Why a ‘skip-level meeting’ is key to building your career

Visibility is critical for career success. However, when many professionals get serious about being more visible, they focus solely on the relationship they have with their bosses, which is a big mistake.

Your boss is one person in the hemisphere of stakeholders. While they do have some control over your career opportunities and growth, they are not the end-all be-all. Should you nurture this relationship? Absolutely! But if you are only focused on being visible and “seen” by your boss, your strategy will fall short. Your boss has their own priorities; while a good boss will want to see their employee excel, they are also likely focused on their own agenda.

I’ve seen it time and time again where a boss moves on to a new role, new company, or (gasp) is fired, and all their direct reports are nervous because they don’t really have close connections with other people in the organization. Essentially, you don’t want to be in a scenario where your boss leaves the company or goes to a different department, leaving you without any other strong relationships with key stakeholders in your company. There are also situations in which your boss isn’t always well-liked or is seen by others as difficult to get along with.

Do you want to be seen the same way just because you report to that person, or do you want to own how other key stakeholders see you? Skip-level meetings are a powerful career advancement tool to create relationships throughout an organization.

What are skip-level meetings?

Skip-level meetings are meetings with your boss’s boss without your boss present. For example, let’s say the VP of sales has four managers who report to him or her. A skip-level meeting would occur when the VP of sales meets with the direct reports of his or her four managers.

Why do they happen?

Skip-level meetings are an important management tool and should not be received as negative or going over your boss’s head. The goal should be to maintain and increase communication so that all parties learn more about what’s happening in the organization from each perspective. Also, skip-level meetings offer opportunities to develop professional relationships, especially if you don’t have regular interactions with senior management.

How do I schedule a skip-level?

I’ll be honest, a good leader schedules skip-level meetings periodically with their team. But it should come as no surprise that many leaders don’t always check in with their broader team members or make it a priority. If skip-level meetings are not part of your organization’s culture, you should consider reaching out to senior managers on your own (but do run it past your boss first and explain why you would like to have the opportunity to meet with their boss). Some bosses might push back on this, but, theoretically, they should not prevent you from requesting a skip-level meeting. Once you have spoken with your boss, here is a sample email you can send to your boss’ boss. Please adapt it to fit your scenario:

Hi [skip-level boss’s first name],

My name is [your name], and I work with [your boss’s name] as [your title]. If possible, I’d like to schedule 30 minutes to learn more about your role at [company name]. I’d love to hear more about your journey and see if you have any tips on my career growth.

When you have an opportunity, could you share your availability over the next few weeks, or can I work with [skip-level boss’s admin’s name] to schedule time with you?

Thank you,

[your name]

What happens during the meeting?

First, keep in mind that you requested the meeting. Even though this is your boss’s boss, it is your responsibility to properly prepare for the meeting and come up with thoughtful questions and discussion topics. A skip-level meeting is not the time to critique or give feedback about your boss. It is also not the time to discuss salary, promotions, or additional responsibilities. Remember, the topics you discuss with your boss’s boss will most likely go back to your boss. Don’t say anything you don’t want to get back to them.

So, what do you talk about? Here are some sample questions to ask. Make changes so it makes sense for you and your organization.

Team alignment

• What are your goals for the department this quarter? This year? Five years from now? How do you think we are going to reach those goals?
• What do you consider to be our team’s top priorities for this year?
• How can our team provide more meaningful contributions to the company?
• What one thing should our team work to improve?

Company growth

• How do you see the company developing in the next three years?
• What initiatives are being considered this year?
• Which competitors are you most concerned about?
• What industry trends concern or excite you?

Professional growth

• How did your career develop at this company?
• What should I focus on at this point in my career?
• What skills am I missing if I want to advance?
• What one thing would you tell your younger self about career advancement?

Another insightful question to ask: What is demanding or consuming most of your time right now? (This is a great way to get information on the skip-level boss’ top priorities in the organization.)

And what happens after the meeting? Always send a follow-up note after the meeting to thank the skip-level boss for their time. And if you said you would follow up on something, make sure you do. Also, consider asking for a quarterly meeting and get it on the calendar as soon as possible.

Arika Pierce is the author of I Can. I Will. Watch Me., as well as a leadership coach and the founder of Piercing Strategies.