Skip Level Meeting Guide for Employees

9 min readJul 15, 2020

Skip level meeting invites can send a chill down the spine of even the most seasoned employee, especially the first time. “Just wanna chat” or “Quarterly check-in” subjects lines on meeting requests can send your mind racing in a thousand different directions all at once, leaving you anxiously wondering what you in store for.

We’ve all been there!

If this is a new experience for you, try and put aside all the panicked feelings and focus on what is really happening; you have a manager (let's call them “the skip”) who wants to gather feedback from you about what they can do to provide you clarity and how they can enable of your career.

The goal of this article is to put you in the best frame of mind to make the most out of your skip level conversation, give you some things to ruminate over to prepare, and share some advice about avoiding common pitfalls. I will go over the most common topics discussed in skip-level conversations, including sample questions that should get you in the right headspace to make the most of your time.

There are a ton of articles out there for leaders on the subject of skip levels; how to run them, what are the goals, what questions you should ask, etc. Hopefully, your skip included an agenda or topic guide for the points they would like to discuss. If so, look over the items, and spend time thinking about the points they bring up. Note down any significant items you want to address to make sure you stay focused and cover all your topics. A good skip level meeting usually has some prompting questions, but adapts to the needs of the employee, letting them set the direction of the conversation.

Not everyone is great about setting agendas or laying out the intent in meeting invites, and all you may have received is some generic message about “checking in” and “wanting to catch up”. Don’t fear! You can still prepare to get the most out of your conversation by thinking about some common themes found in all organizations.

Context Set to Get the Most Out of Your Time

Hopefully, the skip has done their research and is prepared with knowledge of your role, background, and experience in the organization. However, it never hurts to take a moment and set background context beforehand or in the first minutes of the meeting. This will help focus the conversation and correct any inaccurate information. You can do this by sharing a brief summary of your journey, including a timeline for what you have been doing throughout your career in the organization:

“I am currently a Senior Engineer working in the platform team helping build out our billing service where I am focused on scaling issues currently. I started with the company 6 years ago as an intern and was hired here right out of college. I previously worked on the mobile team and then moved on to the machine learning team where I was promoted to sr engineer 2 years ago.”

This short context-setting will help frame career progression conversations outlining what you have expertise in, identify any opportunities you may need to demonstrate abilities or gain new skills, and also sets a timeline for how long you have been in your current role. This seeds your career goal progression conversation with where you are at so you can focus on what's in store for you next.

It never hurts to send any topics you would like to cover including questions head of time. Links to reference material such as project plans, shared company goals, career ladders, or compensation policies you want to discuss, enable you to spend your time talking and not waste it tracking down materials or giving background information during your conversation.

Prepare Your Thoughts, Questions, and Answers

Goals, Company and Personal

Your company has business goals that they are trying to meet.

If you are lucky those goals are spelled out very clearly and frequently revisited, updated, and communicated out using a framework like OKRs or Smart Goals. If so, review the goals and measurement criteria, prepare any questions you might have about how your personal work and the work of your team relate to the goals what the priority of the goals is in your manager’s mind.

If you don’t know what the goals are, a skip level is a perfect time to ask:

Does the company publish goals anywhere that I can see?
How is progress towards our goals measured?
What are the companies priorities?
How did the company fail to meet its potential last year?
What challenges will the company face this year?
How will achieving these goals help the company?

You should also have personal career goals that outline the things you would like to achieve as a professional, the direction you would like your career to evolve towards, and a list of explicit skills you wish to gain and experience you need to gather. If you don’t have career goals, this is probably a conversation you need to first have with your direct manager. I suggest reading over Danielle Leong’s article Setting goals with your engineers that don’t completely suck as a good starting point.

Keep a lookout for opportunities where skills you need to demonstrate and experience you need to gain aligns with the needs of the company. Talk to your skip letting them know of any particular goals or work that interests you and ask to be considered when opportunities arise for participation.

Common Questions Skips Ask Employees About Goals

What professional goals would you like to accomplish in the next six to 12 months, and what makes you say that?
Are you happy in your role? What could make it better for you?
What’s one thing we could do as a company that would impact your personal life?
Who is one person in the company that you’d like to learn more from?

Communication

Different companies have varying levels of success with communication and alignment, and as the company grows, these problems only grow more challenging at scale. Review the latest companywide announcements, recent all-hands meetings, product demos, or company-wide emails, noting down any questions you have or points you want to bring up. Use your skip level discussion as an opportunity to gain clarity on confusing or unclear things. A side benefit of this is it will also aid your skip to know where they could improve communication if common topics show up as confusing and unclear.

Common Questions Skips Ask Employees About Communication

What are you LEAST clear about — in terms of our strategy and goals?
Do you have any questions that, if answered, would help you in your day-to-day?
Is there anything that would be productive for me to re-explain to your team?

Feedback on the Company Direction and Skip Level Leadership

If your skip elicits feedback from you on the company performance, product direction, strategy, or areas they could personally improve on, you will be in the best situation to respond if you have spent a couple of minutes beforehand thinking through what you would like to say. It is easy to ramble when trying to think on the spot and you may miss some of the most important points. Get your ideas down in notes so you can articulate your thoughts clearly and succinctly

Common Company and Skip Level Leadership Related Questions

If you were CEO, what’s the first thing you’d change?
What’s one thing we should start, stop, and continue doing as a company?
What’s one thing we can do to improve the performance of the team?
What is one thing I could do to make your job easier?
What is everyone around me neglecting to share with me?

Feedback on Your Manager and Your Peers

Feedback about others during a 1:1 can be a tricky topic. I would discourage you from using your meeting time to do critical feedback for your manager or teammates. Critical and negative feedback needs to be managed as a separate conversation so that you can keep the focus on the main topic of your current meeting which is YOU!

If you do have critical feedback that you would like to give about your manager or teammates, my advice is first, if possible, try and give the feedback directly to your direct manager as going directly to your skip may end up creating a lot of bad feelings that you then need to navigate. If you have gone to your manager and/or feel you still need to address these with your skip, set up a separate meeting outlining your concerns, steps you feel you have already done to try and resolve them and talk about the impact the negative behaviors have on you and ability to do work. Ask the skip for the next steps, guidance, or a resolution plan.

Keeping this as a separate event allows you to give the topic your full time and attention without feeling like you are compromising on time that should be focused on you.

Positive feedback and shout-outs are more appropriate in a skip level meeting as you are not asking for resolution or next steps, but simply raising awareness. If your skip has a lot of folks reporting to them, it is unlikely they will be able to keep eyes on every little thing and may miss good work done by good people. Note down any shout outs/praise for coworkers and take a couple of minutes at the end of your discussion to share the positive impact folks around the organization are making on you and your work.

Requesting a Skip Level

This all sounds great, but what if your skip never schedules a skip-level conversation and you would like answers to the above, seek clarity, and want to get some face time:

Reach out to your direct manager and ask if there is a pattern for requesting a skip-level meeting that you can follow. Some folks are open to you just dropping things on their calendar, some use request style systems like Calendly or ask you to schedule through their executive assistant. Working within the system will be the best way of getting your meeting as soon as possible.
Create an agenda of the topics you would like to talk about, including links to material you would like to discuss and send it over ahead of time so that everyone has an opportunity to prepare. If you are comfortable with it, share this agenda with your direct manager and solicit any advice they have on the points you are asking about.
Be patient. Calendars are hard and depending on the size of your organization it may take weeks in order to find available space on both your calendars. If something is urgent or time-sensitive, make sure to outline the urgency with a reason why you need your discussion to be scheduled sooner then later.

Take a Deep Breath

Like most things in life, you will get out of it what you put in. Do the work, spend the time and you will be in the best place to get a lot of value out of this and future skip-level conversations. Afterward take a moment to reflect your conversation, write down any notes of things you want to follow up on, think about what you would want to have achieved by your next skip discussion and send an email to the skip reminding them of anything they were going to follow up on for you.

You got this.