Product Management IRL

Product Management IRL

Backstories

Skip-Level Without a Safety Net - Follow Up Story

Delivering updates that earn leadership confidence

Amy Mitchell's avatar
Amy Mitchell
Nov 21, 2025
∙ Paid

What happened after writing a recent Product Management IRL article? These insights are exclusive to premium subscribers of Product Management IRL.

This week’s backstory is about doing skip-level presentations as a product manager:

Skip-Level Without a Safety Net

Skip-Level Without a Safety Net

Amy Mitchell
·
September 16, 2025
Read full story

What Prompted This Article?

One of the side effects of flattening organizations is senior leaders have so many direct reports that they have limited time with the people doing the work. A new thing in my company and in others is “office hours”.

Office hours are a new, low-pressure way for product managers and others to get access to their senior leaders. Sometimes this is called a skip-level, where you have a 1 on 1 meeting with your boss’s boss.

Office hours are less formal than a 1 on 1 skip-level meeting. They are scheduled with more people, so more of the organization can contribute to the decisions in the office hours session.

While the new office hours are less formal, no one is fooled into thinking less preparation is required.

I wrote this article after my boss encouraged me to present to my skip-level boss’s office hours. I usually don’t shy away from presenting my work to senior leaders. But in this case, many warning bells went off.

My boss nudged further to say others at my level present frequently.

I wrote about my new way to prepare for the skip-level meeting. Below is the sweet spot I’m aiming for on the next presentation:

sweet spot of preparation and quality

Here is a short video on the steps to prepare:

What Happened After This Article?

User's avatar

Continue reading this post for free, courtesy of Amy Mitchell.

Or purchase a paid subscription.
© 2026 Amy Mitchell · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture