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5 Ways to Manage Multiple Stakeholder Expectations in Enterprise Customer Onboarding

Align diverse expectations and deliver successful outcomes when multiple decision-makers are involved

Let’s say you're confidently navigating an enterprise onboarding when you slowly start to see conflicting requirements emerge.

You realise that the stakeholders haven’t communicated with each other about your solution.

Their timeline expectations are wildly different.

You’re going to need to backtrack to help them align. Fast.

… And now, you’ve got a headache.

You rub your temple and wonder if you should have just become a yoga instructor instead. 😅

But in all seriousness, the most dangerous moment in any B2B onboarding isn't if the product fails, it's when stakeholder expectations diverge.

It's why experienced onboarding specialists develop a sixth sense for detecting when the VP of Something Important is about to derail your carefully planned timeline with a casual "quick question" that's actually a fundamental objection in disguise.

Let's explore how to transform this complex stakeholder landscape from your biggest challenge to your greatest competitive advantage.

No need for painkillers, I’ve sorted your headache with the project below. ↓

Customer Onboarding B2B SaaS

🧪 The Project: Stakeholder Alignment

These steps are for complex onboardings where alignment is key. You will notice it becomes second nature once you have a template process in place for managing multiple stakeholders.

Step 1: Create a stakeholder org map during the sales cycle

Don't wait until kickoff to understand who's who.

Work with your sales team to identify all key stakeholders before the contract is signed. This gives an important head start to onboarding.

It may even prompt some further investigation that could have been missed.

Track each stakeholder's:

  • Role/title

  • Decision-making power (approver, influencer, end-user)

  • Primary concerns/goals

  • Communication preferences

  • Potential resistance points

  • Document specific success metrics for each stakeholder group

This info will be powerful throughout the lifecycle, so why not get the knowledge early?

🔍 NOTE: Ask your sales team: "Who might block this onboarding if they're unhappy?" These are often the stakeholders who weren't heavily involved in the purchase decision but have significant operational power.

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