Tips for Effective Onboarding and Reonboarding

How long should your onboarding program for SDRs be? I’ve now either trained or onboarded 1000+ SDRs in my career. I’ve built onboarding programs that were 1 week long, and more comprehensive programs that were 4 weeks long. Here’s what I’ve learned: 1. People don’t learn by being overloaded with documentation and videos upfront. 2. Onboarding doesn’t need to just happen in the first few weeks. Breaking down concepts in “micro lessons” over a period of time is more helpful. For example, if you sell 5 use cases, your SDRs don’t need to learn all 5 use cases in the first few weeks of onboarding. Let them master 1-2, focus on those prospects then unlock other personas. 3. People don’t retain information unless there is a continuous learning & re-enforcement loop You SHOULD set up weekly 1-1s, weekly calls reviews and power hours with reps from week 2 IMO. 4. Let SDRs learn on the job. Let them know it’s OKAY to fail. It’s okay to have some role playing up front. In fact, I recommend it. But don’t focus on this TOO heavily. They will butcher some calls and objections. Start practicing on Tier C accounts, don’t put new SDRs on the best accounts right away. With various AI sales enablement platforms like GTM Buddy, you can feed your SDRs real-time content, battlecards and learning as they are actually doing their job. It helps A LOT when it comes to actually learning and retaining information. My recommendation? Make your “official” onboarding for SDRs 1 week long. Include the following: 1. Upfront contract setting expectations for both manager and SDR 2. Day in the life of your Key Personas (Start with 1-2) 3. Main Problems you solve for  4. Basic platform functionality and how it solves problems for personas 5. How to structure your day / manage your time 6. Email / Copy Lessons 7. Cold Calling Lessons + Scripts 8. Using LinkedIn as a channel 9. Role Plays + Certifications for Email, Calls, LinkedIn 10. Overview of critical systems / tech stack Then focus on CONSTANTLY re-enforcing these. #sales #outbound

Most HR teams think their onboarding is solid. → Laptop ready. → Paperwork completed. → First day meet and greet? Check. But here is the truth we see behind the curtain: Most teams skip the parts that matter most for long-term success. Here are two steps most teams forget during onboarding and what to do instead. 1. 𝗖𝘂𝗹𝘁𝘂𝗿𝗲 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝘁𝗵𝗮𝘁 𝗴𝗼𝗲𝘀 𝗯𝗲𝘆𝗼𝗻𝗱 𝘁𝗵𝗲 𝗵𝗮𝗻𝗱𝗯𝗼𝗼𝗸 Telling someone your values is easy. Showing them how the team 𝘳𝘦𝘢𝘭𝘭𝘺 works is the magic. New hires do not struggle with the handbook. They struggle with the unwritten rules. Give them real language instead of vague gestures. For example, instead of asking… "Do you use Slack?" Try saying… "Our team lives in Slack during business hours. We expect same day responses for most messages and a quicker reply if it is from your manager or during core hours." Other examples to spell out clearly: • How often leaders drop in for updates • When cameras are expected on • How people give feedback • When it is okay to block focus time • Preferred communication style (short pings or detailed notes) And pair them with a culture buddy. Someone who can answer real questions like "Is it normal to send a calendar note before messaging the VP?" That saves so much social anxiety and avoids awkward first month missteps. 2. 𝗥𝗼𝗹𝗲 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗮𝗻𝗱 𝗺𝗲𝗮𝗻𝗶𝗻𝗴𝗳𝘂𝗹 𝗲𝗮𝗿𝗹𝘆 𝗰𝗵𝗲𝗰𝗸𝗽𝗼𝗶𝗻𝘁𝘀 A job title is not direction. People want to know exactly how to succeed. → Get specific. → Paint the picture. Instead of saying… "You will lead onboarding." Try… "In your first 30 days, you will run onboarding for three new hires. Success looks like zero missed system access steps, plus a feedback survey score of 4.5 or higher." Then schedule a 30 day check in. Not to judge. To support. Ask questions like: "What has been clear so far?" "What has been confusing?" "Where do you need resources or examples?" And tell them one thing they are doing well. Everyone needs a confidence anchor early. Strong onboarding is not fancy. It is clear, human, and consistent. Which onboarding detail made the biggest difference for you in a new role? If this sparked ideas, share it with another HR pro building better onboarding. #OnboardingTips #HRLeadership #PeopleFirst ♻️ I appreciate 𝘦𝘷𝘦𝘳𝘺 repost. 𝗪𝗮𝗻𝘁 𝗺𝗼𝗿𝗲 𝗛𝗥 𝗶𝗻𝘀𝗶𝗴𝗵𝘁𝘀? Click the "𝗩𝗶𝗲𝘄 𝗺𝘆 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿" link below my name for weekly tips to elevate your career!

When I thought I’d done enough hiring, I missed one small but big thing, and it cost a great employee. Last quarter, I filled an important position in just 11 days. It felt like a win. But 6 months later, that person quit. And I realised, the mistake wasn’t in how fast we hired, but in how little we understood what truly motivated them. I did everything right, job description, skill match, reference check, offer letter. The candidate joined happily. They were talented and responsible. But what I never asked was: 👉 What will make you stay here beyond one year? During his exit talk, he said, I wanted more challenges, a clear path, and a stronger sense of belonging. That’s when it clicked, we hired for skills but didn’t show them the growth journey. Here’s what I should have done from day one: 1️⃣ Growth Plan: Explain what their 6, 12, and 18 months could look like, including new learning or team exposure. 2️⃣ Culture Talk: Share how our company lives its values daily and how they’ll be part of it. 3️⃣ Ownership Chance: Tell them what project they’ll own and how it will make a difference. Because employees don’t just quit jobs, they quit environments that don’t meet their expectations or values. Recent reports also say: Professionals now value purpose, growth, and belonging more than just salary. A good onboarding and role clarity are now key to retaining employees in the first year. So I changed my process, Now ask them: ✔ Why this role? Why now? during interviews. ✔ Share a short growth roadmap at the offer stage. ✔ Have a First 90 Days check-in on culture and impact. ✔ Explain, What success looks like in Year 1 and review it at month 6. Results: ✅ Fast hiring (under 20 days) ✅ Better offer acceptance and retention rate Key lessons for HRs and recruiters: 1️⃣ Start with why, understand what drives the candidate beyond the job title. 2️⃣ Talk about culture and belonging early, not after joining. 3️⃣ Show the path, people stay when they see how they’ll grow and make an impact. Simple frameworks: Why-Impact-Roadmap: Explain the reason, result, and path. Environment Check-In: Discuss clarity, culture, and growth before hiring. 90/180-Day Review: Set early goals and revisit them at 3 and 6 months. #careers #careeradvice #hr #linkedinnewsindia #linkedin

Your first 90 days with a customer can make or break the entire relationship. I've seen it happen too many times: - Great sales process - Solid product demo - Strong contract value - Excited stakeholders Then onboarding happens. And everything falls apart. Why? Most companies treat onboarding like a checklist: - Setup call ✓ - Product training ✓ - Technical integration ✓ - Documentation shared ✓ But here's the truth about onboarding: It's not about your process. It's about their success. After managing hundreds of onboarding sessions, here's what I've learned: The best onboarding isn't standard. It's personalized. Think about it: - Every customer has different goals - Every team has different challenges - Every organization has different paces - Every stakeholder has different priorities Your onboarding needs to reflect this. Here's what works: 1. Start with clear expectations - Define success metrics upfront - Set realistic timelines - Map out key milestones - Align on responsibilities 2. Build a dedicated team - Assign specialists who understand their industry - Create cross-functional support - Have clear escalation paths - Enable quick problem-solving 3. Monitor health signals - Track early usage patterns - Watch engagement levels - Note stakeholder participation - Measure progress velocity 4. Automate the right things - Regular check-in reminders - Progress updates - Resource sharing - Usage alerts But here's where most companies fail: They don't plan for challenges: - Low customer engagement - Complex technical integrations - Unclear success metrics - Resource constraints - Scalability issues The solution? Build feedback loops: - Collect input at every stage - Adjust plans based on signals - Iterate on materials - Improve processes continuously Remember: Onboarding isn't about getting customers to use your product. It's about helping them achieve their goals through your product. The first 90 days set the tone for everything that follows. Make them count. What's your approach to customer onboarding? What challenges have you faced? ------------------ ▶️ 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 1993+ community members! 💥 [link in the comments section]

As Chief of Staff, I designed many onboarding plans. Not for my team. For my CEO’s. Some were veterans stepping into a new role. Others were brand new to the organisation, sometimes even to the sector. Yet the fundamentals stayed the same. They were shaped by many brilliant leaders before me, and I still use them till today. Here’s what worked (I hope you'll try it too!): 1️⃣ Jump right in Have them shadow key people. Let them see the work on the ground. No document replaces lived experience. And the team benefits from a fresh pair of eyes. 2️⃣ Set the context Don’t leave this to HR. Create clarity on what matters, and coach them as they learn on the job. 3️⃣ Outline 30-60-90 outcomes The first three months can feel overwhelming. Give them priorities, not a to-do list. Let them figure out how. 4️⃣ Create reflection spaces Hold a weekly check-in. Ask what they’re learning, what’s unclear, and how they’re shaping their priorities. 5️⃣ Give early visibility At 90 days, ask them to present learnings and plans for the next 6 months to leadership. Let them share what support they need. Time and again, this has worked. For different personalities. At different career stages. PS: Which one would you include in your next plan? #Leadership #Onboarding #ChiefOfStaff #StrategyExecution #OrganizationalCulture

Many of us have recently returned from holidays. Some stayed in hotels or Airbnbs, while others had the privilege of staying with family or friends. As recipients of their hospitality—or as hosts ourselves—it’s hard not to notice the effort and thought that goes into making someone feel welcomed and comfortable in a home. This got me thinking: we spend so much time and energy ensuring our guests feel cared for at home, but do we bring the same care and attention to welcoming new members at work? Often, we focus on the logistical side of onboarding. While these are important, they’re only one part of the experience. What about the human side of onboarding? The part where someone new feels 𝘀𝗲𝗲𝗻, 𝘃𝗮𝗹𝘂𝗲𝗱, and 𝘁𝗿𝘂𝗹𝘆 𝘄𝗲𝗹𝗰𝗼𝗺𝗲𝗱? Here are 𝘁𝗵𝗿𝗲𝗲 𝗹𝗲𝘀𝘀𝗼𝗻𝘀 from hosting at home that we can apply to welcoming new colleagues: 𝟭. 𝗦𝘁𝗮𝗿𝘁 𝘄𝗶𝘁𝗵 𝗮 𝗪𝗮𝗿𝗺 𝗪𝗲𝗹𝗰𝗼𝗺𝗲 First impressions are crucial. Consider creating a personalised "welcome pack" that goes beyond the basics. Perhaps, gather handwritten welcome notes from each team member. This collective gesture shows that the entire team is excited about their arrival. Additionally, if from outside of Singapore, include a packet of tissues with a note to explain why—a nod to the local Singapore custom of using tissues to "chope" (reserve) seats at hawker centers in Singapore. 😅 This not only introduces them to local culture but also adds a touch of humor and warmth. 𝟮. 𝗔𝗻𝘁𝗶𝗰𝗶𝗽𝗮𝘁𝗲 𝗧𝗵𝗲𝗶𝗿 𝗡𝗲𝗲𝗱𝘀 Good hosts anticipate what their guests might need—even before they ask. The same applies at work. Does your new team member have all the tools, resources, and information they need? Have you assigned someone they can reach out to for help? Thoughtful preparation can ease their transition and prevent unnecessary frustration. 𝟯. 𝗣𝗮𝗰𝗲 𝘁𝗵𝗲 𝗦𝘂𝗽𝗽𝗼𝗿𝘁 When someone stays with you, you don’t just welcome them on the first day and then leave them to figure everything out. You check in periodically, ensuring they’re comfortable and adapting well. At work, onboarding shouldn’t stop after the first week. Make it a point to follow up regularly over the first few months. A simple check-in can go a long way in helping someone feel supported and valued. 𝗛𝗼𝘀𝗽𝗶𝘁𝗮𝗹𝗶𝘁𝘆 𝗮𝘀 𝗮 𝗧𝗲𝗮𝗺 𝗘𝗳𝗳𝗼𝗿𝘁 Welcoming new team members isn’t just the leader’s responsibility—it’s something all of us can contribute to. Whether it’s inviting them for lunch, answering their questions with patience, or simply being approachable, we all have a part to play in making them feel at home. Thoughtful hospitality leaves a lasting impression on guests. A warm and intentional onboarding experience helps new colleagues feel at ease, integrate faster, and contribute sooner. What have been POSITIVE and not-so-positive experiences you have had when joining a new team? What type of Welcome did you receive?

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.

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

Standard onboarding is cringe for a new SLT 🙃 When you onboard a new SLT or C-level hire, it is tempting to build something “worthy” of the seniority: lots of sessions, lots of slides, lots of ritual. In practice, I’ve found the opposite tends to work better. Senior leaders do not need polished slides. They need faster access to reality, plus a clean contract about what “success” will mean. This is partly just an adopted style of learning. Having had the practice, they are more self-directed, bring a lot of prior experience, and learn best when the learning is immediately useful and problem-centred. In my own work onboarding SLT members, and in how I was onboarded into my role at Work.Life, the highest leverage moves looked a lot like this: 1) Give them the whole system and don’t try painting it better than it is. On day one, the practical basics matter, but the deeper point is access: documentation, decision logs, strategy decks, org design history, metrics, customer insights, board context, and the unglamorous operating cadence. When that material is searchable and reasonably current, a strong leader will “pull” what they need at speed. 2) Protect curiosity before performance pressure kicks in. It is due diligence. The mistake I see most often is surrounding a new exec with urgency from day one, then mistaking hustle for understanding. The better pattern is to actively create permission for observation and discovery even if the business is impatient. This window can be narrow for a new SLT. You need a deliberate plan to get them to insight faster. Then let their instincts kick in and wait your turn. 3)In the first weeks, senior joiners can surface truths that everyone else has learned to step around. That window closes quickly as they inherit incentives, relationships, and the weight of owning decisions. So I try to create structured, low-ego moments where they can ask naïve questions safely, and where we capture what they notice. 4) Negotiate success early, then re-negotiate it as reality becomes clearer. Exec failure is often framed as capability. In reality, it is frequently misalignment: unclear scope, lack of trust to let go or letting go too early. Have you heard the idea of “negotiating success”? It’s a good one. A simple structure that has worked well for me is: • First 30 days: listen, map the system, name the risks, and resist the theatre of quick wins. • Days to 60: align on priorities, define what to stop, and decide where their authority begins and ends. Have them have a crack at things they can call their own. • Days to 90: commit to a few meaningful moves that match long term goals. Secure a few wins. If you are about to hire a new SLT member, I’d focus less on building a “perfect onboarding” and more on three things: radical access to context, protected discovery time, and a clear, revisited definition of success. #Leadership #ExecutiveOnboarding #PeopleOps #HR #SeniorLeadership #OrganisationalDesign

I’ve spent 300+ hours coaching PMM through onboarding. Here is the most important tip I have: Build your 30/60/90 day plan backwards. 👇 Most PMMs' onboarding plans start with a to-do list: --> Meet with cross-functional teams --> Review past launches --> Read docs The problem with this approach is that you never feel like you’re doing enough, and everything seems equally important. You also have no real sense of how long things will take. It makes it nearly impossible to prioritize your time or align expectations with your manager. When I coach PMMs through onboarding, I tell them to build it BACKWARDS. Start at day 90 and determine, by then: – What do you want to have delivered? – What do you need to have learned? – Who needs to know and trust you? Then work backwards and chunk it down. One of my clients just joined as the first PMM at a 50-person startup. In her second week, she was already getting requests for: -> Improving the ICP and messaging -> Updating the sales enablement decks -> Building a launch strategy 😬 As you can imagine she was pretty stressed and needed a good way to set the right expectations and also plan her work. So we built a new plan, working backwards from day 90, which included: ✅ 3 streams: deliver/learn/meet ✅ Tied each project to an outcome, not just a task ✅ Chunked out each project into smaller milestones ✅ Treated learning as a deliverable, so her ramp time was visible She used that plan to align with her manager, which not only set clear expectations but also showed she could think strategically and take initiative from day one. If you’re onboarding in a startup, remember the key is not to add more, but to work backwards, and then clearly communicate that to set the right expectations. Let me know how I can help. 💪 #productmarketing #newjob #coaching #strategy