BL&T No. 124: Rethinking Skip-Level Meetings

Agency Leadership

This post originally appeared in my newsletter, Borrowed, Learned, & Thought. BL&T is sent weekly on Mondays. In every edition, I share lessons learned in agency leadership, life, and e-commerce. This post does not include all the details shared in the newsletter sent via email. Subscribe here.


"My friend Mark Rabkin shared a tip with me that I love: strive for all your one-on-one meetings to feel a little awkward. Why? Because the most important and meaningful conversations have that characteristic. It isn’t easy to discuss mistakes, confront tensions, or talk about deep fears or secret hopes, but no strong relationship can be built on superficial pleasantries alone."

From "The Making of a Manager: What to Do When Everyone Looks to You" by Julie Zhuo [Book]


In Edition No. 057 of this newsletter (October 2021), I reflected on feeling like I was losing touch with the team and clients. In addition to introducing the executive sponsor role, I started running skip-level meetings with my team. At the time, I wrote:

This week, I'm introducing skip-level meetings. With the permission of the managers on my team, I will be meeting with each of their direct reports on a regular basis. In the meetings, I'll ask questions about how clear they are on our vision for the future, what they're excited about / not feeling great about, and give them room to ask questions on their mind. My hope is to strengthen my connection with the team and:

  • Gather feedback
  • Create greater alignment on our vision
  • Hear their thoughts on higher level leadership topics

Like executive sponsors, skip-level meetings have proven to be an effective way of staying connected to the day-to-day and team experience. While we want team members to feel comfortable sharing their thoughts with their manager, they have appreciated this channel to discuss their experience within the agency more broadly. So far, insights in these meetings have led to insights on client projects, new opportunities for team members, changes in how we work, and initiatives among management.

When I rolled out skip-level meetings just over a year ago, I focused on meeting with the direct reports of the managers reporting to me. Not only has my role expanded to all teams, but I've learned that making time for these discussions across the entire team would have been worthwhile from the start.


The main challenge with skip-level meetings has been coordinating them. When I started having these meetings, my approach was to set up recurring meetings. At first, this worked fine, but as folks moved on and others joined, it became difficult to manage. Meeting with everyone on the team will make this even more complicated.

Starting in February, my plan is to cancel all my recurring skip-level meetings and set up a weekly event on my calendar. Each week, I'll schedule time with someone from the team, referencing a spreadsheet with all team member names listed. Given the team size, I'll aim to chat with everyone every four months vs. my original plan of quarterly meetings.

In addition to changing how I schedule skip-level meetings, I'll also start reminding everyone about the meeting agenda ahead of time. Currently, we just jump on Zoom and begin chatting. While I've enjoyed the casual discussions, I expect that giving people more time to think could only yield better insights.

If you're considering running a similar meeting with your team, below is my agenda for reference.


I start every meeting with a few minutes of catching up: How are you doing? Whats new? How is life outside of work?

I've enjoyed making this time to take a step back and learn more about the team member's pursuits outside of work. For example, a designer recently told me her experience getting back into muay thai and how what she's learning in class has been helpful at work.

After catching up, I ask if there's anything on the team member's agenda. Sometimes, I have a topic to discuss, too. If we surface anything here, we may spend the rest of the meeting digging in together. If not, I jump into my list of questions, covering whatever questions feel most relevant.

  • How are you feeling about your current workload? projects? role?
  • Do you feel like you're growing in your role? Is your progress aligned with your career goals?
  • When have you been most proud of your work and being on the team this quarter? What has been most challenging?
  • What advice would you give to the leadership team about making the company better?
  • How has your relationship with your manager been helpful? Any areas of feedback?
  • Could I be doing a better job outlining the vision and direction for where we’re headed?
  • As a company, do you think we’re behind the curve on anything in particular?
  • What are you most excited about going into the next 3 months? Least excited about?

With about 5 minutes left in the meeting, we align on any next steps and follow-ups.

As a side note, I keep notes from every discussion. These have been great to reference from meeting to meeting. In some cases, I may also review notes with the team member's manager (with their approval) if there is an issue to address.

Thought Starter

What can I do to get more connected to my team and gather feedback?


The E-Commerce Corner

In a recent website audit, we saw customers abandoning the client’s cart to explore other product categories then never checking out. The cart currently looks like the rest of the site with full navigation and featured product categories. Simplifying the cart and keeping it as a designated page for external linking is a worthwhile update; however, introducing a mini-cart slide-out is a more effective way to drive conversion. Mini-carts allow customers to browse with ease and when they’re ready to purchase, make checking out feel seamless.

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