Skip-Level One-On-Ones: Skip Them of Keep Them?

Problem

"When you are struggling with too many reports you are most likely to hire new managers -- either by promoting them internally or hiring externally. The immediate sense of relief that is a result of the delegation of responsibilities might be tainted with the feeling of disconnection that appears as your engineers begin to report to their new EM. Engineers are not only coping with adjusting to the new structure and becoming familiar with a new manager, but they may also feel the same disconnection. On top of that, you are curious about how effective new EMs are, are they up to the task and will they be able to manage the team effectively? Also, will you be able to have an insight into the operational side of the work."

"The immediate sense of relief that is a result of the delegation of responsibilities might be tainted with the feeling of disconnection."

Actions taken

"I could have kept the original one-on-ones with my past direct reports. However, that would be immensely time-consuming and would hinder me from doing other things that I should be doing. In addition, it would also be -- though less -- time-consuming for your engineers who would have not one, but two one-on-ones. More importantly, by surpassing EMs you would effectively undermine their authority as they have been hired to manage the team instead of you."

"By surpassing EMs you would effectively undermine their authority as they have been hired to manage the team instead of you."

"To avoid that, I canceled all my one-on-ones with the skip-level and instead introduced the Open Doors. In pre-Coronavirus pandemics times, I would meet people during the Open Doors in person, and now I try to be as welcoming using remote tools. Overall I’ve been practicing the Open Doors for over a year and it proved to be highly successful."

"I canceled all my one-on-ones with the skip-level and instead introduced the Open Doors."

"Canceling one-on-ones was not an easy thing to do. I didn’t want my engineers to feel abandoned and I sent out an email showing my appreciation of their time and the new relationship they established with their new manager. I also explained to them that I was still around to help but without intention to interfere."

"I didn’t want my engineers to feel abandoned and I sent out an email showing my appreciation of their time and the new relationship they established with their new manager."

"I realized that multiple one-on-ones could be distracting as well as imposing, so I proposed the concept of the Open Doors. Once per month, I would free up some time to invite five to six people to this, entirely voluntary, event. In pre-Coronavirus times, I would be in my office or any other available room and people would stop by if they felt like talking to me. If I would be talking with someone else, they could inquire if it was something more business-related like discussing a new feature and then, they could join in, or if it was something more personal than they should wait. Also, if during the Open Doors we would stumble upon a problem that would require a longer, more private conversation to take place I would gladly schedule a one-on-one meeting."

"I proposed the concept of the Open Doors. Once per month, I would free up some time to invite five to six people to this, entirely voluntary, event."

"The Open Doors turned out to be highly time-efficient and also allowed me to keep up with people and not become detached from them and problems they were encountering. What sometimes happens -- and that happens more often as you climb up the ranks -- is that your managers would report only good things to you. You can minimize this by staying close to the ground and being aware of the potential problems in their early stages. EMs sometimes mistakenly believe that they could solve those problems by themselves without understanding all the ramifications or would just rather cover their mistakes up. There is no need for one-on-ones to avoid this -- an informal chat with your engineers now and then would perfectly do."

"The Open Doors turned out to be highly time-efficient and also allowed me to keep up with people and not become detached from them and problems they were encountering."

Lessons learned

• Try to stay as close to your engineers but be considerate of your and their time.
• Find a format that would fit both you and your engineers. Initially, I tried 15 minutes-long one-on-ones that, though worked for me, didn’t work for my engineers. They found the fixed schedule and infrequent occurrence impractical, so I decided to come up with something less time-bounding and more frequent.
• As a leader, never rely only on your direct reports to tell you what is working and what is not. Talk to your engineers on the ground who can identify problems in their early stages.