Team meetings

How to Prepare for Skip Level Meetings & 1-on-1s

An employee’s meeting with their manager’s manager—also known as a skip-level meeting—is typically seen as an escalation mechanism. The common understanding is that you involve a leader when there is a problem. However, it shouldn’t be. 

Skip-level meetings, when conducted regularly, help employees and leaders to share knowledge. It allows them to share insights that they gain from their unique position and perspective. 

For instance, a customer service associate, being close to the customer, might have insights into their pain points. The COO, being close to the CEO, might know more about the strategy and roadmap for the future. When these two meet, it helps exchange business context.

In this blog post, we explore how you can leverage skip-level meetings to the organization’s advantage as a manager of managers.

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What is a Skip-Level Meeting?

A skip-level meeting is a conversation between an employee and their supervisor’s supervisor without the middle manager being present. It skips one level in the organizational hierarchy, hence the name.

For example, let’s say that you are the city sales head whose direct reports are cluster managers. Each customer manager might have sales development representatives (SDRs) reporting to them. 

A skip-level meeting happens between you and the SDRs without the cluster manager present.

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Benefits of Skip-Level Meetings

In any given week, managers can meet their teams often—in standups, reviews, customer meetings, etc. Whenever an employee faces a challenge, they reach out to their direct manager, keeping a collaborative relationship. 

However, for the next-level manager, this is not the case. They are often distant from the teams of their direct reports and their work. Skip-level meetings bridge this gap.

Benefits of skip-level meetings for employees

Having their voices heard: Often, employees might face challenges that their immediate supervisors can’t resolve. Examples are purchasing an expensive new tool, which the immediate supervisor might not have the authority to approve. 

In such cases, skip-level meetings allow them to raise their concerns to someone with more authority.

Feeling seen: Employees, especially those in the field or away from the office, feel as though they work in isolation. Even if they collaborate with their peers or immediate supervisors, they might not feel part of the larger purpose of their work. 

Skip-level meetings—just like all-hands or company off-sites—help employees feel seen, boosting their morale.

Share insights: Employees on-ground have a pulse of the customer, which is of immense value to the organization. An SDR selling a time-tracking tool might find that customers want the ability to convert these entries automatically into a timesheet. 

Such insights might not reach the product team in the hustle of day-to-day activities. A skip-level meeting offers the place and time to share insights that can be operationalized immediately. 

Understand organizational strategy: Not every employee has clear visibility into corporate strategy. A software engineer might know everything about the feature they are developing but not why it was added to the product roadmap. 

Skip-level meetings help leaders bring their vision and strategy to the entire organization.

Benefits of skip-level meetings for leaders

Identifying unseen opportunities: Leaders can get direct and specific feedback from those on the ground. The finance associate who pays the bills might notice the organization spending too much on duplicate tools. 

On a regular day, they might brush this aside. During a skip-level meeting, they might flag this to the CFO, which can amount to thousands of dollars in savings.

Effective problem-solving: When team communication is filtered by multiple levels of managers, the root cause might get lost. Skip-level meetings can take the leadership to the bottom of critical issues. It can help with workflow optimization as seen from the perspective of the end user.

Access to customer insights: Leaders rarely speak directly to customers unless it is a big/essential account. A skip-level meeting is an opportunity to collect honest feedback about all customers without meeting each of them individually. This is a great way to gather organizational knowledge.

Raising employee morale: Skip-level meetings ensure that employees are seen and heard by organizational leaders. This makes employees feel more engaged and valued. Employees who feel that their work matters will be motivated to do more.

Handle personnel issues: People put up with bad managers because they don’t want to seem like troublemakers. Skip-level meetings facilitate a 360-degree review for middle managers. This way, leaders can address employee concerns and train supervisors to do better.

In essence, skip-level meetings enable leaders to change things. It gives them clearer visibility. It helps them make improvements quickly and effectively. As a result, employees see that their feedback is valued and respected. 

Over time, this creates employee loyalty, which leads to better retention and better financial performance of the organization. 

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How to Prepare for and Schedule Skip-Level Meetings

As a manager of managers, the responsibility of scheduling regular skip-level meetings rests with you. Here’s how to prepare for and schedule skip-level meetings to your advantage.

1. Inform the reporting manager

When your team member sees a meeting request from their manager’s manager, they will wonder: “Are they letting me go?” When your direct reports hear that you’ve been speaking to their team, they’re sure to be insecure. 

So, a skip-level meeting can be emotionally draining for your teams. To avoid putting your teams under unnecessary stress, think about how you want to approach your skip-level meetings. 

Use a process-mapping tool to identify all tasks you need to complete before getting into a skip-level meeting. Here are some steps to consider.

  • Be transparent with everyone
  • Create a cadence for regular skip-level meetings so no one is alarmed when they get a meeting request
  • Conduct the quarterly one on one meetings with your direct reports before the skip-level meetings
  • Inform your direct reports of your skip-level meeting schedule
  • Encourage your direct reports to inform their teams to expect a meeting invite from you

2. Know who you’re meeting with

Let’s say you have five direct reports, and each of them manages a 5-member team. Then, you will have to meet 25 individuals with their personalities, working styles, priorities, and skills. Before you get into a meeting with them, understand them.

Collect details about them in advance. You will be able to find out about their role, responsibilities, goals, and performance so far from your human resources management system [HRMS].

To understand them as a person, you can use something like Clickup’s about me template. Invite them to answer questions about their values, strengths, experiences, and more. 

Clickup about me template
Customizable About Me templates for managers to know their teams better

Use this data to anticipate their issues and consider your responses beforehand. 

3. Schedule skip-level meetings thoughtfully

The best cadence for skip-level meetings is once a quarter. If you leave it for longer than that, you might appear to be disingenuous, merely ticking off a box. Any more frequent than that might be a burden on your schedule.

Meeting 25 individuals every quarter isn’t easy. So, scheduling your skip-level meetings right is critical. We recommend one of the following two methods. 

Batch scheduling: Five 20-minute meetings a day for a week every quarter. While this will occupy you for an entire week, it will help collect all information holistically and contextually. It will also give you the rest of the quarter to take action on the feedback you’ve collected.

Continuous scheduling: Alternatively, you can meet two people weekly throughout the quarter. This helps you spread the meetings over time and monitor progress more closely.

Depending on your span of control, schedule meetings in a way that works for you. Be sure not to club 2-3 people into one session or do group meetings. A good skip-level meeting is always 1-on-1.

4. Keep bandwidth in mind while scheduling skip-level meetings

Remember that you’re not the only busy one in the organization. So, be mindful of your skip-level team’s workload before scheduling a meeting. Your project management tool should be able to tell you how busy team members are.

Clickup’s workload view gives a consolidated real-time view of what each team member is doing and if they can spare 20 minutes to speak to you. 

ClickUp Workload view
ClickUp’s workload view to schedule meetings with skip-level team members

On the other hand, your bandwidth also needs attention. ClickUp’s calendar view helps you see all your appointments in one place, so you can ensure you’re not overwhelmed by too many meetings.

5. Create a skip-level meeting agenda

There is nothing more wasteful than a meeting without an agenda. Considering that a  skip-level meeting is barely twenty minutes long, you need a clear plan. Clickup’s skip-level meeting agenda template is a great starting point.

Clickup skip level meeting agenda template
ClickUp action plan template for skip-level meetings

While planning the agenda, also think of skip-level meeting questions you might ask. Here are a few examples.

If you’re a CFO meeting an accounts receivable associate, you might ask:

  • How many of our customers delay payments beyond the agreed time?
  • How many delays are we responsible for, and how can we fix them?
  • What payment channel is preferred by customers?

If you’re a city sales head talking to SDRs, you might ask:

  • What grievance are you hearing from customers repeatedly?
  • What features do they love?
  • Why do some prospects prefer our competitor over us? 

In every meeting, consider asking:

  • Are you happy with your role, your boss, and your job?
  • Do you have all the tools you need to do your job well?
  • If you had the chance, what is the one thing you’d change about your work?

Share this skip-level meeting agenda with your employees a couple of weeks in advance so they can think about it and come prepared. 

6. Prepare yourself to answer tough questions

Skip-level meetings can be hard on you as well. Your team members will use this opportunity to discuss their concerns (which is what you want, too!). So, be prepared to address them. Collect all your facts and numbers. Decide on what information you’re ready to share with them. 

How much ever you prepare, the effectiveness of a skip-level meeting relies heavily on how you participate in the conversation. Here’s how you can improve that.

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How to Have a Successful Skip-Level Meeting

Start well ahead of the meeting

When you send the skip-level meeting agenda to your team, encourage them to review it and add their items. When they do, be proactive in acknowledging their input. 

This is one of the simplest ways you can establish trust. Your response shows them that you genuinely care about the skip-level meeting and them as a person. 

Bring together the tools you need to run successful skip-level meetings. This could be an AI tool for meeting minutes or summaries, a goal-tracking app, a call-recording software, or your favorite paper and pen.

Come in with clear goals

Enter into the meeting knowing what you and your skip-level team member want to accomplish from this conversation. A tool like ClickUp helps track goals and set a structure for the meeting.

Continue from the previous skip-level meetings

If you’ve had skip-level meetings with this person before, continue from there. Acknowledge your action items and progress since then. If you haven’t been able to resolve a concern, explain why.

When an employee feels like nothing came of the previous meeting, they’re less likely to participate eagerly this time. Reassure the importance and impact of the skip-level meeting.

Have an open mind

While you’ve prepared for this meeting and learned about the person, remember that this meeting is more about them and less about you. So, ask questions and listen patiently without interrupting.

Be open. Do not carry preconceived notions or ideas you’ve heard from others. During the meeting, do not judge. 

Provide feedback

Employees want to hear from you about their performance and what they could do better. Provide feedback on their work and their input to this meeting. Document and share this with them so you can build on it during your next session.

ClickUp Summarize feature for Meeting Notes
Summarize meeting notes in seconds with ClickUp AI

Creating a feedback document feels tedious? Check out Clickup’s AI-powered assistant to summarize your meeting notes, identify action items, and suggest timelines. 

Come away with clear action items

A skip-level meeting is only as good as your action on the discussion points. To ensure that you’re involved and interested, be sure to document meeting minutes. Take adequate notes. If unsure, try one of ClickUp’s meeting notes templates. Make a copy and customize them for the purpose and structure of your skip-level meetings. 

Taking your skip-level meetings one step further, ClickUp Meetings allows you to take notes, manage an agenda, and set action items. Take responsibility for action items and add them to your task management system. Set timelines and other check-ins, if needed.

Keep open communication after the meeting

Don’t wait for the next skip-level meeting. Have an open communication channel with your employees to discuss and complete action items. Use Clickup’s Chat view to collaborate on your tasks in real time.

  • Assign tasks to other team members if you’re delegating
  • Share assets, links, and more
  • Comment on the progress you’re making or challenges you’re facing

You can also create a separate window for skip-level meeting-related chats so they don’t interrupt your projects.

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Ace Your Next Skip-Level Meeting with ClickUp

Skip-level meetings offer visibility into what goes unnoticed during the day-to-day. It helps leaders understand issues more deeply. It helps employees participate better. When done right, skip-level meetings have the potential to boost employee morale, increase productivity, and create a culture of openness and transparency.

Despite its immense benefits, a skip-level meeting isn’t easy to plan, schedule, prepare for, and execute. ClickUp is here to help.

Clickup’s project management software has features to help you run effective skip-level meetings. Whether checking people’s workload, creating meeting agendas, taking notes during meetings, or automatically summarizing them, ClickUp can do them all. 

Run skip-level meetings like a pro with ClickUp. Sign up for free today!

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