5 Helpful Questions to ask in your next Skip-Level Meeting

Published on
September 28, 2023

Skip-level meetings are an important tool for keeping your whole team aligned from the top down. A skip-level meeting is when you meet with your boss's boss, or members of senior management. Sometimes it’s a 1:1, or sometimes your manager's leader will meet with the whole team of direct reports at the same time. It’s called a skip-level meeting because your direct manager usually isn’t part of the meeting. 

The purpose of a skip level meeting is to facilitate communication across different levels of your team, from executive leadership directly to individual contributors. This is a chance for you to get to ask your boss’s boss big picture questions about the projects you’re working on and how they fit into the overall direction of the company. But sometimes it’s hard to think of what to say. Especially your boss’s boss is not someone you interact with regularly. 

Don’t worry, we’ve got your back. In this article we’ll share 5 insightful questions you can take to your next skip-level meeting that are sure to spark some thought-provoking conversations. Plus, you might even earn bonus points for showing up extra-prepared for the meeting. We also have some expert tips to fine-tune your approach, so your next skip-level meeting can be helpful and effective for everyone involved. 

Benefits of skip-level meetings for employees

Skip-level meetings — those unique interactions you have with your boss's boss or senior management — aren't just about catching up on the latest office gossip or building rapport. In Agile environments, they're goldmines for enhancing collaboration, boosting engagement, and refining decision-making processes within teams. 

Opportunity for building relationships

Ever wished you had a direct line to those making the big decisions? Skip-level meetings give you just that. Whether they are one-on-one meetings or group meetings with high-performing teams, skip-level meetings are great for employees.

They create a platform for employees to personally connect with higher-up managers, bridging the usual gaps. Building these relationships isn’t just about networking; it’s about fostering a more unified, cohesive, and super-productive Agile environment. The closer the ties with your direct manager and upper management, the stronger the teamwork overall.

Increased employee engagement

Holding a skip-level meeting where employees can talk and ask questions with top-level leaders is a great way to boost engagement. When your team feels like they have a voice, and their questions and opinions are valued, it unlocks a deeper sense of ownership in the organization.

And as every good leader knows, when employees are engaged, they’re not just checking boxes. They’re brainstorming, innovating, and proactively problem-solving. It's like unlocking a superpower you never knew your team had!

Open and informed decision-making

Remember playing the game Telephone and laughing at how distorted the message became by the end? Now imagine that in a business context—yikes! 

But here's the good news: skip-level meetings can be your direct line of accurate communication. The questions you ask in skip-level meetings can give you crucial insights that shape well-informed decisions. 

Better communication culture

The ripple effects of skip-level meetings are profound. Bad meetings can cause a disconnect, while good meetings can unlock new potential and be a driving force of productivity.

Beyond the immediate benefits of direct communication, skip-level meetings plant the seeds for a culture rooted in open communication and transparency across all levels of the team, and even your whole organization. Better alignment leads to smoother interactions, fewer hiccups, and teams that vibe together. 

5 questions to ask senior leaders in your next skip-level meeting

Now that you know more about skip-level meetings and how they can drive alignment, let’s get you prepared with some great questions to ask the next time you meet with your boss’s boss. Targeted questions promote clear communication and help ground the meeting in a central purpose. And especially in Agile environments, effective communication is crucial to efficient processes and seamless operations.

Here are five questions to consider asking:

1. How does the company’s overall strategy align with the priorities of our team's current sprint or work cycle?

Understanding the connection between the company's macro-strategy and a team's micro-tasks is essential. This question ensures that the team's efforts are in sync with the broader organizational goals, steering clear of counterproductive efforts. 

When a team knows how their current sprint or work cycle fits into the bigger picture, it not only motivates but also channels their focus in the right direction. It's about ensuring that every ounce of effort counts.

2. Are there any changes in the organization's strategic direction that might impact our team's backlog?

Agile is all about flexibility and adaptability. By posing this question, teams can stay ahead of the curve, understanding and anticipating changes that might influence their backlog. Knowledge of upcoming shifts or adjustments allows for proactive planning, ensuring that the team remains resilient and adaptable. 

This not only ensures continuity in the face of strategic changes but also positions the team as forward-thinking and prepared.

3. How can we ensure a strong feedback loop between our Scrum team and the product owner?

A robust feedback mechanism is crucial to driving the Agile development process. Asking this question emphasizes the desire for effective collaboration and communication between the Scrum team and the product owner. Strong feedback loops mean that iterations are informed, user-centric, and aligned with stakeholder expectations. This not only optimizes product development but also fosters a culture of continuous improvement.

4. Are there any company goals or initiatives that may impact our team's ability to deliver value consistently during sprints?

Potential roadblocks or disruptions, if left unchecked, can derail even the most well-planned sprints. 

This question is about identifying those external factors or company-wide initiatives early on. By addressing potential hurdles, teams can strategize, recalibrate, and ensure consistent value delivery during sprints. It's a proactive approach to navigating the complex corporate landscape while staying on track.

5. How can our Scrum team better collaborate with other teams to streamline processes?

Agile teams know: you always want to try to avoid working in silos, because collaboration and alignment are essential for success. Asking this question underscores the importance of cross-functional collaboration, breaking down barriers, and fostering inter-team synergies. 

Collaborative efforts can unlock efficiencies, promote knowledge sharing, and reduce redundancies. By seeking ways to enhance inter-team collaboration, be it additional tools or different structuring, Scrum teams can pave the way for streamlined processes, reduced bottlenecks, and a harmonized work environment.

Tips for employees to help create more effective skip-level meetings

While skip-level meetings offer an incredible opportunity for direct communication with senior leaders, remember: everyone has to work together to make these conversations productive and successful. Your preparation and active participation can turn these meetings from good to outstanding. With that in mind, let’s explore some ways you can get the most out of your next skip-level meeting:

Clarify your goals

Before stepping into the room (or logging into that Zoom call), have a crystal-clear understanding of what you aim to achieve. By setting personal goals, you're giving direction to your contributions. An easy way to do this is with Spinach. Having an AI-powered meeting assistant on your side can help you outline what you plan to say, making it easier to communicate your main goals.

Prepare questions

Coming armed with well-thought-out questions can drastically improve the quality of your skip-level meetings. Not only does it show you're engaged, but it ensures you get the most out of your time with senior leadership. 

Overwhelmed about organizing your thoughts? Spinach can streamline your meeting prep, so you can focus on being present in the conversation, not shuffling through notes or losing track of what you wanted to say.

Be confident

Putting yourself out there can be daunting, but remember, your perspective is valuable! Stand tall, speak confidently, and express your ideas. Plus, you’ll have a confidence boost knowing Spinach has your back, with a structured agenda ready to go, so you'll always know what’s coming next.

Provide examples or suggestions

The power of concrete examples or suggestions can't be understated. They not only make your points clearer but also show you’re invested in the solution. To add an extra layer of gravitas to your suggestions, Spinach can pitch in with data-driven insights, giving you an edge in proposing actionable Agile improvements.

Use Spinach to make skip-level meetings more simple

Your time is valuable, especially on a busy Agile team, and if you take time to have a meeting, you want it to be productive and effective for everyone involved. And remember, in skip-level meetings, everyone plays a pivotal role in driving the conversation, from senior leadership to individual contributors, and everyone in between. By preparing the right questions and confidently voicing ideas, you can elevate the outcome of your next skip-level meeting and drive better communication across your team. 

And with Spinach as your AI-powered meeting assistant, your next skip-level meeting will be a breeze. Spinach can simplify your preparation process by helping you organize your questions and agenda items. Plus, you won’t have to worry about taking notes! You can focus on being actively engaged in the conversation, and Spinach will give you smart meeting notes and insights right after your meeting ends. 

Ready to transform all of your meetings? For a seamless, informed, and efficient approach, check out Spinach today!

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