The Power of the “Undercover (ish) Boss”
- Jun 17, 2025
- 2 min read
There was a show that ran for 12 years on TV called “Undercover Boss.” I’m sure almost everyone has heard of it. I loved the show not only for its pure entertainment value, but also for reinforcing some of the most critical skills needed at the mid to senior leadership level.
These leadership skills centered on listening, but even more important was the concept of going deep into the organization to seek out feedback. In most if not all shows I saw, this feedback unearthed new insights to the leader regarding what was working and what was not.
Logic would imply this happened because the CEO or senior leader had a bad management team that was giving him or her poor or incomplete information. While that could certainly be true, I think the bigger issue was that these businesses didn’t have a robust “skip-level” feedback system. While you could argue that this is the job of the management team, this additional skip-level feedback loop is critical for someone that manages other people leaders. But why?
To answer that, think about it from the other side for a moment. We’ve been taught that when managing up to our boss, we should only share what is needed and keep it simple. This is sound advice, no issues here. But this practice also has an unintentional consequence. For every layer of management, a leader is getting roughly half the story at twice the volume. Image what happens when there is more than one layer of management. It’s like the old game of telephone where the starting message and emphasis gets very distorted when passed from person to person.
Again, the answer to solving this dilemma isn’t to stop distilling data and being concise when sharing information up the org chart. That is critically valuable. It’s also not about eliminating all management layers, although removing unneeded layers is many times needed and will certainly help. The answer? Supplement your management feedback with skip-levels on a regular basis.
A skip-level is just talking to an individual or group of employees that report to another management layer below you. The idea is to do this regularly at all levels, even (and especially) the front-line employees of the business. Here’s what happens when you do:
You see how the business really operates—warts and all.
You understand your managers better: their filters, judgment, and coaching habits.
You get a clearer sense of what’s missing, and why.
Your managers get better. Regular skip-levels create accountability.
And most importantly—people feel heard. Which builds culture, morale, and trust.
A tip: It’s easy to do this when you’re traveling—less so at HQ. Be intentional. Put time on the calendar. Make it a discipline.
Funny enough, when consultants come in, this is usually where they start. They talk to employees, surface insights, and bring back gold. And often, the employees say, “We’ve been saying this for months—nobody asked.”
So don’t wait for a consultant to uncover what you can find yourself. Just ask. Just listen. No disguise required.
