Chapter 3: What "Value" Actually Means to Your Users

If you can't define success from your user's perspective, you can't design a path to it.

Here's a question I ask every team I work with:

What does a successfully onboarded user look like?

The answers I get usually sound like this: "They completed the setup wizard." "They invited a teammate." "They used the core feature at least once."

Those are all things the company cares about. None of them are things the user woke up that morning hoping to accomplish.

This is the fundamental misalignment at the heart of most broken onboarding: the company defines success by what it wants users to do, not by what users actually want to become.

Users don't buy products. They hire them.

There's a framework called Jobs-to-be-Done that reframes how we think about why people adopt products. The core idea: users don't buy your software because they want software. They "hire" it to make progress in their lives.

Nobody wants a CRM. They want to stop losing track of deals.

Nobody wants a project management tool. They want to stop feeling like their team is out of sync.

Nobody wants an analytics platform. They want to make decisions with confidence instead of gut feelings.

The job isn't the feature. The job is the transformation the user is seeking. And until you understand that transformation, you're designing onboarding for the wrong destination.

The three dimensions of user success

Here's where it gets interesting, especially in B2B. When a user "hires" your product, they're not just looking for a functional outcome. They're looking for three things simultaneously:

Functional success: what they can see.

This is the tangible outcome. The report got generated. The invoice got sent. The pipeline got updated. It's the most obvious dimension, and it's the one most teams optimize for. But it's not enough on its own.

Emotional success: what they feel.

Does the user feel competent? Confident? In control? Or do they feel confused, overwhelmed, and like they're wasting their time? The emotional dimension is invisible in your analytics, but it's the reason users quit. Nobody leaves because a feature didn't work. They leave because using the product made them feel stupid.

Social success: what others say.

In B2B, this one is critical. Does the user look good to their team for choosing this product? Does their manager see results? Do their colleagues adopt it, or roll their eyes? A user can get functional value from your product and still churn because nobody else on their team bought in.

Great onboarding addresses all three. Most onboarding only addresses the first.

The "So What?" exercise

One of the simplest tools for getting past surface-level success metrics is to keep asking "so what?" until you hit the real transformation.

Here's how it works:

"Our product helps users create dashboards."

So what?

"So they can see their data in one place."

So what?

"So they can make faster decisions."

So what?

"So they look like the person in the room who always has the answer."

That last one is the real job. The user doesn't want a dashboard. They want to be the person who always has the answer. That's the emotional and social transformation they're actually seeking.

When you know that, you design onboarding that gets them to that feeling, not just to a completed dashboard.

The four forces working on every new user

Every person who signs up for your product is caught between four competing forces:

Push: the pain of their current situation.

Something isn't working. Their current tool is frustrating. Their process is broken. This is what made them start looking for a solution in the first place.

Pull: the appeal of a better future.

Your product promises something better. Faster workflows. Better insights. Less manual work. This is what made them sign up.

Anxiety: the fear of change.

What if this doesn't work? What if I waste time learning something new? What if I look incompetent in front of my team while I'm figuring it out? What if I have to migrate data and something breaks?

Inertia: the comfort of the status quo.

The current way is familiar. It's not great, but it works. Switching costs are real, both in time and in cognitive effort. "We've always done it this way" is the most powerful force in any organization.

Push and pull work in your favor. Anxiety and inertia work against you.

Onboarding's job is to amplify the push and pull while reducing anxiety and inertia. Most onboarding only focuses on pull (showing features) and ignores the other three entirely.

In B2B, there's a complication

The person who bought your product is often not the person who has to use it.

A VP of Sales signs the contract for a new CRM. The sales reps have to use it every day. A Head of Marketing chooses an analytics platform. The marketing coordinators have to learn it.

These two people have completely different jobs. The buyer's job is to solve a strategic problem. The end user's job is to get their daily work done without extra friction.

If your onboarding is designed for the buyer's job ("here's how this platform transforms your revenue operations"), it will fail the end user whose job is "I need to log this call before my next meeting."

Great B2B onboarding accounts for both. It gives the buyer the strategic narrative they need to justify the decision, and it gives the end user a fast, practical path to getting their work done.

The Eyes Light Up moment

There's a concept I love from Wes Kao: the Eyes Light Up moment. It's the point in a conversation, a demo, or an onboarding experience where you can literally see the user's expression change. They go from politely interested to genuinely excited.

That moment is your signal. It tells you exactly where the real value lives for that person.

Pay attention to when it happens in customer calls, in demos, in support conversations. When users' eyes light up, that's the transformation they care about. That's the destination your onboarding should be driving toward.

If you've never seen it happen during onboarding, your onboarding isn't reaching the right moment.

Putting it together

Before you can design a path to value, you need to answer these questions clearly:

If you can answer all of those, you have a map of the real landscape. Not the features your product offers, but the transformation your users are seeking.

That's the foundation for everything that comes next.