Skip-level meetings - where you meet with engineers who report to your direct reports - are one of the most valuable tools in a senior engineering manager's repertoire. They provide unfiltered insight into team health, surface problems that middle managers may miss or minimise, and demonstrate to engineers that senior leadership is accessible and interested. This guide helps you get them right.
Understanding the Purpose of Skip-Level Meetings
Skip-level meetings serve multiple purposes. They give you direct insight into team health, morale, and the effectiveness of your managers. They give engineers access to senior leadership and a channel for concerns that may not surface through normal reporting lines. And they help you calibrate performance assessments by hearing directly from the people doing the work.
The most important purpose, however, is relationship building. Engineers who have a personal connection with senior leadership are more engaged, more trusting of organisational decisions, and more likely to raise concerns early rather than letting them fester. These relationships are an investment in organisational health.
Setting Up Skip-Level Meetings Effectively
Schedule skip-level meetings regularly - monthly or bi-monthly for each engineer. Consistency matters because it takes time to build the trust needed for candid conversations. Sporadic or one-off skip-levels feel more like investigations than relationship building.
Be transparent with your direct reports about the purpose and format of skip-level meetings. Reassure them that the goal is not to check up on their management but to build broader relationships and gather diverse perspectives. Managers who feel threatened by skip-levels may try to coach their reports on what to say, which defeats the purpose.
Keep the meetings relatively short - 20 to 30 minutes - and informal. This is not a performance review or a status update. It is a conversation about the engineer's experience, their perspectives on the team, and their career aspirations.
Asking the Right Questions in Skip-Level Meetings
Start with open-ended questions that invite genuine reflection: 'What is the most frustrating thing about working on your team right now?' 'What would you change about how we work if you could change one thing?' 'Do you feel like you are growing in your role?' These questions signal that you want honest answers, not polished reports.
Ask about the engineer's career aspirations and whether they feel supported in pursuing them. This gives you insight into whether your managers are investing in their reports' development and whether the organisation is providing adequate growth opportunities.
Avoid questions that put the engineer in an uncomfortable position regarding their direct manager. 'Do you think your manager is doing a good job?' is too direct and puts the engineer in a loyalty bind. Instead, ask about their experience - 'Do you feel like you get the feedback and support you need to do your best work?' - which surfaces the same information without the confrontation.
Handling Sensitive Feedback Appropriately
When an engineer shares concerns about their direct manager, listen carefully and ask clarifying questions. Determine whether the issue is a management problem that needs to be addressed, a communication gap that can be bridged, or a difference in perspective that is normal and healthy.
Be clear about confidentiality. If an engineer shares something sensitive, discuss with them how you plan to handle it before taking action. Blindly escalating concerns can damage the trust you have built and discourage future candour. Sometimes the right action is coaching the manager without revealing the source; other times, the engineer may be comfortable with a more direct approach.
Follow through on what you learn. If patterns emerge across multiple skip-level conversations - for example, several engineers expressing frustration with unclear priorities - address the systemic issue. Engineers will quickly stop sharing honest feedback if they see that their input leads to no change.
Avoiding Common Skip-Level Pitfalls
Do not use skip-level meetings to assign work, redirect priorities, or give instructions that bypass the direct manager. This undermines the manager's authority and creates confusion about who is directing the engineer's work.
Avoid creating a 'court of appeal' dynamic where engineers learn they can escalate to you whenever they disagree with their manager's decisions. If an engineer brings a disagreement to you, encourage them to resolve it with their manager first, and only intervene if the issue is genuinely unresolvable.
Share general themes from skip-level meetings with your direct reports without attributing specific comments to individuals. This helps managers understand their teams' experiences while maintaining confidentiality. If a manager receives aggregated feedback that 'several engineers feel unclear about priorities,' they can address it without anyone being singled out.
Key Takeaways
- Skip-level meetings provide unfiltered insight into team health and build senior leadership relationships
- Schedule them consistently and keep them informal - 20 to 30 minutes, monthly or bi-monthly
- Ask open-ended questions about experience and growth rather than putting engineers in loyalty binds
- Handle sensitive feedback with care, clarity about confidentiality, and consistent follow-through
- Avoid undermining direct managers by assigning work, redirecting priorities, or creating appeal dynamics
Frequently Asked Questions
- What if my direct report is uncomfortable with me having skip-level meetings?
- Address their concerns directly and empathetically. Explain that skip-levels are a standard practice that benefits the entire organisation, not a reflection of distrust in their management. Offer to share the general themes you hear (without attributing specific comments) and reassure them that you will not make decisions about their team without involving them. If they remain uncomfortable, that itself may be a signal worth exploring.
- How do I handle an engineer who uses the skip-level to complain about their manager?
- Listen to understand whether the complaint reflects a genuine management issue or a normal interpersonal friction. Ask clarifying questions and encourage the engineer to address the concern directly with their manager first. If the complaint reveals a pattern or a serious problem, address it with the manager as a coaching opportunity. Make clear that skip-levels are not a substitute for direct communication with their manager.
- How many skip-level meetings should I have?
- This depends on your organisation's size. As a rule of thumb, you should have skip-level meetings with every engineer who reports to your direct reports. If this creates an unmanageable number of meetings, prioritise: meet with each engineer at least quarterly, and increase frequency for new hires, engineers going through transitions, or teams where you sense issues. The goal is breadth of coverage, not depth of every conversation.
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