Best Practices for Onboarding That Foster Learning

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?

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 ❗ SOPs are thin, outdated, or missing.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.

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

When people ask me about how to best onboard new employees, I always reference child psychologist Dr. Penelope Leach’s saying, “Start as you mean to go on.” In the world of child rearing that means, if you want to raise a well-mannered teen…make sure your toddler knows not to throw her Cheerios on the floor. The beginning sets the tone for everything that follows. And the same can be said for onboarding at an organization. Onboarding isn’t just showing new hires where the bathrooms are or what’s in their benefits package. It’s your first and best chance to say to a new employee: This is how we work, and this is what matters here. Given the increased focus on AI (pretty much everywhere we look), I wasn’t surprised to start seeing it incorporated into company onboarding. Helen Russell, Chief People Officer at HubSpot, recently shared with Daniel Huerta and Stephen Huerta on The Modern People Leader podcast how new hires experience AI simulations on Day 1 of onboarding—actually within the first hour! HubSpot wants to illustrate that AI isn’t just a side project; it’s fundamental to how they operate. After the stage is set through onboarding, Russell shared a new ritual that helps the AI learning journey stick. It’s called the "MondAI Minute" (get it?). Every Monday, an employee shares a 60-second video of a creative AI use case. What began as a simple share has turned into a friendly competition, with ideas evolving “from deflect to automate to enable.” And finally, starting on day one, HubSpot leaders convey the same message: When it comes to AI, we want you to experiment, take risks, and share what you learn. In other words, we're giving you permission to play. As we read in articles every day, there’s a lot of uncertainty in the world today about AI, its impact on jobs, how to use it, when to use it, and why to use it. Sharing your company’s perspective on AI and giving people the chance to use it in their roles as part of onboarding sends a clear signal: This is part of our DNA. You only get once chance to make a first impression—as a company and as a leader. I’d love to hear from you: what’s unique about your onboarding? Have you started to incorporate AI? Listen to the full episode here: https://lnkd.in/eJWkxEbe

Stop “welcoming” new hires. Give them a win in 30 days instead. When I first hired 8 years back, I thought the best onboarding was all about making new hires feel at home. I was wrong. New hires actually struggle with: → Understanding the business and their role. → Aligning with company culture and expectations. → Getting that first “win” to build momentum. → Building relationships with colleagues. I’ve now completely changed our onboarding process. The only goal is to get new hires to their “first win” fast. Instead of generic training, we work backward from their first big achievement. Here’s the framework: Step 1: Define the “first win” (within 30 days) Every new hire gets a specific, meaningful milestone. 1. It should be important enough that not doing it has a business impact. 2. Something that pushes them but is achievable with team collaboration. 3. It should give them real insight into how we operate. Our new Demand Gen Marketer’s first win was securing Market Development Funds (MDF) from a partner. To do this, they had to: - Work with our internal team. - Engage with a partner manager. - Propose a campaign relevant to both companies. This wasn’t just a task (it was a meaningful contribution). Step 2: Provide context (without overloading them) Most onboarding programs drown new hires in endless presentations. We limit training to what they need for their first win. 1. A 45-minute deep dive on the company’s journey, priorities, and challenges. 2. Targeted learning on only what’s relevant for their milestone. 3. Hands-on guidance instead of passive training. For the Demand Gen hire, we focused on: - Who the partner manager was and their priorities. - How the partnership worked. - What MDF campaigns typically get approved. Step 3: Align them with our work culture Culture isn't learned in a handbook. It’s experienced. Every new hire is paired with a mentor to guide them through: → Quality Standards → What "good" looks like in our company. → Processes & Tools → How we work and collaborate. → Feedback Loops → How we review, iterate, and improve. The result? New hires achieve something meaningful within their first month. They feel pride, momentum, and confidence (not just onboarding fatigue). Great onboarding isn’t about information. It’s about impact. 💡 How do you set up new hires for success?