Written by Scot Chisholm
| Leadership, Management | August 16, 2024
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An executive meeting is a recurring team meeting that includes the most senior leaders within an organization. At the most fundamental level, the executive meeting is about increasing alignment across the team (and company) on a continuous basis.
The purpose of the executive meeting is two fold:
The Chief Executive Officer (CEO) normally leads the executive meeting, which are usually held weekly or every-other-week. As the name suggests, attendees typically include the executives of the organization – for example, Chief Financial Officer, Chief Operating Officer, Chief Revenue Officer, etc.
It’s very common for executives to fall out of alignment with each other throughout the year – even with a clear set of company goals and outcomes. They often disagree on the “how” and the “who” of the strategy and tactics.
This debate should be welcomed by the CEO – to a point. Once a path is chosen, the executive meeting is used to finalize the decision and re-align the executives. This continuous calibration process is critical to the success of any sized organization – and the executive meeting is the best place for this to happen in a healthy way.
Most leaders over-complicate this simple but powerful meeting. It can quickly go from a high-leverage alignment tool, to a waste of everyone’s time.
I’ve sat through more painful meetings than I care to admit over my 20 years leading teams. The usual suspects are:
But the real cost goes much deeper:
These are systemic issues that can kill an organization over time. If you let them slip into the executive meeting, they’ll spread through the whole company, like cancer. This is why I tell the founders that I coach, “you’ve got to keep it tight at the top”.
This is why it’s so critical to get this meeting right.
The executive meeting should not be confused with its cousin, the executive strategy session or “offsite” (as they are commonly called). Executive strategy sessions are longer-range planning meetings where vision, strategy and goals are created, refined and finalized. These meetings are typically held two times a year, separate from the recurring executive team meeting.
Here’s how to think about it: if the executive strategy session is all about aligning on the medium-to-long-range plan, the recurring executive meeting is all about aligning on short-term execution (within a 12 month period).
I’ll write about executive strategy sessions in a future post, but now back to our topic of the day – the executive meeting.
My general rule of thumb is to have 10 or less people attend the executive meetings. From my personal experience, I’ve found that 5-7 people is the perfect size. But, this number will adjust up or down depending on the team composition at any given time.
The most important thing is to ensure that each company function is property represented in the executive meeting (I.e. sales, product, etc.). The CEO should make the final call on who’s in and who’s out, and use consistent logic to draw the line across the company.
Typically the attendee list includes the CEO’s direct reports and/or top functional leaders across the company. By “functional leader” I mean the top leader over each respective function (i.e. head of sales). This could be a “Chief Executive”, but it could also be a “Vice President” or “Director” if you haven’t named a C-level position over that function yet.
Sometimes a functional leader will report to another executive, and not the CEO. These functional leaders should still be included in the executive meeting because they add a valuable perspective that would be missing otherwise. For example, the Head of People Ops may report to the Chief Operating Officer. But as the CEO, you’d want your Head of People Ops in the executive meeting to fully represent that function.
A key thing to understand about executive meetings is that your ideal attendee list is going to change over time as the company matures.
For example, if you’re an early-stage startup, still honing your product-market-fit, your “executive meeting” is simply a recurring meeting with your co-founders (and maybe a couple other key folks). You won’t have a “C-suite” of executives at that point, nor should you.
But as your company grows, you’ll start to assign clear ownership over functional areas within the organization. For example, product, sales, marketing, finance, operations, etc. Some of these early “executives” might be home grown, or you might hire externally to fill gaps. But, by the time your company hits $10M in revenue, you’ll want to have your executive team fully built out, with strong leaders over every function.
But building out your executive team isn’t just about adding people. It also involves removing people that are no longer a fit. This doesn’t mean firing the person from the company, but it does mean mutual recognition that the person is no longer the top leader of their functional area. Otherwise the executive team and meeting will get too large and the attendees become redundant (you’ll have multiple people in a given function).
For young CEOs and first-time founders these are usually sensitive and painful decisions. For example, it’s common for the co-founders to attend the executive meetings early on, but then gradually phase out if they don’t continue to lead a major function. Similarly, a home-grown Head of “X”, that has crushed it for you for years, could hit a ceiling and need to be replaced. These are some of the hardest decisions to make as a leader, but they must be made.
Now I’m now going to detail the perfect executive meeting format after 20 years of trial and error. It’s designed with the meeting purpose squarely in mind:
To ensure the company is on track and the team is aligned.
Anything else is just fluff, and can be discussed elsewhere (through 1x1s, email, slack etc.). Anyone that tells you differently is making the executive meeting too complex (regardless of the size of the company).
Here’s my preferred format:
Length & Frequency:
I’ve learned over the years that a (slightly) less frequent, but longer meeting, is the most productive format for executive meetings. This provides enough time for the team to truly dive into the hard stuff and come away with a clear path forward. Shorter executive meetings push too many decisions, and leave too many conflicts unresolved.
But why 1 hour and 40 minutes for the length? Why not 2 hours, or 1 hour and 30 minutes?
Two hours proves too long for most executive meetings. The meeting drags on and isn’t as sharp. On the other hand, 1 hour and 30 minutes is problematic because executives are able to schedule a full 30 minute meeting immediately after the executive meeting. This creates distracted minds at the end of the meeting when decisions are usually finalized.
Setting the executive meeting at 1 hour and 40 minutes gives everyone a 20 minute buffer after the meeting to digest individually and plan next steps. It also allows for the meeting to go long if needed with important topics. No one wants to end a meeting unresolved.
Schedule: Day & Time
The day and time of the executive meeting is mostly a matter of preference. For me, I prefer it to be on Monday at 1:00 pm. This lets my executives get into the day and prepare for the meeting. But it’s still on Monday, so it sets the tone for the rest of the week.
Regardless, the most important thing is picking a reliable time slot for your schedule. If you always travel on Mondays, then don’t pick Monday because you’ll move or cancel the meeting all the time. Pick a day and time that gives you the highest chance of participation and presence.
Executive Meeting Agenda
Now let’s break down the agenda:
This executive meeting agenda never changes; but, you can trade time between sections as applicable. For example, if all of your goals are “on track” in the Goal Review section, you can spend more time on the Special Topics section (and vice versa).
And remember, you can always end the meeting early if you have extra time. Never fill an executive meeting with low-level admin items just to use the 1 hour and 40 minutes. Always give extra time back to the team and cover the lower-level items via email or slack.
Now I’m going to detail each portion of the agenda in the following sections.
Still with me? Let’s go…
You can play the beginning of an executive meeting two ways:
I prefer the second approach 95% of the time, with the caveat that some situations do call for a more militant approach.
But don’t confuse trust-building with being soft. There will be plenty of opportunities during the meeting to be more direct, or take a hard stance. And that’s exactly why it’s important to warm people up first. Your goal is to create a safe environment before diving into the harder topics.
You can even let folks chat casually for a few minutes and that usually does the trick too.
This may seem like fluff, but it’s actually quite important. This section of the agenda sets the tone for open, honest communication throughout the meeting. It’s a small investment that pays big dividends. Don’t skip this part.
This is, without a doubt, the most important part of the meeting.
If you’ve done your annual planning and goal setting correctly, your company should have a clear set of annual company goals – three or less. Each goal should have measurable outcomes that define the success or failure of that goal.
From there, each team should have created its own goals and outcomes that align to the company’s. The same constraints exist – three or less goals per team. Remember, goals are not supposed to cover EVERYTHING the team does, only the most important items. Goals are not a task list for the year.
OK – back to the executive meeting. The purpose of this section of the agenda is to:
Before the meeting starts, each person MUST update the status of their team’s goals on whatever dashboard the company uses to track progress. Each executive should have three or fewer goals (and measurable outcomes under each). For example, if the head of marketing is an attendee of the executive meeting, then she should update the status of the marketing team goals before entering the meeting.
This is a non-negotiable. I’m stricter on this than almost anything else. Why? Because a lack of status creates a blind spot for the company. If you don’t know how the marketing team is performing, you can’t possibly know how the company is truly performing.
If you read my article about goal tracking, you know that I use a very simple rating system. More is less here.
To rate each goal, you first start by rating each measurable outcome under the goal. Then you rate the goal itself based on how the outcomes are shaping up. Remember, the outcomes should define the success of the goal in numbers. So, if you are “on-pace” for each of your outcomes, then the goal should be “on-pace” too. If you are “slightly off-pace” or entirely “off-pace” with one or more outcomes, then the goal is likely in jeopardy.
If an outcome is slightly or fully off-pace, the executive should jot down what is blocking the success of this outcome or goal. For example, it could be a performance gap, resource gap, dependency issue, etc. The executive should be prepared to raise this during the meeting itself and ask for the group’s help if applicable.
Once each executive updates the status of their goals, then you as the CEO (or your Chief of Staff equivalent) update the status of the company-level goals. You do this right before the executive meeting, using the updates from each functional area to guide the company-level update. If the goals are designed correctly, the status of the functional-level goals will become leading indicators of the company. For example, if every executive marked their goals as “red” – behind pace – then there should be no way that the company goals are “green”. And vice versa.
After you settle into the meeting, I usually kick off by giving a 5-10 minute overview of how the company is doing against its goals and outcomes.
Remember, these company-level statuses are based on the inputs from each executive. So, as you’re giving your company-level overview, you should prop up questions that you’d like the team to dive into when it’s their turn. For example, if one of the company goals went from “green” to “red”, because the marketing team’s goals all went from “green” to “red”, then you want the marketing leader to explain the change and what’s being done.
Important: When giving the overview, avoid the temptation to dive deep on functional problems during your summary. You don’t want to explain-away issues, or solve problems on behalf of other executives (even if you know the answer). This gives them an “easy out” and shifts responsibility away from them as the leader of their function. Each executive must learn how to fully and clearly explain issues, and any corrective actions. Then you can chime in from there. This is very important for creating the right level of accountability, and helping them develop as a leader.
So, you might say something like:
“As you can see, goal #2 went from green to red since the last time we met. From my understanding, this status change was mostly due to the marketing team’s goals changing from green to red. [Marketing Leader] will dive into this in a second, but I want to spend a good amount of time on this as a team so we can get it back on track.”
By the time you’re done with the summary, you will have identified a handful of specific things you want to focus on when you go around the room for functional updates. This keeps the rest of the meeting laser focused on the major issues and resolution.
Next I go around the “horn” and allow each executive to give an update on their team’s goals. Each person’s update might last 5-10 minutes on average. Shorter if their goals are all “green”, longer if their goals are all “red” and need further inspection.
In fact, if an executive has a goal that is fully “green”, we recognize the good work in 30 seconds or less and move on. As an executive team, you should be spending 99% of your time on yellow and red goals, and 1% praising the green ones.
If an executive has a yellow or red goal, they should be prepared to answer:
For the first bullet, this is where the executive brings forward any blockers they have identified. This could be a performance gap, resource gap, dependency issue, etc. The executive should always have a hypothesis on what the issue is.- even if that changes as they learn more. If they don’t have a POV, this is a major red flag.
If an executive has a yellow goal, I’m making sure they have a full handle on the situation and can clearly articulate a plan to get the goal back on track. The team might chime in here or there with a suggestion, but we’re mostly leaving it up to the executive to course-correct and report back.
However, if an executive has a red goal, it opens up a different level of engagement from the team. After hearing the executive out, the team is given permission to ask questions, offer suggestions or volunteer resources. If an executive has a red goal for more than one month (two executive meetings), then I will allot more time for the group to discuss and help the executive. For example, if it’s a serious enough issue, we might dedicate 30 minutes on a single red goal. In these cases, I suggest you borrow time from the Special Topics section (below) to make this happen.
Bottom line: The Goal Review section of the executive meeting is about diagnosing issues quickly, and making sure there is a plan in place to course-correct. Most times the leader can solve the issue themselves (with light assistance from the executive team); but, sometimes the executive is really stuck, and needs heavier support from the executive team to get back on track.
If you’ve designed your goals correctly, nothing should be more important than getting yellow and red goals “back to green”. These are your company’s top priorities for the year after all!
“Get to green” even became a mantra across my companies. It reinforces the need for personal accountability, but also the supportive nature of the team. As an executive, you need to fully own your goals. But at the same time, the rest of the team is there to support you if you’re really struggling. The company can’t win if its executives are losing.
The last part of the executive meeting agenda is reserved for any special topics that you (or your team) want to bring forward. These topics could be related to the company or team’s goals, or something else important.
Example topics might be:
I like to ask the executive team for special topic ideas via Slack the day before. Then I’ll prioritize the top 1-3 as I see fit. If a suggestion relates to a company or team goal, I’ll make sure it’s integrated into the prior Goal Review section somehow.
The key is picking topics that you think the whole team needs to discuss or align on. Again, you’ll want to avoid including lower-level administrative items. These can be handled separately, usually on email or slack.
You’ve now read my core suggestions on how to run the perfect executive meeting! Now onto some bonus tips…
Nothing kills this meeting’s effectiveness faster than executives not updating their goals prior. Make it a cultural expectation that you don’t enter the meeting without your goals updated. I rarely pull moves like this, but I’ll even ask someone to leave the meeting if they come unprepared. It’s that important.
An executive should know where their team stands at all times. If there’s an issue, they should have a strong point of view about why it’s happening and what to do about it. If they’re relying too much on you, or the team for solutions, they may not be the right fit for the executive team (or even your company).
This executive meeting format excels at spotting issues early on, before they become major problems. That’s why it’s imperative to focus on yellow and red goals, and hold each leader accountable for getting things back on track. If you gloss over yellow and red goals, then lack of progress is on you, not the executive.
The executive meeting should drive decisions, not just facilitate discussion. Make sure each discussion topic has clear next steps (especially for yellow and red goals). Use your Chief of Staff (or equivalent) to record meeting actions, and then make sure executives are following through after the meeting is over.
Once your executive team gets used to this format, it makes it much easier to host the meeting without you (if necessary). I usually assign my Chief of Staff as the stand-in facilitator. If you don’t have a Chief of Staff, you can make one of the executives the facilitator. Just make sure to rotate executives if you miss multiple meetings. You want to avoid the appearance of favoritism.
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And there you have it!
A proven template for running the perfect executive team meeting. It’ll take a bit of getting used to, but once you’ve run 5-10 of these, you’ll be a natural… and your company a well-oiled machine.
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