Have you gotten an email from your manager's manager asking for a skip-level meeting? If you secretly panic at the idea of meeting with a senior manager, have no fear.
While it's totally understandable to feel a bit intimidated, skip-level meetings are actually great opportunities for both the employee and the skip-level manager. It allows both sides to gain a better understanding of what's really going on -- good or bad -- across the organization.
Let's walk through everything you need to know about what skip-level meetings are, their benefits, how to prepare, and example questions to make the most of your next skip-level meeting.
What is a skip-level meeting?
A skip-level meeting is a one-on-one between an employee and their manager's manager, without the middle manager in attendance. For example, a Marketing Coordinator (who usually reports to the Marketing Manager) may have a skip-level meeting with the Director of Marketing.
These meetings allow you to connect directly with senior leaders that you may not regularly interact with in your day-to-day work, bypassing the traditional chain of command.
In many organizations, it's not uncommon for the traditional hierarchical structure to create barriers to effective communication -- preventing ideas and concerns from reaching decision-makers. But with skip-level meetings, employees can break through those bureaucratic barriers and connect directly with senior managers.
How often should these skip-level meetings happen? Well, this depends on the size of your organization. This one-on-one meeting between a senior leader and lower-level employees could occur every month, but in larger organizations, your skip-level meeting may be scheduled once a quarter.
No matter their structure and cadence, skip-level meetings provide both the senior leader and employee an opportunity to learn and stay in tune with the pulse of the company. Skip-level managers are able to keep their feet on the ground while employees stay in touch with the company's goals and high-level vision of senior leadership.
Skip-level meeting benefits for employees
Skip-level meetings provide many unique benefits for employees, including:
Direct access to upper-level management
Opportunity to share ideas and innovative solutions with decision-makers
Discover insights into the organization and its goals
Opportunity to share challenges and blockers for your team
Opportunity to discuss career aspirations and growth opportunities
Receive guidance and mentorship from upper-level managers
Gain a greater understanding of the company culture and it's values
Build trust and psychological safety at work
Skip-level meeting benefits for senior leaders
And employees aren't the only ones to benefit from skip-level meetings -- there are many advantages for senior management too:
Gather new ideas and fresh perspectives for innovative solutions
Discover challenges and opportunities for improvement at an early stage
Build connections and relationships with employees
Identify valuable performers with high potential for growth
Identify opportunities to better support and mentor middle managers
Improve workplace culture and satisfaction across the organization
How to have awesome skip-level meetings
So, how do you prepare for a skip-level meeting? What do you talk about, and should you have any questions ready? Let's walk through everything you need to know so you can make an amazing impression with your boss's boss.
1. Create your agenda
Like any meeting, your skip-level meeting should have an agenda to make sure everyone can come prepared for a productive discussion. You're both busy people who have lots to do, and we all know how unstructured meetings end up wasting everyone's time. Make a great first impression with a solid agenda so you can keep the meeting on track, remember all of your important topics, and get answers to the key questions you've been wanting to ask your skip-level manager.
Your senior manager may offer a template or agenda to use, but if not, use this one for your next skip-level meeting:
Skip-level meeting agenda template
1. Introduction
- Introductions (break the ice with some light discussion around personal interests)
- Overview of professional background & experience
- Overview of your roles & responsibilities
2. Progress & performance updates
- Overview of current goals, projects & timelines
- Personal contributions
- Team performance
- Ideas & opportunities for improvement
- Feedback & insights from skip-level manager
3. Challenges & blockers
- Current challenges at work
- Ideas & opportunities for improvement
- Feedback & insights from skip-level manager
4. Company strategy
- Company-wide strategic initiatives & goals overview
- Top challenges the company faces
- Company performance & market position
- Company culture & workplace initiatives
- Ideas & opportunities for improvement
- Feedback & insights from employee
5. Career development
- Career aspirations & goals
- Feedback & insights from skip-level manager
- Employee skill development resources at company
- Career opportunities at the company (current & future)
6. Open forum topics
- Additional ideas, questions, or concerns
7. Conclusion
- Key takeaways
- Follow-up items for employee
- Follow-up items for skip-level manager
2. Prepare your skip-level meeting questions
As we know, skip-level meetings are pretty infrequent, so take the time to prepare thoughtful and relevant questions to make the most of the opportunity. What do you want to know about the company's current state, what the future looks like, or even how your senior leader evolved their career into the position they hold today?
And as always, remember your skip-level manager is a person too, so don't jump in like a robot! Kick off the meeting with some light ice-breaker questions to build rapport and get to know them on a more personal level.
After you have a few minutes to chat about life, it's time to dive into the good stuff.
Here are ten awesome example questions for your skip-level meeting:
I would love to hear your story -- how did you get started with the company and develop your expertise so far in your career?
What's going well -- what are we doing successfully today as a team/organization?
What's not going well -- what are the biggest challenges we're facing as a team/organization?
What do you see as the teams/organizations key priorities -- what are we doing to reach those goals?
What are we doing (or should be doing) to differentiate our company in the market?
What's one thing we could do as a team that would bring the biggest impact this year?
What can I do in my role to better support our mission?
Do you have any feedback on my performance, or notice any areas where I can improve?
Do you have any advice on how I can further develop my skills in my role, or grow within the company?
What's your favorite thing about our organization -- what motivates you every day?
These example questions are awesome starting points -- but remember, it's okay to go off-script or customize your question list before (and during) your skip-level meeting.
3. Consider your challenges
While these meetings offer amazing insights to you as an employee, it's also the perfect opportunity for you to share blockers for yourself and the team. Before the meeting, organize a list of your top challenges to share with your skip-level manager. They're collaborating much more broadly across the organization and could very likely have run across similar scenarios in the past and have an awesome solution up their sleeve.
If you're struggling with an issue or challenge that's bottlenecking the rest of your project or your team -- bring it up with your skip-level manager. You may find that this problem isn't unique at all. It may have already been approached by a few other teams. If your skip-level manager doesn't know the fix off the top of their head, they can put you in touch with the team that's already found the solution.
And sharing tough challenges not only shows that you're thinking about the problem -- but that you care about your work too. Bring your senior leader up to speed on how you've tried to solve the problem, why it didn't work, and any ideas you have for potential solutions to try next. Your skip-level manager will appreciate your proactive approach and can likely provide valuable insights or potential solutions to help you and your team thrive.
4. Share your career aspirations
Long-term goals -- we all have them. And your skip-level meeting is the perfect opportunity for free mentorship around how to achieve them. Your skip-level manager has been in, if not exactly, a similar role as you are today -- and has gone through the career navigation ahead of you. Use your skip-level meeting to discuss your career path, new skills you should be focusing on, or what other opportunities may be available through the organization.
For example, a software engineer may be experienced and interested in machine learning, though that might not be the focus of their team. The skip-level manager may know of another group working with that technology that's seeking more talent for their project.
5. Discuss your projects & responsibilities
While skip-level meetings are primarily focused on high-level topics, it's likely the senior manager will want to learn a bit more about your day-to-day job. This is where you can share a quick overview of what you're working on, what's going well, and any challenges you're up against. Your skip-level manager may have some tips on how you can enhance your work, align more with company goals, and maximize your direct impact.
Of course, discussing current projects is something you're also doing in touch-base meetings with your direct manager -- and this should not be the same conversation. Save the nitty-gritty details of your projects for your direct manager, your skip-level meeting should be more focused on progress updates.
6. Seek feedback & guidance
Don't be afraid to ask for feedback -- it's how we grow. By requesting feedback on your performance, you can better understand where your strengths are and if there are any areas where you can improve. And unless you're dropping the ball on some pretty basic requirements necessary for keeping your job, the feedback for improvement is likely just going to be around developing work skills to help you become more productive in your role -- researching tips, time management hacks, communication methods to leverage in your team, etc.
While your direct manager is a great resource for feedback around individual performance on tasks and projects, this skip-level discussion is where you can get more high-level guidance. They likely have unique insights into the challenges, performance, and roadblocks facing your team as a whole.
7. Share innovative ideas
Have an interesting idea for your product, a process, or a problem? It's hard to battle through the same challenges every day when you see a clear fix that can be done -- of course, the challenge is finding time to prioritize the change.
Working on the ground floor exposes you to many challenges and opportunities that you're uniquely positioned to discover -- and your skip-level manager wants to hear about them.
Skip-level meetings give senior managers the chance to gather valuable insights around potential innovations they otherwise wouldn't run across in their role. And having a broader understanding of the company and its operations, your senior leader will have a good idea of how feasible and impactful it could be for the company.
Of course, you'll want to be conscious of any past discussions you've had with your direct manager around your idea, and make sure to fill them in on your skip-level manager's feedback after the discussion. And while every idea may not be a home run, you never know -- it could just change the future of your company.
8. How to talk about your manager or work issues
Now to the tricky part -- how to appropriately express concerns around your work environment. This is something you're going to want to think about before your meeting, especially if you're fired up about something -- you don't want to be shooting from the hip with built-up emotions.
If you have any concerns or issues related to your manager, work environment, team dynamics, or organizational practices, the skip-level meeting could be a chance to speak about them with a key decision-maker. But skip-level meetings are not the place to complain about your direct manager unless something is seriously going wrong.
Take that innovative idea you've had in your pocket, say you've brought it up to your manager a dozen times, and they continue to claim it's interesting but never prioritize it. However, your skip-level manager seemed to find it fascinating -- this doesn't mean you should drop everything and jump in. Instead of undermining your direct manager's authority by kicking it off without permission, tell them about the enthusiastic conversation you had. It's an excellent opportunity to open that discussion back up and share the feedback your skip-level manager provided.
Remember, your direct manager is the person you report to, and you have to work with them every day. Keep your communications respectful and professional so you can keep strong relationships with both of these managers. However, your skip-level manager may occasionally ask for feedback on your manager, and you should, of course, share your thoughts so your senior leader can obtain insights on how to better mentor their direct report (your manager).
Skip a level & boost communication 📢
Skip-level meetings are valuable methods for improving communication and fostering a sense of collaboration within an organization. Employees want to work in a transparent company and have a strong understanding of its goals, challenges, and opportunities -- and senior leaders gain incredible insights by connecting with the people who are getting the hard work done every day.
Approach your skip-level meeting with the preparation you need to knock it out of the park -- a well-thought-out agenda, valuable questions, and any ideas you want to run by your manager's manager.
Did we miss anything? How do you prepare for skip-level meetings? Tweet us @reclaimai to let us know!
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