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Tools for Time – Henry Shapiro & Freedom Matters

Henry Shapiro Freedom Matters

Good time management requires facing up to our constraints

Henry Shapiro is a co-founder at, an intelligent calendar assistant and time management platform used by over 13,000 companies worldwide. In this conversation, we talk about some of the practical ways in which time constrains us, and how to manage those constraints.

We discuss:

  • the importance of shifting from a task to a priorities-based approach to managing time
  • how good time management requires facing up to our constraints
  • how to manage the balance our own demands with those of others
  • the importance of allocating time for good habits
  • how AI can help us with time, and where it can go too far

Host and Producer: Georgie Powell Sentient Digital

Music and audio production: Toccare Philip Amalong


Henry: Every company that we’ve talked to, their impetus is all around actually improving their employees’ productivity. And they’re running surveys and literally asking them, do you think we have too many meetings? Do you have enough hands downtime during the week? Do you get enough time with your family? 

Because people have a lot of choices, right now, the labor market is still, at least for now, in a place where, like, it’s very hard to attract and retain great talent in tech. 

And so more and more companies, I think, are understanding that if you burn people out, and you run them ragged, don’t give them clear incentives to care about their work or clear space for them to live their lives, they’ll go somewhere else.

Georgie: Welcome to Freedom Matters, where we explore the intersection of technology, productivity, and digital well-being. I’m your host, Georgie Powell. And each episode, we’ll be talking to experts in productivity and digital wellness. We’ll be sharing their experiences on how to take back control of technology. We hope you leave feeling inspired, so let’s get to it. 

This week, we’re speaking with Henry Shapiro. Henry is co-founder at, an intelligent calendar assistant and time management platform used by over 13,000 companies worldwide. Prior to founding Reclaim, Henry was VP and GM of Product Management at New Relic, where he led development of observability solutions for tens of thousands of customers. 

Today, as part of our series, exploring the tools that we use, we’re discussing time. We discussed the differences between a task versus a priority’s approach to time, while recognizing constraints is important, and how technology can make good habits easier to achieve. 

Henry, welcome to the Freedom Matters podcast. It is an absolute delight to be here with you today. 

Henry: Thanks for having me. 

Georgie: Now, we are obviously running a season about the technology tools that we use. And we wanted to talk to you about time, and how different technology tools help us to interpret and manage our time. So, let’s just maybe start, I’m going to start with quite a big question, what you think about time and the role that time plays for you. Kind of what is time to you?

Henry: That’s a very broad and philosophical question, very existential.

Georgie: Straight into the details here.

Henry: When I was in high school, my art teacher put a piece of paper over the clock that was in the room and just wrote time is an illusion on it. That should explain a good amount about how I think about it. 

No, actually, somewhat seriously on that point, I think we’re very inclined in our work. And if you — I’ve mostly worked in product and engineering teams, where when you sit down to plan out like the sprint for the week, there’s this very big aversion in the engineering community to doing actual estimation, like hard time estimation. 

And saying, I think this ticket is going to take a day and this one’s going to take a few hours, and this task is going to take me two days. There’s some good reasons around it. There’s some sense in the engineering community that would lead to bad outcomes from a business standpoint. 

But even just setting that aside, I think the reality that we’re all contending with is we all only get 24 hours in a day. And we only get so many hours in the day that we want to work. And we need a certain amount of time to spend with our families. And we need a certain amount of time to sleep and exercise and take care of ourselves. 

And so I think there’s this tendency in workplaces, and this is like a — I think it’s born out of agile engineering, agile culture of don’t focus on time, just focus on your priorities and what you need to get done. And I think there’s a lot of power in that. But we still have to always rein ourselves in. 

And there’s a great book that kind of keyed off on the same idea of the theory of constraints, like that you have to have a sense of there are limits to what I can get done in a week and there are limits to how much capacity I have. And I need to make sure that as I’m thinking about my priorities, I’m also thinking about how much time I’m going to have. 

Which seems like a very basic concept, like something that we should all really understand. But I think in modern work, we’ve lost that a little bit and tricked ourselves into this idea that, no time is not really — that’s not really the point. It’s not about how many hours you have in the day, it’s about what you’re focusing on or what matters. The reality is like we can’t change those certain physical limitations that we have. 

What really, I think, inspired us to create Reclaim was realizing that companies and people, they want to do so many things. They want to be the best versions of themselves across work and life. But what is so often forgotten is the role that the calendar and the schedule and time plays in our ability to do that. 

And how much of a constraint that puts on us, not just the constraint we put on ourselves by occupying our own time, but the constraint that other people demand of us by putting time on our calendars and demanding things from us.

Georgie: Really interesting. So, I think what you’re saying is actually the opposite of what your teacher said in terms of time is illusion. [crosstalk]

Henry: Time is not illusion.

Georgie: Time is not illusion, it is the limiting factor to the way that we live our lives. [crosstalk]

Henry: That’s right. Sorry, Mr. Casey, it’s not an illusion. 

Georgie: We need to square up to it and manage it much better and be aware of the constraints that come, not just in terms of our own ideas of what we want to do, but also what other people want to be doing with us as well. 

And in your experience, we were talking before this call about how so often we’re getting this wrong, right, because we’re not recognizing that time is the constraint. It basically means that the way we end up living our lives is perhaps not how we intended. Can you explain that a little bit more to me?

Henry: Yeah. I think that if you don’t embrace the idea that there are limited hours in a day, and you don’t embrace the idea that you only have so much capacity, this is to me how burnout basically, initially manifests itself. There’s so many variables that lead to people, what are they calling and quiet quitting. 

But I think it typically starts with people losing track of almost like the happy segments of their life that have to be there in order for them to be fulfilled and balanced. And so I think starting with the concept of what are the rough timeframes of the day where you actually get your best work done? 

What are the timeframes of the day where you take meetings? What are the timeframes of the day where you’d like to spend time on yourself and spend time with your family? What are the timeframes of the day where you don’t want to be connected to anything, and you just want time to isolate your brain a little bit and recharge, if that’s important to you?

Even just doing that core work of really starting to allocate them in your day, I think is an important first step in recognizing that constraint and using it to your advantage. 

And I think the other thing, and this is more to the point of realizing that you are not the only person who controls this. And I think this is where productivity sort of gurus and productivity mantras have led us astray in the modern world is they painted this like rosy picture. And you see, every three months, there’ll be some article that’s like Elon Musk and Jeff Bezos do these five things. And they say no to everything, and they go heads down for all day. 

Yeah, I imagine if you’re Jeff Bezos or Elon Musk, you can do whatever you want. You can probably say no to any meeting out there and no one’s going to — You could probably take the whole week off and go into a cave and do whatever you want. But we I think, forget middle managers, senior leaders in organizations, they have people relying on them. 

And so the very concept of just just say no to everything, and just be really ruthless with defending your time, I think there’s truth to that idea. I think you do need to set those boundaries. But the reality is, if the CEO puts a meeting on your calendar, you’re not going to go say, sorry, these are my deep work hours, can you please find another time? 

We are ultimately in control of where we spend our time. But depending on the relationships we want to have in our work and in our personal lives, we don’t ultimately have complete control. There is a certain amount of like, obligation and duty that we have to fulfill through where we spend our time.

Georgie: But how do we do that? How do we draw the line between the demands of our work and personal life, and between our own priorities and those of others.

Henry: So, we have a very, I’d say flexible model at Reclaim of how we think what we call core collaboration hours. And this is something that more and more organizations are embracing now. Dropbox have recently rolled out this, what they call virtual first toolkit that it was when they, like many companies, have made the decision to go fully remote. And they established this set of what they called core collaboration hours. 

And the idea was, create a spot in the day, and it really shouldn’t be more than four to six hours. And in our case, it’s 10:00 AM to 02:00 PM Pacific, where you’re generally expected to be around and available for your colleagues. That’s where we tend to have any meetings and it’s also, it works for different time zones. 

And outside of those hours, how you spend your time is up to you. And the expectation is we’re not generally going to have meetings outside of these hours. We’re not going to expect that anyone is around to answer this or that question. And it has a couple of really positive effects, at least for us. 

One is, it will naturally restrict, and this can be uncomfortable for companies and uncomfortable for them to stick to. It naturally restricts the total number of hours you can spend in meetings in a given day. And then the other thing I think it frames is this idea that, and I’m not the first person to say this, work life balance is a fluid concept. 

There are people who are tremendously burnt out on their work because they’re not feeling fulfilled by it or they’re not feeling great about what they’re doing or they’re just not feeling great about their career, whatever it might be. And they may not be working more than 30-40 hours a week. It may not be because they’re really pushing themselves that hard. 

There are definitely, obviously, folks who push themselves in terms of hours to the point of burnout. But my sense is that if you really love what you’re doing, work life balance can mean that you work an eight to five or nine to five job. And after 05:00 PM, you’re offline. And that some weeks is how I operate. Or I’m like, I need a week to recharge, and I need to make sure my evenings are allocated for my family. 

And some weeks, it’s hey, we’re working on something that’s really important. And I’ve set expectations with my family that I’m going to be working some kind of off hours. And the way we end up folding in that time is at different hours during the day. 

But I do think establishing for companies like, what are your core collaboration hours? When do you expect people to really be online? And then really, what are your personal hours? And where do you expect that people are going to be offline and doing their own thing? 

And a lot of what I just talked about is codified into the product that we built. We’re very much in the business of trying to help people structure their days and their work weeks around that set of concepts.

Georgie: Yeah, because I was going to say, it’s fantastic this level of flexibility that we all have now, but it puts so much more pressure on us as individuals to take responsibility for our time. 

Let’s talk a bit about the tech and how the tech is starting to get to a place where it can help us to do that.

Henry: At a core level, we want people to be able to express what matters to them, their preferences, their priorities, and have a system that will accommodate those needs. So, whether those needs are for personal or professional objectives that you have, we’re in the business of basically making time in your schedule for that, and doing it in a way that is flexible and intelligent and adaptive. 

Early on, when we started the company, like, there were really two kind of primary objectives that we had. 

The first thing we really wanted to address was this sort of feeling that I think a lot of professionals get as individuals where they get to the end of a week, and they’re like, what the hell was that? What did I do? And I feel like I just spent 50 hours in meetings. And now I actually have to work this weekend, because I didn’t get anything that I actually need to get done this week. 

You know, the calendar, I think, in many ways is like as companies get bigger, it becomes this debt that everyone has to pay down every single week. And we really want to make the calendar a space that people don’t view that way. That they view that the calendar is actually a space that really reflects the entirety of what they care about across both their work in their life, and really gets them thinking about where their time is going. And helps them understand their capacity to my earlier point. 

At a broader, more kind of enterprise oriented level, there’s this pain, I think that we really want to help organizations with which is helping them to understand how their priorities are connected to time, and how their resources are connected to time. 

Georgie: But I still feel like there’s a lot of onus on the individual to be very disciplined in trying to determine how they want to prioritize their time.

Henry: Yeah, it’s funny when we first built the product, very first prototype of reclaimed was, tell us what your top five priorities are and we will allocate time for them. And we tested it with like VPs of product, engineering managers, CEOs, like pretty experienced mature professionals. 

It was honestly pretty astounding to us how few of those people could actually describe their priorities. Because I think often humans were not inclined to think of things in terms of like priorities. We’re inclined to think of them in terms of tasks. I need to do this thing today. I need to do this thing this week. 

And so our onboarding is very oriented around this idea of let’s just do a couple of really simple things that are really universal. 

First thing is, let’s make sure your personal appointments get reflected on your work calendar. Second thing is let’s make sure you have lunch. Third thing is let’s make sure you have just a little bit of time to catch up on email and catch up on your Slack and things like that during the day. And that’s it. Like that can be as far as you go with the product to start out. 

What people I think start to, and we hear this from users all the time, I’ll have user conversations, I’d say at least once a week where I hear something to the effect of I just ate lunch five days in a row for the first time in two years, because of just having it on the calendar and having it be flexible [crosstalk] and able to kind of move around.

Georgie: And someone else has set it for them as well. I wonder if that makes a difference too. Because I always put lunch in, but — because I’ve put it in, it just seems to vaporize.

Henry: There’s a little bit of pressure around, yeah, Reclaim is kind of urging you to do this thing and take this time. The other thing is I’m sure when you put lunch down, you probably, I’m guessing, you put it at noon, or one o’clock or wherever you eat lunch every day. And the reality is sometimes things come up. 

And so our concept of lunch which we would call habit in our product, you can basically give us a range of time. And the next thing they start to do is think about what are the other things I want to make sure I do regularly? Do I want to make sure I’m spending at least an hour every week doing a little bit of networking? 

Do I want to make sure I spend at least 30 minutes exercising three times a week? They start to think about what are the routines that I sort of aspire to do during my week. And that tends to build up towards a map of what they want their work week to look like. 

And then they start thinking about tasks, which is the other side of our product where they can start to describe, okay, here’s something that I need eight hours to get time for. And I know I’m going to be struggling to find that time over the next three weeks. So, I’m going to tell Reclaim that it’s due in three weeks, and I need eight hours and Reclaim’s just going to go find the time for me. 

And that becomes powerful because A, you actually get the time to work on the task. And B, you start to really understand what your capacity is. 

One of the first aha moments that our users have, that they describe to us is, I didn’t realize how much I was taking on until I really started entering it all into Reclaim and understanding how it all added up on the calendar.

Georgie: Yeah. Interesting. But still, that prioritization hasn’t really happened. But I guess as you go through that process again, and again, you start to see in the habits and the way your week’s planning out, it forces you in a way to understand what your priorities are more. Is that what you see happening?

Henry: The biggest area and this is an area that I think over time, we’re going to get better and better at as we see more and more behavioral data on which habits they’re skipping every week. 

And there’s a workflow that we get very excited about, which is, hey, you haven’t done this in a while kind of workflow of, hey, it’s been three weeks since you last exercise, you should probably get that on your calendar this week, we’re going to prioritize it at the top. And so there’s all these little things that we’ve looked at from a kind of machine learning and intelligence standpoint. 

But generally, what we see from users is like, they want to be in control. A lot of the time they’re people who’ve been managing their own calendar for decades, in some cases. They fancy themselves experts in doing that, and they’re looking to get away from the toil of managing it, but they still want to be in ultimate control of if I say I want to eat lunch at three o’clock and Reclaim scheduled it for two, don’t fight with me about it. I know best where I want to spend my time. 

And so that’s really what we anchor on is like, people ultimately are the best arbiters of where they should be spending their time. And we’re there to help make it easier for them to just make those trade offs.

Georgie: That’s a really interesting point. I’m glad you raised it because one of the questions I was going to ask you is exactly that around autonomy. Like in the digital well-being sector one of the biggest criticisms of technology and the tools we use today is increasingly they’re taking away our autonomy. 

So, it’s quite interesting to hear you raise that. I wonder, in other areas, one of the things we’re talking about this season with tools is thinking about consequence scanning. So, thinking about these new tools we’re using and the unintended consequences of these tools and how those consequences can subsequently have other consequences. 

And just talking to people about how they think more broadly about how the tools might be affecting people, even when they’re not even using the tools.

Henry: Yeah. Yeah, I think for us, the biggest thing that we, I wouldn’t say worry about, but it’s a thing that we have talked about a lot as a thing we never want to end up falling into. Although, there are companies out there that do this kind of thing. And that’s basically what I would call fine grained productivity tracking, or like micro, some people would call it micromanagement. 

There are people who use our product, and they use it for, I’m going to take five minutes and brush my teeth, and I’m going to take seven minutes and prepare for bed. More power to them. If they want to use the product that way, for some folks, that’s really a very powerful way of making sure that they stay on task. 

But I’d say the majority of our users and certainly our users who are in professional scenarios, where every week you look at their calendar, 60 to 70% of the time’s already taken, like by other meetings, recurring meetings, people asking them for their time, so — they’re really not fighting for 100%, they’re fighting for like that 30% to just be filled with some stuff that they want to get done. 

So, for them, it’s, I need to make sure I have a few hours to catch up on some important tasks, I need to make sure I have some time for lunch, I need to make sure I have some time for some important habits. But they’re not obsessed with this idea of I need to make sure I’m tracking down to the minute how much time I’m spending on each thing. Or I need to make sure that every single minute of my day is structured, just so or else I’ll go off the rails. 

We think that’s generally not like a great way. Because then become almost so dependent on the tool to guide you that you forget about the power that you do have as an individual to really drive your agenda and drive your own priorities. 

And I think the same thing is true of organizations. There are companies out there who have put systems in place for things like keystroke tracking and seeing how much time you’re spending on YouTube and see obviously a whole very extreme case of productivity tracking. 

Our greatest fear for a tool like ours is that it would ever be used in that way. Because ultimately, we do want enterprises to care about their time. We do want them to care more about their accountability, frankly, than necessarily putting it on employees. 

Companies ask a lot of their teams. They’ll ask them to take on the OKRs, from this quarter, while they’re still finishing up the OKRs from last quarter, while they’re also dealing with a hundred little fires that the executive team may not even be aware of, because it’s just happening on the ground. And I think that’s important information for them to know. 

Here’s some data that tells us how much time people are actually spending on this thing and here’s the stuff that’s distracting them and keeping them from getting that time. And it never is like YouTube or anything like that. People generally come to work with very good intentions of doing their best work. 

It’s usually, yeah, the organization’s asking people to balance what is maybe an insurmountable amount of work. And they are making these trade-offs little by little whether you realize it or not. 

So, it’s like this, if you trust in sort of the human nature of how these things could be used to improve our lives, both at an individual level and a company level, I think they can be incredibly powerful, and they can actually be ways of driving better decision making and better accountability up and down the chain.

In a sort of nightmarish Black Mirror university would be like we’re micromanaging ourselves. And we’re micromanaging our companies to the point where the trust is eliminated. We don’t have faith in people to make good trade offs and make good decisions.

Georgie: And spontaneity is dead. 

Henry: That’s right. Yeah.

Georgie: But what happens when competition doesn’t have the same concerns about a dark mirror of the future when our calendar’s become more intuitive at planning every last second of our life? Is there a risk that other products will go where has said they won’t?

Henry: Look, at the end of the day, the reason I think social media apps can do what they do is they have these very clear incentives. Where it’s you get this massive service where you get to post and see other people’s content and just have this immense trove of information at your fingertips. The trade off is you are the product, like you are the thing that we’re selling, basically. 

I think in the context of our world, for what it’s worth, every company that we’ve talked to, their impetus is all around actually improving their employees’ productivity. And they’re running surveys and literally asking them, do you think we have too many meetings? Do you have enough hands downtime during the week? Do you get enough time with your family? 

Because people have a lot of choices, right now, the labor market is still, at least for now, in a place where, like, it’s very hard to attract and retain great talent in tech. 

And so more and more companies, I think, are understanding that if you burn people out, and you run them ragged, don’t give them clear incentives to care about their work or clear space for them to live their lives, they’ll go somewhere else. 

So, I think it’s genuinely important to companies to figure that puzzle out. And I think also, they’re concerned about it from a company productivity standpoint. But I don’t think they’re looking at it as it’s this employee’s fault, or it’s that employee’s fault, I think they’re looking at his look, this is just what happens, companies get bigger. 

And culturally, we start trending more and more towards meetings, and so many things flying around, and it’s just the nature of the beast. And let’s try to decrease the likelihood that overruns us entirely. 

So, at least for now, every sign I’m seeing is pointing towards companies actually really wanting to utilize this type of tech as like a way to genuinely help, yes, make the company more productive, but also like increase retention, which really means, like, making employees happier.

Georgie: Using this tool, you built it because you realize that you guys had a problem in the last company that you had. How do you feel about your time management now?

Henry: That’s a great question. I was a VP of Product, never had an executive assistant or an assistant or anything like that. My co-founder Patrick never did either. And so this is, in many ways, Reclaim is far more help than any of us had managing our own calendars. 

You’ve been in, I’m sure, roles like that and known people in roles like that, you may not be as high ranking or as meriting of an EA as say a CEO is but your calendar is about as crazy.

What Reclaim and generally like focusing on this problem has given to me is probably the biggest thing was routines. Like, I was a chronic over-worker at New Relic. And still that’s the thing that I think everyone who’s ambitious struggles with, right, is not knowing when they’re pushing themselves a little too hard. 

We often think in terms of tasks, like I need to finish this thing, or I need to check this thing off my list. But routines are actually really important because they’re things that you never really checked off. Like they’re things you do during — on a regular basis throughout the week. 

But making sure that hey, I exercise three times this week, or I ate lunch five times this week, or I got time to read a book this week, keeping yourself anchored in those types of things, that’s probably been one of the biggest and that’s my particular feature and Reclaim. That’s the one that I tend to spend the most time. 

And then one on ones, that was the other thing that I think we also forget about is when you become a manager, and you have a team of even 12 people, 10 people, like not even that big of a team necessarily, you’re probably going to end up with somewhere between 15 and 20 one on ones. And so we forget that even those are like 30 minutes apiece, you’re talking about, like 10 hours. And if you’re doing it weekly, that’s 25% of your workweek. It’s pretty intense. 

So, another element that I found very useful is really around how we manage our one on one meetings. And even just the concept of I go on vacation, or this person goes on vacation, and Reclaim just finds the next best time. And having the ability to sort of let the system schedule those things flexibly throughout the week and make changes as things get booked over. 

We obviously have a vision of where we want to go in the enterprise, and we want to get there and help businesses with this problem. But we fundamentally believe that enterprises don’t use products. We believe people use products. And especially in this space, like time is a very personal thing. And productivity is a very personal thing. 

And so we built the product from the very beginning for individuals to be able to sign up for it.

Georgie: So, freedom advocates of the four-day workweek, and we spoke with Alex Tang. And this just feels like a place where a product like Reclaim can really help solve a lot of problems.

Henry: I mean, we have companies right now that are using our product to roll out a no meeting space, which is not quite a four-day workweek, but inches in that direction. 

Because if you accept the idea that no meeting day means genuinely no meetings, my day is entirely my own, people could take that day and just go have a personal day, if they want to. It gets rid of the obligation that oh crap, I have to be online because there’s a meeting at three. So, we’re seeing people inching towards it. 

You know, the four day workweek is one of these, like, big band aids that I think companies are afraid to rip off even though there’s so much good proof around it being effective for companies. But even just no meeting days, I think, start to push in that direction because they let people start experimenting with the idea of, well, what would it look like if we effectively didn’t really work together more than four days a week? 

Georgie: Yeah. 

Henry: What if we gave everyone one day of space where they just got to do their own thing?

Georgie: It kind of needs to be no meetings, no comms.

Henry: Yes. Yeah, that’s a good point. That’s a very good point. 

One of the other things we built out in the product was this Slack status sync feature that will basically sync your Slack status to your calendar. And so it will auto categorize different types of meetings. And so you can also set do not disturb for different categories. 

So, if you’re in a personal commitment, or meeting with a customer, you can set it to do not disturb. If you’re in like deep solo work, you can set it to do not disturb, you can customize the message that shows for each category of work. 

And so we think a lot about like outside of the calendar, what are the signals that tell people that you are or are not available to communicate? And can you use that as a way to set other kinds of boundaries beyond just your time, right, where it’s like look, my calendar’s kind of saying, like, please, please give me two hours here.

Georgie: Fascinating. I’m definitely going to try it. Henry, thank you so much for your time today. You’ve been a fantastic guest for the Freedom Matters podcast. We’re really so grateful to have had you.

Henry: Thank you. Thank you for taking the time. I appreciate it.

Georgie: Thank you for joining us on Freedom Matters. If you like what you hear, then subscribe on your favorite platform. And until next time, we wish you happy, healthy, and productive days.