At Archova, we help senior leaders and people managers build high-performing teams and drive results through practical systems and effective leadership behavior. In this article, we answer the question of how to run skip-level meetings that strengthen your organization rather than make it more political.
Skip-level meetings let you talk directly with employees who report to your direct reports. When done well, they surface information that gets filtered out on its way up. They reveal patterns long before they show up in attrition data or quality issues.
But here is what often happens
You schedule coffee with someone two levels down to get unfiltered information about how work actually happens. Sounds like a good idea, but the problem is that their manager finds out after the fact. What felt like good leadership and well-intended just taught your direct report that you’re doing things behind their back. This scenario plays out constantly, and most leaders don’t realize the damage until it’s too late.
Skip levels only work in high-trust organizations
Before you implement skip levels, you need to assess whether your organization is ready. Skip levels require leaders who are secure enough not to feel threatened by feedback or discussions about their team’s work that they are not privy to. There needs to be a shared understanding that skip-level meetings are intended to help support the team, to learn about challenges and opportunities early, and to build a culture of transparency and accountability. Without this foundational understanding and the trust that everyone involved acts in alignment with this purpose, skip levels will create the perfect conditions for distrust and defensiveness.
“Skip-levels are for the leader’s learning, not for evaluating the person you’re speaking with or bypassing their manager.”
Skip levels give you three things most leaders can’t see from the top
Let’s say three people in different parts of your org mention the same process being slow. That’s a signal, not noise. One person having a bad week is just a data point. When you hear the same friction point from three or more people in unrelated contexts, treat it as a structural problem that needs your attention. These patterns are exactly what skip levels are designed to surface.
Skip levels also make leadership visible and accessible. In organizations that have grown quickly, senior leaders can feel distant. These conversations remind people that you’re paying attention to more than dashboard metrics. They demonstrate that next-level leadership is supportive and available to individual contributors.
Plus, the best skip levels help you spot talent surprises that could be leveraged to enhance someone’s career experience. There are always people doing great work who aren’t loud about it, or whose manager hasn’t figured out how to showcase them yet. Skip levels give you a window into strengths and capabilities that don’t always show up in the usual reporting structure.
The open forum trap destroys the value immediately
Here is the big red flag: The fastest way to ruin skip levels is to schedule them without boundaries. When you don’t set clear intentions, people walk in thinking it’s a mentoring session, a venting opportunity, or a chance to complain about their manager.
Before any skip level, state the purpose explicitly in writing to both the employee and their manager. If you’re there to understand execution challenges, say that. If you’re collecting feedback on a specific initiative, make that clear upfront.
“The best conversations focus on patterns, risks, and opportunities rather than venting or evaluating individuals.”
One approach is to frame skip levels as “get to know you and your work” conversations where you’re looking for how to support the work rather than collecting information on the manager. This keeps the focus on business value while building rapport. Some organizations make these informal with coffee or a meal involved, using a few standard questions but mostly building trust and another line of communication. The key is having organic and authentic interactions so there’s real value, not theater.
Reacting in the moment teaches people to bypass their manager
What to watch out for: When someone mentions a problem in a skip level, and you immediately fix it or send an email, you’ve just shown everyone that escalating to you gets faster results than working with their actual manager. This comes from good intentions but creates terrible incentives.
Example: An employee tells you a tool doesn’t work. You email IT right away to show you’re responsive. Now everyone knows that going around their manager is more effective than following the chain.
Route all action through the manager. Say “I’m going to talk to your manager about this and they’ll follow up with you on next steps.” This keeps ownership intact and reinforces the chain of leadership. Your skip levels should strengthen the manager’s authority, not undermine it.
Now, on that same note of action. Overdoing it is as bad as underdoing it. Nothing kills credibility faster than silence after skip levels. You need visible follow-through. One effective approach used at Lockheed Martin involved senior leaders returning to the employees who were invited to skip-level meetings to report on actions taken. The leader would follow through on commitments and close the loop so participants could see real progress. About halfway through the year, HR would provide a survey to get feedback on what was working and what needed adjustment. This kind of structured follow-through turns skip levels into a tool for increasing employee engagement and retention instead of just another meeting on the calendar.
Triangulation is poison
Another behavior to watch out for is triangulation. This happens when skip levels become a way to pass feedback about someone without addressing them directly. An employee complains to you about their manager instead of having that conversation face-to-face. This breaks trust and teaches people that the way to handle difficult conversations is to avoid them and escalate sideways.
Example: Someone tells you their manager doesn’t listen to them and isn’t available. You take notes and plan to address it without the employee ever speaking to their manager first.
When someone brings feedback about their manager, your default response is to coach them to have that conversation directly. Ask “How much does your manager already know this is an issue for you?” and help them prepare to deliver the feedback themselves. The goal is to build their capability to handle difficult conversations, not to become the middleman.
“If you clearly define the purpose of the skip level and expectations, and the employee starts to share feedback about their manager, coach that person to have a conversation with their direct manager first.”
The exception is when someone fears retaliation or when you’re explicitly collecting 360 feedback and everyone knows that’s the purpose. In those cases, the process should be transparent. When skip levels are built into the culture as an organic and healthy way to collect 360 feedback, that can work well. The key is that all parties understand the goals and format so there’s no mystery about the process.
Structure matters more than frequency
I often get asked how often to hold skip-level meetings. Fortunately or unfortunately, there is no right answer for this. For new hires that are key to your department, it might make sense to have skip levels every 4-6 weeks to help them integrate and feel connected. For other employees, it might work better to meet quarterly, bi-annually or annually depending on your context and goals as well as the size of the team and your available time.
There is also no clear best practice on whether or not skip levels should be held on a regular schedule or not. Some leaders vary their approach based on what’s happening. They might prioritize certain teams in Q1 based on current work and move others to Q4. The key is being intentional rather than rigidly adhering to a calendar.
One leader shared with me that he only accepts skip-level invitations if the person confirms they’re going to teach him something he doesn’t yet know. That pre-requirement keeps the meetings focused and valuable.
Other organizations keep skip levels informal and organic rather than standing meetings. They might have one-off conversations outside standard chains of command when there’s a specific reason. There’s no single right answer on cadence as long as you’re clear about intent and consistent enough that people understand the pattern.
Three groups need different playbooks
Senior leaders: Tell managers before you schedule skip levels. Share the format and explain why you’re doing it. This is non-negotiable for maintaining trust. In the meeting, ask business-first questions about systems, patterns, and friction. Listen for themes across multiple conversations, not one-off issues. Keep conversations focused. After the meeting, close the loop quickly by sharing what you heard and what you’re doing about it. Bring managers into the follow-up or your skip levels will hurt trust instead of building it. If you’re not consistent in your approach, people start guessing why you’re meeting with them, and the whole process becomes political.
Managers: Normalize skip levels by framing them as support, not surveillance. Make sure your boss has told you the purpose and format. If you feel left out of the conversation about your employee’s growth or strategy, that comes down to the emotional intelligence of the senior person running the skip level. Ask for clarity upfront. Help your team prepare by encouraging them to think about what they want to share with the senior leader, i.e., your boss. After skip levels happen, ask your boss for a summary of themes (not verbatim quotes) so you can course correct. The key is having organic and authentic interactions so there’s real value.
Employees: Show up with business value, not complaints. Pick one specific thing that would make a difference if changed, explain where the problem shows up and what it costs, and offer one concrete suggestion. Keep your manager in the loop about what you plan to discuss. If feedback about your manager comes up that you weren’t planning to raise, mention it to them afterward. Remember that skip levels help you feel seen, heard, and valued while giving you another line of communication with senior leadership. This is your opportunity to build rapport with leaders you might not get to work with regularly and to showcase your thinking on the business.
How to apply this
Assess your organizational readiness by evaluating whether there is enough trust on the team where skip levels can be held without leading to political drama or defensiveness.
Define the purpose of your next skip level in 2-3 sentences and send it to both the employee and their manager at least a week before the meeting.
Review your last three skip levels and identify one theme that came up more than once, then decide who owns the next action and set a deadline to close the loop with participants.
