4 Pitfalls of Skip-Level Meetings

marc davis
5 min readMar 16, 2016

Skip-level meetings, where a manager meets with employees that indirectly report to him or her (e.g. employees reporting to managers that report to this manager), can offer many benefits, including:

  • Insights into the organization that may not have been visible to the manager previously.
  • A different perspective on his/her direct reports.
  • An ability to build real rapport with folks deeper in the organization (which can have many unforeseen benefits down the road.)
  • Deeper understanding of what work is getting done in your org, and where possible opportunities lie.

However, skip-level meetings come with their own unique set of challenges. Below I’ve compiled a list of four pitfalls you’ll want to be aware of as you consider setting up skip-levels.

Pitfall #1: Beware of hidden agendas.

Most employees you meet with will be sincere and genuine, but every now and then you may encounter someone with a hidden agenda. I once had skip-levels with an employee who was actually gunning for the job of his manager, and tried to use our discussions to his advantage. For example, he would “innocently” ask about a certain idea that his manager had nixed (unbeknownst to me), and if I voiced some casual interest in it, he would then meet with his manager and tell him that I had approved the idea. While this may be a somewhat extreme example, it makes a broader point.

Pitfall #2: Watch out for inequity perceptions.

Some managers may have dozens (or more) of employees reporting up through their org. Even meeting with each employee just once per month for 30 minutes could consume substantial bandwidth on your calendar. It becomes very tempting to “pick and choose” who to meet with based on factors ranging from likability, perceived competence, functional interest, and so on. However, if you start down this path, be aware that other employees will notice, and it will become an issue.

If you have too many folks to easily handle within your current calendar constraints, you have a few basic options, including: 1) reducing meeting lengths from 30 minutes to 15 minutes; 2) reducing the frequency of meetings (say from 1x per month to 1x per 6 weeks); 3) rotating by groups of people (for example, during one quarter, you meet with 2 people from each group you manage; then the next quarter, you meet with 2 different ones.) To make this work, you’ll need to explain the policy up-front to your teams. Also, this third option suffers from creating longer periods where you don’t have interaction with portions of your team.

Pitfall #3: Take care you don’t issue accidental orders.

While this may seem like a similar subject to “beware the manipulator”, it’s actually quite different. As a leader in your org, employees automatically presume that you have significant knowledge, experience and wisdom, and it makes perfect sense that they’d want to tap into it. So they’ll often use you as a sounding board to bounce ideas off of. I’ve had several instances where a well-intentioned employee ran an idea by me, and I might have said something like “that sounds neat!”. Unfortunately, these employees then went ahead and started to implement these ideas without first running them by their own managers. This resulted in my managers feeling that either I was undermining their authority, or that their employees were.

While not providing your opinion is a non-starter (if you have to wear a “feedback straight-jacket” then what’s the point?), you do have to be careful about how what you say gets interpreted. What I’ll typically do is say something like “That sounds like a great idea, but that’s just my 2 cents. Go ahead and run it by your manager, and get his/her take, as she owns the decision here.” In certain cases (depending upon the idea and also the employee), I may also drop a note to that employee’s manager saying something like, “Hey, in my 1:1 with Sue, she ran an idea by me (e.g. “new product feature”). I thought it had merit, but told her to sync with you. Your call.”

Pitfall #4: Be very careful on how you handle employee feedback on their own manager.

Sometimes during a skip-level, you’ll receive unsolicited feedback from a team member regarding his or her manager. While the purpose of skip-levels isn’t to spy on your own directs, these meetings can provide excellent insights into how to continue to grow your own directs’ managerial capabilities.

However, you need to be careful about how you bring any such feedback back to the manager in question. If it’s something that the employee should/can be addressing directly with his or her manager, I’ll definitely encourage them to do so. However, if it’s a problem that isn’t resolving, or something where the employee doesn’t feel comfortable taking it directly with her boss, then you’ll have to figure out the best approach.

Some other useful tips:

  1. Also think about meeting with people in other groups you work closely with (for example, a product director may decide to grab coffee with some some of the software developers.)
  2. Keep the meetings informal; I prefer to go for walk-and-talks (versus sitting down in a room, which can be more formal)
  3. Vary the agenda. Sometimes you can talk about business, but I’ll often explore their personal side, and also share details about my own personal life. A major benefit of skip levels is the opportunity to form real connections.
  4. Be aware of the “opening up” index. Some folks are naturally more forward and willing to open up. Others will only convey “Everything’s great.” People that are high on the “opening up” scale are invaluable, as they can provide real insight into organizational dynamics. People on the other end of the scale may either have a trust issue (which can be addressed over time), or simply have a philosophy that nothing good ever comes from opening up to senior management (perhaps rooted in their real experiences!) For that latter type, you’ll want to invest additional time building trust, but also listen very carefully, as there may be indirect hints of problems that need addressing.