Every onboarding hits a blocker at some point. A stakeholder goes on holiday. IT deprioritizes the SSO setup. A key decision-maker changes. The question isn't whether you'll face blockers — it's whether you have a systematic playbook to resolve them before they compound into churn.
This playbook covers the three most common types of blockers and exactly how to handle each one.
Blocker Type 1: IT delays (the most common)
In B2B SaaS, IT delays are the #1 most common onboarding blocker. SSO, domain authentication, compliance setup — these require IT involvement that was often never properly arranged during the sales process.
Day 1 prevention: Identify the IT contact separately from the business contact at kickoff. Send their task list directly to them with a specific deadline (Day 5). Do not route IT tasks through the end user or buyer — they rarely have the technical context or authority to move IT quickly.
If blocked after Day 5:
- Send a direct escalation email to the IT contact — specific task, specific deadline, specific impact of not completing it
- CC the buyer on the escalation — this applies social pressure without being confrontational
- Offer a 15-minute call to walk IT through the setup — most IT teams delay because the requirements aren't clear, not because they don't care
- Flag the account as at-risk in your tracking system
Blocker Type 2: Stakeholder dropout
The buyer going silent mid-onboarding is the second most common blocker. They were engaged during the sale and kickoff, then disappeared. End users are confused about priorities. The CSM is unsure whether to push or wait.
Prevention: Set expectations at kickoff that you'll need the buyer for three specific touchpoints — the Day 14 first-value check-in, the Month 1 progress pulse, and the Day 60 buyer re-engagement. Get these on their calendar during kickoff.
If blocked after Day 21:
- Send the "Two things I need from you" email — keep it to two bullet points maximum, make it easy to respond
- Contact their EA directly if they have one — EAs can often get a 15-minute slot that the buyer themselves would ignore in email
- Connect through LinkedIn if email is bouncing or being ignored
- Document all outreach attempts for the renewal conversation
Blocker Type 3: Internal client politics
Sometimes the blocker isn't technical — it's organizational. A team member is resistant to the new tool. A department head wasn't involved in the purchase decision and is pushing back. Internal priorities have shifted since the deal closed.
How to identify it: Low end-user adoption despite good IT setup and responsive buyer. Users logging in but not completing tasks. Feedback that users "already have a way of doing this."
How to handle it:
- Arrange a team-level call — not a training session, but a genuine conversation about what's not working
- Find the internal champion at the end-user level, not just the buyer level
- Document specific wins and share them internally through the buyer
- Lower the activation bar — focus on one task that's genuinely easier with the new tool than without it