Alicia Diamond

Chief of Staff Blog

Actionable advice, tips, and musings from a 2x Chief of Staff

How to Run an Executive Team Meeting That Doesn't Suck

Ah, the executive team meeting. Based on your personal experience, that phrase might invoke one of two reactions: dread or curiosity.

In my experience, despite the differences between executive team meeting formats at various companies, two truths prevail:

  1. No one outside of the executive team understands what happens in the meeting. And often, in the absence of understanding, there is fear. 

  2. Attendees feel obligated to spend some portion of the meeting making themselves look good in front of their boss and their competitors (read: peers).

I’ve sat through exec team meetings every week for the last 4 years. Some good, most okay, some downright bad. The better meetings all happened to include a meeting leader focused on making the most out of the time. The worst? They relied on the group to figure it out on the fly. We were in the exec team meeting after all! If we couldn’t figure it out, who could?

If you’re just starting out, or curious about leveling-up your own leadership team’s regular meeting, I propose the following advice:

Keep your agenda simple and oriented around your top company goals. Topics that don’t easily fit underneath one of your top goals probably don’t belong in this meeting.

Keep your agenda simple and oriented around your top company goals. Topics that don’t easily fit underneath one of your top goals probably don’t belong in this meeting.

  1. Reign in the topics

    To prevent a meeting that is simply a live theatrical version of each department’s weekly status report, verbalize the expectation for approved topics. Ask for topics that: 1) require the brains of the entire group, not just one or two individuals 2) require assistance from the entire group to remove blockers 3) align with the company’s goals.  

    To make sure the topics align to goals, I suggest a pre-templated agenda (a simple Google Doc will work) that structures each topic under one of the company’s current goals. If it doesn’t fit under a goal, the meeting owner should thoroughly vet the topic and its broad importance before distracting the rest of the group with it. 


  2. Designate a meeting owner

    The CEO is often the de facto leader of this meeting, but based on his/her personality a deputy might be best to lead and keep the meeting running smoothly. Might I suggest a Chief of Staff for this role? 

  3. Channel Bezos and require thoughtfulness ahead of time

    I’ve been known to chant “those who can’t write, can’t think”. At face value, that’s a bit harsh, but hear me out: I’m not asking for gorgeous prose, I’m asking for a well-structured argument. It takes time to write something clearly. It also takes (everyone’s) time for someone to ramble while introducing an idea. The former is a much better use of everyone’s time. If the topic owner can’t structure a solid, data-driven argument to support their own opinion, he or she shouldn’t (yet) be bringing it to the exec team. 

    The best executive team meetings I’ve seen are used for discussion, not for education. A well-crafted email distributed prior to the meeting, sent well enough ahead of time for the team to fully digest, will make for a better conversation and a more confident decision-making process. The decisions brought to the executive team meeting shouldn’t be rushed. If they were easy decisions, they would have been made at another level, right?

  4. Actively create talking points for the attendees to socialize

    Your execs should make a habit of sharing information with their teams immediately after the exec team meeting. This can happen via Slack or via their own weekly meeting. It’s important for the company to know what the exec team is talking about because 1) it encourages them to get curious about how the exec team makes decisions - which is the ultimate hack to scaling culture, and 2) it encourages open and honest communication. The most important part of an executive’s job is to effectively communicate with his or her team. Most of your job is to distill and reinforce. As I like to say, “hit people over the head repeatedly” with a message until it sticks. Bulleted talking points - not a script - help the execs to understand key takeaways and the agreed-upon appropriateness of what to share now vs later. These can easily be developed on the fly as each topic is discussed and decided upon. Add a reminder to your agenda template “what do we tell our teams?”

  5. Schedule time to think “operational big picture”

    HBR, linked below, recommends splitting strategic and operational conversations. I love this idea, and I’ve seen it work successfully, but I recommend taking time more than once per quarter (or whenever your strategic planning sessions regularly occur) to think about operations from a macro perspective. If your strategy is shifting, but you’re approaching ops from the same old tired way, you might never achieve your potential. Schedule time to do a post-mortem on operational issues with a focus on learning and improving - what went wrong at the exec level that contributed to this failure? Go through a “blank paper org chart” exercise - the org chart equivalent of zero-based budgeting. If you had to start over again today, with this team, how would you organize everyone and why? 

Not enough for you? Here are other ideas that caught my eye:

  • From HBR, on the topic of sharing thoughtfully prepared materials ahead of time: “all reading materials have been distributed to participants at least five days before each CEC session. Whenever possible, standard templates are used to display important financial, market, and competitor information. This gives each CEC member time to carefully review materials before the meeting and quickly get up to speed on important issues. Second, a standard cover sheet is included with all materials specifying precisely why people are being asked to read them—for information purposes only, for discussion and debate (in which case, the key issues are highlighted), or for making a decision and deciding a course of action.”

  • From HBR, on the topic of prioritizing agenda items: “Successful companies prioritize the problems and opportunities on top management’s agenda according to the “value at stake”—that is, according to the impact that resolving each issue will have on the company’s long-term intrinsic value (the net present value of the company’s future cash flow discounted at the appropriate risk-adjusted cost of capital). This can be done through a broad sensitivity analysis using the company’s valuation model; numeric precision is not the object of this analysis, only a general understanding. Typically, lower levels of the organization should address the low value-at-stake issues.”

  • To learn more, visit: https://hbr.org/2004/09/stop-wasting-valuable-time