Why Most Onboarding Fails Before It Even Starts
Most onboarding fails before it starts.
Customers leave the first call already thinking, “This is going to be painful.”
Another reason is they’re designed for the company, not the customer.
That results in endless calls, bloated decks, and customers checking out halfway through.
You don’t need more “energy” on calls.
What you need is a system that gets customers to value faster.
Here’s how to fix it.
1. Quick Wins > Full Tours
Don’t walk customers through every feature.
Give them one small action they can complete in under 15 minutes.
Examples:
Update profile settings
Connect a single data source
Invite one teammate
That’s enough.
Quick wins create confidence.
Confidence fuels momentum.
Momentum keeps accounts alive.
I explained why failing to deliver those early wins creates silent churn that teams only notice too late.
💡Example: A payroll software company I worked with asked new admins to run a “test payroll” in week one. It wasn’t real money, but it gave them confidence they could trust the system before touching live employee data.
As simple as that. You’ll find a step-by-step version of this idea in my customer onboarding checklist guide.
2. Stop Running Marathons
A 3-hour training call is onboarding suicide.
Customers retain almost nothing.
Break it into 3–4 shorter sessions, each tied to a clear outcome. Think of it as “sprints,” not “lectures.”
That same principle powers the customer success fundamentals framework. Keep actions small, repeatable, and measurable.
3. Personalize From the Start
Generic first steps kill excitement.
Show the customer’s actual use case right away.
If they’re in finance, walk through a finance workflow. If they’re in retail, show retail. This signals relevance, and relevance drives adoption.
💡Example: A well-known project management platform swapped its generic “task setup” demo for industry-specific workflows. Marketing teams saw campaign boards, IT teams saw sprint boards. Engagement in the first 30 days jumped by 40%.
See? It’s the same personalization playbook I broke down in detail here: personalization strategies in Customer Success.
You’re reading the free edition of The CS Café.
What follows is not more tips. It’s the full playbook that companies I work with use to turn onboarding into a retention engine.
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