Overcoming Challenges In Client Onboarding

Think your onboarding process is smooth and simple? Here’s what it actually feels like from the customer’s side. This is a real-life example I'm currently in the middle of: ✅ Sign up for new service we're really excited about and are eager to get started with quickly. ✅ Receive email with 9 "simple" steps to get started. Looks easy enough at a glance! ✅ Carve out time in the afternoon to work through them. 🚧 Immediately hit a wall: I can't proceed until Daniel Zarick signs the contract. Stuck until that gets done. ✅ Contract finally signed! Okay, I'll work through the next steps later this afternoon after my calls. 🚧 Next step is granting access to some tools. But which email address should I grant access to? Ping the team to ask and wait for a reply. 🚧 Need to provide "a few voice of customer examples." We've got thousands. Unclear what they're looking for. Ping them again to ask for clarity. 🚧 Need to schedule a kickoff call. No meeting link provided. Should I be reaching out to find time? Will they let me know when they're ready for me to schedule? I set aside an hour to tackle this list. The result? I completed ONE out of NINE tasks. 😲 And just like that, we're delayed by a day. At least. What looks like a "simple list of things to do" on paper quickly becomes a complex web of dependencies, permissions, and unclear expectations. To truly enable your customers from the get-go: ✅ Provide all necessary context upfront—don’t make them ask for clarity ✅ Clearly define each step: what's needed, who’s responsible, and by when ✅ Give them the tools and instructions to actually complete the steps in one go Remember: Every moment of customer confusion is a loss of momentum and a potential delay in your onboarding timeline. And that's why we built Arrows: https://lnkd.in/guZwtrNS

Last week we had our first churn 💔 It hurt, especially considering that Mailability.io is a SaaS bootstrapped company with no funding. After a few months of successfully winning and onboarding numerous clients, seeing revenue value from day 1, we saw a client walking away, for the very first time. Without even giving us a chance. We just completed the implementation, went live and started seeing the first $$$ coming in. The next day the phone rang. They said their team was too small to handle another solution, and so they left. After a few failing tryouts to get the client back, our first reaction was disappointment. A few hours later we've already agreed that we will turn this negative experience into a customer experience learning-opportunity goldmine. Since Thursday, we have had 4 debrief meetings. In these meetings we identified the reasons for this churn and suggested effective ways to handle them. And even though there's probably nothing anyone can do to reduce churn risk to 0, it was definitely a must have experience for us as a company. Here are 4 key learnings💡: 1. While ICP is crucial, champion attention is key (even after signing) 🏆 While this client fell perfectly within our ICP, we missed a crucial aspect during the sales process. We wanted to win this client so much that it blinded us from seeing that they just didn't have the attention span to invest their time and energy in a solution like ours at this time. Learning - identifying potential engagement issues early on, can save precious time later (which is our most important asset). 2. Knowledge gaps cause confusion 🤔 The client shared with us that they didn't fully understand critical areas of the solution during the sales process, which caused them to enter the onboarding phase with technical knowledge gaps.  Action - added two additional slides to our sales decks. One explains how our solution works end-to-end. The second explains the onboarding process and the time required from the client during this phase. 3. Choose the communication channel that works best for your client 💬 We work with Slack to communicate with most of our clients, but in this case it didn't work smoothly. It took us a few days to realize that communication wasn't streamlined and moved to email. Learning - while suggesting your preferred communication channel, ask the client for their preferred channel of communication and follow their lead. 4. Clean and organized onboarding process with $ value from day 1 🤝 We've identified the weaker areas of our onboarding process and corrected them with clear objectives and action points.  - Added a few product recap slides to the onboarding deck to make sure everyone is aligned. - Added a clear timeline of required tasks, starting from high-impact / low time investment ones.  - Identified milestones requiring the client to review and confirm our setup, before launch. What have you learned from your churn experiences? Share in the comments!

After 5 years helping 800+ companies streamline onboarding, here's the most underestimated way I’ve found to eliminate delays: Prescriptive playbooks. Most onboarding failures happen before customers even start using your product. We dump endless configuration options on them and ask them to figure out what they want. I know a software vendor in our space who gives a spreadsheet with 800 rows for their customers to fill, before they can “start” implementing. The result? Analysis paralysis, delayed launches, and frustrated users wondering if they're doing it "right”. Customers do sometimes blame themselves for these delays, but they’ll steer away from your software and software in your space if they have this experience Ever notice how many tools give you templates instead of a blank page? There's a reason for that. Smart companies use more prescriptive and preset configurations: For ex, Slack: Suggested channels and workflows This leverages two psychological principles: → People are more likely to use tools when they feel they've already started → Once started, momentum keeps them going Instead of asking "What do you want to set up?" start with, "Based on companies like yours, here's what we recommend." Map your customer types to proven configurations. Present these as the starting point. This approach eliminates decision fatigue, ensures customers benefit from your best practices, and de-risks launches with proven setups Your customers don't want infinite choices. They just want confidence that they're set up for success.

🧠 The Psychology Behind Successful Customer Onboarding A hard truth I've learned as a CS leader is that perfect features mean nothing if your onboarding fails. Another hard truth: Psychology matters more than process. You must focus on human behavior rather than just feature adoption. Here are my three principles to live by in onboarding: The Momentum Principle: We discovered that customers who achieve value in the first 48 hours are 3x more likely to become long-term advocates. So we redesigned our onboarding to focus on quick wins before complex features. By breaking down the journey into smaller, achievable milestones, we create a pattern of success that builds confidence and momentum. The Ownership Effect: When customers invest time in customizing their setup, they're significantly more likely to stick around. We now encourage early personalization through guided setup sessions. Rather than doing it for them, we coach customers through the process. This has increased product stickiness by 47% and reduced early-stage churn by 34%. The Contextual Learning Framework: We stopped treating onboarding as a linear checklist. Instead, we now adapt the journey based on user behavior and role. Our data shows that contextual learning – delivering guidance at the moment of need – increases feature adoption by 68% compared to traditional training methods. The results speak volumes: Time-to-value was reduced from 45 days to 15 and adoption rates increased by 56%. Successful onboarding is about building confidence and creating habits. Every friction point isn't just a technical issue; it's a psychological barrier waiting to be understood and removed. Are you designing your onboarding for features or humans? #CustomerSuccess #SaaS #Onboarding #CustomerExperience