What is a leadership meeting?

A leadership team meeting is a recurring meeting that includes the most senior leaders within an organization or team. At the most fundamental level, the leadership meeting is about increasing alignment on a continuous basis. The tighter the alignment at the top of the organization, the better the team will perform at every level. This makes it one of the most important meetings you’ll run as a leader.

The purpose of the leadership team meeting is three fold:

1. Ensure the team remains aligned on the company’s vision & priorites;
2. Ensure the company is on track against its annual goals and key metrics; 
3. Provide a forum to remove any blockers that may stand in your way.

The Chief Executive Officer (CEO) normally leads the leadership meeting, which are usually held weekly or every other week. As the name suggests, attendees typically include the leaders of the organization – for example, Chief Financial Officer, Chief Operating Officer, Chief Revenue Officer, etc. 

It’s very common for leadership to fall out of alignment throughout the year – even with clear vision and priorities. The team often disagrees on the “how” and the “who” of the tactics. Or runs into blockers that must be removed. This continuous calibration process is critical to the success of any sized organization – and the leadership meeting is the best place for this to happen in a healthy way. 

The cost of bad leadership meetings

Most leaders really screw up their leadership meetings (I was there once too!). They can quickly go from a high-leverage tool, to a waste of everyone’s time. The usual suspects are:

• No defined structure
• Too many people invited
• Not enough problem solving
• Decisions unclear or unmade
• No follow through on agreed upon actions

But the real cost goes much deeper:

• Lack of team alignment
• Delayed decision-making 
• Blocked goals and outcomes
• Declining motivation and morale 
• Confusion throughout the organization

These are systemic issues that can literally kill an organization over time. This is why I tell the founders I teach in Highland how important it is to stay “tight at the top” – keeping your leadership team as aligned and in synch as possible. Even a small crack at the top will create large misalignments further down the org chart. But a well-run leadership meeting makes sure those cracks never appear – or if they do – they’re patched up quickly before turning into a more serious problem.

Leadership meetings vs. leadership offsites

The leadership meeting should not be confused with its cousin, the leadership offsite. Leadership offsites are longer-range planning meetings where vision, strategy, and goals are created and refreshed each year. These meetings are typically held 2-4 times a year, separate from the recurring leadership meeting. 

Here’s how to think about it:

1. Leadership Meetings — recurring meeting that aligns the leadership team on short-term execution.
2. Leadership Offsites — longer, less frequent meetings that align the leadership team on medium to long term vision, strategy & goals

Speaking of leadership offsites, I just did a Masterclass on the topic for my Highland community - if you're a founder or CEO and want access to this Masterclass and the accompanying Guide, reach out to us here. 

Now for the rest of the article, we’re going to focus on building the perfect leadership team meeting for your company…

The Perfect Leadership Meeting Structure

First, let’s start by reviewing the overarching structure of the perfect leadership meeting (perfected, in my view at least, after 20 years of trial and error). This structure cuts out all the B.S (tangents, politics, low-level items, etc.) and focuses on the stuff that truly matters – making sure the team stays aligned and hits its goals! Nothing more, nothing less.

Here’s the overarching structure of the leadership meeting:

Length & Frequency:

I’ve learned over the years that a (slightly) less frequent, but longer meeting, is the most productive cadence for leadership meetings. Shorter meetings push too many decisions and leave too many issues unresolved. The extra time allows for depth – allowing the team to truly dive into the hard stuff, remove blockers, and develop a clear action plan.

But why 1 hour and 40 minutes long? Not 2 hours, or 1 hour and 30 minutes? 

Two hours proves too long for most leadership meetings. The meeting drags on and isn’t as sharp. On the other hand, 1 hour and 30 minutes allows attendees to book a 30 minute meeting immediately after the leadership one. This creates distracted minds at the end of the meeting when decisions are usually finalized. 

Setting your leadership meeting for 1 hour and 40 minutes gives everyone a 20 minute buffer after the meeting to digest (and put into motion) any action items that they’ve been assigned. It also allows you to go a few minutes longer if you’re in the middle of a decision. While you should always try to end on time, I have no problem running over by a few minutes to clarity a decision, rather than pushing it to the next meeting. Pushing just slows the execution speed of the company down.

Schedule: Day & Time

The day and time of your leadership 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 still sets the tone for the rest of the week.

The most important thing is picking a reliable time slot for your schedule. If you travel on Mondays, then don’t pick Monday because you’ll end up canceling the meeting all the time. Always pick a day and time that gives you the highest chance of participation and presence. 

Who Should Attend

My general rule of thumb is to have 10 or less people attend the leadership meeting. 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. 

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, marketing, product, etc.). Their title could be a “Chief Executive”, or it could also be a “Vice President” or “Director” if you haven’t named a C-level position over that function yet. The person’s title is less important than their functional responsibility.

Sometimes a functional leader will report to another executive, and not the CEO. This is a perfectly acceptable set up; but these functional leaders should still be included in the leadership meeting because they add a valuable perspective that would be otherwise missing. For example, your Head of Human Resources (HR) may report to your Chief Operating Officer (COO). But as the CEO, you’d still want your Head of HR in the executive meeting. Otherwise, you’d be taking your people advice from your COO, who is much less connected to the details of the function.

Ultimately its up to the CEO to make the final call on who’s in and who’s out. Just make sure the major functions are represented, and that you’re using consistent logic so there’s no special treatment.

Leadership Meeting Agenda

Here’s an overview of the leadership meeting agenda. The sections never change – but, the discussion within each section will change based on your progress and blockers.

The ‘Get to Green’ (G2G) section is the most important part of the leadership meeting. This 60-minute section is used to “unblock” any goals or metrics that are off track. To do this effectively, you need to make sure a small amount of pre-work is done prior to each leadership meeting.

Pre-work

To get the most out of each leadership meeting (especially the G2G section), there’s a few important things that need to happen before anyone enters the room:

1. Company dashboard needs to be updated
2. Team-level dashboards need to be updated
3. Attendees add items to ‘Get to Green’ list (in shared doc)
4. CEO prioritizes ‘Get to Green’ list by urgency (in shared doc)
5. CEO selects top 3 for discussion in next meeting (shares via Slack)

Your dashboards should track your top goals and metrics across the company, and across each functional team. Then you update the status of each goal, outcome, or metric to show how you’re pacing towards your targets. Here’s my simple grading system for updating status:

🟢 = On pace (pacing to 100% achievement or above)
🟡 = Slightly off pace (pacing to 80-100% achievement)
🔴 = Off pace (pacing to under 80% achievement)

This grading scale is part of the goal system that I personally use (and teach) called WhyGos - Why, Goal, Outcome. I found it to be a significant upgrade over OKRs, EOS Rocks and others. Try it out (for free) and let me know what you think! 

Regardless of the goal system you use, your dashboards should always be updated with the current status before stepping into the leadership meeting. This is a non-negotiable. I’m stricter on this than almost anything else. Why? Because a stale dashboard means stale information, and stale information means the team is operating at a disadvantage. This should never happen.

The CEO should take responsibility for the company dashboard (with help from their head of finance, ops or chief of staff). Then, each functional leader should take responsibility for updating their own team dashboard as well. Any trouble areas (red & yellow items) should be added to the ‘Get to Green’ list – a running list of ‘off-pace’ goals and/or metrics that may need further discussion and resolution.

This G2G running list is usually maintained in a simple Google doc by the Chief of Staff (or equivalent). Then the CEO prioritizes the list and selects the top 3 items for discussion in the upcoming leadership meeting (communicating the selection via Slack so the team comes prepared). For example, the Slack message might be as simple as this:

For the Get to Green section tomorrow, I want to focus on these off-pace team goals because they’re causing the company WhyGos to fall behind too. Please come prepared to discuss blockers and how the team can help you remove them.

1. Marketing WhyGo #2
2. Product WhyGo #1
3. Sales WhyGo #3

OK, now that we’re done with the pre-work, let’s dive into the details of each agenda section…

1. Settle In (5 minutes)

It’s important to create the right environment first – the right vibe in the room – before jumping into the harder stuff. I’ll usually share a personal story, a company win or give someone some quick props (and let others do so too).

But don’t confuse this trust-building step 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. 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.

2. Company Progress (10 minutes)

In this section the CEO brings up the company dashboard and frames the meeting, focusing on how the company is doing since the last time the group met. But rather than simply reading the dashboard (which the leaders are expected to do prior to the meeting), the CEO should focus on anything that has changed since the last meeting (both positive and negative). If anything went “green” since the last meeting its a great time to give some props and positive feedback. Then on the other hand, the CEO should point out new or recurring trouble areas, especially ones that have been included in the G2G section of the agenda. I also like to include the ‘why’ behind choosing those top three items for discussion and resolution.

For example, a company-wide goal may have gone from green to red since the last time the group met. So, I might say something like this:

As you can see, company WhyGo #1 went from green to red since the last time we met. From what I understand this was due to a few team-level WhyGos falling behind. Most notably Marketing WhyGo #2 went from green to red as well. This is a big shift and I wanted to get on this right away. The head of marketing will give more context in a second, but I’m hopeful after today we can get this one back on track.

3. Team Progress (20 minutes)

This section focuses on progress at the functional (team) level. If you’ve set your goals correctly, each functional leader will have their own WhyGos that they’re tracking in a team dashboard. Each leader brings up their dashboard and does the following:

1. Gives update on any Actions from last meeting (that they owned)
2. Gives update on any red & yellow items (green items are skipped)

This “around the horn” process should take less than 5 minutes per person. Ideally only 2-3 minutes per person. Deeper discussion is reserved for the G2G section that comes next. If any of the person’s items were chosen for discussion in the Get to Green section, they can skip those items for now.

For #1 — Actions are essentially “next steps” from prior meetings with assigned ownership. So, if the functional leader had any assigned Actions, they should update the group on their progress against the task or assignment. Ideally you want most of these closed out from the prior meeting (roughly 75% of actions are usually closed out within one meeting cycle, and 25% take two). But if it extends longer than two meetings than there’s likely a problem.

For #2 — If a functional leader has a yellow or red goal, they should be prepared to answer: 

• Why is this goal behind? 
• What’s the plan to catch up?
• What help do you need from the team?

Usually the red items are brought into the G2G section, so this section tends to focus on the yellow ones. So with these, I like to make sure the person has a full handle on the situation and can clearly articulate a plan to get the goal or metric 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. If the goal remains yellow for too long, the CEO may decide to elevate it to the G2G section to prevent it from going red.

4. Get to Green (60 minutes)

This is, without a doubt, the most important part of the meeting. This section is used to “unblock” any goals or metrics that are off track. Typically the CEO selects red items to start with, but yellow items will make its way into this section too (especially recurring yellow items).

The Get to Green (G2G) list is usually maintained in a simple Google doc that the leadership team has access to. The CEO prioritizes the list based on urgency and selects the top three items for this section of the leadership meeting. If you successfully “unblock” the first three, you can always move down the list as time allows.

Before I get into the flow of the section, its important to define what I mean by a “blocker”. A blocker is something that’s holding the leader back from hitting their target. This could be a performance gap, resource gap, customer issue, dependency issue, etc. The functional owners should always have a hypothesis on what the blockers are – even if they don’t have a full corrective plan in place yet. If they don’t have a POV on what’s going on, this is a red flag and possible performance issue.

Ok, now that we’ve defined what a blocker is, here’s what should happen in this section. For each G2G list item:

1. The functional leader who owns the goal or metric provides context on the situation and clearly identifies the blockers that are holding the team back from success. If the leader already has a corrective plan in place, they can walk the team through it.
   
2.  The team creates an Action Plan to unblock the goal or metric and get it to green again (ideally by the next leadership meeting). If the functional leader already started a corrective plan, then the team can vet that one and add to it. If not, the team works together to create a new Action Plan. Either way, the Action Plan will include various next steps (“actions”) with a clear owner for each. These Actions should aim to be completed by the next meeting. If all actions are completed successfully, the team believes the goal or metric will get to green.

“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 a leader, 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 struggling. The company can’t win if its leaders are losing.

5. Actions (5 minutes)

The last section of the leadership meeting agenda is wraps everything up:

1. Review Actions and ensure everyone is clear on ownership & expectations
2. CEO provides a few parting words that sums things up & leaves on a positive

Leadership meeting bonus tips

Now onto some bonus tips… 

Come with updated goals, or don’t come at all

Nothing kills this meeting’s effectiveness faster than attendees 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. 

Attendees should have “command” of their business

A leadership meeting attendee (often called 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 meeting is your early warning system

This leadership 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. 

Drive decisions and track actions

The leadership 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. 

Don’t cancel this meeting

Once your leadership 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. 

Attendees evolve over time

One key thing to understand about leadership 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 “leadership meeting” is simply a recurring meeting with your co-founders (and maybe 1-2 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 the 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. 

Here’s the hard part though. Building an 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 attendees) will get too large and redundant (i.e. you’ll have multiple people from a given function attending).

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. 

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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