Making the most out of meetings with your skip level manager

[ernest-phillips]

What is a skip-level manager

In most organizations, you will have a regular one on one meeting with your direct manager. However, there are other types of manager meetings that can be just as impactful, if not moreso on your career. These are meetings with your skip-level-manager. A skip-level-manager, your manager's manager or someone that is typically one level above your direct manager. While finding time for another meeting might seem unnecessary, these conversations can be game-changers for your professional growth.

Let me share my own experience. I didn't start my career at GitHub as an engineer - I began in Support as a Technical Support Engineer. I enjoyed the work, but during a conversation with my director of Support, he challenged me to think about where I saw myself in five years. When I shared my goal of moving to Engineering, he didn't just listen - he actively helped make it happen. He helped me create a plan, connected me with the right people, and advocated for me when an engineering position opened up. That relationship with my skip-level manager made all the difference in my career transition.

Let's explore why investing time in these relationships isn't just worthwhile—it can provide insights, opportunities, and alignment that go beyond your day-to-day work.

Why Building a Relationship with Your Skip-Level Manager Matters

It's easy to get caught up in your daily work - completing tasks, hitting team goals, and improving processes. I know I did when I worked in technical support - I was focused entirely on helping customers and closing tickets. But I learned an important lesson: doing great work alone isn't always enough to advance your career. Sometimes you need someone with a broader view of the organization who can help guide your next steps.
Getting your work noticed matters - both for you and your team. When you build a good relationship with your skip-level manager, you have someone who can see and share the impact of your work beyond your immediate team. It's an opportunity to:

• Get Your Work Noticed

  Building a reputation beyond your immediate team is crucial. Skip-level managers can advocate for you and your work at higher levels of the organization. By sharing your accomplishments and challenges directly with them, you ensure your contributions are visible to decision-makers who might not otherwise see your day-to-day impact.

• See the Bigger Picture

  Your skip-level manager operates at a higher level, focusing on the long-term vision and strategic goals of the organization. Conversations with them can provide valuable insight into how your work fits into the bigger picture.
  This broader perspective can make your quarterly or yearly goals more tangible. You’ll gain a clearer understanding of why those goals matter and how your efforts contribute to the organization’s success. This alignment not only makes your work more meaningful but also positions you as a proactive contributor to the team’s success.

• Get Expert Advice

  Skip-level managers have usually walked the path you're on. They've either done your job before or managed many people in your role. Whether you're stuck on a challenging project, working toward a new skill, or thinking about your next move within your organization, they can share valuable insights from their experience. If they don't have the answer, they often know who does and can connect you with the right people.

• Open New Doors

  When you broaden your scope and invest in these relationships, you’re not just building a connection—you’re building a bridge to new opportunities. Whether it’s learning about a potential role, gaining access to cross-functional projects, or receiving mentorship, your skip-level manager can play a key role in your long-term development.
  When you take time to connect with your skip-level manager, you're not just adding another meeting to your calendar—you're creating chances to grow, understand where the company is headed, and shape your career path. It’s a simple step with far-reaching benefits, both for you and your team.

How to Build a Relationship with Your Skip-Level Manager

Building a relationship with your skip-level manager might feel daunting, but it’s actually easier than you think—and you have more control over it than you might realize. Taking the initiative to connect with them not only helps build rapport but also demonstrates your commitment to your career and the organization’s success.

1. Take the First Step

One of the simplest ways to get started is to schedule a meeting. Check to see if they have open slots in their calendar specifically for connecting with team members. Don't feel limited to only your manager's manager! You can look beyond your direct reporting line to connect with leaders whose work interests you (these might be directors, VPs, or have other titles depending on your company's structure) or whose teams collaborate with yours. If there isn't dedicated skip-level meeting time on their calendar, you can try to schedule the meeting yourself. Just make sure to give them a heads up, and check their bandwidth for such a meeting. This can be as simple as sending a short message explaining the purpose of the meeting and any context they might need.

For example, if you're working on a project that spans multiple teams, you might want to connect with the director overseeing that broader initiative. Or if you're curious about a different area of your organization, reaching out to that team's director can give you valuable insights and expand your network.

2. Come Prepared

Your skip-level manager’s time is valuable, so preparation is key to making the most of your meeting. Outline a general theme or key topics you’d like to discuss beforehand. Sharing this agenda in the meeting invite or a quick follow-up message helps set expectations and ensures a more engaging conversation.

Here are some examples of questions you might ask:

• Strategic Goals: What are you most excited about accomplishing this year?
• Personal Development: Are there ways I can better showcase my skill set or the projects I’m working on?
• Leadership Perspective: What is the most challenging part of your job?
• Fun and Connection: What’s your favorite ice cream flavor?

Feel free to tailor your questions to your goals—whether it’s gaining insight into the organization, seeking advice, or simply getting to know them better.

3. Own the Conversation

While these chats can go in many directions, don't be afraid to guide the conversation toward what matters to you. Bringing your own questions and topics shows you're thoughtful about your role and where you want to go.

Don’t hesitate to share updates about your work, ask for feedback, or seek guidance on challenges you’re facing. Even light, informal conversations can help build rapport and make future interactions more natural.

4. Follow Up

After the meeting, consider sending a quick thank-you note summarizing any key takeaways or action items. This small gesture not only reinforces your appreciation but also keeps the relationship warm for future interactions.

By taking these steps, you’ll not only foster a meaningful connection with your skip-level manager but also create opportunities to learn, grow, and align more closely with your organization’s vision. Remember, the relationship is what you make of it—so take the reins and make it count!

Managing the Manager Dynamic

Meeting with your manager's manager may feel awkward, or you may feel as if you are stepping on their toes by having conversations with their manager. You don't have to talk about your direct manager with your skip-level, unless you want to. This goes back to your ability to control the flow and direction of your conversations. This is your time, after all.

There may be times when you do want to discuss your relationship with your manager. This can be in regards to a myriad of topics ranging from the amount of time you meet with them to how their particular management style may or may not be working for you. When these conversations happen, focus on constructive solutions rather than criticism. For example, instead of saying "My manager doesn't meet with me enough," try "I feel I'd benefit from more frequent check-ins to stay aligned on priorities—do you have any suggestions?

Building Relationships Beyond Engineering

The benefits of building a relationship with your skip-level manager aren’t limited to engineers or even individual contributors. This approach can be valuable across all roles and parts of the organization.

My personal experience illustrates how relationships with skip-level managers can open doors, provide guidance, and foster growth across various roles. Whether you’re in Support, Marketing, HR, or another part of the organization, these relationships can help you align your goals with the company’s vision and take meaningful steps toward your aspirations.

I hope this post has eased some of the anxiety or skepticism you might feel about connecting with your skip-level manager. When you approach it as an opportunity to get to know another person in your organization—who just happens to be your director—it becomes less intimidating and more approachable.

Remember, this relationship isn’t just about seeking guidance or visibility for yourself. It’s also about sharing your unique ideas, experiences, and contributions with a broader audience. It’s a two-way exchange that can benefit both you and the organization.

So, why wait? Take that first step and schedule your skip-level meeting today. Your skip-level manager may already have time blocks on their calendar for these kinds of conversations—take advantage of them!

Start building that connection today. You’ll be surprised at the insights, opportunities, and growth it can unlock for both you and your team.