Skip Level Meetings Are About Insight, Not Distrust

How to gain unfiltered perspectives and build trust without undermining your managers

You're leading one or more engineering teams. Maybe you just inherited a new team, like a client I spoke with recently. He struggled with a classic leadership dilemma: "Do I talk directly to the engineers reporting to my new manager, or do I only go through him to signal trust and support?".

It’s tempting to respect the chain of command to avoid stepping on toes. Let your managers do their jobs without getting in the way. You clearly want to empower your managers and don't want to set the example of someone who micromanages or bypasses them.

The problem is that you're flying half-blind if you only talk to your direct reports. You're missing the ground truth. And you're missing great opportunities for leading and inspiring people who don't directly report to you.

I've made that mistake more than I'd like to admit, so I didn't hesitate to suggest my client establish semi-regular skip level 1-to-1s with people in the team they had just inherited.

Skip levels are a powerful tool that, when deployed carefully, can make the overall organization more effective.

Why You Need to Be Doing Skip-Levels

I believe skip level should be part of any leader's standard toolkit as soon as they inherit or establish a team with a layer of management between them and the individual contributors on the ground.

There are many reasons why I believe so. Let's explore them one by one.

1. You get the unfiltered reality. Any competent person equipped with the best intentions can only observe, process, synthesize, and communicate a small portion of the reality they observe. Conscious and unconscious biases are always at work at every step of the process. You'll always get a partial view of reality when you limit your intake to a single source. Talking directly to individual contributors — or other layers of managers — will give you different perspectives on what is happening. It'll still be filtered and processed, but collecting observations from many sources can form a more nuanced and better-informed picture of reality. Establishing truth is one of the most complex human challenges, and I always recommend that leaders watch the classic movie Rashomon¹ for a brilliant and painfully accurate reminder.

2. It helps you see deeper issues before they become trouble. Engineers on the ground often see the patterns first. The painful deployment process everyone complains about. The inter-team friction causing endless debates and bike-shedding. The unreasonable workload that has become a source of sarcastic jokes and fuels frustration in the whole team. Skip levels are your early warning system for systemic issues that your direct report might not consider critical enough to escalate. They might be doing that with the best intentions or deliberately hiding problems from you. Receiving the signals from the team will allow you to address them in frank conversations with the manager. In the best case, you'll calibrate on what's worth escalating or work together to address some of the issues you discovered. In the worst case, you'll realize you need to monitor what the manager is doing due to emerging trust issues.

3. You get a real sense of team health. Engagement surveys are helpful but can't give you the complete picture. Hearing directly from engineers about their motivation, frustrations, and wins is an order of magnitude richer in meaningful signals. Granted, the investment required is also significantly higher, but I argue it's worth every minute if done correctly. In a direct conversation with team members, you can gauge morale, spot potential flight risks, and understand what engages your people far better than relying solely on your manager's assessment. You're not replacing your manager's work. You're complementing it.

4. You build trust and rapport. When a senior leader takes the time to listen to an individual contributor, it sends a powerful message, particularly in organizations promoting the values of transparency, accessibility, and feedback. Taking time away from your supposedly busy agenda for people not directly reporting to you shows that you care about their contribution, well-being, and opinion. They will get to know you better and build the trust they might need in the future. Having formed the rapport makes it more likely they'll proactively escalate situations that require your attention and that you might not be directly seeing. You're not building a network of spies but rather of well-intentioned informants.

5. You identify talent and potential gaps. Skip levels help you calibrate. You can spot high-potential and high-performing individuals. You can discover and encourage career aspirations that your manager might not have surfaced. You can get a sense of whether someone might struggle to keep up with their responsibilities and whether that might be due to a lack of competencies, support from their manager, or both. These are all helpful data points to improve your ability to develop, retain, and reward talent in your organization.

Okay, But What About the Risk of Undermining My Manager?

In my experience, this is the #1 reason leaders shy away from skip levels. And it's a valid concern. You should always support and empower people reporting to you. If done poorly, you can dramatically disempower your managers and create chaos.

The solution isn't avoidance; it's doing them correctly.

Let's start with something foundational: you have the right to speak with absolutely anyone in your organization, regardless of who they report to. As a leader, you have the duty to do whatever it's in your power to ensure the organization as a whole is set up for success.

That, to me, has two straightforward implications.

First, if someone argues you don't have the right to go and talk with someone in their team, that's their problem. They might lack confidence or have something to hide. Don't let it get in the way of exercising something genuinely at the intersection of your rights and duties. At the same time, work with them to understand where the problem is coming from and help them overcome it. Just don't let it stop you from establishing those conversations.

Secondly, talking to someone should not be implicitly interpreted as stealing their attention or changing their priorities. You must be careful not to fall into the temptation of sidestepping your direct reports by directly instructing their people on what they should do, how, and when. That would be a disaster that would disempower your managers and undermine your credibility with the whole organization.

Think about how skip levels can contribute to implementing an approach of inspected trust² across your organization. You should probably start by inviting your manager to have skip levels with your direct reports.

That said, here are some simple rules I recommend you follow to maximize positive impact and minimize side effects.

• Rule #1: Talk to Your Manager First. Be transparent. Tell them why you're doing skip-levels. Frame it as support for them and the team. "I want to get a broader perspective to see how I can best support you," or "This helps me understand the ground-level reality of our challenges." Make sure they know you're doing this regularly across your organization and that you're not checking up on them specifically. Address their concerns or pushbacks before moving forward.

• Rule #2: Share Back Themes. After your rounds of skip levels, synthesize the themes you heard (process issues, morale trends, common suggestions) and share them with the manager. Bring them up in your 1-to-1s, invite them to provide their perspective, and jointly work on diagnosing and solving the underlying issues. This will help your manager be more effective, and they'll see the value in your support.

• Rule #3: Set Clear Expectations. This is probably the most crucial rule to avoid undesired side effects. Tell the employee the purpose isn't performance management or daily task direction. Remind them that it's their manager's job and that you don't intend to interfere. It’s about their experience, the bigger picture, challenges, and careers. Clarify confidentiality: You'll keep personal feedback private, but systemic issues might need to be shared. Invite them to use the space to ask you any questions.

• Rule #4: Don't Solve Their Manager's Problems. Resist the urge to jump in and fix things that fall under the direct manager's scope. You'll be tempted to do that until you build a strong discipline around it. Instead, coach the employee on how to approach their manager or offer to help facilitate a conversation with the two of them. Redirect operational stuff back to the proper channel unless it's feedback about the manager or a serious issue.

• Rule #5: Focus High-Level. Ask about strategy, culture, development, process, and roadblocks. Avoid getting bogged down in tactical details around recent deliveries or technical choices. Ask questions that will help them surface underlying issues, such as "Where do you spend most of your time?" or "What's one thing you wish leadership understood better about the work your team is doing?" etc. Occasionally, use powerful questions such as "If you had the power to change one thing in this organization, what would that be?". Don't take the answers too literally, but watch out for surprising ones or common themes emerging across different people.

Inherited a New Team? Start skip-levels early

For my client inheriting that new team? Skip-levels are non-negotiable.

It's the fastest way to get to know the full context, mapping out the team's different people, talents, and personalities. They help you quickly get a sense of the team's health, whether there are major interpersonal issues among its members or tensions and frustrations with the team's manager.

As the team's manager is likely also newly reporting to you, spend the required time to build that rapport, explaining how you usually work with your teams and why you believe skip levels are an essential part of it. But don't fall for the temptation of delaying the moment you start practicing them, as you'd like to let things settle first.

Instead, get started quickly and respectfully.

Schedule those meetings.

Talk to your team's team.

Be brave, respectful, and delicate enough to seek the ground truth.

You, your managers, and your entire organization will be better off thanks to your taking action.

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1. Rashomon is one of the masterpieces of the Japanese director Akira Kurosawa. It tells the story of a crime and the challenging attempts to establish the truth of the events. It is a classic movie everyone should watch at least once in their life. Find out more on the movie's Wikipedia page.

2. Will Larson often discusses Trust per se not being a management technique and advocates for a sort of trust and verification he calls “inspected trust.” Read more about it in this article.