Communicate transparently with the employee's direct manager that you will be conducting a skip-level meeting, explaining the purpose and that it is a standard leadership practice, not a reflection of concern about their management.

Familiarize yourself with the employee's position, tenure, current projects, and recent performance highlights so you can have an informed and meaningful conversation that demonstrates genuine interest in their work.

Develop five to eight thoughtful, open-ended questions that invite honest dialogue about the employee's experience with their team, their manager, the organization's culture, and their career aspirations.

Define what you want to learn from this meeting and share a brief agenda with the employee beforehand. Clarify that the purpose is to build connection, gather candid feedback, and understand their perspective.

Choose an informal, private setting for the meeting. Consider having coffee or taking a walking meeting to reduce formality and power dynamics that might inhibit open and honest conversation.

Inquire about how the team is feeling collectively, whether the culture feels supportive and collaborative, and if there are any undercurrents of frustration, confusion, or disengagement that leadership should be aware of.

Ask whether the employee feels well-informed about company direction, team decisions, and changes that affect their work. Identify any communication gaps between leadership and front-line employees.

Understand how well the team members work together, whether there are any silos, conflict, or collaboration challenges, and what could be done to strengthen team cohesion and productivity.

Ask the employee whether the organization's stated values are reflected in day-to-day operations, management decisions, and team behavior, or if there are disconnects between what is said and what is practiced.

Probe for organizational barriers such as bureaucratic processes, unclear decision-making authority, inadequate tooling, or misaligned incentives that are preventing the team from performing at their best.

Explore whether the employee feels their direct manager provides adequate guidance, removes obstacles, gives them appropriate autonomy, and creates an environment where they can do their best work.

Ask the employee whether they receive regular, specific, and actionable feedback from their manager, and whether their manager invests time in coaching their professional development and career growth.

Gently probe whether the employee perceives their manager's decisions about work assignments, recognition, performance evaluations, and opportunities as fair, transparent, and consistent across the team.

Ask whether the manager is approachable, responsive, and communicates effectively. Understand if the employee feels comfortable raising concerns, asking questions, or challenging ideas with their direct manager.

Assess how well the employee understands the organization's strategic direction, their team's role in achieving it, and whether they feel their individual work connects meaningfully to the bigger picture.

Ask about the employee's career goals and whether they see a viable path for growth within the organization. Understand what opportunities or experiences they feel would accelerate their development.

Pose this question to surface the employee's highest-priority concern or suggestion. The simplicity of asking for one change often elicits the most honest and impactful feedback.

Ask what senior leadership could do differently to improve the employee's and the team's effectiveness, whether it is better communication, resource allocation, strategic clarity, or removing organizational barriers.

Give the employee a platform to share creative ideas, process improvements, or innovations they have been thinking about. Demonstrating interest in their ideas builds engagement and may surface valuable insights.

Express genuine appreciation for the employee's time and honesty. Reinforce that their feedback is valuable, will be taken seriously, and that they should feel comfortable reaching out to you in the future.

After the meeting, record the main themes, concerns, suggestions, and positive observations shared by the employee. Distinguish between individual feedback and systemic issues that affect the broader team.

Communicate relevant themes to the direct manager in a way that is constructive and aggregated, without attributing specific comments to the employee. Frame feedback as development opportunities rather than criticisms.

For systemic issues raised during the skip-level meeting, develop a concrete action plan with timelines and owners. Communicate back to the employee that their feedback led to specific actions being taken.

Set a follow-up skip-level meeting, typically quarterly, to build an ongoing relationship with the employee and demonstrate that these conversations are a sustained leadership practice, not a one-time event.