Outlook Calendar for Reclaim is almost here! Join the waitlist

Reclaim.ai Blog

Productivity tips, calendar hacks, & product updates from the Reclaim team.

Skip-Level Meeting: 2024 Questions & Tips Guide
January 18, 2024

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.

Guide overview:

What is a skip-level meeting?

A skip-level meeting is a one-on-one meeting 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, the traditional hierarchical structure often acts as a barrier to effective communication, hindering the flow of ideas and concerns to  decision-makers. This strict hierarchy sometimes results in employees rarely having the opportunity to interact with senior management, creating a significant disconnect within the organization. However, the introduction of skip-level meetings offers a solution to break through these bureaucratic barriers, enabling direct connections between employees and senior managers. This, in turn, fosters improved communication and idea sharing, ensuring that everyone in the company remains aligned with the organization's vision and goals.

The frequency of these skip-level meetings should be tailored to the size of the organization. In smaller organizations, skip-level meetings could occur on a monthly basis, where larger organizations may only be once a quarter. Regardless of their structure and cadence, skip-level meetings benefit both senior leaders and employees by providing an opportunity to gain insights and stay attuned to the company's pulse. Senior managers can keep their connection with the frontlines, while employees remain engaged with the company's overarching goals and high-level vision set by 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

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 (as an employee)

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 (template included)

Like any meeting, effective skip-level meetings should have an agenda to make sure everyone can come prepared for a productive discussion. You’re both busy people with 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:

  1. I would love to hear your story – how did you get started with the company and develop your expertise so far in your career?
  2. What’s going well – what are we doing successfully today as a team/organization?
  3. What’s not going well – what are the biggest challenges we’re facing as a team/organization?
  4. What do you see as the teams/organizations key priorities – what are we doing to reach those goals? 
  5. What are we doing (or should be doing) to differentiate our company in the market?
  6. What’s one thing we could do as a team that would bring the biggest impact this year?
  7. What can I do in my role to better support our mission?
  8. Do you have any feedback on my performance, or notice any areas where I can improve? 
  9. Do you have any advice on how I can further develop my skills in my role, or grow within the company?
  10. 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 one-on-one 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).

How to conduct skip-level meetings (as a senior manager)

If you’re a senior manager, skip-level meetings are an amazing tactic to encourage open communication, build rapport, and gain insights into the organization's dynamics. Here are key strategies to conduct skip-level meetings effectively:

1. Establish clear objectives

Skip-level meetings aren't just chats for the sake of it. They're designed to achieve specific goals. These goals could be anything from getting feedback, grasping how the team operates together, lending support, boosting morale, or keeping everyone on the same page about the company's big goals.

And yes, having a clear agenda for these meetings is critical (feel free to use the skip-level meeting  agenda template we linked earlier). It keeps things on track and guarantees that the time spent in these meetings is productive and beneficial for everyone involved.

2. Create a comfortable environment

Always remember that speaking with a skip-level manager might make some employees a bit jittery or uneasy. When people feel too nervous or uncomfortable, it can put a damper on the discussion. As a skip-level manager, do your best to create a relaxed and open vibe during these meetings.

Let your team members know that the aim is to have a genuine and honest conversation. Make it clear that their thoughts and feedback are highly valued and that the discussion is confidential. 

3. Listen actively

Richard Branson once said "Listen more than you talk. Nobody learned anything by hearing themselves speak." Well, that's something really handy to keep in mind for your skip-level meetings.

When you're in those meetings, focus on being an active listener. It's not about taking the spotlight; it's about giving your team members the floor. Encourage them to speak up and share whatever's on their minds – whether it's ideas, worries, or suggestions.

4. Acknowledge & address concerns

If your direct reports bring up any problems or worries during the meeting, always acknowledge them. It's super important to show that you're taking their feedback seriously. Don't just brush it off – that’s only going to increase the concern of the employee and potentially amplify their workplace stress.

Once these concerns are on the table, try to tackle them together.  And if you promised any specific actions during the meeting, make sure to follow up. It shows you're true to your word and committed to making things better.

5. Regularize skip-level meetings

Once you get your skip-level meetings going, don’t let them fall off the calendar. It’s up to you to make these skip-level meetings a regular thing (every quarter at the very least). By doing this, you're keeping everyone engaged and encouraging an environment where people feel comfortable sharing their thoughts openly. And the key to building these relationships with employees is keeping them alive. 

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!

Trend Reports

Smart Meetings Trends Report (145+ Stats)

Setting Priorities Report: Top Work Challenges (50 Stats)

Workforce Trends Report: +100 Stats on Employee Productivity Analytics

Meeting Scheduling Trends Report: 130+ Scheduling Links Stats

Burnout Trends Report: 200+ Employee Stress Stats by Department

Task Management Trends Report: +200 Stats on Managers vs. Individual Contributors

Productivity Trends Report: One-on-One Meeting Statistics

Ready for an
AI calendar?

Auto-schedule your tasks, habits, breaks, & meetings on Google Calendar.

Start scheduling →

It's free! 🎉

Get the latest productivity trends from Reclaim

Something went wrong. Please try again.

Ready to reclaim your time?