinion, onboarding programs need to shift away from focusing on content and move toward sequence and intent. Stop prioritizing information completeness and instead design around progressive capability. New hires should start doing real things earlier. Do small things first, then bigger ones. The training doesn’t disappear; it gets reorganized around the doing rather than the knowing. Here’s a reframe that changes how I think about onboarding entirely: new hires should be selling from day one. What they’re selling evolves. Day 1–10 – Selling themselves internally. Learning the business, earning trust, building relationships. Understanding how the organization actually operates and not just what the org chart says. (And ideally not asking where the coffee machine is for the fifth time.) Day 10–30 – Selling curiosity externally. Joining calls, asking smart questions, observing experienced reps navigate conversations. Not pitching like a caffeinated product brochure. Listening. Reading the room. Developing instincts. Day 30–60 – Selling pieces of the deal. Running discovery. Owning the recap. Setting next steps. Still supervised, still supported. Think of it as a learner’s permit where you have real driving in controlled conditions. Day 60–90 – Selling full-cycle. Pipeline, deals, forecasts; basically the whole beautiful, complicated mess. Accountable for outcomes, supported by the system, coached by the manager. Actually in the game. Designed this way, onboarding isn’t a waiting room before the job starts. It is the job, at progressively increasing altitudes. The new hire is never a spectator. They’re always a participant. The only question is what role they’re playing this week.

I once worked with a team that was proud of their onboarding process. New hires got swag bags, welcome lunches, and long orientation decks. But here’s what no one was tracking: How long it took those new hires to make a real impact. In one case, it was 90+ days before someone delivered their first key result. Not because they weren’t capable—because we hadn’t built a runway for them to land on. So we reworked onboarding completely. Not as an HR checklist. As a business acceleration strategy. We asked questions like: • What does success look like in the first 30, 60, 90 days • What’s their first deliverable that actually moves the needle • Who are the people they need to build trust with quickly • What tools, data, or decisions are they missing to get started • How do we shorten the time from “welcome” to “impact” The result? Time to productivity was cut in half. Confidence went up. Retention improved. So did results. Because when onboarding is done right, it’s not about orientation. It’s about acceleration. #HRRealTalk #OnboardingMatters #EmployeeExperience #TalentDevelopment #NewHireSuccess #HRLeadership #PeopleStrategy #TimeToProductivity #WorkforceEnablement #FutureOfWork

Stop onboarding. Start everboarding. Most companies still treat onboarding like a one-time event. Day 1 → Week 1 → maybe a 90-day check-in… and then? Nothing. But the data (and experience) says that’s where performance actually starts to diverge. The concept of “everboarding” flips that model: 👉 Continuous skill development 👉 Ongoing manager engagement 👉 Reinforcement tied to real work—not generic training Because retention and performance aren’t won in onboarding. They’re won in the months that follow. This is especially critical in high-volume environments where: Early attrition is highest in the first 30–90 days. Role clarity and confidence drive safety + productivity. Manager consistency varies widely. If you’re only investing upfront, you’re missing the biggest lever. The shift isn’t complicated—but it is intentional: Treat the first year like a structured journey, not an event Align L&D with real performance signals (not completion rates) Hold frontline leaders accountable for development, not just output AI and automation will streamline hiring. But what happens after the hire? That’s still your competitive advantage. Onboarding gets people in the door. Everboarding determines whether they stay—and succeed.

Are we setting new hires up for success or just throwing them in the deep end? Too often, companies pride themselves on flashy onboarding but lack real strategies for employee growth. A smooth transition for new hires should be more than just a checklist; it’s about shaping them to thrive within the company's unique ecosystem. Here’s an example of how to structure the process for true impact: ⏩ Personalized Onboarding: Every new hire’s background and skills are different. Why isn’t onboarding? ⏩ Mentorship Pairing: Matching new hires with mentors who are invested in their long-term development. ⏩ Continuous Feedback Loops: Weekly check-ins that are used to adapt training and resolve obstacles before they become frustrating. ⏩ Voting on Training & Growth Options: Let new hires vote on training topics and growth paths that matter to them, ensuring they’re motivated and engaged. ⏩ Clear Pathways for Growth: A map of potential roles and skills needed so no one feels trapped in their current position. ✅ Growth is a team effort, not an individual endeavor!!! ✅ Imagine if each new hire knew they weren’t just filling a role but were being actively prepared to advance. 🤔 Are we doing enough to make them part of the future? 💡 Shouldn't we always strive for growth and retention? 📈

If you are rushing your new CSMs’ for taking on accounts in their first week or two, you might be setting them up for failure. You might think that onboarding is only for your customers, but it is equally important for your CSMs. Good onboarding can make your CSMs more confident, competent, and productive. Bad onboarding can lead to frustration, confusion, and churn - both for your CSMs and your customers. Before a CSM can have a meaningful conversation with a customer, they need to master a lot of skills and knowledge, such as: - Market Knowledge: Understanding the industry trends, challenges, and opportunities that affect your customers and your product. - Product & Technical Knowledge: Learning the features, benefits, and best practices of using your product, as well as how to troubleshoot common issues and answer technical questions. - Demos & Simulations: Practicing how to showcase your product’s value proposition and address customer objections in various scenarios. - Shadowing: Observing how other teams interact with customers, such as Sales, Solution Architects, and Support, and learning from their techniques and feedback. - Auditing Accounts: Reviewing and analyzing customer data, such as usage, satisfaction, goals, and health scores, and identifying areas of improvement and risk. - EBRs: Preparing and delivering effective executive business reviews that demonstrate your product’s impact, align with customer objectives, and uncover new opportunities. - Soft Skills: Developing trust and rapport with customers, asking open-ended and probing questions, listening actively, communicating clearly, and managing expectations. Only after completing all these steps, are they ready to face a customer and deliver value. Onboarding a new CSM can take a while, but it is worth the investment. Companies that truly care about customer success won’t settle for any less. How do you onboard your CSMs? I would love to hear your thoughts. #CSM #CustomerSuccess #Onboarding ------------------ ▶️ Want to see more content like this and also connect with other CS & SaaS enthusiasts? You should join Tidbits. We do short round-ups a few times a week to help you learn what it takes to be a top-notch customer success professional. Join 720+ community members! 💥 [link in the comments section]

Nearly 20% of new hires leave within their first 45 days. It’s not because they aren't talented, it’s something very common. It’s because businesses set unrealistic expectations from day one. Without proper onboarding, mentorship, or training, it’s impossible to expect new employees to perform at their best immediately. Here’s how you can set them up for success: 1. Encourage open dialogue from day one ↳ Make sure new hires feel comfortable voicing their thoughts early and often. 2. Clarify job roles upfront ↳ Define their responsibilities clearly to avoid confusion. 3. Pair them with a mentor ↳ Connect them with someone who can guide and support them. 4. Design a thoughtful onboarding experience ↳ A structured plan helps them navigate their role more confidently. 5. Acknowledge small victories ↳ Celebrate early achievements to boost morale and build momentum. 6. Provide ongoing feedback and learning ↳ Continuous support helps new employees grow and excel in their roles. 7. Promote work-life balance ↳ Ensure they know that personal well-being is valued alongside the work. 8. Set achievable goals ↳ Give them realistic targets that respect the learning curve of a new position. 9. Check in regularly ↳ Regular touchpoints allow you to track their progress and offer guidance. 10. Exercise patience ↳ Growth takes time, and being patient builds trust and commitment. 11. The companies that win are those that see new hires as long-term investments. After all, no one can grow without the right tools, support, and encouragement. #Growth #HR #Business #Strategy #Investment #Goal