The Art of Skip-Level Meetings: Purpose, Pitfalls, and Best Practices

Leaders understand the importance of effective communication within an organization and how easily the real message becomes diluted as it trickles down the management chain. 

But what if there was a way to bridge the gap between executives, managers, and employees? 

Skip-level meetings are exactly that. These meetings aim to enhance communication, foster employee engagement, and drive organizational performance. 

Purpose of Skip-Level Meetings 

Unlike traditional one-on-ones, skip-level meetings intentionally bypass the immediate supervisor, allowing senior leaders to connect directly with staff at least two levels below them and enable them to directly acquire feedback. 

Goals of Skip-Level Meetings 

If executed correctly, the skip-level meeting is designed to: 

Build Trust: Mutual trust is accomplished through intentional engagement, such as candid, transparent conversations, and feedback on concerns and actions, with lower-level employees. 

Gain Insight: An astute leader will be able to understand their team’s dynamics and unique challenges and gauge morale, motivation, and trust. 

Support Teams: With more trust and insight, senior leaders can better address concerns, offer guidance, and align vision and impact across the organization. 

Benefits of Skip-Level Meetings 

Some of the obvious benefits of these conversations, when done on a regular basis, include: 

Employee Engagement: Lower-level employees feel valued and appreciated by attentive and interested senior leaders. The conversations allow for a better understanding of what life is like in the trenches and assure employees that management is listening and aware, leading to a more connected and involved workforce. 

Productivity Lift: The increased engagement resulting from regular, well-executed skip-levels leads to more productive employees, which, in turn, positively impacts the bottom line. 

Talent Identification: Personal involvement at lower levels exposes senior leaders to potential talent, resulting in nurturing and developing their team within the organization. 

Unintended Consequences 

Unfortunately, poorly conducted skip-levels can work against the very goals they were designed to achieve.  

Threatened Middle Management: Leaders may find it tempting to conduct these discussions more like an inquisition and come across as “checking up” on the intermediate manager. In this case, the conversation destroys the manager’s authority and credibility and puts the employee in an inappropriate place of power. They may believe their responses could either get their manager in trouble or get themselves in trouble. If this happens, the employee will not share openly or abuse the opportunity to improve their performance. 

If there are concerns about the intermediate manager, the fact that a skip-level is happening can put them in a defensive and uncomfortable position. Leaders must be clear about the practice of skip-levels with their direct reports and encourage their input on what topics to discuss. The important piece here is not to give the impression that these meetings attempt to bypass the employee’s immediate supervisor but to listen, learn, and support. 

Unrealistic Expectations: A leader must walk a thin line of concern and interest with promises to act. The intent is to get a better bottoms-up view of the team and its management without throwing anyone under the bus. The focus on questions like: 

Just as important are those same questions in reverse. Affirming the employee on what you see them doing well and how it helps you in your role is incredibly empowering. Telling them what you need from them individually and as a team so you can do your job better will get you better information and create a relationship and reputation as a leader who listens and recognizes the team’s value to your organization. 

Devaluing the Employee: Under the pressure of daily business, the temptation to postpone or cancel meetings can be intense. However, the message this sends to employees is that they aren’t important. 

Even more, the employee sees it as a personal devaluation and a statement about their priority with you.  

Likewise, if you commit to an action, make sure you circle back with them with an update. If no progress has been made in a while, it is even more important to let them know that you haven’t forgotten but aren’t making the progress you expected. Essentially, follow up with them as you expect them to do with you. Anything less, and you can destroy months of trust-building.  

Common Mistakes to Avoid 

Lack of Preparation: Failure to plan discussion topics and questions leads to unproductive meetings and sends a message that the meeting is not important. Part of planning is understanding who you will be talking to. Talk to their immediate supervisor. Be sure of their role and responsibilities, what they do well, and what they contribute to the team. Use this opportunity to discover more about their aspirations and development opportunities. 

Lack of Follow-up: As mentioned earlier, nothing speaks more loudly about your commitment than follow-up. If you say you will do something, model the accountability you need from your team and show yourself trustworthy. 

Cancellations: Regularly canceling skip-level meetings sends a negative message. Prioritize these commitments to maintain trust and transparency. Resist this temptation at all costs. If you must reschedule, make it personal.  Do it yourself rather than pass it off to your assistant.     

Investigation: Questions are important for good conversation and providing insight. However, if the questions sound probing or more like an inquisition rather than a genuine interest in understanding the employee’s situation, it can create a very uncomfortable experience. The employee will be guarded in their answers, wary of what you will do with the information and how it will reflect on them. Use open-ended questions that focus on helping the employee be successful. 

Best Practices to Master Skip-Level Meetings

Create a Welcoming Environment: Meeting with a senior manager can be intimidating. It is up to you to put the employee at ease. Be relatable and approachable. Keep your scheduled appointment and be on time. 

Ask Open-Ended Questions: Encourage open dialogue by asking questions that invite them to show their best. Then, work into the concerns, but from the perspective of improvement, not fault-finding. In return, provide feedback to them about what you see in them personally, the team, and what you need to do your job better.  

Avoid Triangulation: It’s not uncommon for concerns or issues about others to bubble up in the conversation. Avoid getting in the middle and encourage them to address the issue directly with the people involved.   

Follow-up: We have already emphasized the importance of the leader following up on the commitments made, but it is equally important that the employee do the same. Note any commitments made and agree on a follow-up date before concluding the meeting. If neither party has provided a timely update, assure the employee that it is okay to check in with you regarding the status. Accountability goes both ways. 

Embrace these meetings and see your team become more connected, more productive, more satisfied, and far less likely to leave. 

If you are uncertain on where to begin, you can schedule a call with us and we can discuss and guide you on taking the first step.  

Book a Call with KMP Consultants