Today’s topic is for the scenario when a customer is adamant about a particular way of working.
As the expert in onboarding your product, you will have a proven way of successfully onboarding a customer.
We usually reiterate this to customers throughout the onboarding phase but sometimes they can be set in their ways.
This is usually because they have experienced poor onboarding with a previous vendor and don’t want to repeat the same painful process.
This, is a valid concern.
Communication of the context of YOUR particular onboarding process is important.
If this doesn’t reassure them completely then sometimes you may need to meet in the middle.
The steps below are how I suggest you navigate it for a strong ongoing partnership.
Meet me in the middle? I’ll write it, you implement it? ↓
🧪 The Project: Strategic Redirect
This framework transforms potential conflict into collaborative problem-solving. Use it to navigate scenarios where the customer pushes back on your standard process.
Step 1: Time machine question
Don’t immediately counter their idea. Why not entertain it to find out more?
Ask something like:
"That's an interesting approach. Can you walk me through what success looks like for your team in 90 days if we follow that path?"
This does 3 things:
Shifts focus from tactics to outcomes
Reveals their actual goals (often different from their stated ones)
Creates space for you to align their vision with reality
Step 2: Highlight patterns
Look to share insights from your experience with many successful onboardings.
"You know what's interesting? About 80% of our customers initially want to do exactly what you're suggesting! The most successful we have seen are the ones that do [insert objective] because they see [insert optimal outcome].”
Then pause. Let them think on it, and ask you for more information.
It will be even more powerful to have case studies ready to send over to support your claims.
This approach positions you as a data-driven advisor.
Step 3: Pilot option
If they're still keen on their original approach then you have the option to offer a chance to test it out.
"Okay, I understand that you feel strongly about this approach. How about we run a small pilot? We'll implement your approach with one team/feature/workflow for two weeks, measure the results, then decide how to scale. How does that sound?"
Set clear success metrics upfront.
Most pilots naturally reveal why the alternative approach works better, but customers feel ownership because they ran the experiment.
Be prepared that this pilot could also be successful!
Go into it hoping for the best. Don’t try to prove a point. 😏
Highlight that this could elongate their onboarding and get them to sign off on that in writing.
Be sure to acknowledge their openness during these interactions.
This reinforces the deeper than surface level partnership you are trying to build.
The deeper you can dig into opinions, struggles, and hesitancy the more likely you can provide a highly successful onboarding experience.
"I really appreciate you sharing your thinking with me. It actually helps me understand how we can better support teams like yours. Let’s keep this going so we can both adjust for the best outcomes as we go.”
This maintains the relationship and leaves the door open for course correction.
🤓 The Analysis
New customers have incomplete information at the start and try their best to succeed.
Our job in onboarding is to fill those gaps with options, ideas, support, and advice that we know will provide the outcomes they need to be successful.
So, be open to alternatives and think on your feet during conversations.
What to expect by making these changes:
Deeper customer partnership & trust
Faster & clearer time-to-value
Faster time to additional revenue
Reduced escalations
