March 9, 2023

How to Not F*ck Up Your Meetings

How to Not F*ck Up Your Meetings

Episode 30: Let’s face it…most meetings suck. Even when they’re set up with all the best intentions, they often end up being a waste of everyone’s time. So what can be done? Alex Lieberman (@businessbarista) has 7 important lessons to keep your meetings under control. By incorporating these lessons, you’ll know when a meeting is needed or not (Hint: Most of the time, it’s not). 


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Alex Lieberman (@businessbarista)

Jesse Pujji (@jspujji)



Alex Lieberman: What's up, everyone? This is Alex, and I am back with another journal-style episode of The Crazy Ones. People have been loving this shorter, more personal format of the show. So Jesse and I are keeping it going once a week to start. By the way, Jesse and I have been absolutely floored by all of the emails we have gotten from hundreds of you, and we've gotten to know so many of you. If you haven't yet done so, please email us at You can literally just say “Hi.” It's two letters, H-I, and we will respond to you. Think about it this way. Would you more regret taking 15 seconds to send that email, or not taking 15 seconds to send the email and wondering what a conversation with Jesse and I could have turned into? So shoot us an email now at or after you listen to this episode. 

On this episode, I am going to talk about meetings. Why? Because most people suck at meetings, so I'm gonna talk about when you should have them and when you shouldn't, how to make meetings worth everyone's time, and things you can do to make meetings at your company better starting today. Let's do this. What's up, everyone? I'm Alex Lieberman. 

Jesse Pujji: Yo, this is Jesse Pujji.

Alex Lieberman: And this is The Crazy Ones. There are over 7 million Google and 13,000 Giphy search results for the phrase “hate meetings.” And that is because most people suck at meetings. Now, this isn't a sexy topic, but it is an absolutely vital one. Whether you're a startup founder, a startup employee, or a corporate professional, you are going to be dealing with meetings for the next several decades, so it's worth getting good at them. Plus, as Steve Sinofsky, who's the former president of Windows at Microsoft, shared, in the course of building a company, the most important tool you have to create a culture of shared values is communication. And meetings are critical to communication. And based on my own experience having thousands of hours of meetings at Morning Brew, many of which were not effective, as well as tons of time spent researching this very topic, I am going to give you seven timeless lessons for taking controlled meetings and making them work for you versus against you. So let's do it. 

Lesson one: Meetings are a last resort, not a first option. A meeting is a form of communication in a company that has the highest opportunity cost of time. So the bar should be super high for when you call a meeting, otherwise you're at risk of wasting time, taking people out of their productive workflow, and not respecting the time of a number of people. It requires everyone to synch up their calendars, which at times means moving things around to accommodate the meeting. And a one-hour meeting with five people isn't a one-hour meeting. That's so, so important to understand. It's a five-hour meeting in terms of the trade-off for all people that are in attendance. And I find meetings are oftentimes a lazy attempt to get something done. Something needs to be done. And the easiest thing to do is for you to just throw time on a calendar instead of just doing the thing now. And you should take this rule even more seriously when you're setting up recurring meetings. Now you're talking about not just taking an hour of someone's time this week, you're talking about taking an hour of someone's time into perpetuity. So here's a quick shortcut as you think about when to have meetings versus not. Any time you call for a meeting, you should default ask yourself one simple question: Can this be an email? And put the burden of proof on yourself to justify why it shouldn't be an email versus why it shouldn't be a meeting. Meetings are a last resort. 

Lesson number two: Make meetings two-thirds as long as you think they need to be. One of the worst practices is when a meeting goes the full time just because that's what the calendar said, and we all do this in life. When we give ourselves a certain amount of time to finish a task, we always, inevitably take up the entire time. But the odds are you could just get the same thing done in less time if you had a stricter boundary that you had set. So moving forward, if a meeting is 30 minutes, actually schedule it for 20 minutes, and if a meeting is 60 minutes, schedule it for 40 minutes. It respects everyone's time and forces you to keep things on track, versus allowing tangents to happen because you know that there's more than enough time allocated for the meeting. And what this also means is that the meeting leader or an appointed person should own the role of facilitating the meeting. That means making sure the agenda is followed, not allowing tangents to derail the meeting, and pushing things forward once a decision has been made. And I love this rule because it's one of the simplest ways to bring down the cost of a meeting. 

This rule also just reminds me of a business idea that I’ve wanted to see built forever. Basically, you know, in doing research for how to make meetings better and having bad meetings of my own, I've always had this visual in my head of just like a meter ticking up as time goes on. And that meter is basically the aggregate cost of that meeting in terms of people's salaries. And so a business idea that I've always had is, what if someone created an add-on that plugs into Google Meet or Webex or Zoom? And basically what you do is you plug into the meeting, before you start it, how many people are gonna be in that meeting, what the salary is of each person. And so as you're having the meeting, ticking up in the top right corner of your Zoom or of your Google Meet is a dollar value. And that dollar value is associated with basically the per minute cost of each employee, times the number of meeting minutes that meeting has gone on. And so ensure what it does is it holds you accountable to looking at that dollar value and saying to yourself, is it worth still having this meeting or not? Because you're seeing how much it is costing the business by you having five people in this meeting, either spending the time well or not spending it well. So if anyone out there likes this idea and wants to build it, the idea is yours. It's free to steal. I would love to see someone build this and I'd love to use it in my own life. 

Okay, lesson three: Follow the two-pizza rule. At Amazon, Jeff Bezos created a very simple model for making meetings more efficient: two pizzas. If two pizzas cannot feed the group that is meeting, your meeting has too many people. Far too many people would default to, “Oh, let's just get another pizza. Let's instead be able to feed people with three pizzas.” Or if it's an in-person meeting and not everyone can fit inside of the meeting room, “Oh, let's just get a bigger meeting room so we can fit more people.” That is not how you should think about it. How you should think about it is, if two pizzas can't feed the group, your meeting has too many people. And roughly speaking, this means your meetings shouldn't have more than five to seven people. Fewer people in a meeting means several things. It means lower cost. Fewer people means fewer salaries taken up by a 45-minute weekly product meeting. It also means lower opportunity cost of the other things that those attendees could have been doing if they didn't have to join your meeting. 

A smaller meeting also means more ownership and autonomy. The people that do attend the meeting end up feeling a greater sense of ownership, since they know their contribution matters and they wouldn't have been included in the meeting if they weren't responsible for pushing things forward. And a smaller meeting also means greater presence. And what I mean by this is, every additional person means fewer people in the meeting that actually contribute to the meeting, and more people just watching the meeting as passive onlookers. Having an additional person also increases the odds of someone not being present to what's going on in the meeting, whether that be them playing on their phone or browsing on their computer. And the second you get one person not paying attention, we are accustomed to herd mentality. So you will get several people doing exactly what that one person is doing. Less people in a meeting is better. 

Lesson four: If, as the meeting leader, you have not shared a meeting agenda, meeting goals, meeting roles, and meeting prep with folks prior to the meeting, you should not expect the meeting to go well. And it's crazy to me—people just expect meetings to go well without any of the necessary prep going on. Just when else in life would you expect anything to go well, if you haven't set expectations or planned ahead? As a meeting leader, if you are asking people to give their time to you, it is a nonnegotiable that you take on the responsibility of creating the best chance for the meeting to succeed. That means every single attendee should know what the agenda is for the meeting, what purpose they individually serve in the meeting, if there's any homework or brainstorming they need to do prior to the meeting.

So going back to Amazon, Amazon requires for meetings a memo to be written by the meeting leader. Typically, it's a six-page memo, because Amazon has a culture, a writing culture, of all thoughts are written down prior to talking about it. And then what would happen is in Amazon's meetings, people spend the first 30 minutes of the meeting reading that memo before discussing. So people should know in your meeting if there's homework or brainstorming that needs to be done. And then finally, what the desired outcome should be for the meeting. 

And so just to use an example for my backyard game business, The Plunge, we have a weekly meeting right now that has a very simple agenda. One, what did we accomplish this week? Two, where did we fall short of our expectations? And three, what are our priorities for the next week? I lead the meeting and I provide commentary on go-to-market and our growth strategy for having a successful Kickstarter campaign. Danny, who's my partner, provides commentary on product and operations, because that's his focus. And if you're asking yourself right now, couldn't these items that I just discussed be an email? Because you know, in a lot of cases, everything I just mentioned doesn't necessarily have to be a meeting. You're not wrong. The reason that we are doing this weekly meeting right now is because we're in the really early days of this business of The Plunge. And I think of this meeting time as rapport and communication-building between my partner and I. But post-product launch, this meeting will inevitably be turned into a weekly email. So that's lesson four, which is set expectations, set the agenda, have people know their roles, and have actionable takeaways. If you don't have those things, you should not expect the meeting to go well. 

Lesson five: Meetings are not for most things. Meetings, at the end of the day, are for something very simple: Three to five people attend a meeting to make an important decision that has cross-organizational implications. Meetings are not for catch-ups. And I'm not suggesting you don't do catch-ups with someone or people at your company. It's important for building relationships, but I wouldn't consider that to be a meeting. A meeting has a very specific desired outcome. It involves three to five people, max seven, and it leads to an important decision that must be made. Meetings are also not for initial brainstorms. Those should be done independently and then shared over docs or email, and then you can come together to make a joint decision around that brainstorm via a meeting. And brainstorms should always happen before meetings. It gives you time to think creatively, but it also gives people time to pressure-test the ideas that are brainstormed. So at the end of the day, if you think about it, when have you ever really come up with a great idea if a brainstorm is the meeting? Because it's impossible to think of things on the spot. You want the time to think for yourself, and then you can discuss those ideas with a group of people to ultimately lead to a decision.

And finally, meetings are not for status updates. Those should be sent via email. If people have questions on the updates, those can be answered over email as well. And if questions on the updates turn into a debate, that leads to an important decision to be made by several people. That is when a status update can turn into a meeting. When the update had questions, when those questions couldn't be answered and a decision needed to be made, that decision can then be discussed in a meeting. 

Lesson six: Treat meetings like a product. The riskiest thing that we can do is just to maintain the status quo. Treat a meeting like a product, solicit feedback, and make it better. Similar to what I was saying before about meeting prep, people just assume meetings will be great, and they'll just get better on their own over time, and that's not how the world works. That would be like launching a product into the world and then going onto autopilot, not measuring engagement, not soliciting feedback from your customers, none of that. And so doing just the same thing over and over and expecting things to get better makes absolutely no sense. A meeting is a product, and its customers are its attendees. Would you ever think about not making your product better for your customers? Of course you wouldn't. So don't think about not making meetings better for your attendees. You should go into meetings always thinking with a critical lens: How could this be better next time? And you should solicit feedback from the people in your meeting. You should ask them three very simple questions. And these three questions will lead to information that will make your meetings way better over time.

You should ask them if they think the meeting was a good use of their time. You should ask them if they think the goal of the meeting was accomplished, and you should ask them if they would do anything different for the next meeting. 

And last but not least, lesson number seven: Meetings are ephemeral. Make sure you preserve their learnings. When you have a meeting, it is only being experienced by the people present in that meeting. But if we go back to my definition of when it makes sense to have a meeting, you should have really important decisions and discussions that come out of every meeting that you have. So whether it's for people that couldn't attend the meeting for whatever reason, or people who the meeting's outcomes impact, memorializing the meeting is just as important as having the meeting itself.

So you, as the meeting leader, or an appointed facilitator, should always take meeting minutes and make it glaringly obvious to people not in attendance what the major outcomes were. If people read your minutes and they have lots of questions, it probably means you weren't clear enough with how you articulated the meeting's outcomes. And by the way, keeping meeting minutes is also a great force function to keep the meeting on topic and not go on tangents, because it will be pretty embarrassing to write a whole bunch of minutes that have nothing to do with the actual purpose of the meeting. 

And that, my friends, is the seven timeless lessons for how not to fuck up meetings. Now, I would love to hear from you. What is the most pressing challenge you're experiencing in your career or your business right now? The thing that is preventing you from falling asleep at night, or the thing that you wake up stressing about? Jesse and I want to talk about these topics on an upcoming episode of The Crazy Ones. So shoot us an email at, and I will get back to you as soon as possible. Thanks again for listening, and I'll catch you next episode.