Joint Skip-Level Meetings

Problem

I had a team under me of high-performing entry-level people who I wanted to keep engaged and motivated. I also wanted to create opportunities for them to learn and grow. Joint skip-level meetings between frontline people and me turned into venues that galvanized the team, made them more productive, and helped them with their career growth.

Actions taken

First off, I had to intentionally leave out the middle management layer who were their immediate supervisors and who were doing their performance reviews. If the middle layer would be included, the group might be hesitant to ask questions. Also, by excluding them, I eliminated most of the boss-employee relationship. I would often be unaware of what the middle management would say, and if my answer contradicted theirs, my group of entry-level people would bring it up, and we could together discuss the disparity. But, I would never give a conflicting direction or undermine the middle layer’s authority.

I named our joint skip-level meetings “Team Collaboration Meetings” as they were atypical staff meetings targeting early-career people. These events were essentially biweekly fora where entry-level PMs would have access to someone at the executive level to stir up their interest, allow them to ask questions, and encourage them to grow further. Our discussions were diverse and engaging; we would talk about what they learned in the last two weeks or what new skills they wanted to acquire. I would also have them identify their peers who were doing great in some areas, and people who were struggling in those areas would connect with them. That would allow people not just to share what they learned but to teach others and elevate anyone else on the team.

We would also discuss their challenges and pain points. I would often ask them if they understood why they were doing what they were doing. They would bring up their day-to-day concerns like, How I make sure that engineers would understand my user story or How to gain trust by a senior architect who is 20 years senior, and I would help them frame their conversations.

After a while, we also incorporated a reading club session where we would dissect the books I thought every product person should read. For example, I organized debates to get into details of How to win friends and influence people, a seminal book by Dale Carnegie. Every time we would meet, we would review a couple of chapters, and someone would give a synopsis of a chapter debate.

Our joint skip-levels became incredibly successful, and people were looking forward to it. They knew they could ask any question and get an honest answer on business, product, or customers. It didn’t take too much effort on my part to put it together, but that team thrived because of the interaction they had with someone on the executive level. They were developing fast, were super effective, and that didn’t get unnoticed by the C-level executives who were wondering what my approach was. Many of my early-career PMs moved on, and their careers propelled quickly. I had fresh grads who would become senior PMs within three years and who were able to put their skills to the test.

Lessons learned

• I did it free-form and could probably have used a bit more structure with the meeting. I allowed team members to nominate topics for discussions in advance, and I would be able to come prepared with data or else. Letting them drive the topics -- and me being along for the ride -- was more beneficial than me telling them what they should ask and learn.
• You should commit to building a good working relationship with one level down because when something bad happens, they won’t be afraid to walk into your office and have a candid conversation. Some people told me that they never talked to their VP before. Having an open-door policy is not about having it for the sake of it, but having it so that people can use it. I never wanted to be one of those off-limits executives, but one of those executives who are opening lines of communication.
• By leaving the middle management out of the equation, I wanted to create a space for entry-level PMs to raise their concerns. With their bosses present, they would be reluctant to do so. I wanted them to have a facetime with me and to see where certain decisions are coming from.