#8 – Inbox zero & time management for productivity | Sam Corcos, Dr. Casey Means, & Ben Grynol

In this episode of A Whole New Level, Casey Means Ben Grynol, and Sam Corcos sat down to talk about inbox zero, time management, and how they think about shaping the principles of communication at Levels.

Why Sam is a proponent of inbox zero

Sam was using Gmail’s zero product Inbox before Superhuman came out and changed the game.

I started doing inbox zero…The biggest thing that I noticed for myself was the anxiety reduction that came with it. This is one of the things we talked about in the effective communication podcast is how the stack of ambiguous tasks was something that cause a lot of anxiety for me. And not knowing how much work I needed to get done, if I was dropping balls.

Reducing anxiety through inbox zero

Casey has experienced productivity boosts without the “gray cloud” of unopened emails sitting in her inbox.

I would say my anxiety level around communication has gone down quite a bit since August, which is when I really adopted finally inbox zero. And I think that it really is what you talked about. Which is as opposed to this just looming gray cloud of ambiguous tasks that a lot of which live in your inbox, in the body of these emails. I’m just waiting for that magical time, that optimistic time when you think you’re going to get to it. It’s all gone. It’s all scheduled into your calendar. And you can actually clear the inbox and know that everything’s been accounted for. So it’s been a major change. And yeah, I think I’ve been able to actually be a lot faster with communication without that gray cloud of a huge inbox hanging on top of me.

Transitioning from the medical field to a fast paced startup

Before Levels Casey didn’t use email a huge amount but felt the stress of maintaining digital health records.

In the medical world, email wasn’t really a big part of my life. There would actually be days that would go by where I wouldn’t check my work email because so much of what was dictating my schedule in my life was actually the electronic health record and the communication with patients on there. So in a sense, that was kind of my inbox. But with that, kind of similarly to the business world, there are a lot of physicians out there with dozens or hundreds of chart notes or patient communications that just have not been completed yet and feel a huge burden and weight on their shoulders about this. And actually, I believe the leading factor involved in what is rampant physician burnout is essentially electronic communications and working with the electronic health record. So it’s kind of no different a lot of ways from the business world where I feel like this is a really root cause stressor for a lot of people, figuring out how to manage their inbox.

Transitioning to a new process for task management

Being intentional about how tasks are managed has unlocked a new level of efficiency to be unlocked.

Basically when something would come in an email that needed to be done, I’d add it to that list. And then the email would sit in my inbox until at some point it got done. So that was a terrible system. It’s almost embarrassing mentioning it, but I’m saying it in full transparency because you’ve got to start somewhere. And I think that sometimes when you don’t have good systems coming in, you can kind of just, a year can go by where you’re kind of doing things the wrong way. And this looks totally different to of course how I’m doing things now. But that progression from that to now which is inbox zero, really using calendaring to manage my tasks. It was definitely a six to eight month process and a lot of conversations with Sam. And I think that process, we can go into it in more detail. But from getting from there to now and the stress that’s taken off from moving away from the to-do list to a system of using the calendar and the inbox as a way to triage tasks has been game changing for me.

The impact of closing the loop

The process Sam uses for managing tasks from his inbox has been eye opening and stress relieving for Casey.

the big game-changer things that happened was that Sam actually started sending me Loom videos of him processing his email and showing how he takes things and puts them into his calendar. And it was I would say completely revolutionary for me to watch him process email versus knowing how I do it. It was faster, it was more efficient, there were shortcuts. He was delegating. He was sending emails to other people to loop them in early. He was closing the loop, even if he wasn’t ready to complete the task, but at least telling people that he saw it. And this was the timeframe. He was setting realistic guidelines of when he would get back to them based on looking at his calendar. And all of that was mind blowing to me.

How to force constraints on what you can accomplish every day

Adding todo’s to the calendar makes it easier to be realistic about how much time you have.

It’s really just about triaging information. The goal of putting something on your calendar is to force yourself to be realistic within the constraints of what you can actually accomplish in a given day. I think one of the biggest conceits that I’ve seen in people in leadership, in any company I’ve worked at is this assumption that comms just sort of happens. And very few people prioritize it or block off time to do it. And they just sort of try to fill in email in the margins between major tasks that they’re doing. When for most people in leadership, it really is their main job

Ben’s biggest learnings from calendaring

Having tasks on a calendar makes it easier to see how time is being allocated.

The biggest learning for the calendaring is, I guess there are two of them. One of them is accountability. So it’s time accountability to myself. If you’re really diligent about it and you keep track of everything down in 15 minute increments, you can see how you spent your time and you can go, “Am I spending my time in the best possible way for this team to be effective?” The other side of it is optics. So this is I think the biggest benefit is being able to see each other’s calendars. And you can just look into mine and you can be like, “There isn’t a ton of room to just throw eight hour projects, just throw this randomly saying, ‘Hey, we need this tomorrow.’” Even if it was urgent, sure. We’d make it happen. But you can sort of see where time is being spent. And I think that’s been helpful for everybody to be able to see the actual work being worked on.

Working in Threads and a need for reminders

Casey describes how the Levels team has shifted away from Slack.

I think we’re coming to a conclusion here that we might need a recommendation for Threads to do the reminder function. Because this all resonates with me so much. Just with Threads, what I am doing since it is basically a secondary inbox, is that when there’s any task that I know is going to take me more than about 10 minutes, I will put it on the calendar. Something I really need to do a deep review on. But in that system, it will just sit on the inbox homepage until that’s done, even if it’s two weeks in the future. And there is something so different about that than the inbox zero feeling where it’s just knowing that it’s there and you can see it every day, it feels like that gray, amorphous cloud again. So being able to get rid of it and have it come back only when you need it I think is a huge cognitive unload that I think it’d be really positive and something that’s superhuman. Does a really great, great job of.

Learning specific skills for inbox management

Inbox management is kind of like a sport that needs specific skills and training.

I started seeing email just as I would see a sport. You literally need specific skills to do it well, and we don’t actually learn those as an American adult. You don’t get trained on how to do it well. So in superhuman, that could be shortcuts, smart phrases, setting up your desktop appropriately to be able to move windows around in the most efficient way. So Sam in August, I think it was August, was actually at my house for about a day and sat down with me for two or three hours, and literally just watched me do email in person. And in about an hour, he completely transformed my desktop.

Superhuman as a tool for flow state

Ben shares an anecdote that led to the design of Superhuman

Rahul always talks about this. Rahul Vohra co-founder of Superhuman. That he designed, anecdotally, here’s a little story he tells and he told it on the Acquired Podcast shortly after Rapportive had been acquired by LinkedIn. He got himself a little toy, which was a Lamborghini. I can’t remember which model it was, but he used to drive it through the canyons. And he said he would drive it a little faster than the speed limit. Not much, but just a little bit faster. And that would put him into this deep flow state. So he had this insight one day where he’s like, “I want to design an email product that puts me in a flow state that feels like I’m driving a Lamborghini through the canyons.” And that’s really what it feels like.

The role of leadership: removing blockers from others

Often moving into a leadership role means a shift in the things that are most important.

So I think that the biggest principle is that if you’re in leadership, communication is probably your number one priority over all other things. Unblocking others. It’s making sure that people have the things that they need in order to get work done. Because if you’re in leadership, you are probably the blocker for a lot of things.

Being clear on who has the ball

Sam highlights the importance of ensuring communication systems set clear expectations.

So the metaphor that I think of in my head is it’s important to know who has the ball on any given task. Ben, you’re particularly good at taking the ball and then deciding that we don’t want to do anything further with it. So there were a lot of open tasks where we’ve decided that we would think about it, and then you would be responsible for it. And then you start looking into it and you say, “I think we should not do this.” And then we don’t. And that’s great. As opposed to it just sort of silently going away without any real sense of resolution.

Increasing visibility for deadlines in remote teams

Especially for remote teams knowing when things will happen is critical.

I think the comment around being able to inform stakeholders around deadlines is I think a really important one because this is especially important for remote teams. People need to know that everyone on the leadership team is reliable. And let’s say the deadline is Friday, and you get a really important press interview that comes up, and you bump into Tuesday. If you don’t have any way of telling the person to expect it later, they might be blocked by that thing. And they might need to change something in their calendar. And if all they hear is, “Casey just didn’t do the thing. And I don’t have any visibility as to why.” It decreases people’s confidence in execution and in reliability.

Adapting to moving into a leadership role

The impact of moving into a leadership role and strategies for learning delegation.

You’ve repeated that mantra so many times Sam which is that, “Casey, you need to be doing what only you can be doing at the company.” So I shouldn’t be going in and trying to take work that someone else on the team who is even more capable than I am doing that can do. So that’s been really impactful for me. Really trying to focus on the things that I’m really passionate about doing, but also the things that only I can do as the medical doctor at the company. So that’s been one thing.

I think the second thing, this is getting ultra personal here, but it’s a podcast. So I think we should. Is that honestly, I’ve been in therapy for the past year. And I started therapy after my mom died in January. And it’s funny. A lot of things I talk to about my therapist is these types of concepts around being a people pleaser, not wanting to say no, having trouble delegating, and actually just breaking through some of those barriers. And just better understanding what it means to be part of a team and to grow into new challenges and new opportunities in the company, and how that’s okay. So I think it’s been a bit of leadership training both through interactions with you Sam in coaching, but also through examining some of the reasons why it’s hard to delegate, and why it’s hard to say no, and why it’s hard to tell people you can’t do something. And realizing what the positive sides of that are and why you do need to lean into that I think, as you move into a leadership and a management role.

Recommendations for better communication

Ben’s top takeaways from improving communication at Levels

When it comes to messaging, have better tooling. So Superhuman is a great one for email. Be honest about prioritization and time management. If you’re spending your time communicating about something and choosing to say yes or no, be honest about the what you’re working on, your prioritization of those tasks. Be fast. And that doesn’t mean to be reactive to recency, but be fast in the sense of 24 to 48 hours professionally is probably reasonable for a medium priority message. Be transparent. So always be honest about it. And be specific and direct. Not necessarily thorough, but be specific. “Question Casey, will you have this press thing done by tomorrow?” Don’t bury the lead. And then close the loop once it’s done.

Casey Means: Something about Sam’s videos, his Loom videos that made an impression on me. It was like he was literally breathing heavily while doing email. It was so focused, and I realized this is not an afterthought. This is like get in the zone as if I’m doing any other tasks, super, super focused, like a sport. And when I kind of changed my framework around that, I think it was really helpful.

Ben Grynol: I’m Ben Grynol, part of the early startup team here at LEVELS. We’re building tech that helps people to understand their metabolic health. And this is your front row seat to everything we do. This is A Whole New Level.

Ben Grynol: Inbox zero. It’s other something you get behind, or you don’t. Either you’re the type of person who can look at their phone and see 29,337 unread messages and be okay with it, or you can’t. There’s not really an in-between. And the idea of processing and triaging information, really the foundation of communication. Well, there are all these things that can be really hard to get behind. Everyone’s going to have a different way of going about their tasks, and that’s fine. The important thing is do you get to an end goal that works, and is it the most effective way for you to manage what you do?

Ben Grynol: And so Sam Corcos, CEO and co-founder of LEVELS, Casey Means, Chief Medical Officer and co-founder of LEVELS, and I. Well, the three of us sat down and discussed all these different principles of communication. The way that we think about email, specifically inbox zero, the way that we’ve managed our comms, our internal communications, and the way that we can take these insights to help each other to keep learning and really getting better as we communicate more as a team. The conversation reinforced that. Communication really is the foundation of any great relationship, whether personal or professional. So, here’s where we started.

Casey Means: Okay. In box zero, this is a sensitive topic. It’s a fun topic. It’s something that I think we’ve probably discussed as a team more times than you can count on two hands. But, I think between the three of us, we all have such different ways of managing communications and tasks to be effective in the way that we prioritize things. So there’s a lot of lessons learned just in I guess the outlook on inbox zero, and then how we’ve all come to this point that we manage it, and even the way we manage it today.

Casey Means: So I know Sam is a huge proponent of inbox zero, and he’s been really helpful in getting our team ramped up around that. So Sam, how did you start to think about inbox zero? And when you did it, did you ever revert back to these old habits or old ways of doing email?

Sam Corcos: Yeah. I started doing inbox zero. Gmail came out with a product called Inbox, which they eventually killed. I’m not entirely sure why. I guess it didn’t get enough traction. But it was basically superhuman before superhuman. It was the first real inbox zero tool. The biggest thing that I noticed for myself was the anxiety reduction that came with it. This is one of the things we talked about in the effective communication podcast is how the stack of ambiguous tasks was something that cause a lot of anxiety for me. And not knowing how much work I needed to get done, if I was dropping balls.

Sam Corcos: The thing that I’m especially curious about, because I know Casey and I have talked a lot about this topic of time management in communications and inbox zero in particular. And I’ve noticed a significant jump in communication and what I perceive to be a reduction in stress from Casey’s side of things. I’m curious to hear if there are any big learnings in the last few months.

Casey Means: I mean absolutely no question. I would say my anxiety level around communication has gone down quite a bit since August, which is when I really adopted finally inbox zero. And I think that it really is what you talked about. Which is as opposed to this just looming gray cloud of ambiguous tasks that a lot of which live in your inbox, in the body of these emails. I’m just waiting for that magical time, that optimistic time when you think you’re going to get to it. It’s all gone. It’s all scheduled into your calendar. And you can actually clear the inbox and know that everything’s been accounted for. So it’s been a major change. And yeah, I think I’ve been able to actually be a lot faster with communication without that gray cloud of a huge inbox hanging on top of me. So yeah, certainly happy to dive into what the system was before we got to inbox zero and the progression towards actually getting there. If you want to get into some detail on that Ben, I’m happy to elaborate.

Ben Grynol: Yeah. I think that that would be, going into some of the backstory is really interesting. I’ve always been curious because you came from a world where I’m going to make an assumption that communication in the medical field is very different than a air quotes fast paced startup, especially one that is remote and relies on communication. Right? It’s probably more volume than would take place in the medical world. So what was that like coming into this environment, and then what was the sense of reluctance to fully adopt the inbox zero?

Casey Means: Yeah, it was interesting. In the medical world, email wasn’t really a big part of my life. There would actually be days that would go by where I wouldn’t check my work email because so much of what was dictating my schedule in my life was actually the electronic health record and the communication with patients on there. So in a sense, that was kind of my inbox. But with that, kind of similarly to the business world, there are a lot of physicians out there with dozens or hundreds of chart notes or patient communications that just have not been completed yet and feel a huge burden and weight on their shoulders about this. And actually, I believe the leading factor involved in what is rampant physician burnout is essentially electronic communications and working with the electronic health record. So it’s kind of no different a lot of ways from the business world where I feel like this is a really root cause stressor for a lot of people, figuring out how to manage their inbox.

Casey Means: But when I came to LEVELS, but first it was just the five of us, the co-founders. So there wasn’t quite as much email. And then as responsibilities and areas that I was working on expanded and as we started working with more external partners, and as I started really managing content which had a lot of external partners with freelance writers, editors, and things like that. Definitely email started ramping up quite a bit after the first few months.

Casey Means: So what I kind of defaulted to was sort of my, what I would consider my high school college and med school kind of way of managing tasks, which was the to-do list. Which I love the way Sam talks about to-do lists. It’s this really overly optimistic way of thinking that you’re going to kind of get everything done, but really it just creates this just amorphous list of tasks that aren’t really prioritized.

Casey Means: And I was looking back at some of the things I was initially using for my to-do list. And I basically had a Google Doc called Casey’s Priorities I would update every week. And the last time I updated this was in October of last year. So I used it for over a year at LEVELS. And before my one-on-ones with Sam, I would generally update it so I can get a sense of what was on my plate.

Casey Means: And it was usually about three typed pages for each week. And it essentially was bucketed into all the areas that I was working on. And then underneath those buckets, all the tasks that week that I had to do. And then I highlighted the ones that were top priority.

Casey Means: So you’re looking at three types pages, it’s super overwhelming. .And kind of just deciding, “Okay, at this moment, these are the ones that need to get done first.” So in October it was content, hiring, podcasts, advisory board management, research, PR media, conferences. And then other team needs, which was sort of a catch all. And then under each of those, maybe three to 20 bullet points.

Casey Means: So this was really causing a lot of anxiety. And I feel like most of the time I was talking to Sam on our one-on-ones, I’d be like, “Oh my gosh Sam, there’s so much on my plate. I’m not sure where to start.” And he would really help me strategize. And those documents in one sense were useful because they actually helped us really realize where we needed to hire. And I think from those documents, actually kind of directly led to us hiring people like Mike Haney to take over a lot of the editorial and content side, Tom to really take on a lot of the partnership stuff. And so they were useful for understanding that, but they were not useful for task management.

Casey Means: And basically when something would come in an email that needed to be done, I’d add it to that list. And then the email would sit in my inbox until at some point it got done. So that was a terrible system. It’s almost embarrassing mentioning it, but I’m saying it in full transparency because you’ve got to start somewhere. And I think that sometimes when you don’t have good systems coming in, you can kind of just, a year can go by where you’re kind of doing things the wrong way. And this looks totally different to of course how I’m doing things now. But that progression from that to now which is inbox zero, really using calendaring to manage my tasks. It was definitely a six to eight month process and a lot of conversations with Sam. And I think that process, we can go into it in more detail. But from getting from there to now and the stress that’s taken off from moving away from the to-do list to a system of using the calendar and the inbox as a way to triage tasks has been game changing for me.

Ben Grynol: I mean, it’s wild because it seems really busy, right? Everybody who has that much work on their plate, it’s like, “Oh my goodness, I’m so busy.” But it gets down to this root of things being unplanned work, right? If the majority of your time, 95% of your time is bogged down in unplanned work, and Sam has tons of thoughts on this because it pertains to company building, it pertains to eng, it pertains to name it. Unplanned work can clog up the manufacturing system pretty quickly. And I think that’s where the outlook on having a really efficient way of managing your time and being accountable for it is what makes things progress.

Casey Means: Yeah, definitely. And I think one of the many, many ways in which Sam’s an incredible leader is that you can go to him with some of these problems. And really, I see him as a coach in a lot of this.

Casey Means: So it was pretty fascinating to see how things progressed. Really the first shift, because Sam really I think associates email and task management together. And I was not really viewing things that way, like how email could be directly feeding into how I structure my time. And now, I see them as very much one in the same. Because many of the tasks where I’m going to have to devote time to comes in through email.

Casey Means: So some of the big game-changer things that happened was that Sam actually started sending me Loom videos of him processing his email and showing how he takes things and puts them into his calendar. And it was I would say completely revolutionary for me to watch him process email versus knowing how I do it. It was faster, it was more efficient, there were shortcuts. He was delegating. He was sending emails to other people to loop them in early. He was closing the loop, even if he wasn’t ready to complete the task, but at least telling people that he saw it. And this was the timeframe. He was setting realistic guidelines of when he would get back to them based on looking at his calendar. And all of that was mind blowing to me.

Casey Means: So those initial Loom videos, I’d say maybe I don’t know, you probably sent me five hours worth over the course of a few weeks. And those felt like coaching and watching game days from a sports team. And I loved it.

Casey Means: And then he asked me to send him Loom videos of me doing email. And he actually coached me through those. And basically at multiple different timestamps said, “Hey Casey, you could have definitely sent this email to XYZ and had them do that. Write back to this email, tell them you can’t look at it until your calendar opens up.” And really giving me this play-by-play how I could be doing it differently. And that was definitely one of the biggest steps forward in me gaining the skills to actually be a good email processor and figure out how to take things from the email, put them in my calendar, create that closed loop system, and then get the email out of my inbox.

Ben Grynol: Yeah. We got to go down the path of this calendar thing, because it’s something that Sam has done for a couple of years now. There’s a nice first round piece of boat. It’s very counter-intuitive, or it was. I’ve adopted it now. It was very counter-intuitive to the way that I worked. And that’s back to this first statement of hey, we all have different ways of processing information and doing it efficiently. I’ve always had a to-do list that I use on a notepad. But prioritize it where it’s like super happy to just delete things off of it. And try to be efficient about core deep work or core project work versus unplanned and now we’re punting this. But Sam doesn’t use a to-do-list. So my questions around this calendaring exercise, and how do you pair that with this whole thought of inbox zero when taking it on?

Sam Corcos: Yeah. It’s really just about triaging information. The goal of putting something on your calendar is to force yourself to be realistic within the constraints of what you can actually accomplish in a given day. I think one of the biggest conceits that I’ve seen in people in leadership, in any company I’ve worked at is this assumption that comms just sort of happens. And very few people prioritize it or block off time to do it. And they just sort of try to fill in email in the margins between major tasks that they’re doing. When for most people in leadership, it really is their main job.

Sam Corcos: So making sure that you prioritize communication. This is one of the things that Casey mentioned is that I know that Ben and Casey, you have different methodologies for scheduling things. I do it more in the way that Casey does now, which is if somebody sends me an email and it asks me to do a thing, I will mark the email as complete, but I will put it in my calendar. So I’ll block off, say an hour to do the thing that was in the email. Whereas Ben, I know you use the email system itself to set a reminder for yourself in the future. I get a lot more clarity on what I have upcoming and what my bandwidth is through using calendars. But whichever system works for each individual’s fine.

Sam Corcos: So I am actually curious Ben, because I know that you’ve been experimenting with using your calendar more over the last month or so. Have there been any learnings from that process?

Ben Grynol: Yeah, so here’s the biggest thing is it was terrible at first, right? Because the optimal calendar for me was zero meetings let’s assume a week. And this is not a perfect state, but no meetings at all. And every day has just completely opened chunks of time to do really deep focused work. And knowing that you can adapt that, you can be malleable when needed if some unplanned work comes up that happens to actually be high priority. Not something that seems like it’s a high priority, but it actually is. Where it got really hard is when I was trying to do what you had suggested where it’s like an email comes in, or some message comes in from somewhere, and you block off time to address it in your calendar. And I was trying to do that. But where it was really difficult was I couldn’t adapt to well, I have to punt this thing forward. It just wasn’t working.

Ben Grynol: So what’s worked better is to open up the calendar so that it doesn’t have these blocked off chunks of time for certain things. It’s knowing that I’m going to accomplish a number of core projects and fill in, like you’ve got your rocks and filling it in with the sand around it, which is the emails.

Ben Grynol: But the biggest learning for the calendaring is, I guess there are two of them. One of them is accountability. So it’s time accountability to myself. If you’re really diligent about it and you keep track of everything down in 15 minute increments, you can see how you spent your time and you can go, “Am I spending my time in the best possible way for this team to be effective?”

Ben Grynol: The other side of it is optics. So this is I think the biggest benefit is being able to see each other’s calendars. And you can just look into mine and you can be like, “There isn’t a ton of room to just throw eight hour projects, just throw this randomly saying, ‘Hey, we need this tomorrow.’” Even if it was urgent, sure. We’d make it happen. But you can sort of see where time is being spent. And I think that’s been helpful for everybody to be able to see the actual work being worked on.

Ben Grynol: One more point is back to this whole email thing and this I don’t know if you want to call it, a weird system. But it just seems to be, what has worked is when an email comes in, it’s not about processing it reactively. But I tend to batch things. So it’s like I’ll turn off platforms, communication platforms for hours at a time if I’m not processing. And then when I go to batch, let’s say I spend an hour and a half or two hours just doing comms, just hammering through them. I’ll process everything. And then even if the thing is processed, I’ll set reminders for myself of followups to stay on top of things. Or follow-ups for closing the loop. Like somebody intros, somebody on our cap table makes an intro to somebody else. I’ll set the reminder for four weeks just to close the loop with that person to be like, “Hey, wanted to let you know the conversation went really well. Here’s what we talked about. One, two, and three. Appreciate it.”

Ben Grynol: That’s the way that I use email as far as tooling goes so that my brain never has to think about ever doing any tasks. I basically use it as, I use it so that I can actually not be super smart, just transactional about everything. And it makes things a lot easier.

Sam Corcos: Yeah. I think the biggest one is around the ambiguity of the big stack of tasks. I think this is what Casey touched on. That’s definitely something that I feel as well. Right now, we’re using Threads instead of Slack. And one of the challenges when you have a list of followups, you can’t push those in future date. Right now I have a list of I think 30 Threads that require my input. But about half of them don’t need my input for at least a week. And it’s definitely causing me some stress just knowing that there’s a high probability I will drop a ball because I don’t have a way to triage that information.

Ben Grynol: Yeah. I’m on the same page. That takes up brain space. When I see that, that gives me a sense of anxiety because it feels like not inbox zero. Whatever the opposite of inbox zero is, that’s what it feels like. And I think I’ve got 29 right now, right before we hopped on this. And one of them is a thread that you had sent me earlier today, Sam. And it was like, “Hey, let’s revisit this in every quarter.”

Ben Grynol: So what I do in email is just set the reminder and it’s gone away. I don’t even need to think about it. It’ll be zero. I’m at inbox zero. But instead, that thing’s going to sit there in my purview for like ever in perpetuity until we address this thing, which could be multiple quarters. And it doesn’t take very many of those to stack up where all of a sudden you’re like, “Whoa, there are 50 of these things,” and you can’t figure out which ones to prioritize because it’s a block of things with no date associated to them.

Casey Means: I think we’re coming to a conclusion here that we might need a recommendation for Threads to do the reminder function. Because this all resonates with me so much. Just with Threads, what I am doing since it is basically a secondary inbox, is that when there’s any task that I know is going to take me more than about 10 minutes, I will put it on the calendar. Something I really need to do a deep review on. But in that system, it will just sit on the inbox homepage until that’s done, even if it’s two weeks in the future. And there is something so different about that than the inbox zero feeling where it’s just knowing that it’s there and you can see it every day, it feels like that gray, amorphous cloud again. So being able to get rid of it and have it come back only when you need it I think is a huge cognitive unload that I think it’d be really positive and something that’s superhuman. Does a really great, great job of.

Casey Means: But yeah, I think one of the biggest breakthroughs that Sam helped me with. Being in a leadership position, knowing that email communication is going to actually be a significant part of my job can’t just fit in around the edges, which I think is what we all try to do. Putting actually three hours of straight email processing on my calendar every single day. And now that I have that and I know I’ve got that buffer time to do email, and considering email now to be a part of my job that I actually see as a real important task, it is so, so much easier.

Casey Means: So I’m doing the like I just mentioned, if it’s less than 10 or 15 minutes or so, I will just process whatever’s in the email during that block, during that hour block, or one of those three hour blocks. And then if it seems like it’s going to be more than that, like I’m actually having to edit a document or whatnot, review a strategy document, it goes on the calendar. And then I think like Ben does, I set the reminder for that email to come back the day that I’m going to be working on it around the time that I calendar it for.

Casey Means: So yeah, I think that’s just something that is a definite takeaway for me is schedule the time on your calendar so you’re not overly optimistic about what you can do, and let email kind of just be a second tier thing when it really is not.

Ben Grynol: If it took, so you said it took like 18 months to like really grasp onto this and you would try, and then revert back to old ways and try again. In August, right? Because I think that’s what you said August of this year is when you really embraced it, what was that catalyst for change where you’re just like, “Okay, I’m done with this. I have to adopt this new way of communicating or processing information”?

Casey Means: It was several things. I think the first was I think at a certain point, you just get sick of complaining about the same things. I think that’s what. I was like, “I just do not want to have another one-on-one with Sam where I’m complaining about the same thing.” And Sam is so helpful. And the real catalyst was we’d been exchanging these Loom videos back and forth, which I feel like really helped me build my basic skills for actually how to be a good email processor. And I started seeing email just as I would see a sport. You literally need specific skills to do it well, and we don’t actually learn those as an American adult. You don’t get trained on how to do it well. So in superhuman, that could be shortcuts, smart phrases, setting up your desktop appropriately to be able to move windows around in the most efficient way.

Casey Means: So Sam in August, I think it was August, was actually at my house for about a day and sat down with me for two or three hours, and literally just watched me do email in person. And in about an hour, he completely transformed my desktop. So totally changed my hot keys, and my hot corners, and set up multiple desktops instead of one desktop, and had me put different programs in each desktop so I wasn’t totally cluttering my one desktop. Got the sidebar to disappear, so it wasn’t in my space. All these things that just made it much more of a focused place on my desktop, and then watched me do some email for a little while and gave me some of those pointers, like we’d been doing through Loom. But something about doing it in person and kind of, I feel like almost seeing the cringing of some of the things I was doing and really I’m like, “Yeah, I got to do better.” Was great.

Casey Means: So what resulted from that time together in person, which was really what I considered just to be some of the best coaching of my life. I said, “Okay, I feel like I have the skills by Sunday at whatever 9:00 PM. I’m going to be at inbox zero. I’m going to send you a note at that time, be held accountable for this.” And I did. So then I do think getting to inbox zero no matter what it takes, even if it means sitting down with someone in leadership at your company who’s really good at it and getting real help. Getting to that inbox zero was such a monumental thing because I had been living with 500 emails in my inbox for months, and months, and months. And getting to that and then starting fresh was transformational. Because then, there was no burden, no overhead. And from then on, everything that came in, I could apply the skills to.

Casey Means: I could either calendar it. I knew how I wanted to be approaching emails that were incoming. So that was, from there actually, I have not reverted. And it’s been now a few months and I don’t see it going back because the foundation and the skills are there now.

Casey Means: So I really do see it almost like a sport. And something about Sam’s videos has Loom videos that made an impression on me. It was like he was literally breathing heavily while doing email. It was so focused, and I realized this is not an afterthought. This is like get in the zone as if I’m doing any other tasks and super, super focused, like a sport. And when I kind of changed my framework around that, I think it was really helpful.

Ben Grynol: Yeah. That’s so funny, but it’s so true though. Because I mean everything, as soon as you get in the process of doing it and you get, Rahul always talks about this. Rahul Vohra co-founder of Superhuman. That he designed, anecdotally, here’s a little story he tells and he told it on the Acquired Podcast shortly after Rapportive had been acquired by LinkedIn. He got himself a little toy, which was a Lamborghini. I can’t remember which model it was, but he used to drive it through the canyons. And he said he would drive it a little faster than the speed limit. Not much, but just a little bit faster. And that would put him into this deep flow state. So he had this insight one day where he’s like, “I want to design an email product that puts me in a flow state that feels like I’m driving a Lamborghini through the canyons.” And that’s really what it feels like.

Ben Grynol: As soon as you get processing email or any type of communication really efficiently, you get into a deep flow state where everything is hotkeys. It’s snippets, it’s reactions. It’s about how fast you can get through things while still being thoughtful. The other side of it is that just because you can do things quickly, doesn’t mean that you do. And I think this is where Sam’s been working with a number of people on the team to set expectations around communication. Right? So it’s like we might have the ability to process things. But if we’re not responding N number of days, that might not be helping the rest of the team. So Sam, how are you thinking about it when you’re trying to break down remotely? You’re trying to break down where to help people and what is going to benefit the team the most as it pertains to processing versus communication expectations.

Sam Corcos: Yeah. I think some of it is first, it’s whether people want me to help them. Casey and I have talked about it a lot, and she wanted my input. I think another is whether there are balls being dropped or not. So we can take your example then of the system that you have in place. Approximately zero people in the company mentioned that they’re concerned about you dropping balls. So whatever system you have in place, it’s definitely working. So there are other places where I get feedback that communication is not where it needs to be, or there’s some ambiguity around execution or timeline. And we just need to increase the cadence of communication. I think it’s especially important in remote teams like ours to have an unreasonably high cadence of communication, much more than people are used to in jobs that they come from before.

Sam Corcos: Josh talked about this in a previous podcast where his lack of communication was causing a lot of tension earlier on in our relationship as co-founders. And he had this recognition that how could Sam know what I’m doing? Because I’m on the other side of the country. So there’s no looking over the shoulder, there’s no casual conversations. It’s just somebody who’s completely off grid. And then they come out of the cave.

Sam Corcos: So I think that the biggest principle is that if you’re in leadership, communication is probably your number one priority over all other things. Unblocking others. It’s making sure that people have the things that they need in order to get work done. Because if you’re in leadership, you are probably the blocker for a lot of things.

Ben Grynol: Yeah. The tough thing with it too is, and there’s no right answer to this. It’s just being respectful of everybody’s outlook. So objectively, yes, I agree. If you’re in a leadership position, your job is to communicate, to unblock, to get things done, and to move things forward.

Ben Grynol: The challenge is that you could send hypothetically, so let’s use you and I as an example. You could send me 250 we’ll just call them emails even though we use Threads both 250 messages tomorrow. And let’s assume they’re relatively transactional. I wouldn’t even think about it. It would just be processing. You just do it. But to somebody else, they might think, “Oh my goodness, I’m so overwhelmed,” that they go into shutdown mode and then they don’t know which one to start with.

Ben Grynol: So it’s knowing that everybody’s got a different preference for email. And I think when we decided to switch to Threads like Sam and I had our hand in the air we’re like, “We love email.” Just I don’t know, it’s a weird thing I guess. But we just both really enjoy. It’s an enjoyable thing to do. This sounds totally maniacal right now.

Sam Corcos: We’re definitely outliers on the team.

Ben Grynol: But it’s funny because other people, like Miz was notorious for saying like, “I have a lot of gripes with email. And that’s completely fine. Josh, same thing. He’s not a huge fan of email. But I think it’s because of everyone’s way of processing it is going to be totally different. So when more people are hyper communicators, it’s really good. But you also need the right tooling to be able to manage that communication. Right? So it’s like if you have, when it’s only Sam putting out, we’ll see. He’s pushing out 30 emails a day to the team. And then there’s different response times from everyone else. Well, if you have three Sams or three people with a high communication cadence coming in and they’re all pushing out 30 emails, that’s where we started to see things break is like, “Oh my goodness, there’s a very high communication cadence. A lot of information needs to be processed. What are we going to do about it?” Knowing that email is not the right platform for the way that we needed to communicate as a remote team.

Ben Grynol: So it’s interesting to see how that happens from a tooling perspective. But if we get back into expectations for communications, and I’m genuinely curious because I don’t know if the outlook on followup and the outlook on reasonable amount of time to respond is going to differ here. So Sam, I’m curious. What do you think is a reasonable amount of time to give someone to respond to an email?

Sam Corcos: I think it depends on the person and the role. I think 24 hours is probably reasonable. I think one of the things that’s often underappreciated, and I think this is something that Casey and I talked about is it’s okay to give someone a response. And that response is, “I’m not going to be able to answer this for five more days.” The goal is not to avoid failure. It’s to avoid silent failures, where that communication gap causes a lot of stress for the other party. So if Ben asks me for something, if I just respond with, “I don’t have time to look at this until Thursday, is that okay?” The answer is usually yes. But if I just don’t respond and they wait until Thursday, Ben doesn’t know if I even got the message or if I’m avoiding it for some reason. There’s too much ambiguity.

Sam Corcos: So the metaphor that I think of in my head is it’s important to know who has the ball on any given task. Ben, you’re particularly good at taking the ball and then deciding that we don’t want to do anything further with it. So there were a lot of open tasks where we’ve decided that we would think about it, and then you would be responsible for it. And then you start looking into it and you say, “I think we should not do this.” And then we don’t. And that’s great. As opposed to it just sort of silently going away without any real sense of resolution.

Sam Corcos: But I’m curious about one thing to hear from Casey on one of the things that I’ve always struggled with. And I know this is something that’s taking up a lot of your time right now, since you’re really the point person on all of the press that we’re doing.

Sam Corcos: When I was going through my calendar, and my emails, and all of the tasks on my list with Miz a couple of months ago, we had the recognition that I have maybe one or two unscheduled events per week. It’s really very few. We went through 100 communications via email and Threads. I think it was actually just email in this case. But all 100 of them were asynchronous, and none of them were time sensitive. So that was an interesting observation.

Sam Corcos: In your particular case, a lot of what you’re doing right now is very much time sensitive. It’s a reporter wants to talk to somebody now or tomorrow, and it’s harder to schedule around that. How have you managed that? Because that’s something I’ve always struggled with myself, and my solution is just to avoid it.

Casey Means: Well I think one of the first things is being a little bit more comfortable saying no to things. So it used to be in the beginning of the company that anything press related that came in, we’d kind of drop everything and do it. And now we’re being a little bit more selective about opportunities. And now, we’ve hired Mike Haney our editorial director, who’s now really the point person day-to-day for the first pass on press stuff. So to have that help with another person who can help fill in for things that are semi-urgent is a huge help. And a lot of times him and I will go back and forth about like, “Can you do a first draft for this type of thing, for these answers? And I’ll do a quick review,” or vice versa. So having that tag team is really helpful.

Casey Means: But I think from a calendar perspective, you really taught me this lesson. Which is that sometimes if I’ve got a day that’s full of blocks, I can potentially move a task that’s non-urgent to a subsequent day or even maybe next week if it’s really not time sensitive, but does have to be done. And then I can write that person, whoever else is a stakeholder in that task or project a note saying, “Hey, something came up. Would it be okay with you if I got this to you on Tuesday?” And a lot of the times, that’s not a problem. If it is a problem then have to reevaluate.

Casey Means: So then of course, sometimes things just kind of end up adding blocks, maybe cutting into email time or whatever to get some of those time sensitive stuff done. But those are kind of the main ways that we triage this stuff. So having help and support, moving blocks around, and just making sure to close the loop on that, and learning to say no more to some of these things that are not necessarily going to be great leverage for the business, or necessarily super critical or existential for us right now.

Sam Corcos: Yeah. I think the comment around being able to inform stakeholders around deadlines is I think a really important one because this is especially important for remote teams. People need to know that everyone on the leadership team is reliable. And let’s say the deadline is Friday, and you get a really important press interview that comes up, and you bump into Tuesday. If you don’t have any way of telling the person to expect it later, they might be blocked by that thing. And they might need to change something in their calendar. And if all they hear is, “Casey just didn’t do the thing. And I don’t have any visibility as to why.” It decreases people’s confidence in execution and in reliability.

Casey Means: Absolutely. I mean, I think that the closing the loop is the key thing. And I think in a remote asynchronous company, it’s like closing the loop is everything. Even if the closing the loop is saying that you can’t do it right now. I think that can sometimes be the hardest part for people. And actually, I’ll just speak for myself. I think that was a hard part for me early on, which is that a lot of the time closing the loop means that you’re saying, “I can’t get to this right now,” or, “I need to push back this deadline. Does that work for you?” And I think for people who are in the sort of people pleaser category, that can be really, really hard.

Casey Means: So I think that’s just something that we’ve all got to get more comfortable with. Really realizing and buying into the fact that it’s always better to know what’s going on and have a clear answer, even if that answer is no, versus just having something in the linger. It’s always worse that way. And it’s such a fallacy in our minds that we convince ourselves that it’s better to just let it fade away or whatever.

Casey Means: So that’s something that I think has been a shift for me as I’ve gotten more confident saying no. Again, as the company has grown, it’s been interesting because in the very beginning again, it was five of us. We were doing everything ourselves, and we were both having to be strategists and leaders, but also individual contributors because there were so few people. Now we have 35 people or so, and there’s a lot bigger team to sort of help and take on work. So you do end up having to pass things to the appropriate team to route information to say, “No, I don’t have bandwidth for this, but let me connect you with XYZ.”

Casey Means: And I think this is not all about just skill with email as a tool or as an art, but it’s also about that confidence in evolving roles over time and feeling comfortable. Just being honest with yourself and other people about what you’re capable of, what you can do right now, what you can’t, what your bandwidth is, and being comfortable delegating as a team grows.

Casey Means: So I think there’s a lot of that psychological stuff that’s also embedded in why we have challenges with emails that good leadership can help you deal with, and face, and be honest about, and kind of grow into. So you’ve been hugely helpful to me in that regard Sam, and you as well Ben. But I think there’s definitely a part of it there as well where closing the loop is not just about laziness or not having good email hygiene, but actually more a deeper rooted not wanting to disappoint people, which is a fallacy because it’s always worse to not let them know.

Sam Corcos: Yeah. I wonder, you have a lot more time-sensitive things that come up than I do. Do you have like a heuristic that you use to … one of the things that I try to make sure that I’m following is to make sure that I don’t let recency determine priority. Do you have any heuristics that you use for when a press piece, or a press opportunity, or something that’s time sensitive comes out that you use to try to prioritize those things?

Casey Means: One of the great things now is that there’s a team around me that can help me prioritize and triage. So because we have such a strong relationship with Jack Taylor PR, and Tom, and Mike are both working with me on press, I can now get input on an opportunity like, “Hey, how important do we think this is? What do we think the reach is? Is this worth doing?” And everyone on the team’s aware of how bandwidth constrained we are. So they’re not going to pile on unnecessary stuff.

Casey Means: So one of the heuristics, I mean first of all, it’s definitely getting input from the team on how valuable this opportunity is? And does it align with our written press strategy? Our press strategy has shifted between the beginning of this year and now. Last year, beginning of this year, and now. Where initially, we really wanted to make sure that we were sharing our message in the top tier reputable outlets that people turn to for trusted advice. And we were very fortunate to achieve that. And then secondarily, we really want to build domain authority and make sure that we have strong backlinks coming to our site.

Casey Means: So there’s different things that we’re trying to achieve that shift over time. We initially were really telling the story mostly about LEVELS and about our product. And we’re shifting a bit more into sharing more educational stories about metabolic health and niche topics within metabolic health that are relevant to individuals.

Casey Means: So because of that, we have to evolve in terms of what opportunities we’re taking on. So it’s not just about yes to everything. It’s actually really aligned with what is going to be aligned with our strategy and not just what’s a shiny object. So we have a big team that helps us stay accountable to our strategy that allows us to say no confidently when that’s the right move. And if it’s not, then we obviously look at the calendar and find time to do it. And again, these are often 24 hour turnarounds, and bump stuff that may be lower priority.

Casey Means: And then I did a last thing is that we’ve created really great systems for making some of these press responses as efficient as possible. We have an amazing corpus of past responses in notion for all the different articles we’ve been a part of and interviews. And all of that is documented, recorded, and organized. So that allows for JTPR to potentially take a first pass at doing some answers on my behalf that I can then review, or for Mike or Tom to do a first pass.

Casey Means: So we’ve set ourselves up to make these things not like reinventing the wheel every single time. Although sometimes of course, we’re going to get novel questions that we have to do original answers to. But trying to just basically create systems that let us be more efficient with these answers.

Sam Corcos: Yeah. It sounds like delegation is the answer to that. Because a lot of those things are figuring out ways of having either an automated system, or having somebody take the first pass to free up more of your time. That’s something that I’ve been practicing a lot, really for probably the last eight years. I’ve had, a lot of people on the team don’t know this, but Laurie who works with us as a contractor has actually been my EA for almost eight years now, maybe more than eight years. And I actually hired Laurie after reading Tim Ferriss’ 4-Hour Workweek where he talks about delegation as a superpower, and realizing that I didn’t have the skills needed to be able to delegate.

Sam Corcos: So I hired Laurie, not really having anything for her to do. Just with the intent of figuring out how to get better at delegating. And that was a really useful exercise in just flexing that muscle and learning how to phrase things and to set people up for success to be able to delegate effectively.

Sam Corcos: And I’m curious Casey in the course of the last call it six months, you’ve been delegating a lot more stuff. I’m curious if there was a mental shift for you that got you more comfortable with that.

Casey Means: Yeah. I think the mental shift, a lot of it came down to conversations with you and Josh. And then, also a lot of the reading that I was doing and we were doing as a team. Reading things like High Growth Handbook and that famous article about giving away your Legos at a startup. And several things like that that helped me conceptualize how my role needs to change as the company grows.

Casey Means: Again, with the people pleaser gene and really just wanting to add value, it can be hard sometimes to move from the doing it all yourself to delegating psychologically. Well, this is different value. This is unknown value. Is this okay? Should I give this up? Or is it going to seem like I’m not doing what I’m good at and what I’m here to do? And that’s I think a real trap that you can get into psychologically that can stunt your ability to grow as a company is growing, and as you’re bringing on new people.

Casey Means: And I think one of the things that’s been most impactful for me is just being in such awe of people on the team that we’ve brought on, and seeing how they work, and how they can just take the baton and do it so much better than I can. And I’m thinking about you Ben, and Mike Haney, and Tom, and JN, and Miz, and people we’ve brought on who it’s just like have taken these things that initially were kind of my own. Like initially, Josh and I were figuring out how to get on podcasts, and we were totally flailing. And then Tom comes in and we get on 120 podcasts. And Mike comes in, I’m trying to publish one article every two weeks. And then Mike Haney comes in and we’re publishing three articles a week.

Casey Means: So that confidence building of realizing oh man, this is really exciting to work with people who are so good and feeling comfortable. It just necessitates that you kind of give up what you were initially doing and continue to move into the role of what only you can do.

Casey Means: And you’ve repeated that mantra so many times Sam which is that, “Casey, you need to be doing what only you can be doing at the company.” So I shouldn’t be going in and trying to take work that someone else on the team who is even more capable than I am doing that can do.

Casey Means: So that’s been really impactful for me. Really trying to focus on the things that I’m really passionate about doing, but also the things that only I can do as the medical doctor at the company. So that’s been one thing.

Casey Means: I think the second thing, this is getting ultra personal here, but it’s a podcast. So I think we should. Is that honestly, I’ve been in therapy for the past year. And I started therapy after my mom died in January. And it’s funny. A lot of things I talk to about my therapist is these types of concepts around being a people pleaser, not wanting to say no, having trouble delegating, and actually just breaking through some of those barriers. And just better understanding what it means to be part of a team and to grow into new challenges and new opportunities in the company, and how that’s okay.

Casey Means: So I think it’s been a bit of leadership training both through interactions with you Sam in coaching, but also through examining some of the reasons why it’s hard to delegate, and why it’s hard to say no, and why it’s hard to tell people you can’t do something. And realizing what the positive sides of that are and why you do need to lean into that I think, as you move into a leadership and a management role.

Casey Means: So those are some of the things that I think have been helpful, but a lot of it stems from just being continually astounded by our team and how amazing people are. And being comfortable passing off things to people and seeing how they run with it, and make it just 10 times better.

Sam Corcos: Yeah. I can definitely relate to the people pleaser aspect. It used to get me in a lot of hot water. I would say yes to everything. And I would just massively over commit myself to projects that I’d be doing. And the worst part of it was it would end up just being worse than saying no, because I would just let everyone down. And that was a hard thing to get over from me for sure.

Casey Means: I’m so curious to hear what your journey was through moving through that.

Sam Corcos: Yeah. It’s been a long time. I can’t think of any specific moments where it clicked for me. It was more out of necessity where I really value being reliable, and being someone that people can trust, and being high integrity. And it felt like committing to all of these things and dropping balls was causing me to fail at it.

Sam Corcos: Come to think of it, one of the things, I sort of backed into using my calendar. I was doing a lot of contract work for software development. And when you are a contractor and you’re billing hourly, you have to rigorously keep track of how you spend your time. So I started using my calendar to budget my time and to keep track of my time as an accountability mechanism out of necessity. Because otherwise, I wouldn’t know who to bill or how much.

Sam Corcos: And I noticed that doing that really made it clear how much I could actually get done in a given week. And if I knew that I had to commit 20 hours to a project and I blocked off 20 hours on my calendar, and then somebody comes to me with a new project, I could say much more confidently, “I can totally work on this, but not for another two and a half months.” Or we’re going to have to figure out some different arrangement with this other commitment that I have. So I think it was more of a necessity than anything coming from being a contract software developer.

Casey Means: Another thing you just said there that reminded me of something that was helpful for me was conversations where you basically said when you’re thinking about how to choose to spend your time, assume that your time is worth X amount of money per hour. And you kind of I think created an arbitrary value, but that was what I should orient my mind around in terms of this is the value to the company. So if you don’t think what you’re doing is worth that amount of money, then it’s like it should be going to someone else. We may need to hire a contractor to help with this or something like that.

Casey Means: And somehow knowing okay, if I’m working on something that definitely doesn’t need to be done by me, and could be done by someone else. And I could probably hire someone for a decent amount of money to do it, knowing that there was a monetary value associated with it really was helpful for me. Because I was like, “Yeah, maybe we should hire a marketing freelancer or something to help with this particular project.”

Casey Means: So just really like you said, knowing the value of your time, and then that being a helpful way to prioritize whether you’re working on the right stuff. It’s something I think about pretty frequently still. And we do have access to capital right now. And there are many really talented people who want to work with LEVELS. So there’s that opportunity to get things potentially off your plate that are not things that are the best use of your time right now. So, yeah. So that’s just I think another kind of framework to potentially talk to the leadership at your company about, and sort of think about how you should be thinking about your time, and when you should be outsourcing or delegate.

Sam Corcos: Yeah. Another framework that’s been helpful for me with regards to delegating is, it’s almost like using imposter syndrome to one’s benefit where you visualize somebody who is in the same position. So hypothetically in my case, I would think who’s another CEO of a startup in a similar stage? And then I think would it be reasonable for that person to do this thing? And if the answer is yes, then I need to just do it and not feel like I’m not worthy, or that I’m an imposter. I found that as a mental model has been really helpful for me.

Casey Means: I mean, that’s been a helpful one when you’ve told me about it. Because I think there’s a few times when you’ve said to me, I’ve said, “Oh my gosh, I can’t send that email.” It sounds like I’m shirking work or I’m saying no, and I should just do it. It’ll take me five minutes. And you say, “If I Sam sent this email, would you think I was being lazy?” And I’m like, “No, of course not. You’re so busy. And you have so much on your plate, and of course someone else could.” He’s like, “Yeah. So how is it different if you’re asking for help with something or saying that you don’t have bandwidth for it right now?” And I think there is something really powerful about visualizing another person doing something and whether that’s reasonable, or expected, or whatnot. So that mental framing has helped me a lot kind of build the confidence to ask for help, delegate, etc.

Ben Grynol: It’s funny that, I want to go deeper on I guess the sense of being a people pleaser as it pertains to wanting to do everything. Because I think of it in a similar yet totally different way. So similar way, yeah, sure everybody wants to please people. Nobody gets up in the morning they’re like, “I hope I disappoint a whole bunch of people today. That would just be insane.” But, the only way to actually scale your time is through delegation. That’s just a fact. That’s the only way you can scale your time is by having a whole bunch of people that you trust to be able to do a bunch of great work. And that’s awesome. But the way that you actually please people isn’t by doing it yourself. It’s by being involved in more things getting done. That’s called progress, right?

Ben Grynol: So if you are building a house, and you’re trying to do all the framing yourself, and you’re pouring the cement foundation, and you’re wiring it and doing the plumbing, it’s like that takes you three years let’s say independently. You might as well make the nails while you’re at it and cut down the trees. Why not? That would be insane. But as soon as you delegate and you’re like, “We’ve got a plumber, and we’ve got the electrician, and we’ve got the contractor running point on the project, and we’ve got the framers,” you’re involved in that. And this is why people are happier is because they’re like, “Oh great, this thing’s getting done.” And then the other side of it is you’re actually a people pleaser for all the people who are contributing to the thing getting done. Because intrinsically, they feel trusted. They feel like they’re doing a good job. If they assume they are doing a good job and you’re letting them operate with autonomy. And all of a sudden, the people pleaser has gone so wide, the roots are so deep because all the people contributing to this one thing extrapolate that to 10 things going on at once.

Ben Grynol: You’ve now made instead of two people happy through two projects, you’ve made 100 people happy because there are 10 projects with 10 different people involved. And it’s like wow, that’s what’s called impact. So when thinking about scaling time and delegation and being a people pleaser, that’s the only place my mind goes where I’m like, “How can we make more people happy?” And you’re like, “By just doing more stuff, that’s okay work. And then people should be happy.”

Ben Grynol: It’s funny to hear the connection to wanting to do it oneself. I think that’s natural. That’s the human mind. But overcoming that and as soon as you see the other side of the mountain, you’re like, “Whoa, this is a pretty different way of executing.”

Casey Means: Totally. I think once you get past that mental block, it’s a lot of freedom, and you see the opportunity on the other side. But I do think it’s like that step of relinquishing a little bit control and then just seeing how much fruit can be born from that. And you do such a great job with that Ben, being involved in so many different projects. And just being very diligent about documentation, about project updates, about closing the loop, and really just kind of making sure everyone’s unblocked. So you can be involved in lots and lots of different things and empower lots of different projects. Well, seeming to be pretty cool as a cucumber. So it’s admirable.

Ben Grynol: Well, I think we can bring this home here with a couple of, carve out a couple recommendations on how people can be better at comms. But there’s definitely a misconception. And we will highlight this again, which is you cannot over-communicate. It is nearly impossible to over-communicate. So if you think you are, do 10 times more of the communication that you are. And you’re still probably not communicating enough. There is a point where somebody has to tell you, “Casey, I don’t need you to send me a picture of your coffee every morning. Even if we’re best friends, it’s like that might be a little much. You sent me 972 pictures today and messages. That’s a little much.”

Ben Grynol: But in general, when it comes to communications. And the reason to bring this up, I’ll go down a bit of a rant here because this is uncovering the curtain here. My one life gripe, probably my biggest one, and Pam would attest to it is bad communication. Both personally and professionally. That is a jab. That hurts me so much that I can’t even, I wish I could express how much it really … it’s painful.

Ben Grynol: So the reason I say it is that right now, we’ve been talking about professional communication. But it does relate to personal life too. So if you say, and this is Tom Kelley wrote this book gosh, 15, 20 years ago. It’s called The Ten Faces of Innovation. I believe that’s what it’s called. Anyways, he’s got this thing in it called the doorbell effect. And it’s when you are communicating with someone and you know, like Sam and I have had a thread. And Sam and I are talking, we’ll tie it into personal life. Sam’s my best friend and neighbor. He’s my neighbor. And we’re talking about going out for a bike ride on the weekend. And we’ve been doing this all week. And then he just drops off the face. And you wouldn’t expect it from Sam, because he would communicate. But somebody drops off the face and you’re like, “I’m ringing the doorbell. I know the person’s inside the house. And why aren’t they coming to the door? I can see them through the window.”

Ben Grynol: And that’s probably one of the most frustrating things in life, whether it’s personal or professional is not closing that loop or not saying, “Hey, this thing is done.” Putting some sense of resolve on the communication. So I think that’s probably one of the most important things when it just comes to comms. Not email, just comms is making sure that you’ve got a sense of resolve to whatever it is, no matter how big or small it seems.

Ben Grynol: Here’s a couple of recommendations, and feel free to add to any of these is how can people be better at comms? Well when it comes to messaging, have better tooling. So superhuman is a great one for email. Be honest about prioritization and time management. If you’re spending your time communicating about something and choosing to say yes or no, be honest about the what you’re working on, your prioritization of those tasks. Be fast. And that doesn’t mean to be reactive to recency, but be fast in the sense of 24 to 48 hours professionally is probably reasonable for a medium priority message. Be transparent. So always be honest about it. And be specific and direct. Not necessarily thorough, but be specific. “Question Casey, will you have this press thing done by tomorrow?” Don’t bury the lead. And then close the loop once it’s done. Great. Here’s a takeaway. So anyways, that’s my rant on that. But if you guys have anything to add to how to be better at comms or email, fire away.

Casey Means: I love those takeaways, Ben. I would say the only ones I would add are don’t be afraid to ask for help. I think we’re in a challenging environment in our lives right now where there is such an abundance of communication streams. We all are on five or more channels of ways that people can communicate with us. And they’re all different, and it’s hard. So find people who are better than you at it. I.e., Sam Corcos and Ben Grynol. And get help, and be honest about your struggles.

Casey Means: I think some of the biggest breakthroughs for me were when I just was like, “You know what, it’s embarrassing Sam. But this is my inbox. Here it is.” And then you can get support just like with anything else. So I would say just don’t be afraid to ask for help. And then maybe also examine some of the underlying reasons why you’re struggling with certain aspects of communication, like saying no or delegating. Those may be more parts of your personality that you need to examine, and work through, and get to the root cause of so that you can communicate as effectively as possible and scale yourself and your time as effectively as possible. So getting to the root cause, asking for help are two additions I would add to Ben’s.

Sam Corcos: Yeah. I think I would add make comms your number one priority if you’re in leadership. Keep it as simple as that. If you’re an engineer, you might get one email per day, especially at our company. So it’s not really a big deal. But if you’re in leadership, it needs to be your number one priority. If you’re overwhelmed and things are overtaking your communication time or your email processing time, you need to reduce your workload to make that the priority.

Ben Grynol: Hey, Sam didn’t get a phone call. He was supposed to get a phone call. What’s with that?

Sam Corcos: It’ll be sometime today. We’re on west coast time, so it could be anytime in the next three hours.