Customer Support

During a leadership meeting at Amazon, the head of customer service reported that average customer wait times were under sixty seconds, despite growing complaints of long hold times.

Jeff Bezos decided to test it.

He picked up the phone, dialed Amazon’s 1-800 customer service number on speaker, and waited with the entire executive team.

Ten minutes later, no one had answered.

What leadership thought was true differed from what customers actually experienced.

The military’s term for the disconnect between what leaders believe and what’s real is known as ground truth.

Ground truth refers to the on-the-ground realities that differ from the assumptions, filtered information, and flawed reporting that often guide decisions from higher command. It erodes wherever feedback loops are long, complex, or broken.

Reality gets lost in translation.

Business is no different.

Lack of ground truth leads to poor or ill-timed decisions, especially as teams grow and layers multiply.

I learned this lesson the hard way in my first startup. One of my partners was brilliant in his domain but a terrible people leader. We first saw the cracks when one of our best team members quit. When we asked why, he said he could no longer work with my partner and backed it up with clear, objective examples that caught the rest of us off guard.

I’d like to say we learned our lesson then, but we didn’t. It took almost losing a few more good people before we finally accepted the ground truth we’d been avoiding.

In my own ventures and in advising others, I’ve seen the same pattern repeat: the absence of ground truth is the root of many poor or untimely decisions.

So how do you minimize the risk?

Here are five practices I use to try and stay grounded and connected to reality.

How To Stay Grounded

Mind The Mixed Signals

When Jeff Bezos retold the story of calling Amazon’s own customer service line during that meeting, he added a simple but profound insight:

“When the data and the anecdotes disagree, the anecdote is usually right. Not because the data is bad, but because you’re measuring the wrong thing.”

Not that the data is always wrong but conflicting signals can be a warning.

As the old saying goes, “What gets measured gets managed”.

What gets managed should matter.

Business can fall into the trap of optimizing for what’s easy to measure instead of what’s actually true.

That’s why I often question how closely important metrics track reality AND whether or not the reality they are measuring actually matters.

Do The Rounds

As a business grows, every founder faces a tradeoff:

continue working in the business and risk micromanaging and limiting growth

or to work on the business and risk losing touch with reality.

You can delegate almost everything but awareness.

The more layers you add, the easier it becomes for filtered information to replace firsthand insight.

That’s why it’s critical to stay intentionally connected to the front lines without trying to run them.

To gauge my potential lack of ground truth I ask myself the following:

• How many contacts have I had with customers?

• How many relationships do I have with employees on the front lines (sales, customer service, etc.) or at least two levels removed from me?

• How often do I ask open questions about any area of the business? Did I proceed asking the Five Whys?

Your job isn’t to control every detail but to stay close enough to the work to sense when something’s off before it shows up in the numbers.

Great leaders must zoom out to build the proverbial factory but still make time to walk the floor.

Stay Flat

As organizations grow, so does the distance between leaders and employees, strategy and execution, assumptions and reality.

Every new layer added between you and the front lines becomes another potential distortion of truth.

Staying flat doesn’t mean avoiding structure; it means minimizing layers between information and action.

It’s about creating direct lines of communication, where truth can travel quickly and unfiltered.

The companies I’ve worked with who do it best:

• Keep hierarchies light - avoid silos as much as possible

• Direct communication - encourage team members to surface issues directly

• Reward open communicators - especially those who speak up early, not those who protect appearances

• Model open dialogue - both in real life and in communication forums (Slack, Teams, etc.)

Receive Bad News Easily

I’ve made it a personal goal in both business and in life for people to want to tell me bad news.

I want to be the first person people come to with problems. Why?

When information flows freely, problems surface early.

When people fear my reaction, the truth hides until it’s too late.

It’s not always easy but to receive bad news easily I practice the following:

• Mind the response gap - If I can sit in the space Covey mentions for even a few seconds, I can manage my response. My goal is not to be inauthentic, but to choose instead of being controlled by impulsive reactions.

• Encourage open dialogue - I don’t quell arguments, debates or other difficult conversations.

• Protect truth tellers - I never punish anyone for telling the truth.

Allow For Uncertainty

Deny uncertainty, and you distort reality.

Ground truth isn’t static. It changes as markets move, people evolve, and new information emerges.

There are direct and subtle ways I create systems and cultures that are designed for uncertainty:

• Experimental frame - I frame projects and initiatives as experiments. Experiments are to make discoveries and test hypothesis, not to predict the future.

• Short feedback loops - I like to keep feedback loops as short as possible so projects can adjust quickly, especially in the beginning

• Reward adaptability - I praise people who change their mind in light of new evidence and maintain a growth mindset around failure

When you normalize uncertainty, you don’t lose control but gain adaptability.

The Next Step

Over the years, I’ve focused less on chasing ground truth and more on removing the conditions that obscure it.

The layers, assumptions, and filters that creep in as businesses grow are what distort reality the most.

I’ve learned that clarity often isn’t found through more data or better dashboards but through staying close to the work, asking better questions, and creating an environment where truth can surface quickly.

Because in the end, the goal isn’t to have perfect information; it’s to see things as they really are and adjust as they change.

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.