Moving from satisfaction metrics to aspiration discovery

Yesterday, I shared the concept of aspirational intelligence to kickstart the year. It is the ability to identify and act upon the aspirations of customers and employees in ways that drive strategic decision-making. I believe it’s the capability that will separate thriving organizations from struggling ones in 2026.

But understanding aspirational intelligence conceptually is one thing. Putting it into practice is another.

Today, I want to give you something immediately actionable: five questions that can transform how you understand your customers. These aren’t survey questions or NPS follow-ups. They’re conversation starters designed to surface what your customers are truly reaching toward.

Why Traditional Discovery Falls Short

Most customer research focuses on problems and preferences. We ask about pain points, feature requests, and satisfaction levels. We measure effort scores and likelihood to recommend. All of this is valuable, but it’s fundamentally backward-looking or present-focused.

Pain points tell you what’s broken today. Feature requests tell you what customers think they need now. Satisfaction scores tell you how well you performed yesterday.

None of this tells you where your customers are heading.

Aspirational intelligence requires a different kind of inquiry. It requires questions that illuminate trajectory, the future, or the direction customers are moving and why that destination matters to them. When you understand trajectory, you can position your organization not just as a problem-solver, but as an essential enabler of your customers’ futures.

The Five Questions

These questions work in executive conversations, Customer Success check-ins, sales discovery, and even product research. They can be asked directly or woven naturally into dialogue. The key is genuine curiosity about the answer, not checking boxes, but truly listening for what’s beneath the surface.

Question 1: “What does success look like for you in three years?”

This question seems simple, but it’s remarkably rare in business conversations. We ask about quarterly goals and annual targets, but we rarely invite customers to articulate their longer-term vision.

The three-year horizon is intentional. It’s far enough out to encourage aspirational thinking, but close enough to feel concrete. One year feels tactical. Five years feels abstract. Three years occupies the sweet spot where customers reveal what they’re actually building toward.

Listen carefully to the answer. Are they describing incremental improvements or fundamental transformation? Are they focused on operational metrics or identity shifts? The language they use tells you everything about their aspirations.

A customer who says “I want to reduce costs by 15%” is describing an outcome. A customer who says “I want our team to be seen as strategic partners to the business” is describing a trajectory. Both are valid, but serving the second customer requires understanding something deeper than their current challenges.

Question 2: “What would make you proud to have accomplished?”

This question cuts past rational goals to emotional investment. Pride is aspirational by nature. It connects achievement to identity. When customers articulate what would make them proud, they’re telling you what matters most.

The answers often surprise. Executives who spend meetings discussing efficiency metrics will suddenly talk about building teams, creating opportunities for others, or leaving a legacy. Individual contributors will reveal ambitions their managers don’t know about.

This question also surfaces the difference between imposed goals and personal aspirations. Customers might be measured on certain KPIs, but what would make them proud often transcends those metrics. Understanding this distinction helps you serve the whole person, not just the role.

Question 3: “Who do you want your organization to become?”

Notice the framing: not “what do you want your organization to achieve” but “who do you want your organization to become.” This subtle shift invites identity-level thinking.

Organizations, like people, have trajectories. They’re becoming something, whether intentionally or by default. When you ask customers to articulate who their organization is becoming, you gain insight into the transformation they’re pursuing.

Some customers will describe capability shifts: “We want to become a data-driven organization.” Others will describe cultural aspirations: “We want to become a place where the best talent wants to work.” Still others will describe market positioning: “We want to become the company that defines our category.”

Each of these aspirations implies different priorities, different success criteria, and different ways your organization can add value. A customer pursuing data-driven transformation needs different support than one focused on talent attraction, even if they’re buying the same product.

Question 4: “What’s the gap between where you are and where you want to be?”

Once you understand the destination, this question illuminates the journey. It invites customers to articulate not just their aspirations, but their honest assessment of the distance they need to travel.

This is where vulnerability enters the conversation. Customers who answer honestly are sharing something important: an admission that they haven’t yet arrived. This requires trust, and the conversation itself can build that trust when handled with care.

The gap they describe tells you where you can create the most value. Sometimes the gap is capability, they lack skills or tools. Sometimes it’s credibility, they need proof points or external validation. Sometimes it’s clarity, they know where they want to go but not how to get there.

Understanding the nature of the gap helps you position your value proposition appropriately. You’re not just selling a product; you’re helping close the distance between who they are and who they’re becoming.

Question 5: “What would have to be true for you to look back on this year as transformative?”

This question reframes the immediate future in aspirational terms. It asks customers to define transformation on their own terms and identify the conditions that would make it possible.

The phrase “what would have to be true” is powerful because it surfaces assumptions and prerequisites. Customers often reveal dependencies they haven’t articulated, like organizational buy-in they need, resources they’re lacking, or changes in their environment that would unlock progress.

This question also creates a natural opportunity for partnership. Once you understand what would have to be true, you can explore together which of those conditions you might help create. You move from vendor to collaborator in the customer’s transformation.

Putting It Into Practice

These questions don’t work as a checklist. Firing all five in sequence would feel like an interrogation. Instead, weave them into natural conversation. Use one or two in your next executive business review. Drop another into a Customer Success check-in. Let them inform your discovery process in sales.

The goal isn’t to collect answers in a database. It’s to develop your own aspirational intelligence to perceive and understand the trajectories of the people you serve, and drive customer success and loyalty.

Over time, patterns will emerge. You’ll start to recognize common aspirations within customer segments. You’ll develop intuition for the language that signals deeper ambition. You’ll build relationships that transcend transactions because your customers will feel genuinely seen.

The Aspiration Behind the Question

Here’s the deeper truth: asking these questions is itself an act of aspirational intelligence. It signals to your customers that you care about more than their current contract or this quarter’s usage metrics. It communicates that you see them as people on a journey, not just accounts to be managed.

In a world where every vendor claims to be customer-centric, this kind of genuine curiosity stands out. It builds trust. It creates loyalty. It transforms relationships.

Start asking. Start listening. Start understanding what your customers are really reaching toward.

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Chris Hood is an AI strategist and author of the #1 Amazon Best Seller Infailible and Customer Transformation, and has been recognized as one of the Top 40 Global Gurus for Customer Experience. His latest book, Unmapping Customer Journeys, will be published in April 2026.