1:1 meetings for CEO's

As a CEO, you will be asked to join a lot of meetings. When the company is small, information flows surprisingly well and freely. The alignment you have with the entire company can be quite strong. As the company scales, communication becomes harder. Depending on the scale of the company, it may feel like the CEO job evolves to an endless bounce from meeting to meeting. You might even debate how useful some of these meetings are, but, from an ROI standpoint, perhaps the most valuable meetings become your set of 1:1 meetings with your direct reports. While there is no perfect way to run a 1:1, I thought I would share a primer on how to think about these meetings. 

What is the 1:1 meeting: your direct report 1 on 1 is the recurring catch up. This meeting should be owned by your direct report and ideally they are driving the meeting. There are many meetings / ways that you can communicate information down in the organization. This meeting is the closing of that feedback loop - it is their time to share feedback with you and in doing so, it allows you to understand where there is or is not alignment in the organization. Often you will have items you want to discuss but try to cover your items after they have been able to get through their list. 

Ideally this meeting is a standing recurring event so that it can be easily scheduled around and so that adequate prep can be done beforehand. Your report can decide to skip the meeting if the agenda is light but avoid endless rescheduling as it could build a perception that the report’s time or role is not valued in the company. 

At the early stages of the company and when you are building trust with your direct reports, the 1:1 should be weekly. As the company matures, you can experiment with every two weeks - though you may find that it is easier to keep a weekly schedule and skip whenever needed. As a side note, I think CEO’s should also do skip-level 1:1’s at a regular interval - perhaps quarterly - to make sure that they are interfacing with the next level of the company in continued efforts to “close the feedback loop.”

Personalize based on style: the 1:1 should be different based on how you like to interact with your team and on how your direct report likes to communicate. For example, some of your reports will want to be in a conference room with a screen or whiteboard while others will prefer a walking meeting free from other distractions. As the number of direct reports scale, it becomes helpful to have your report create an agenda for each meeting and be able to review this in advance. You can use a running document where you and your report put items into the agenda.

What to cover: the 1:1 is a good check in that can sometimes bubble up serious issues. Because you don’t know where the issues may be, you should think of your role as a guide more so than an interrogator. Your goal is to help your report introspectively think about what is happening around them and uncover areas of alignment or misalignment. Ask open ended questions that allow your report to take the conversation to wherever they want. 

Questions that I find helpful:

  • What are you working on? - the purpose here is to make sure that whatever the top priorities are in the org are being re-iterated by your direct reports. If someone says they are working on something that is wildly unimportant, you know that better alignment is needed. 

  • How are you doing? - a good example of how a very open ended question can lead to a productive conversation. Your direct report will take this question in whatever direction is top of their mind. 

  • What can I do to help? - are there blockers that your direct report is struggling with? Or less tactically, are there strategic questions / issues that he/she wants to discuss with you. 

  • How’s your team doing? - similar to “how are you doing,” the purpose is to get a sense of the overall health of the team and whether there are opportunities / issues to double click on. 

If you have other ideas on 1:1 meetings and how to make them run better, I would love to hear about them. And if you’re struggling with this topic and could use a sounding board, please reach out to me (Gautam at M13.co).

Gautam Gupta