Day 10: Somewhere between “create kickoff deck” and “enable integrations,” we lost sight of the hu…

Somewhere between “create kickoff deck” and “enable integrations,” we lost sight of the human side of onboarding.

Here’s what I wish made it onto every SaaS implementation checklist—because it’s rarely the tools or timeline that derail a project. It’s the people stuff:

✅ Is the client emotionally ready to start?
The folks tasked with implementation are often inheriting a decision they didn’t make. If they’re still processing “why this tool,” you’re already behind. Before diving into tasks, ask: do they feel ownership, or are they just executing?

✅ Have we identified the real decision-maker?
The person scheduling the meetings isn’t always the one calling the shots. Without clear stakeholder alignment, every milestone risks being vetoed late in the game. Find the person who defines success—and make sure they’re in the loop early.

✅ Do we agree on what “done” actually looks like?
If the team is delivering to a vague vision, you’re building on shifting ground. Nail down what MVP means to them—not just what you assume it is. Clarity here saves rework and resentment.

✅ Have we addressed the “we’ll know it when we see it” trap?
This is the silent killer. Ambiguity disguised as flexibility. Push for definition, even if it’s imperfect. A shared draft beats a mystery ending.

Because project success isn’t just about deliverables.

It’s about navigating the messy, unspoken expectations that live between the lines.

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