The Secret to Skip-level One-on-ones
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The Secret to Skip-level One-on-ones<br>How to Build a Great Engineering Culture: Article 5
Mark Grebler<br>May 28, 2026
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So you’ve been working hard and instilled the engineering culture that you want. From your perspective, everything is going smoothly. All of a sudden, a person from one of your teams leaves. A month later, another person from the same team leaves. You start to investigate and realise, too late, that the team is in shambles and things are seriously wrong. But all the while, the signals you were getting from your direct report leading the team, and the team metrics were that everything was ok, and just needed some minor improvements. It turns out that the leader was managing up (you) well, but was a destructive leader from the perspective of his team.<br>How did it get this way without your knowledge, and what could you have done to prevent it? One answer is to have skip-level one-on-ones and know how to get the right information from them. Regular one-on-ones with your direct reports are a well-accepted way to coach and guide your teams, but one of the key things (that is well-known, but not actually well adopted) to building a great culture is having regular one-on-ones with the people reporting to your direct reports (your skip-levels). But skip-level one-on-ones that just go through the motions are not enough. You have to probe deeply in them, often by actually questioning potential issues without waiting for your skip-levels to proactively raise them. While the example above is an extreme case, the same structural gap exists in subtler forms, and skip-level one-on-ones are designed to catch both.<br>Thanks for reading Mark Grebler’s Substack! Subscribe for free to receive new posts and support my work.
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“I sometimes feel like I’m the only Engineering Manager that gives a s**t,” one of my Engineering Managers (EM) said to me.<br>“What do you mean?” I asked.<br>What followed was an in-depth discussion, which led to the point that the EM wasn’t happy with the performance of one of the other EMs (not all the other EMs, which his initial statement suggested). He thought that the other EM hadn’t taken enough ownership of the team’s delivery and that the team was struggling. This was a valuable discussion that helped me understand the EM’s concerns about the other EM, which I then needed to validate. I was fortunate that the EM was willing to open up about his concerns, but most of the time, your reports will not be so willing to raise these sorts of issues (and even less likely with your skip-level reports).<br>I then went to my skip-level reports (the ones that reported into the potentially problematic EM) to try to understand the situation deeper. Asking some high-level questions about how the team was going yielded a few concerns about developer experience (DevEx), but not any information about the EM themself. It wasn’t until I said something like “I’m a bit worried that your EM hasn’t supported the team enough to uplift their DevEx, which has contributed to the team’s problems”. Once I said that, the skip-levels opened up, and I understood deeply what the problems were, which allowed me to support the EM to resolve the issues.<br>Probing deeply in one-on-ones: How to actually get useful information.
Skip-level one-on-ones can be a valuable source of information for you, but in order to effectively get information from them, there are a couple of ingredients needed. Firstly, the person needs to trust you enough to be willing to open up and provide valuable information (otherwise, you run the risk of getting superficial information that is unlikely to help), and the other is that you need to be able to probe effectively enough to ensure you are eliciting valuable information. We won’t delve into building up trust in this article beyond that it takes time and requires you to be authentic, show vulnerability and listen deeply, but we will look a bit more at how to probe. When asking questions initially, start broad (like “what’s on your mind”), and then escalate if that doesn’t yield anything.<br>If you have a suspicion that an issue exists (cultural, people-related or something else), then there is a technique that can help gain information that may not be forthcoming. If, after starting broadly and then probing, they still do not give any information about your concern, it may be because they do not want to throw their colleagues or boss under the bus, or because of the power differential between you and your skip-level. As in, they may not want to be the person in the team who exposes a concern. This can be highly problematic. I’ve had times when almost everyone in a team has the same concern, but nobody is willing to raise it because of that fear. For example, everyone in the team has a concern about one particular team member, but to each individual, it doesn’t feel like a huge concern. But when everyone has...