#38 Stop Admiring Leaders for Listening to Customers

The CEO of one of the companies I work with recently did something that, on paper, really shouldn’t be remarkable. Over the course of three months, he made more than 60 contextual interviews with users across Europe. He observed them in action, listened carefully, asked thoughtful questions, and came back with insights that potentially will change the company’s value proposition, positioning, and even product strategy.

What’s most striking to me isn’t the quality of the insights, although they were impressive. It’s the fact that this kind of work is still seen as unusual, even exceptional. Something worth celebrating.

And I get that. It’s rare to see leaders dedicate that kind of time and energy to understanding customers first-hand. But maybe that’s the real problem. Understanding the people we serve shouldn’t be framed as visionary leadership. It should be as normal and expected as knowing how finance or operations work.

When Leadership “Discovers” the Customer

We’ve all heard the stories. The ones where a leader is celebrated for connecting with customers.

Howard Schultz returns to Starbucks and puts on a barista apron. Herb Kelleher joins the Southwest Airlines crew on flights and baggage runs. Walt Disney walks the park like a guest. Ingvar Kamprad visits IKEA stores anonymously to observe customers and talk with staff. Jeff Bezos famously leaves an empty chair in every meeting to represent the customer.

These stories are powerful. They’re human, symbolic, and often told with admiration.

But they also reveal something troubling: that actions as basic as spending time with customers are still considered bold or admirable leadership. When in reality, they should be a normal part of how we make decisions. They should be embedded in how companies operate, not treated as strokes of genius.

The strange thing is, we already have entire professions built around understanding customers. People who are trained to explore behaviour, uncover needs, make sense of messy realities, and translate insights into something actionable. Researchers. Designers. Strategists. Insight leads.

So why are these people rarely present in boardrooms or around executive tables?

Challenging Power

One explanation, as previously mentioned, might be power. When Jeff Bezos leaves a chair empty, it sends a message. But the chair can’t speak back. It can’t challenge assumptions. It can’t say, “That’s not what our users are telling us.”

But someone who works with insight every day can. And that changes things.

In many leadership teams, there’s this unspoken belief that the CEO or founder just has a special instinct for what customers need. When that image becomes central to someone’s role or identity, being challenged by someone with actual expertise can feel uncomfortable.

It can also be uncomfortable to introduce someone who holds you accountable to what is actually true. That’s what good insight work does. It doesn’t just confirm what we hoped was right. It often reveals what we’ve missed.

So yes, maybe this is about power. But there are other explanations worth considering too.

Other Forces

Many executives simply haven’t worked closely with people in insight roles. If you’ve never seen great research change a decision or reframe a problem, it’s easy to underestimate what it can do. In many cases, leaders rely on proxies such as sales calls, CRM dashboards, or anecdotal feedback and believe they already understand the customer. Or they fall back on their own past experience, which is usually too limited and often outdated.

In some organisations, insight sits deep inside product, design, or marketing teams, with little visibility at leadership level. In others, it’s seen as too slow or too vague to be useful when big decisions need to be made fast. Leaders under pressure for short-term results may find it easier to invest in marketing or sales than in developing deeper understanding.

There’s also a cultural element. A compelling story from a founder or a single customer anecdote often carries more weight than a behavioural pattern uncovered through dozens of interviews. Add to that a persistent bias toward numbers over qualitative data, and it’s not hard to see how insight gets devalued or overlooked.

Finally, there’s a talent dimension. Many insight professionals aren’t trained or encouraged to step into strategic roles. They’re seen as experts in delivery, not as partners in direction-setting. That becomes a self-fulfilling cycle.

No More Empty Chairs

We don’t need more symbolism. We don’t need more empty chairs or performative empathy. We need people who actually understand how to understand people, sitting in the rooms where the most important decisions are made.

I’m not saying every company should add a researcher to its board. But if no one in your leadership team is fluent in customer insight, not as an abstract value but as a craft, then you’re likely making expensive decisions in the dark.

There are people who do this work every day. Who sit in users’ homes. Who watch how products are actually used. Who map unmet needs and rethink broken assumptions. Who bring nuance, depth, and relevance to strategy.

That work is not guesswork. It’s not magic. And it’s not optional, at least not if we want to build things that matter.

We don’t ask leaders to guess how finance or operations work. There are clear roles, clear processes, and the right people in the room. So why are we still expecting leaders to guess what customers need?