How to Fall in Love With a Stranger

In 1997, a team of psychologists led by Arthur Aron, Ph.D. and Elaine Aron, Ph.D. created a framework now famously known as the 36 Questions. The questions are a sequence of prompts designed to help two strangers grow closer.

The secret wasn’t just in the questions themselves, but how they were structured.

The questions were grouped into three escalating levels of intimacy, each revealing a deeper layer of a person’s identity.

The first set contains surface level questions that serve as the warm up.

Questions such as, “Given the choice of anyone in the world, whom would you want as a dinner guest?”

The second and third sets delve much deeper, such as:

“If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven't you told them yet?”

As each person reveal more about themselves, the likelihood of both making a connection increases.

When you think about your customers, there’s a direct parallel.

Across the companies I’ve worked with I’ve noticed a pattern. The most successful ones know their customers very well.

They can tell you exactly who they serve, what their customers care about, and what problems are solved by purchasing their product or service.

The underperforming companies? The description of their customer avatar is often fuzzy, assumed or overly broad.

The numbers speak for themselves. The under-performers have less growth, higher customer acquisition costs, lower margins and longer sales cycles.

I wanted to understand how well my clients understood their customers so I created a simple framework inspired by the three levels from the 36 Questions.

If a company can easily describe their customer at every level, then they understand their target avatar with clarity, depth, and precision.

Level 1 - The Measurables

“What gets measured, gets managed” the common business phrase espouses.

Our first level focuses on the common, easily observable and measurable aspects of our customer avatars; demographics and psychographics.

Demographics

Demographics build the basic profile. Most companies understand their customers at this level.

For consumers as customers it includes:

• Age

• Gender

• Income

• Education

• Job title

• Geographic location

Business customers can include:

• Industry or Sector

• Revenue

• Market segment

Basic demographics are a necessary starting point but only scratch the surface.

Psychographics

Psychographics group individuals by interests, hobbies, social media habits and lifestyle patterns (to name a few) instead of basic demographic categories.

Netflix, for example, regularly leverages the power of psychographics.

Take two Netflix subscribers who are interested in watching the popular show, Stranger Things. Depending on the viewing patterns of each subscriber, Netflix will show them different splash screens.

If one subscriber often watches romance films, the splash screen might display scenes from the show that emphasize relationships.

If the other subscriber has a history of watching exclusively horror, they will show frightening or intense scenes.

Same show, but Netflix understands each customer may relate differently to the content based on their psychographic associations.

Psychographics are less frequently discussed for business customers but include industry norms, risk tolerance and professional identity among others.

Both demographics and psychographics are a great start but unfortunately where the less successful companies stop.

Level 2 - The Drivers

It’s easy to categorize people or businesses.

What’s harder but infinitely more valuable, is understanding why they decide to buy.

High-performing companies excel here. They have a clear grasp of the problems their customers are trying to escape and the motivations pulling them toward a better future.

Problems

One of the biggest sources of wasted spend in any business is a weak understanding of the customer’s problem.

Products get built that no one wants because they solve nothing meaningful.

Marketing money disappears because the messaging sells features instead of addressing the customer’s pain.

When a company can’t articulate the real problem, the customer won’t see the real value.

Motivators

People don’t buy products, they buy progress.

Motivators are the forces moving someone from their current state to a future they believe is better. They can be intrinsic (improving health, gaining clarity, saving time) or extrinsic (market pressure, competitive shifts, economic or technological change).

The stronger the motivator, the faster the decision.

Companies that understand their customers’ problems and motivations share one trait:

They spend a lot of time with their customers.

Not just sales.

Not just support.

Everyone.

From the CEO to product development, they maintain direct, ongoing contact and treat customer insight as a core operating loop.

A famous example comes from the Four Seasons Hotel chain. Their daily employee huddles, attended by staff across the entire hotel, center on sharing customer successes and challenges so feedback flows into daily operations. It’s an extreme case, but it illustrates the culture required to truly understand your customer.

When companies reach this level of insight, their product becomes more than a solution.

It becomes a bridge to the customer’s desired identity and future.

Level 3: Alignment

As much as the 36 Questions can uncover connection, perhaps more importantly they identify when two people would never connect.

Better to realize the inability to connect after 36 questions than thirty-six years of marriage.

Relationship coaches refer to this as vetting and the process is just as important in business.

Alignment occurs across two dimensions: Values and Behaviors.

Values

The easiest way to know if there is risk of value misalignment is when companies simply don’t communicate their values.

If the employees don’t understand the company’s values there is almost zero chance customers will.

I recently made an important decision to leave traditional health insurance to join a crowd sharing plan. Of course, I ran the numbers and did my due diligence. One of the things that made it an easy decision is the company, CrowdHealth, is very forthcoming with their values and why they think the current healthcare system is broken. I align so much with their message that I regret not starting the company myself.

When companies are clear on their values, it makes it easier for customers understand the value proposition they offer.

When values align, everything from sales to adoption moves more smoothly.

Behaviors

Expressing values is one thing. Living up to them is another.

This is where behavior becomes the ultimate test of alignment.

If you claim to value transparency but hide fees, customers will feel the mismatch. If you promote speed but your onboarding takes weeks, that disconnect will show up in churn and stalled deals.

Customers reveal who they are through how they make decisions, how they adopt new tools, how they respond to friction, and how they follow through after the sale. Their actions show whether your product naturally fits into their world or whether you’ll constantly struggle to earn their attention, commitment, or trust.

Businesses who don’t live up to their values or ignore misaligned customer behavior will attract the worst customers and scare off the best ones.

Great businesses know who they serve and who they don’t. Great businesses decline business and fire customers who they know they can’t serve wholeheartedly.

The result is a business where sales cycles shorten, customer satisfaction strengthens, and growth becomes more predictable. I’ve seen this occur not because a company is pushing harder, but because they’re aligned with the people they’re meant to serve.

The Next Step

Understanding your customer at all three levels—Measurables, Drivers, and Alignment—gives you a sharper picture of who you’re truly built to serve.

Most companies stop at Level 1 while the best ones go further.

Why?

Similar to the 36 Questions framework, the deeper levels reveal as much about your company as it does about the customer.

And, like any relationship, you may find that getting the customers you want requires becoming the version of a company they’d choose.

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.