Skip-level meetings — conversations with the person two levels above you — are rare, relatively high-stakes, and full of potential. Most people waste them by being either too passive (treating it as an update meeting) or too strategic (trying to use it to advance an agenda). The most effective skip-level meetings are genuine, specific, and well-prepared.

Understand the Purpose Before You Walk In

Skip-level meetings exist for different reasons in different organizations. Sometimes they are structured listening sessions the senior leader does routinely. Sometimes they are sparked by a specific project, transition, or concern. Sometimes you have requested it yourself.

Knowing the purpose shapes your preparation. If it is routine, you can come with questions and genuine conversation. If it is sparked by something specific, you need to have thought through that thing carefully.

If you are unsure of the purpose, ask directly before the meeting: “I want to make sure I come prepared — can you help me understand what you are hoping to get from our conversation?”

Know What You Want From the Conversation

The biggest mistake in skip-level meetings is having no ask and no agenda. Senior people’s time is limited — they respect people who use time well, and they remember people who clearly knew why they were there.

Before the meeting, decide: what are the one or two things I most want from this conversation? It might be:

• A clearer understanding of organizational direction and where my team fits

• Feedback on a piece of work or a project I have been leading

• Visibility — making sure this person knows who I am and what I am working on

• Input on a career question or direction I am navigating

You do not need to announce your agenda explicitly — but having it gives structure and purpose to how you engage.

Come With One Substantive Observation or Perspective

Skip-level meetings that are only information exchange tend to be forgettable. The ones that are memorable are where the person being met with says something genuinely interesting — a perspective on the business, an observation about their team, a well-framed question about the direction.

Prepare one substantive thing to bring. Not a complaint and not excessive self-promotion — a genuine, thoughtful perspective or question that reflects your engagement with the work at a level above the day-to-day.

Be Strategic About What You Share

A skip-level meeting is not the place to raise concerns about your direct manager, vent frustrations about organizational issues in an unfiltered way, or share information that would undermine your team’s coherence. Those things have other channels.

Be honest, be specific, and be thoughtful about what you are choosing to surface. Information shared in a skip-level meeting has a longer reach than it might feel like in the moment.

Follow Up After the Meeting

A brief thank-you note within a day or two — with a specific reference to something from the conversation — closes the loop professionally and keeps you in the senior leader’s mind beyond the meeting itself.

Frequently Asked Questions

Should I tell my manager I am having a skip-level meeting?

In most organizations, yes — if skip-level meetings are not routine. Surprising your manager with a conversation they were unaware of creates unnecessary political risk. Most managers are fine with skip-level meetings when they know about them in advance.

What if the senior leader asks about my manager?

Be honest, be fair, and be measured. This is not an opportunity to surface every frustration. Stick to what is factual and relevant. If there is a genuine relationship issue influencing your work, it can be raised — but carefully and specifically, not as a general complaint.

How formal should a skip-level meeting be?

Take your cue from the senior leader and the culture of the organization. Most skip-levels are semi-formal — professional and purposeful but conversational. Over-preparing a formal presentation tends to feel stiff.

What if the meeting is initiated because the senior leader has concerns about my work?

Come prepared with your honest assessment. If there are legitimate concerns, acknowledge them directly and come with a clear sense of what you are doing about them. Defensiveness in a performance-related skip-level rarely helps.

How do I make a skip-level meeting useful if I have never met this person before?

Bring a bit of context — what you work on, how long you have been in the role, what you are currently focused on — to establish shared baseline quickly. Then get into genuine conversation rather than continuing the introduction for the full meeting.