Time to chase Calendar Zero
“There’s this concept called inbox zero, where everyone tries to get to their inbox down to zero. But I would suggest that a more noble pursuit is that of calendar zero”.
I chatted to Howard Lerman this week. I was blown away by this discussion – it captured exactly what is wrong about current work, and why back-to-back meetings are going to lead to many organisations missing the opportunity of this vital moment.
This is an essential listen – about where work is imminently going and how Howard’s philosophy is building his fascinating new product Roam to serve the company of the future.
Read all about the way that work is about to change in the newsletter
The AI 2027 predictions are the wake up call we didn’t know we needed
Microsoft explains why we need to ready ourselves for the reinvention of work
Konstantine Buhler on ‘always on’
Full transcript on the website
Book recommendation: A Pattern Language: Towns, Buildings, Construction (Amazon commission link to giving about 8 cents to your free podcast)
Transcript
Bruce Daisley
Firstly, Howard, could you introduce yourself to me and explain your journey to get to Rome? and like what brings you here really?
Howard Lerman
First off, thanks for having me on your show here. I’m a serial entrepreneur, so I founded a company called Yext. And when we founded Yext, we were two people in a room, and then we were eight people in a room. And when we were small, even up to 30 people in the same room, we had short, fast conversations all day, and the idea of scheduling an internal meeting never happened. Because if I needed to talk to someone, I would just walk over to them and we’d have… Or if I saw two people talking that I thought knew that I thought were working on something that I had something to offer, would just sort of shout it out and we’d have a you know, we’d sort of hash it out right there. But then as the company grew, we ended up globally distributed with people around, with over 2000 people around the world. And my calendar became crammed up with 30 and 60 minute back to back zoom calls all day long. would even commute to the office to HQ, you know, 45 minute commute. I’d sit there on a zoom. Some of the people would be in the same building. on a video call with people down the hall, you know, on a different floor. and so
The company, you know, ultimately went public and I learned a lot about how to run a company, but I always just wanted to get back to that 30 people, 50 people in a room, kind of short, fast feeling of, you know, being able to have a conversation right now and collaborate as opposed to let’s schedule a meeting next week.
And so kind of things that used to take two people in a short collaborative environment, five minutes right now ended up being scheduled for next week. And so Roam, I made because I realized that we were about to enter a new era and I just wanted to get back to that old way of working.
Bruce Daisley
The one thing that I found captivating about your philosophy is you say no standing meetings, no recurring meetings. Look, firstly, everything you’ve just articulated there, I’ve worked in a team of 30 people and you’re exactly right. We didn’t have any meetings, it was so energizing. And the thing you described there is such a powerful experience of being part of a small team that when you lose it, when you become…
enmeshed in that sort of corporate stasis of having loads of scheduled meetings and your calendar doesn’t feel like your own. think what you’re describing as the vision is beautiful. But your philosophy when it comes to Rome is there’s no recurring meetings. Or as far as I understand it, I don’t speak for you. Talk to me about why you came to that philosophy. Because that seems like such an important lesson for the moment we’re in actually, beyond your technology.
Howard Lerman
Well, let’s take a step back. when I was running Yext , you get a lot of advice when you’re scaling. And when you’re a founder of a company, there’s different skills you learn during different phases of the company. So when you’re two people trying to find product market fit, it’s pretty different than when you’re trying to figure out how to do global sales, for example, and hire people in the UK and France and Japan and so on and so forth. And you get a lot of advice. And one of the main things that you get advice from people who are who sound smart and they’re authoritative is that you should, as a good manager, if you’re learning to be a manager, the first thing you do is you set up a one-on-one recurring meeting with everybody on your team. And I did this for a while because I was running this company and I was in my mid-20s and I’m trying to be a good manager, as I was told by the people that knew what they were talking about.
And it turns out that if you have eight or 10 direct reports, which by the way is what they also experts advise you to have, you know, no more than eight direct reports and delegate. It turns out Bruce, basically all that advice is wrong. That you shouldn’t delegate very much that you shouldn’t have one-on-one recurring meetings and that you should have a broader span of control. And so at Yex, as I was building the company, I had, you know, between 30 and 40 direct reports. I did not have one-on-one recurring meetings. I will still talk to people one-on-one, but if you have a one-on-one meeting with someone once a week, let’s say it’s 30 minutes and you have 10 direct reports, which is in this suggested kind of zone, you’ve clogged your calendar with five hours of meetings. If you do, if you do an hour meeting, which some people do now you have 10 hours of one-on-one recurring meetings. Now, you know, may have 10 or you may have 50 hours to work in a week or 60 and so all of a sudden 20 % is lost to these one-on-one meetings which and the thing is meetings are like a gas. They will expand to the amount of time you give them. So if you have an hour in your calendar for someone to talk to you, you will sit there for an hour and you will both sit there for an hour and you will come up with reasons why that person may walk in happy
Howard Lerman
and leave unhappy and nothing will get solved and there’ll be no shared learning. And so I came out and said this, I wanted to clear my calendar, not have one-on-one meetings. And everyone said I was crazy until it became the soup du jour when we started hearing about Jensen Huang and Brian Chesky.
Bruce Daisley
That was what I was going to bring up to you. Jensen Huang is probably the poster child for this philosophy, right?
Howard Lerman
He really is. And it’s kind of funny and it’s not ironic because he is obviously at Nvidia enabling this AI boom. And so let’s fast forward to today. I mean, we were sitting at the dawn of an entirely new era of work, a dawn of a beginning of infinity, if you will, where… you’re going to see an I predict an entirely new kind of company. And it’s really fascinating because SMBs have classically struggled to compete against enterprises that have enormous resources to throw at any problem. can hire people to solve a process. They can have enormous R and D budgets to conduct deep research and hire teams of PhDs to come up with new technologies or new pharmaceuticals. And I believe AI is going to be a great leveler to try transform these SMBs into it makes new things possible with them. So AI will help the enterprise big companies by by by making there be cost centers that are more efficient. the enterprises have already been able to do a lot of stuff where AI is going to really help companies is in helping them make new things possible that they couldn’t previously afford. And so all of a sudden you’re going to have a new crop of existing businesses who adopt these technologies and new kinds of businesses that are founded on them that are able to just go way faster to achieve things that they previously couldn’t have done before and even complex things. And as a consequence of that, I think the model for running a company is going to be fundamentally changed forever. You’re going to have lower spans of control, for example. A founder or a CEO or an executive, I think it’ll be way easier for them to manage 30, 40, 50 people with AI, with scheduling, with summaries that are happening, with automated emails being drafted with greater visibility. The internet obviously with, know, communications makes the span of control and the hierarchies less necessary. So you’re just going to have flattened hierarchies within organizations. You know, I think also these types of organizations are going to move faster. They’re going to be not scheduling 30-minute meetings. They’re going to be having ad hoc.
Howard Lerman
meetings as necessary and sort of flying through the day as opposed to waiting and queuing things up until a one-on-one meeting next week, which is do it right now. I think another property that we’re going to see Bruce in the future going forward with this new type of business is always on. Constantine Bueller from Sequoia Capital wrote a great piece on this. The AI agents don’t sleep. And so as they demand products and services and they consume them or purchase them, they’re going to be on all the time. And in a global environment, you’re going to see AI agents communicating, purchasing products and services, and companies are going to basically have hours that are always on and being able to move faster and faster and faster. think global access to talent from anywhere. There’s a lot of people that are extremely talented outside of London, outside of New York, outside of the traditional centers of technical excellence, for example, financial excellence expertise. you’re going to see globalization being able to bring distributed companies together. But I just I see a future where people and AIs are working side by side in virtual spaces to achieve more than always on type of environment.
Bruce Daisley
What was really interesting by, and the thing that captivated me and genuinely like the approach was like an organic interest from what I saw. But I loved this. I’ve not used your product, but what I loved about it was that it presented the serendipity of wandering the corridors of an office building. And you saw two people inside a room having a conversation or you were able to witness all of the aggregations of people.
And it definitely brought to mind the sense that when you’re a small company, you’re watching a couple of people in a room and you stick your head in the, know, what you guys talking about. And, and I just love to capture your sense of how you built about the architecture of your product and how you believe that the, uh, the, the functioning of an organization changes as it scales. like, you know, I could definitely see the use case for sub a hundred person company.
And do you think that changes as an organization exceeds that? Talk to me about the way that you turned your philosophy into a product.
Howard Lerman
You know at Yext we were a very in-office company. In fact, we have a big building downtown in New York City with 200,000 square feet. In London, we had, you know, great office space where people would come every day. And I would suggest that what we’ve endeavored to do is to replicate all of the experiences that one might have in a physical office, but do so virtually. Now, they’re a little bit different, but… When you walk around the office that we had in New York, you would see conference rooms, you’d see private offices, you’d see, there was an auditorium, there was a room where people would play games. And so in Rome, what we’ve endeavored to do is replicate each of those types of experiences. And they’re fundamentally different. Let me give you one example. In a theater, you can sit, when you sit next to someone in the theater and someone’s talking, the presenter’s talking.
Part of being in a theater is being part of the audience and experiencing the energy of the people around you, the guy next to you, the people behind you. Maybe people are clapping, maybe they’re booing, maybe everyone’s laughing. You can make offhand comments to the people next to you in a live theater environment. That’s not possible in just a video conference call, but it is possible in the Rome Theater, which we designed to let you whisper to the people next to you in a way that the presenter can’t hear. And they can clap and there’s amplification as more and more people clap or laugh or boo, the sounds increase or decrease proportionate to the number of people doing that. that that experience and that sort of shared feeling of being in the same place is brought in an immersive way to the audience, but also into the to the presenter. So that was that was a source for us, you know, almost having operated in a real place for so long. The inspiration I suggest came from a
There’s actually a book called A Pattern. What was that book called? I’m trying to blank it. Christopher, it’s about how to build cities. And so we looked at that and we played SimCity. But yeah, the company visualization and being able to see who’s talking to who and jump around is all part of the future of work experience that we envision.
Bruce Daisley
A pattern language?
Towns Buildings Construction by Christopher Alexander. Okay, interesting. And so what does that book teach you?
Howard Lerman
Yes, that’s it. Alexander, right? Christopher? precisely right.
Well, it’s actually, it’s one of the greatest, it’s one of my favorite books. And it’s about how to design cities.
And it gives these universal truths, which are just so brilliant, but they may be things like the ratio of cars to, you know, roads to buildings. And frankly, that book actually inspired SimCity. So the, don’t know if you ever played SimCity, but that was, yeah, that was one of my favorite games. In fact, you can in Rome build your, we have little Easter eggs, but you can build your map in a way that’s pretty similar to how you can build your city.
Bruce Daisley
Of course.
Howard Lerman
you can move around who sits next to who. And that was kind of the, a little bit of the inspiration for how to construct your city like you would construct an office floor plan. But yeah, Christopher Alexander’s pattern language was a source of inspiration for us in how to actually come up with the original design.
Bruce Daisley
You’ve raised a really interesting question there. One of the things that I’ve often felt was that we are very intentional about the way we build our physical offices. know, like we wouldn’t allow the real estate where people stepped into our space to be anything other than a reception. We would greet people that this would be the place that we present ourselves to people. And yet when it comes to our calendars, which is similarly a bit of real estate, we allow them to be designed in a totally ad hoc way that anyone can, build whatever they want in any part of the real estate of our calendar. And there’s no intention, there’s no design. And so you, you, you pose a really interesting question there, that there’s a philosophy, this notion of how we build towns or cities or offices, but we don’t bring that same discipline to the other finite resource that we apply to our, our working lives, which is our calendar.
Howard Lerman
Well, we’re very focused on capturing and generating wealth. and saving money, but it turns out that our most valuable resource by far are the very limited seconds and minutes that we have. And people are a little bit overly generous with the way they give out their time. I will actually say that one pattern I’ve seen from some of the most successful people I know, and this is, talking about the centimillionaire, the billionaire folks that have succeeded in a huge way, is they don’t really keep calendar. They don’t schedule very much at all. It doesn’t mean they don’t do anything. Let’s not get confused into thinking that putting stuff on a calendar is actually staying, you know, being productive. What many of, and I was actually talking to one of them yesterday, he’s a repeat founder, one of his companies is worth, I kid you not, 10 billion dollars, and I was asking for his advice on something. And you know, it’s like, what time he just calls me. Like I don’t get to pick when, when I don’t get the schedule of time with him. He’s, know, I’m going to get the call and then I drop whatever I’m doing and I’ll talk to him for 15 minutes when he’s feeling like it’s ready to go. And so
And he sort of famously doesn’t keep a calendar. And so there’s this concept called inbox zero, where everyone tries to get to their inbox, their email inbox cluttered with crap, down, you know, delete, delete, delete, so I can get to inbox zero. That feels like I’m done with my tasks. But I would suggest that a more noble pursuit is that of calendar zero, where…
Bruce Daisley
Wow.
Howard Lerman
It doesn’t mean we don’t do anything. It just means that we are in complete control of our time, which is the most valuable thing that we have.
Bruce Daisley
Wow. mean, look, I’m so enamored with that because there’s something very relatable to it. know, was, I was today, I was chatting to somebody who worked at a colossal tech firm, probably the defining tech firm of our era, but the tech firm that has allowed every single innovation to pass it by. It had a 10 year advantage in AI and that’s gone. It had self-driving cars, two decades before everyone else and that’s gone. And the thing that defines that organization is that everyone has calendar, 100%. Everyone is back to back. And what has therefore come as a consequence of that is they’ve missed all of this, all of the gorillas that are walking past them, all of the opportunities that are there in the room, they’ve missed all of them because they are, they are full, calendar full. And it’s like, what you describe there is just a perfect.
recognition that we need to realign the way that we think about busy, the way that we think about productivity. Fascinating that you would anchor that as the heart of your product. So how are people using your product? How are people talking about product? How is that informing the way you’re developing it?
Howard Lerman
Well, one of the cool things, and there’s a concept when you develop a product called dog fooding. And the cool, that means you use your own product. you know, Bruce, I made, we made Roam for ourselves. That was where Roam got started. We made it for ourselves because we wanted a way to be all around the world and be able to feel like we’re in the same room from anywhere.
And some of us had moved to different places in the United States after the X journey. And the only way that we could bring and be together was in this virtual HQ kind of environment. And so I would suggest that we are the dog fooders of this product. so like, and a lot of founders like always ask me like, do you know, do I have, what should I make? Do I have product market fit or not? And my advice to them is always to make a product for yourself.
because if you make something for yourself, you have at least satisfied a market of one. And then you know that there’s something that there’s probably other people like you, if you’ve satisfied yourself. And so we use our product all day, every day we live in it. And the coolest thing is that our customers do too. Our customers, I’ll give you some stats. The average meeting time in Rome is just eight minutes long.
Now I want you to think about the last time you scheduled an eight minute meeting. It doesn’t happen. But you may have had an eight minute phone call. You may have had an eight minute chat with your coworker. You may have had an eight minute chat with your wife. You may have had a two minute chat with your kid.
That’s how people interact naturally. They don’t carve up blocks of time and sort of like say, we’re going to talk, we’re going to talk about this topic for 30 minutes. Well, when you do that, it’s going to take 30 minutes. So our customers fluidly use Roam all day, every day, and they’re doing so to achieve ultra productivity. Not only when you, when you, when you speak with someone for just eight minutes is it’s not only that your time,
Howard Lerman
has been compressed that you’ve saved time and what used to take 30 or 60 minutes has now been compressed to eight, you also get things done faster and so you’re able to do a lot more with a lot less. Now our vision is to have this all-in-one HQ and we haven’t talked a lot about AI but
Roam is very shortly coming out with, and we are here playing with them ourselves and have baited this with some of our customers, with AI agents that can also collaborate with people in natural ways, like voice, for example, and do so in the virtual office. And we have an AI assistant that…
is able to, and I should talk about this for a second too, the other, just one other side point, the benefit, another huge benefit of having a digital work environment versus physical work environment is that you can transcribe all the meetings. Now, let’s just talk about what that means for a second. We’ve seen the explosion of meeting tools like Otter and Fireflies. There’s one in the UK called Granola, which people love. Fathom. When you’re on a computer or digital surface, we can transcribe what’s going
going on in a meeting and then AI can do stuff with that later on. And one of the things that, great features of Roam is when you have an internal meeting.
we send you a summary of everything that happened and all the participants get that summary in a chat group. And we’re gonna take that to the next level with AI agents and assign action items to people after the meeting. And then for some of those action items, AIs can actually get them done. And this is where things get really interesting because let’s say one of the action items from the meeting, this is always tongue in cheek, but is to schedule another meeting.
Howard Lerman
Well, if we have access to your calendar, which Bruce, you mentioned, and Roam does have access to your calendar through our lobby feature, then an AI agent can analyze everyone’s calendars and clarify stuff, and maybe if there’s an external person, bring them into the fold with email, but schedule the meeting automatically and draft an email automatically.
or even follow up with someone. One of the key things that happens after me is I got to follow up with Jill and I got to remind Sally that I got to get something back from her or get an asset. And so the AIs can do this for us.
That feature is coming out really soon. And so what you’re going to see, I believe pretty shortly within the workplace, that’s what people that I talk to that are so excited about this change. We’re at this point, this really interesting point right now where
The technology is legitimately good enough to achieve things that we’ve been talking about for decades, but we’ve not fully realized that yet. And so that’s about to happen. It’s not like, the sci-fi, know, LLM technology could in the future do these sorts of things. Like these things can happen now. They are starting to happen now. They’re good enough. And over the next few years, we’re going to witness an unbelievable transformation in the way companies work, where people and AI agents are working side by side in more virtual spaces to achieve more than ever.
Bruce Daisley
What I’m really struck by, and look, I’m so grateful for your time today. What I’m really struck by is that this goes beyond technology though. The compelling part of your offering is that, you know, there’s a number of other organizations that might present this, but I think the compelling part of your offering is it’s grounded in such a clear sighted philosophy of where work thrives, where work succeeds, what energizes us about work that…
that’s driven the product to be very differentiated to maybe a dozen other products in an adjacent space. I’m really compelled with your vision of what we are energized by when it comes to work. Is that your own vision? How is that sort of a collective vision? How have you got to here?
Howard Lerman
You know, Bruce, we have an amazing team of inventors that live and work in our own environment every day and talk to our customers. And when we demo, we demo in our own environment. And I just, I think there’s such, I have such incredible optimism for the future and the way that, and I, and I’m glad that you’ve hit on this Rome really does have a human feel to it. And so in this era of AI where all the AIs are talking to each other in the back and
potentially even inventing their own languages to communicate with each other, which we can’t understand, there’s still going to be a human element in all of this. And there’s going to be human creativity. These LLMs just use statistics to compute what they already have seen. And so it is incumbent upon we as human beings to come up with the new ideas that will, and with the assistance of AIs do them faster and better. But
I want to be able to still collaborate with humans because I think that we as thinking machines are our best when we are inspired by others and
there’s no better way to be inspired by others than being present with them. Like I’m inspired by talking to you and it’s exciting. And so being able to replicate, but you are in the United Kingdom, I’m in the United States, we’re doing this from around the world. And so being able to put that into a package and being able to take that to the next level is a key part of everything we do.
Bruce Daisley
I love it. I’m inspired by what you do and I’m compelled by the vision that’s brought you to here. best of luck with the product, Howard. And I’m so grateful for you taking the time to talk to me today.
Howard Lerman
Thank you, Bruce. I look forward to delivering the office of the future.
