How to Run Skip Level 1:1s 🔀

Why you need them and how to have good ones

Skip level 1:1s are, in my experience, one of the most underrated practices in engineering management. They are often added very late to the arsenal of teams’ processes, while some companies do without them altogether.

Today I will talk about them, and I will do so by experimenting with a style of article that is a bit different than usual.

In fact, I am starting with a story—a real world one—and will use it as an anchor to cover why and how you should have skip level 1:1s on your team.

We will talk about:

• 📔 Matt, Dave, and Jane — our case study.

• 🔍 What are skip level 1:1s — definitions first.

• 🧑‍💻 For reports — goals and benefits for reports.

• 👑 For managers — goals and benefits for managers.

• 👌 How to have good skip level 1:1s — frequency, agenda, how to act on items, and more.

Let’s go!

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📔 Matt, Dave, and Jane

Many years ago, one of my best friends — let’s call him Matt — got his M.Sc in computer science with a focus on machine learning. Right after university, Matt joined a well known local company as a ML Engineer, with the promise he would work on the flagship company's product.

However, he was soon assigned to work on other, unrelated areas. He created simple internal tools, refactored parts of the company website, and hammered bugs in legacy code he had little knowledge of.

After the first few months—where, he thought, he was just onboarding—Matt started inquiring his manager, Dave, about his path. Dave’s answers were kind of unconvincing and Matt couldn’t figure out either when he would start working with ML, or the more general company roadmap.

After more months, he finally asked for a meeting with his manager’s manager — Jane.

Jane was blissfully unaware of the whole situation, while Matt was already stressed and a bit disengaged. Jane seemed to sincerely care about that and said to Matt that he could probably contribute to a ML project that was currently being reworked, starting next quarter.

Eventually, Matt was indeed assigned to some of that project’s tasks, but he still remained swamped with the rest of the internal tooling work, which Dave seemed to care more about.

Over the following months Matt tried to juggle between both lanes of work. To do so he often overworked, while his relationship with Dave degraded considerably.

After a little more than a year since Matt had joined the company, he reached out to Jane again to tell her he was deeply unhappy about his job, his expectations weren’t met, and he couldn’t get along with his manager. He was about to quit.

Jane acted swiftly — after less than a month she moved Matt to a different team, under a different manager. Meanwhile, Matt took a long summer break.

After the break, Matt sat down with his new manager—an upbeat, warm guy—who told him about the great ML work they would do together, starting that day.

Matt smiled, thanked him for the opportunity, but resigned the same day anyway.

Aside from the redacted names, this is a 100% true story.

Let’s review everything that went wrong with Matt’s experience, and let’s see why and how skip level 1:1s are related to this 👇

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🔍 What are skip level 1:1s

Before getting back to Matt’s story, let’s pin down some definitions.

Skip level 1:1s are recurring meetings between an employee and their manager’s manager.

While there is a ton of literature on traditional 1:1s, there isn’t nearly as much on skip levels. In fact, in the real world you encounter different scenarios. Some companies don’t have them at all — like in Matt’s case — while others have them in shapes and forms that vary wildly, e.g. in frequency and structure.

But why should you set them up in the first place? Let’s see what they are useful for, both from the reports and the managers’ angle.