How to Talk to Your Skip Manager Without Going Around Your Manager

The default assumptions that keep people silent, what skip managers actually want, and how to use skip-level time to unblock work and grow

The first time I realized how much people underuse their skip manager, it was during a bad month.

We were in the middle of a release that had a regulatory deadline attached to it. The kind where “a week late” isn’t a joke, and “we’ll catch it next sprint” gets you a meeting with Legal. One of our teams was quietly stuck. Not blocked in a dramatic way. No incident. No escalation. Just slow, grinding friction: unclear priorities, a dependency that kept slipping, a product decision that kept changing shape. Everyone looked busy. Nothing moved.

I found out by accident.

I was the manager’s manager in this case. I dropped into a review meeting because someone was out, and I could feel it in the first five minutes. The engineers were polite, careful, and tired. The manager was doing that thing good managers do when they’re trying to protect the team and keep leadership calm at the same time. Everybody was “fine.”

After the meeting, one of the staff engineers caught me in the hallway and said something like, “I didn’t want to go around my manager, but… we’re not going to make it.”

That sentence shows up in some form every few months in most organizations. And it’s usually followed by a story where everyone was trying to do the right thing and still left a lot of value on the table.

Skip relationships are one of the easiest ways to speed up trust, clarity, and career growth inside a company. They’re also one of the most misunderstood.

A lot of people treat their skip manager like an emergency exit: break glass only when things are on fire. And when the fire finally shows up, the relationship isn’t there. The context isn’t there. The trust isn’t there. So the conversation gets weird fast. It becomes an investigation, or a complaint session, or a vague “just wanted to make you aware.” Nobody leaves feeling good.

What I’ve learned, on both sides of the table, is that the best skip relationships don’t feel like escalation. They feel like alignment.

The missed opportunity starts with a set of default assumptions people carry, usually without saying them out loud.

One assumption is that reaching out to your skip manager is disloyal. That it signals your direct manager isn’t doing their job. That you’re trying to play politics. I’ve watched strong engineers avoid skip contact for a year because they didn’t want to look like they were “going around” someone. Then they hit a wall, and the first skip conversation happens under stress. By then, it’s hard to avoid the vibe of escalation, even if that wasn’t the intent.

Another assumption is that skip managers are too busy for you. This one is almost always wrong. Yes, their calendars are a mess. But if you’re a solid IC or a new manager in their org, you are part of what they’re accountable for. Your output, your retention risk, your growth, your ability to execute under constraints. When skip managers ignore those signals, it catches up later as attrition, missed delivery, quality problems, or “mysterious” morale dips. A fifteen-minute conversation today is usually cheaper than the cleanup six months from now.

Then there’s the belief that skip 1:1s are a trap. People assume the skip manager is collecting intel. That anything you say will be used against you. That candor will get you labeled as “difficult.” Sometimes that fear comes from real organizational scars. Sometimes it’s just anxiety filling in the blanks. Either way, it pushes people into a careful, bland, low-information conversation that helps nobody. The skip manager walks away thinking everything is fine. The report walks away thinking the skip manager doesn’t care. And the gap stays.

There’s also a quieter assumption I see with ambitious people: “My skip manager will notice my work if I just keep delivering.” I used to believe this. It’s comforting because it keeps you in control. Put your head down, ship, and recognition will find you.

In practice, skip managers don’t have enough bandwidth to infer your intent from your tickets in a board. They see outcomes, and they see patterns, but they don’t automatically know what you want more of, what you’re trying to learn, what kind of scope you’re ready for, or what support would remove friction. If you don’t tell them, they guess. And their guess is often shaped by whoever is loudest in the room, not whoever is most ready.

All of those assumptions lead to the same behavior: people keep skip managers at arm’s length, then wonder why decisions feel random, promotions feel opaque, and priorities shift without warning.

Now let me flip it around, because I’ve been the skip manager too, and I’ve had plenty of skip reports who didn’t know what I was hoping for.

When I set up skip 1:1s, I wasn’t looking for gossip. I wasn’t looking for a shadow performance review. I wasn’t trying to catch anyone contradicting their manager.

I wanted signal.

In a healthy org, the information that reaches a skip manager is filtered. That filtering is not malicious. It’s normal. Every layer summarizes. Every manager protects their show. Every leader tries to keep noise down and confidence up. That’s part of the job.

But it means I’m always at risk of being the last person to know something that matters. The work is slipping. The architecture is brittle. The team is burning out. The roadmap is fantasy. A partner team is quietly refusing to cooperate. The quality bar is eroding because deadlines are fixed and scope isn’t.

Direct managers can surface those things, and good ones do. But even good managers sometimes wait too long, because they’re trying to solve it first. Or because they don’t want to look like they can’t handle it. Or because they’re new and still learning which problems are “normal hard” and which ones need help.

A skip relationship gives you a second sensor. Not to bypass the manager, but to make the system less fragile.

When I met with skip reports, I was open to a few kinds of conversations.

I wanted to understand what work felt like on the ground. Not the status update, but the friction. Where are decisions getting stuck? What’s causing rework? Where are we burning time because ownership is unclear? If you’re an IC, you see process debt before any dashboard does. If you’re a manager, you feel misalignment before it becomes an escalation.

I also wanted to know what you cared about and what you wanted next. People often under-share here. They’ll say “I want to grow” or “I’m open to more responsibility,” which is fine, but it doesn’t give me anything to work with. The useful version is more specific: “I want to lead a cross-team effort,” or “I want to move toward staff-level scope,” or “I’m trying to get better at influencing product decisions,” or “I’m considering management but I don’t know what I’m signing up for.” Those are conversations a skip manager can actually support.

I was also open to hearing when your manager was doing something that was unintentionally hurting you. Not as an accusation, but as a reality check. Managers, especially in regulated environments, often over-rotate on control when risk is high. They get tight on reviews, tight on approvals, tight on who can talk to whom. Sometimes that’s needed. Sometimes it’s just fear disguised as rigor. Skip managers can help coach that back into balance, but only if they know it’s happening.

And I wanted you to tell me when you saw a better way to run part of the org. Not “we should change everything,” but a practical improvement rooted in the work. A recurring meeting that produces no decisions. A handoff that creates delays every time. A platform dependency that needs a clear owner. A policy that made sense two years ago and now mostly causes workarounds. When someone brought that kind of observation with concrete examples, I took it seriously.

Here’s what surprised me early in my career: skip reports often assumed I would react defensively to that input. In reality, I usually felt grateful. Because it’s rare to get clean signal, and it’s even rarer to get it from someone who is close to the work and also thoughtful about the business constraints.

Of course, not every skip manager is good at this. Some are insecure. Some don’t build trust. Some treat skip 1:1s like a complaint hotline and then punish the manager indirectly. People aren’t imagining those risks. They happen.

So the practical question becomes: how do you work with a skip manager in a way that builds value and keeps relationships clean?

Start by being clear in your own head about your intent. If your intent is to “win an argument” against your manager, that energy shows up. It comes out as sarcasm, loaded framing, selective facts. Skip managers can smell it, and it forces them into referee mode. Nobody wins there.

If your intent is to help the team win, the conversation sounds different. You bring facts. You name trade-offs. You acknowledge what you might be missing. You explain how the issue is affecting delivery, quality, risk, or morale. And you ask for help in removing a constraint, not in “fixing your manager.”

I used to coach people to think in terms of: “What decision, clarity, or connection would change the outcome?” That keeps the conversation grounded.

A strong skip conversation also respects the manager relationship instead of pretending it doesn’t exist. If you’re raising a concern that your manager doesn’t know about, you should have a good reason. Sometimes the reason is valid: you tried, it didn’t land, and the impact is serious. Sometimes it’s because you’re uncomfortable with conflict. That’s human, but it’s also a growth edge. Skip managers tend to respond well when you’re honest about that: “I should be able to have this conversation with my manager, but I’m not doing it well yet. I’d like your advice.”

When someone said that to me, I didn’t think less of them. I thought, “Okay, this person is coachable, and they’re trying to act like an adult.”

Another useful pattern is to make the conversation about the system before you make it about people. “We keep changing scope late and it’s creating rework” lands differently than “Product is a mess.” “We don’t have a clear owner for this dependency” lands differently than “That other team is useless.” Same underlying pain, different signal quality.

And if you want a skip manager to invest in you, bring something real. A decision you’re trying to influence. A cross-team issue you’re stuck on. A career move you’re considering. A risk you see with evidence. A request for feedback on how you’re showing up. You don’t need to over-prepare, but you do need to show that you’re not there to vent.

On my side, as a skip manager, I also learned to set expectations explicitly because people don’t know what the “rules” are. When I didn’t say anything, they filled the silence with the assumptions above. So I started telling skip reports, early and plainly, what I was open to: talking about priorities, career growth, friction in how we work, and concerns that might become delivery or risk issues. I also said what I wouldn’t do: I wouldn’t use the conversation to blindside their manager, and I wouldn’t treat it like a secret channel. If something needed action, I’d usually say, “How do you want to handle this with your manager?” and we’d decide together.

That last part matters. People worry that any skip conversation will automatically become a confrontation between leaders. It doesn’t have to. Most of the time, the right move is to help the report get more effective with their direct manager, not to replace that relationship.

The staff engineer I mentioned earlier? Once we talked, it turned out the team wasn’t blocked by incompetence. They were blocked by a missing decision at a higher level and a dependency that needed a clear escalation path. Their manager was trying to solve it quietly. The engineer was trying to be respectful. Both were acting with good intent. The gap was that nobody had built a working channel with the skip manager before the pressure peaked.

We fixed it quickly once it was visible. We made a call on scope, got the dependency team aligned, and adjusted the plan so the regulatory deadline was protected without burning the team down. The engineer didn’t “go around” anyone. They gave the org a signal it needed earlier.

What I’d tell my past self now is simple: skip relationships are part of how execution works at scale. They’re not politics. They’re not therapy. They’re a way to reduce blind spots and speed up alignment.

If you haven’t talked to your skip manager in a while, you don’t need a big reason to start. A short note that says you’d value fifteen minutes to talk about how the quarter is going, what you’re working on, and what you’re aiming for next is usually enough. Then show up with one or two real topics and the intent to help the org win.

Do that a few times a year, and you’ll notice something shifts. Decisions feel less mysterious. Your work has a clearer line to the bigger picture. And when the hard moment comes—and it always does—you won’t be trying to build trust in the same conversation where you need help.