Course contents

Four modules. One question bank. A repeatable way to run these meetings.

Each module includes short video lessons, a downloadable worksheet, and a practice scenario. Together they take you from understanding why people stay quiet to closing the loop after you've acted on what you heard.

Module 01

Reading the Room Behind the Reporting Line

This module starts with a simple question: why do people tell a skip-level things they'd never say to their own manager? The answer isn't usually about trust in the individual manager. It's about risk, hierarchy, and how information tends to move upward in most organizations.

You'll work through the common reasons employees filter feedback, including fear of being seen as difficult, uncertainty about whether anything will change, and simple politeness that smooths over real complaints. Understanding these patterns changes how you interpret silence in your own meetings.

Why psychological distance from a manager can loosen tongues, and why it can also tighten them
Reading body language and pacing cues that suggest more is being held back
Setting a tone in the first two minutes that lowers the stakes of speaking honestly
A short worksheet for mapping who on your team is least likely to speak up, and why

Module 02

Asking Questions That Open the Door

Most skip-level meetings fail at the question stage, not the listening stage. "How's everything going?" invites a polite, forgettable answer. This module works through the mechanics of questions that invite something more specific without feeling like an interrogation.

You'll look at the difference between closed and open framing, why sequencing matters more than any single clever question, and how to follow up on a vague answer without making someone feel cornered. There's also a section on reading when to let silence sit instead of filling it.

The difference between "surface" questions and "pattern" questions
How to follow up on a vague answer with a second, gentler question
When to name what you're noticing instead of asking another question
Practice scenarios based on common deflections, like "everything's fine, really"

Module 03

Meeting With Managers in Mind, Not Around Them

This is the module directors tend to skip and shouldn't. Skip-level meetings can quietly damage a middle manager's authority if they're handled carelessly, even when the director's intentions are good. This module works through how to prevent that.

Topics include how to talk to your managers before you start doing skip-levels regularly, what to do when an employee criticizes their manager by name, and how to route feedback back through the manager so they're strengthened by the process rather than blindsided by it.

Framing skip-levels to managers so they don't feel like a performance review of them
A short script for redirecting personal criticism into something constructive
Deciding what stays confidential and what needs to reach the manager, and how
Warning signs that a skip-level habit is becoming a shadow reporting channel

Module 04

From Anecdote to Pattern to Action

One comment about a broken process is an anecdote. Five comments across three teams, said in different words, are a pattern. This module is about the discipline of tracking what you hear across meetings so you can tell the difference, and then doing something with it.

You'll also cover closing the loop: how to summarize themes without exposing who said what, how to decide what's realistic to act on this quarter, and how to communicate back in a way specific enough that people recognize their own input in the result.

A simple template for logging themes across meetings over time
Deciding what's an isolated frustration versus a structural issue
Writing a closing-the-loop update that feels specific, not generic
Handling the case where nothing can realistically change right now

Included resource

Inside the question bank

The bank isn't a script to read from. It's a reference organized by theme, so you can pull two or three relevant questions before any given meeting instead of starting from a blank page.

Workload and pacing

"Walk me through what a hard week looks like for you." "What's the first thing that gets dropped when things get busy?"

Growth and recognition

"When did you last feel genuinely proud of something you finished here?" "What skill are you building that nobody's asked about?"

The manager relationship

"What does your manager do that you wish happened more often?" "Is there anything you've decided isn't worth bringing to them?"

Process friction

"What's a step in your work that everyone quietly works around?" "If you could delete one recurring task, what would it be?"

Team dynamics

"Who on the team do people go to when something's actually wrong?" "What's changed about the team's mood in the last few months?"

A whiteboard covered with handwritten notes and arrows mapping recurring feedback themes

Each question entry in the bank includes a short note on why it tends to work, and a common deflection you might hear back, along with a gentle way to follow up.

Format and pacing

Self-paced

No fixed schedule. Work through modules in the order that matches your own calendar and upcoming meetings.

Short lessons

Each lesson runs long enough to cover the idea properly and short enough to fit between meetings.

Practical worksheets

Every module includes a worksheet meant to be used before or after a real skip-level, not filed away.

Reusable reference

The question bank is designed to be revisited repeatedly rather than read once and set aside.