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

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

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.

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

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?

Your senior hire isn't working out. Before you write them off as a bad hire, look in the mirror: Did you set them up to succeed? Most leaders skip right to “it wasn’t a good fit.” But before you make any moves, answer these questions honestly: 🔴Did you explain your expectations initially? 🔴Did you agree together on what great looks like? 🔴 Did you make sure they were clear on their role? 🔴Did you discuss how you can best work together? One of the CEOs I coached was frustrated with a C-level hire who wasn't hitting his stride after several months in the role. (By the way, that IS frustrating.)  But then he realized he hadn't been clear with the new hire about his expectations and the way they should work together. His solution? Re-onboard the executive. Here's how: ➡️ He outlined how he works as a leader. Decision-making style, communication preferences, work rhythms. ➡️ Articulated the top goals for the company and the role. Non-negotiables and priorities for both business results and how work gets done. ➡️ Created space for the executive to share what THEY needed from him. Clarifying expectations isn't one-way. What support, resources, or context do they need to succeed? ➡️ Identified 2 quick wins they could achieve together in 30 days. Wins build momentum and confidence. ➡️ Mapped out key relationships and internal dynamics. Nobody gets important things done alone. Who needs to be involved and how best to engage them? ➡️ Shared the unwritten rules of how things get done. Every company has hidden cultural norms. Who to loop in; level of preparation for discussions; speed vs. consensus all need to be spelled out. After just a few months that  "underperforming" leader became one of his strongest leaders. Here’s the thing: Senior people assume they know how to operate inside a new culture. And with their new boss. But every situation is different. Without explicit clarity, they fill gaps with assumptions from their last job. (Wouldn’t you do the same?) It's your job to be clear, not theirs to read your mind. Most companies don't onboard well at any level. So take a moment to reset. Re-onboarding creates shared understanding and often saves what looked like a bad hire. Do this with one direct report, or even better do it with your whole team.

Everyone talks about onboarding new customers. Nobody talks about reonboarding your old ones. If you're lucky enough to have customers who’ve been with you for 2+ years, it’s time to hit pause and audit. Because while your product evolved, many of them didn’t. They're still operating with old workflows, outdated training, and missed opportunities for impact. Who should you prioritize? Start with customers who: ➡️ Haven’t expanded in the last 12+ months ➡️ Haven’t logged into new features ➡️ Show signs of stagnant adoption ➡️ Have new stakeholders who weren’t around at onboarding ➡️ Were onboarded before your CS org/process matured Here’s what I've done to kick this off: 1️⃣ Run a deployment audit Identify feature usage gaps and map against current best practices. 2️⃣ Re-engage stakeholders Confirm if the original champions are still involved and who needs a reset. 3️⃣ Tailor updated training Highlight new features, improved workflows, and relevant use cases. 4️⃣ Reset goals + KPIs Align on where they’re going next, not where they’ve been. 5️⃣ Rebuild your success plan Give them a “Day 1” experience, grounded in today’s strategy. Use this as a guide but adjust based on your business. This isn’t just retention, it’s renewal insurance. This is expansion through enablement. This is Customer Success in motion. Are you giving your oldest customers your newest thinking?