At some point in your career, you will realize that your direct manager is not the only person who matters for your trajectory. Their manager - your skip-level - often has significant influence over promotions, team assignments, and how you are perceived at a level you cannot see from where you sit.

The engineers who move fastest in large organizations usually have genuine relationships with people two levels above them. The question is how to build those without making your direct manager feel undermined or making yourself look like you are playing politics.

Why This Feels Risky

The concern is valid: going around your manager can damage the relationship that matters most in your day-to-day work. If your direct manager finds out you are meeting with their boss separately, it can create distrust.

The answer is not to avoid the skip-level relationship. It is to build it transparently, with your manager in the loop.

The Right Context for a Skip-Level Request

The most natural contexts for requesting a skip-level 1:1:

You are newer to the team. Many skip-level managers expect to meet new team members in their first 30-60 days. If yours has not scheduled something, asking is not unusual - it is showing initiative.

You are in the middle of career planning. “I’m thinking through my career development and would value 20 minutes of your perspective” is a legitimate and common ask. It positions the meeting as a learning opportunity, not a complaint session.

You have visibility on something cross-functional. If you are leading something that has organizational impact beyond your team, connecting with your skip-level about it is natural and expected.

They have expertise you want to learn from. “I’ve been reading about [topic they care about] and would love 20 minutes to ask you a few questions” is a genuine ask that most senior leaders respond positively to.

How to Ask

The key: loop your manager in first.

“I’d like to get some time with [skip-level] to get their perspective on my career development. Is that something you’d support? I wanted to make sure you’re in the loop before I reach out.”

This does two things: it signals that you are transparent, and it gives your manager the chance to help set up the meeting (which is often faster than a cold outreach anyway).

If your manager responds positively, ask them to either facilitate an introduction or confirm it is fine for you to reach out directly. Then reach out:

“Hi [name] - [your manager] mentioned it would be valuable for me to get some time with you. I’d love 20-30 minutes to get your perspective on [specific topic]. Would you have availability in the next few weeks?”

Short, specific, easy to say yes to.

The Meeting Itself

Most engineers approach skip-level meetings as a performance. They want to impress. They prepare too much polished content and not enough genuine questions.

The skip-level meeting works best as a genuine conversation with a senior person whose perspective you value. Come with 3-4 real questions:

  • “What do you see as the most important thing the team needs to get right in the next 6 months?”
  • “What does someone operating at [next level] look like from your perspective? What behaviors are you watching for?”
  • “Is there anything you’d want to know that you feel like you don’t have good visibility on from my team?”
  • “What’s the most common mistake you see engineers make at my career stage?”

These questions invite substantive answers and position you as someone who thinks about the organization, not just their own work.

What Not to Do

Complain about your direct manager. This is the fastest way to destroy trust simultaneously in two directions. If you have a genuine issue with your manager, there are better paths.

Use the meeting to advocate for your promotion. It feels opportunistic and puts the skip-level in an awkward position. This is your manager’s job, not theirs.

Try to make a strong impression through polished presentations. This is a conversation, not a performance review. Be natural.

Treat it as a one-off. The value is in a relationship over time, not a single interaction. After the meeting, follow up with a brief thank you note and something concrete: “I’ve been thinking about what you said about [X] - it changed how I’m thinking about [Y].”

Building the Relationship Over Time

A skip-level 1:1 every 3-4 months is the right frequency for most engineers who are not directly reporting to them. Too often feels like you are bypassing your manager. Too infrequent means the relationship never develops.

Between formal meetings, small interactions maintain the relationship: a substantive comment on something they shared in all-hands, a brief Slack message when something they worked on has impact on you, or sharing a relevant article with a specific note about why you thought of them.

These are genuine, not performative. The line between the two is whether you are sharing because you actually think they would find it useful.

The Transparency Principle

Every interaction with your skip-level should be something you would be comfortable discussing with your direct manager. Not because you have to tell them everything, but because if you would not, that is a signal the interaction has crossed into uncomfortable territory.

The managers who are most supportive of their reports building skip-level relationships are the ones whose reports are transparent about it. The ones who feel circumvented are usually right that something felt off about the approach.

Bottom Line

A skip-level relationship is not political maneuvering - it is a normal part of being effective in an organization. Build it transparently with your manager’s knowledge, approach the meetings with genuine curiosity rather than performance, and maintain it over time through small consistent interactions. The engineers who have good skip-level relationships almost universally got them by being direct about wanting them, not by engineering accidental encounters or working around their managers.