Leaders need to know customers and front-line workers well, and to deeply understand their reality. But usually, they are safely distant from that experience.
As individuals, a new year invites new intentions. Lose weight, travel, save more money.
Organizations are similar. At any temporal threshold— whether the next quarter or January 1 — we craft new goals. Those goals are typically outcomes, like revenue, new customers or ARR.
The next step is action, because that is our human nature. We love to be doing something — and so we jump over more strategic considerations. Therefore, goals morph into (say) marketing, product or sales projects.
And so, fundamental questions go unasked. Two questions are especially important.
The first, of course, is that of “what is our strategy?”. I’ve written tons about that. For example, here and here.
But the second critical question is ontological—that is, a matter of being.
Who (and how) must I be as a leader to support those goals?
In my last essay I suggested that one critical change that most leaders need to make is to become more comfortable and more effective at saying “no”.
I promised a second suggestion. Here it is:
Spend much more time with your customers and front-line employees.
The Slippery Slope
When Brian Thompson, CEO of United Healthcare, was murdered last year, the response on social media was callous and cruel.
Cold-blooded murder is heinous under every circumstance. Whatever issues anyone has with United, Thompson was a human being, with a family and a life — and his murder should shock and appall all of us.
While the reaction was repugnant, it was not surprising. Most Americans who use their health insurance have problems getting what they need. And when people feel like they are paying a company who then makes their health worse, they become enraged.

https://www.kff.org/health-costs/issue-brief/americans-challenges-with-health-care-costs/
As I watched the saga unfold, I was struck by United’s response. They announced three specific actions:
- Block all comments on social media
- Reinforce Executive Security
- Remove all identifying information from their website.

United Healthcare website.
Notice the lack of links to any information about leadership in this screenshot.
Taking measures to protect life makes sense. But hiding them from the public doesn’t.
It suggests an underlying problem.
The company’s leadership is so far away from its customers and employees that it can’t see beyond its executive suite or shareholders.
Who Are We and What Business Are We In?
If your customers are so enraged by your business that they applaud the murder of your CEO, something has gone terribly wrong.
My guess is that Brian Thompson (like most insurance CEOs) never spoke with a patient facing ongoing pain or even death due to a health insurance denial. Avoiding those conversations makes it easier to take decisions like that. It ensures psychological distance from the worst consequences of Draconian business practices.
When I was watching the public response from United, I was waiting for them to hint at some introspection.
They are ostensibly in the business of health. People love doctors, because they help them get well. But they view insurance companies as their enemies — institutions that obstruct their getting well.
That should provoke introspection. What does it mean to say you are in the healthcare business, if those in need of healthcare see you as an obstacle to it?
Maybe if the C-suite spent time with their customers, they would alter their approach.
Too Easy a Target
Obviously, health insurance is an easy target for the accusation that CEOs are at a remove from their customers. But it happens in every kind of organization — even start-ups.
Once a subordinate team performs sales, supports customers or deals with the fallout from changes to product, policy or process, it’s all too easy for executives to remain aloof, looking at dashboards or courting investors.
More Easy Targets
Beginning in the mid-18th century, French soldiers wore red trousers. The red pantalons became a symbol of French culture.
… the military dress… was part of the identity of ….France itself. It meant bravery, honor ,virility. The coward hides, the hero rises.
When the uniform was first selected, it was important to be able to distinguish allies from enemies on the battlefield. That started to change during the late 19th century, when arms began to kill from a distance. Countries adapted, creating uniforms that would blend into the background and reduce visibility.
As early as 1870, in the lead up to the Franco-Prussian war, a French military doctor named Morache experimented with colors. He concluded that muted colors like black and brown were least visible in battle, while red and white were more apparent. He recommended changing the uniforms. His findings met obstinacy.
Le pantalons rouge were a cultural shibboleth.
Finally, in 1911, vocal opposition to the uniforms grew. General Michel had observed German soldiers and seen how their gray uniforms reduced visibility. He and the troops clamored for change.
But even then, the Minister of War said “Eliminate the red trousers? Never! Le pantalon rouge, c’est la France!”
Finally, after much debate, there was agreement to revise the uniforms in favor of ones that were both more comfortable and less visible.
But the decision came too late.
300,000 French soldiers lost their lives in the just the first few months of World War I.
The government ministers did not understand that war had changed, and that the Napoleonic style of fighting was obsolete.
How could they? They were in Paris, safely away from the front lines.
The Map is Not the Territory
Of course, the French politicians could have tried to learn the soldiers’ experience; just as CEOs of health insurance companies could spend time listening to customer service agents and talking to patients.
But that would demand that they look away from their focal point — the stock price, political landscape, or sales margins.
Talking to customers seems like a waste of time when there are agents to do that.
But the separation between corner office and front-line can cause horrible consequences. There are the deadly ones, like the thousands of French deaths, but there are also basic strategic failures.
In the Trenches
Imagine you’re a new customer success agent in a SaaS startup. A substantial part of your pay depends on upsells, renewals and retention. But soon after onboarding you discover that every call seems to be about technical problems with the data. You try to help clients get better results. But you quickly realize that the problem is the product.
Even as you help customers fix one issue, another emerges. Upselling seems like a pipe dream. You’re just trying to stem the stampede out the door.
The heads of product and revenue are disinterested in this feedback. They are sure that the issue is a combination of user error and your poor technical skills.
It isn’t.
Ultimately, you will fail in the role.
But the company will also fail because clients are jumping ship. They may hire successive new reps expecting them to be better. But the reps are not the problem. The founder and leadership team are busy trying to raise the next round, so they continue to assume customer success performance is to blame — until the damage is so severe that they must confront it.
Often, too late.
If the founder spent time on customer calls, and talking to reps, he would identify a product issue. But instead, she sees it as a performance issue. She is looking at a scorecard, not reality. That scorecard only shows outcomes, not root causes.
Scorecards are merely maps. Maps are very different than the territory they seek to describe. [Click to tweet]
Go to the Trenches
There is a simple corrective. Spend significant time on the front line. Visit with existing customers — especially unhappy ones. Listen to and know your most entry-level employees — those who are harangued by angry customers.
You and I have an opportunity to remove our psychological distance from the worst facts about our lives and businesses. Or we can remain safely ensconced in the safe isolation of being the boss. But the choices yield very different outcomes.
Whether you are a small business owner or a tech founder, knowing and feeling the worst of everything matters. If your reps are telling you that the market does not believe your product is unique, take them seriously and spend time looking through their eyes.
What you hear may offend your sensibilities, but knowing about it and understanding it matters. After all, anyone who feels that way is unlikely to buy. And your own confidence in your product is not enough to generate revenue or a customer base.
Staying psychologically close to customers and employees doesn’t always mean bad news. It may reinforce the choice to add a new feature or unearth a successful framing a new rep is using to close bigger deals.
Yes, it will take time away from something else in the short run. But in the long run, it can save the future of your business — and create the foundation for longevity and growth.
We all deserve longevity and growth