User Onboarding Best Practices

❌ ERP is NOT DONE at Go Live ❌ Too many companies treat Go Live like the finish line. 🏁🏁 Reality check: ❌ Users still don’t know how to use it. ❌ Reports don’t look right. ❌ Bugs keep piling up. ❌ Business leaders wonder why efficiency hasn’t improved. The most successful ERP projects: ✔️ Have a post-Go Live support plan. ✔️ Invest in ongoing training & adoption. ✔️ Keep experts/contractors on board for stability. ✔️ Keep improving & optimizing—not just maintaining. Go Live isn’t the end: It’s the beginning of making ERP work for your business. Strap in 🤣🤣 What's the longest time you've seen to stabilize after Go Live? 👇👇 #D365 #ERP #MicrosoftDynamics #DigitalTransformation

I will admit that one of the most omitted aspects of creating a new feature (or product) is making sure the user knows how to use it. At the same time, you can only make one first impression. How to make it great? Let's face it: It's very hard to onboard users. People have very little time right now and are used to instant gratification. Thus, if the product requires some effort to use, you may see a very upset user on the other end. At the same time, not all products can be reduced to a single button called "solve my problem". So, how to onboard a new user in a way they actually engage? 1) Start with a great text copy There is nothing worse than a technical copy that is not written with your client in mind. Separate it into easy-to-complete steps so the user can learn and move to the next step easily. Remember, the user is not an expert yet like you are. Also, invest into professional translations, so the copy is great for everyone! 2) Set the production value of onboarding materials very high If your onboarding videos look and feel professional, you will build your brand image and user confidence. While creating such videos used to be expensive, nowadays tools exist that will help you automate and speed up the process, such as this post's partner: Guidde! Guidde allows you to create how-to videos quickly based on the screen recording of the process you wish to document. Using AI, Guidde will automatically generate the storyline with highlights, and add text to voice and multiple CTAs, saving you many hours of work. 3) Make it easy to repeat training People forget or skip onboarding steps accidentally. If it is difficult to access the training materials again, you might avoid a lot of user frustration. Not to mention support calls or tickets that could have been avoided. 4) Add micro onboardings While onboarding is associated with getting the user started using a product, that can also apply on a feature level. Take this into account when planning a new release, so it's stellar and accessible from day one! 5) Make it easy to speak to human support While your onboarding will surely be great, a lot of your users will prefer to talk/write to a human being. Make it easy to find contact info. Bonus: monitor the issues that come with this. Rather than hide support contact, eliminate the causes that led to those calls in the 1st place. Thus: 6) Care for onboarding funnel as a product Monitor onboarding usage and later client engagement. Look for steps/materials in dire need of improvement and monitor the metrics once those are introduced. As I said earlier, you can only make one first impression! Make it count :) So, did you find this useful? How do you build your product so that it's welcoming to new users? Sound off in the comments! #productmanagement #productmanager #onboarding

Stop building 90-day onboarding programs. You don’t have 90 days. You don’t even have 45. In today’s world, you have 2–3 weeks before frustration creeps in and your customer starts second-guessing their decision. Why? Because AI has reset expectations. 👉 Sign up for ChatGPT: get answers instantly 👉 Fathom: meeting notes summarised immediately 👉 Gamma: presentations from one upload and one prompt Customers are being trained to expect immediacy. They don’t want to “wait for onboarding.” They want to see value the moment they hit Sign Up. And this is where most traditional onboarding playbooks fail: They’re built around the vendor’s process and team capacity, not decreasing TTV. So what should CS leaders do? 1️⃣ Redefine Day 1 Value Forget “full rollout.” Define the first outcome your customer can see in 14 days that validates their decision. 2️⃣ Compress the critical path Cut ruthlessly. If a step doesn’t lead to visible progress in the first 2 weeks, move it to later. 3️⃣ Agentify Onboarding Any set-up that can be done by an agent from prompting and existing documentation, shouldn't be done manually. 4️⃣ Stack the team early Invest your best effort upfront. Highest-touch in the first 2–3 weeks prevents costly churn rescues later. 5️⃣ Measure value, not just milestones Track the time to the first “aha” or the first outcome, not just task completion. ⚡ AI has changed the clock speed of customer experience. If you’re still anchoring onboarding around 90 days, you’re too slow. And this is for our product teams too. You can't keep building products that take 6 months to get any value from. We need to find smart ways to unlock value from day one. Because the countdown doesn’t start when onboarding ends. It starts the second your customer signs. And we should get comfortable with the fact that onboarding never really ends. New tools come out, and we want customers to always be deploying, adapting, evolving. It's what we call everboarding. The old 90-day onboarding framework isn't built for the speed our customers need to see value today. It's time to throw it out and reinvent it. 📩 Want more tips on how to build an AI-first CS team? Then you’ll love my newsletter. Unconventional Growth is for the CS pro who wants to deliver results and have real impact in the age of AI. There’s over 17k of us (and growing!). #CSM #onboarding #CustomerSuccess #RevOps #CustomerRetention

ERP vendors won’t tell you this. But I’ve seen it kill more projects than budget or scope creep. Here it is: Most ERP failures happen after go-live. During what I call “The ERP Void.” Everything looks perfect on paper. Go-live is announced. Champagne is popped. Then, reality hits. Here’s what actually happens post go-live (but no one prepares for): → Finance can’t close books because opening balances weren’t validated. → Procurement grinds to a halt because approval hierarchies were half-tested. → Inventory shows 0 even when the warehouse is full. → Users go silent. Not because they’re happy, but because they’ve gone back to Excel. And vendors? They’re long gone. On to the next deal. From my 25+ years of rescuing ERP disasters, here’s what I now mandate before go-live: 𝐒𝐭𝐚𝐠𝐠𝐞𝐫𝐞𝐝 𝐆𝐨-𝐋𝐢𝐯𝐞, 𝐍𝐨𝐭 𝐁𝐢𝐠 𝐁𝐚𝐧𝐠 → Go live module-wise or geography-wise. It saves careers. ‘𝐃𝐚𝐲-𝐢𝐧-𝐭𝐡𝐞-𝐋𝐢𝐟𝐞’ 𝐒𝐢𝐦𝐮𝐥𝐚𝐭𝐢𝐨𝐧𝐬 → UAT is not enough. Simulate an actual business day—POs, SOs, invoices, MRP runs, reconciliations. Find the chaos before it finds you. 𝐅𝐢𝐧𝐚𝐧𝐜𝐞 𝐅𝐢𝐫𝐬𝐭. 𝐀𝐥𝐰𝐚𝐲𝐬. → If finance isn’t ready, nobody’s ready. Prioritize core financials, then scale. 𝐇𝐲𝐩𝐞𝐫𝐜𝐚𝐫𝐞 𝐁𝐮𝐝𝐠𝐞𝐭 = 10% 𝐨𝐟 𝐓𝐨𝐭𝐚𝐥 𝐏𝐫𝐨𝐣𝐞𝐜𝐭 𝐂𝐨𝐬𝐭 → Bake this into the contract. No hypercare, no deal. 𝐒𝐞𝐭 𝐚𝐧 𝐒𝐋𝐀 𝐟𝐨𝐫 𝐔𝐬𝐞𝐫 𝐂𝐨𝐧𝐟𝐮𝐬𝐢𝐨𝐧 → Yes, confusion. Not bugs. Measure how long it takes for a user to get unstuck. That’s your real adoption metric. If your ERP vendor isn’t planning for what happens after go-live, they’re not solving your problem. They’re just delivering a system. The real ERP work begins when the dashboards go live. What’s your plan for the ERP Void? ♻️ 𝐑𝐄𝐏𝐎𝐒𝐓 𝐒𝐨 𝐎𝐭𝐡𝐞𝐫𝐬 𝐂𝐚𝐧 𝐋𝐞𝐚𝐫𝐧.

I improved retention and onboarding success by making a change to the first step in the onboarding process. A few years (and a few companies) ago, I made a small tweak to the way we onboarded new customers—a tweak that ended up making all the difference. We stopped diving headfirst into the technical implementation. Instead, we started with what I called a Partnership Kickoff. This one shift transformed the customer experience, boosting retention and improving onboarding success rates. Here’s why: The Partnership Kickoff brought intention to the relationship right from day one. Instead of rushing to “get things done,” we: 1️⃣ Engaged all the key stakeholders in the partnership 2️⃣ Discussed goals and confirmed success criteria upfront 3️⃣ Set proper expectations on BOTH sides 4️⃣ Clarified roles and responsibilities for onboarding and beyond 5️⃣ Created space to ask questions and address concerns This wasn’t just a feel-good meeting. It was about getting ahead of risks, ensuring alignment, and setting the stage for success. Here’s the secret sauce: ⚫️ Set expectations early Sales aligned on the importance of this meeting, and CSMs communicated the who, what, and why in their first email. ⚫️ Use a New Customer Intake Form We asked customers to provide key information upfront—no assumptions or overreliance on Sales handoffs. ⚫️ Prep the right way Sending the kickoff deck in advance meant our meeting focused on conversation, not presentations. ⚫️ Lead with goals and expectations Capturing customer goals was the priority, setting the tone for how we’d measure success. ⚫️ Clarify next steps We left every kickoff aligned on what happens next and who’s doing what. The result? Customers felt heard, understood, and set up for success. It wasn’t magic, but it sure felt like it. That small change? It delivered BIG impact—the kind every CS leader dreams about. Are you being intentional about how you’re starting your partnerships? If not, maybe it’s time to rethink step one. ________ 📣 If you liked my post, you’ll love my newsletter. Every week I share my learning, advice and strategies from my experience going from a CSM to CCO. Join 12k+ subscribers of The Journey and turn insights into action. Sign up on my profile.

"It's the customers fault." ...said the CSM when asked why onboarding is taking so long. But it's never the customer's fault. Trust me, I've been there. It's frustrating when you know the customer will achieve great things -- as long as they complete that one onboarding task. As long as they provide the API key. The CSV file. The user list. But what is really missing here is not customer commitment. What's missing is Joint Accountability™. Looking at it from the customer's point of view: They have just purchased something from you. There is a default expectation that you will do things for them. They give money. You provide service. Simple. This is a pitfall that leads to unrealistic expectations and inevitable disappointment. Because as we all know, most SaaS companies need their customers' help to get them going. How do we then achieve Joint Accountability™? 1. Set realistic expectations, early. As early as the sales process, it needs to be clear what the customer is expected to do once they sign the contract. Sales teams are often afraid of this kind of transparency, but in truth, rather than slowing down sales cycles -- it helps the customers make decisions faster. 2. Documenting responsibilities and progress throughout onboarding. Make it clear what customers are expected to do, when they are expected to do it, and why it is important. Let them know what happens if they don't do their part. With everything documented, it's easier to hold people responsible when the project halts. ❗️This last point is the real secret key to Joint Accountability™: 3. Make everything visible for everyone. Managing projects in the same view as customers make it very hard to hide from responsibilities. And the what, when and why of every task become crystal clear. Internal project management have thrived with frameworks like this for years. It is time Customer Success caught on. This is why we created Shared Workspaces in Startdeliver. Our customers simply embed their customer projects into their own products. For the end user, it helps them onboard quicker without adding yet another tool they have to login to and keep track of. ------ So next time you get that classic customer success onboarding frustration, ask yourself. Did we do everything right from the start? Did we create Joint Accountability™? PS. Shoutout to Lincoln Murphy who started talking about Joint Accountability™ in Customer Success years ago. You can listen to the two of us riffing on an array of Customer Success topics on out podcast: Impact Weekly, available where you get your podcasts. #customersuccess #csm #customersuccessonboarding #customeronboarding

Is There a Simpler Path to Customer Outcomes? Here's a pattern I keep noticing: CS teams are tracking more data points than ever. We have dashboards for everything... engagement scores, feature adoption, support interactions, product usage patterns. But when I ask CS leaders what predicts their customers' success, the answer is usually simpler than the data suggests. It's not about customers using every feature. It's about them completing a few key actions that drive their business forward. What if we're overcomplicating this? Think about your own experience for a second. When you adopt a new tool, do you explore every feature? Or do you find the 2-3 things that solve your immediate problem and stick with those? Your customers are doing the same thing. So here's the question worth asking: ▶️ What are the critical few actions that actually predict business outcomes for your customers? Not product engagement. Business results they can point to. Here's how to find out: 👀 Look at your most successful customers. What did they do in their first 30, 60, 90 days that others didn't? 🗣️ Talk to them. Ask what made the difference. You'll probably hear about 3-5 specific things. Now make those things easier to find and complete. Build your onboarding around them. Celebrate when customers hit those milestones. But here's where it gets interesting: ♻️ This isn't a one-and-done approach. Think about it like habit stacking: the concept James Clear talks about in Atomic Habits. You don't try to change everything at once. You start with one small action, make it part of the routine, then layer on the next. The same principle applies to customer outcomes: ▶️ Start with the one action that drives their most immediate business result. Help them integrate it into their workflow. Once that becomes routine, celebrate the win and introduce the next value-driving action. Then the next. Each action builds on the previous one. Each success creates momentum for the next milestone. What this means practically: ❌ Your customer journey isn't a checklist they complete once. ✅ It's a progression of value that compounds over time. Month 1: They solve their immediate problem. Month 3: They've built that into their routine and are ready for the next outcome. Month 6: They're stacking multiple workflows and seeing exponential value. You're not just helping them achieve one outcome. You're helping them build a system of continuous value creation. The result? Customers move faster because the path is clear and incremental. Your team has better focus because you're guiding one step at a time. Success becomes more predictable because you're building on proven behaviors. And retention improves because value keeps compounding. ❌ Sometimes the answer isn't more data. ✅ It's more clarity about what actually matters, and a system that helps customers build on each win. StepUpXchange JanYoungCX

Most PMs obsess over technical milestones while elite PMs are laser-focused on end users. The difference? Forget Gantt charts or status reports. It's about understanding who actually determines your success. Let me be blunt: No matter how perfectly you execute the technical aspects, if end users hate your solution on the first day of go-live, you've failed. Enterprise IT projects live or die by user adoption. Period. Yet we spend countless hours on technical requirements while treating user readiness as an afterthought. Take Courtney, for example—a hypothetical ICU nurse who is going to be using a new system, which you will be implementing. Here's the uncomfortable truth: Courtney doesn't care about your project plan. She cares about whether she can do her job on Monday morning. Elite PMs know this. They reverse-engineer her success from day one. Here's what that looks like for Courtney for this 4-month enterprise IT rollout: 𝗧-𝟬: Courtney logs in successfully and can work effectively. (The actual moment of truth.) 𝗧-𝟮: Courtney completes training with confidence, not confusion. 𝗧-𝟭𝟰: Courtney registers for training because she understands its value. 𝗧-𝟯𝟬: Courtney's training schedule is released with enough notice for her to plan around it. 𝗧-𝟰𝟱: Courtney's training is developed based on real workflows, not technical specs. 𝗧-𝟲𝟬: Courtney is matched to her future role with clarity about what will change. 𝗧-𝟵𝟬: Courtney sees her future workflows in a non-production environment and gives you accurate (and, if necessary, brutal...) feedback. 𝗧-𝟭𝟭𝟬: Courtney's future workflows are designed for efficiency, not just technical functionality. 𝗧-𝟭𝟮𝟬: Courtney's current workflows are understood deeply, including pain points and workarounds. Two critical insights here: 1. Everything STARTS with Courtney, not the technology. 2. User readiness begins on day one of your project, not the final sprint. Average PMs celebrate when the system passes QA. Elite PMs celebrate when users can perform their jobs without calling the help desk. The technical aspects matter, of course. But they're just table stakes. The real differentiator is whether your end users feel prepared, supported, and empowered when they first log in. If you're not planning for end-user success from day one of your project, you're not just behind. You're playing the wrong game entirely. ~~~ What's your strategy for ensuring users are smiling, not cursing, on go-live day? Or if you're outside IT, how do you apply this end-user obsession in your domain? Drop a comment below. ⬇️

40-60% of first-time users never come back. Most companies focus on one type of onboarding support and neglect the other. Some build great in-app experiences but never follow up when users drop off. Others send tons of emails but their product experience is confusing. The best PLG companies use both product bumpers (inside the app) and conversational bumpers (outside the app) working together. Here are 11 bumpers that could double your activation rates: Product Bumpers (Inside Your App) 1. Welcome Messages Restate your value prop and set expectations for what users will experience. Make them feel invited, not lost. 2. Product Tours Eliminate distractions and give users only the options they care about. Use profiling questions to launch them into the right part of your product. 3. Progress Bars Show how close users are to completion. They'll know onboarding won't take long and they're just a few steps away. 4. Checklists Break big tasks into bite-sized steps. Pre-fill some items before users see them to boost motivation. 5. Onboarding Tooltips Provide just-in-time guidance, but don't drown users in tooltips. Keep it simple and guide them only through the critical steps. 6. Empty States Turn blank dashboards into clear next steps that lead users closer to value. Conversational Bumpers (Outside Your Product) 7. External Messaging Emails, texts, LinkedIn - meet users wherever they spend their time. The best messages provide clear next steps to re-engage. 8. Knowledge Base Give users instant answers to common questions. They solve problems independently while you deflect support tickets. 9. In-app Messaging When users need to ask specific questions, let them message your team in-app for near-instant solutions. 10. Community Forums Let users help each other. Notion does this brilliantly - users share templates that simultaneously increase adoption, engagement, and retention. 11. Training & Specialists Close the knowledge gap with coaching calls, academies, or cohorts. For high-value users, assign specialists to speed up time to value. Pro Tip: If you're just starting, give 10-40 signups per week the white-glove treatment. Welcome emails, onboarding calls, trial extensions - do everything to get them to value. Find what works, then automate it. Manual emails become automated. Common questions get added to your knowledge base. The unscalable path is how you identify the scalable path. What bumpers are you using today?

Every ERP go-live has a ghost. Not a bug. Not a broken formula. A phantom pain. Finance feels it first — when the close takes twice as long, even though automation “went live.” Ops feels it next — when reports are technically correct but emotionally wrong. Everything reconciles. Nothing makes sense. That’s the hidden cost of ripping out muscle memory. Old systems had friction, but they also had rhythm. People knew the quirks — which buttons to double-click, which exports to trust. New systems remove the friction but erase the rhythm, too. The result? A business that’s operationally faster but cognitively slower. ERP leaders love talking about data migration. Few talk about habit migration. You can’t patch it with training. You re-engineer it with feedback loops. Daily “micro-audits.” Live shadow dashboards that compare system data to old instincts. A two-month window where human judgment outranks automation. Because every ERP rollout has two implementations — one technical, one neurological. Ignore the second, and your shiny new platform becomes a prosthetic no one wants to use.