By Matt Dal Santo
Best-selling author Rick Pastoor has been helping people improve their productivity with his best-seller ‘Grip: The Art Of Working Smart’. The former product manager has now also ditched his day job and is working on his own start-up, to continue his mission of giving people more time to do more meaningful work.
Rick, it's been over three years since Grip hit the bookshelves, virtual or physical. What's been the number one feedback you've received from all the readers?
I felt, when I was first writing it, that the emphasis should be on the second part of the book or maybe the third part, which goes more into detail about goal-setting and the bigger plans in life. Turns out, most people are struggling with the first part. Like how to have a good week and how to manage everything that’s coming our way daily. We need all the help we can get, right? And I guess, that's where I was basically assuming that this was common knowledge and that I was just putting it into paper, like just to get a little bit of a template. But actually, most people were saying, “This saved my life”. For me, starting with the calendar is something that I found was lacking in most books. These were mostly about to-do lists, note-taking or email management. I love those kinds of books and I read all those and you probably do too. But I found the time management aspect of it, like starting with your calendar and what you do with it on a given day or a week, is crucial and transformative, if you do it right. But also, you really need to start with it.
Have you found anyone who gave you feedback disagreeing with some of your principles or were sceptical?
Of course, I continually get those. I think the majority of people say, “I cannot live with the rigid schedule because there's too many things that happen, and that I need to jump on” and “There's too many urgent things happening that I kind of missed. And therefore, I cannot make a schedule for the week. I can’t decide up-front”. And there is that part which is connected to how much room you have for, like, optionality. For the surprises that happen along the way, how much time and space do you allow yourself to be creative, and just, at any given morning decide, “Okay, today I'm going to do a whole different thing”. Of those two things, one is more low level, about too many loose ends. The other is about more creativity. And the two really come together when I ask “How does this work? How does this approach work for you?”. And some people are saying “I'm completely fine, I never dropped a ball. I'm stress-free”. Then I’m replying, “Go for it, man. Don't change it if that's the case.”
Often, of course, that's not what's actually happening. People are stressed. People feel overwhelmed and they want to be creative, but they aren’t because they don't have any kind of structure in place to fall back on. What I'm then arguing is, if you want to be more creative, if you want to make spontaneous decisions, you need to know what you're saying “no” to. And for me, that means having a schedule in my calendar to give me a clear view on what I'm saying “no” to, if I dismiss all that. If you don't have that in your calendar, you don't know what you're saying “no” to. The only thing I'm doing is, I'm making things very explicit. And that often transforms their perspective and they’re saying, “Okay, let me do this experiment, see what happens and then take it from there.”
Do you find this is specific to a segment of people that find it really appealing, like, could it be for product managers or corporate executives?
I thought at first it would be young people, that are go-getters or with high motivation, that would be really resonating with them. But, I actually found that it's from all kinds of different places. Even people who are no longer part of the workforce. They’re over 60. They’re saying “Okay, I need this too because my time is more limited than ever. I know I need to be thoughtful about how I spend my time”. And there’s also, which is surprising to me, a lot of women! And I think the reason is that Grip is definitely not written in a typical ‘management’ kind of language. What I found is, a lot of people say things like, “Hey, I like it that it's so dense, it's really concrete and it's not like the typical management stuff that you find”. So, I think what really surprised me was to see that women have to balance a lot of stuff that we, men, often don't have to. I really try to have an equal split at home but we still live in the time or age where women bear the brunt of work. I would love to have that changed! Then, more than ever, you need to have some kind of an idea of how you want to spend your week. Which is helpful.
I like how the book really delves into quite a few topics. Is there anything that you, in hindsight, wished you had included or planned to follow up?
So, I think in hindsight, I didn’t add much in the third part of the book. I should’ve spent more time backing up with scientific insights, or just scrap it all together and refer to some other book. For example, there’s some stuff about habits where I would now refer to James Clear. His is way broader and more in-depth. I did not add a lot there. In hindsight, I might have skipped most of the third and spent more time in the first two sections of the book. Making sure there are methods to apply to different kinds of settings. The thing that I would love to expand on, in future, which I’m not doing now is: ‘How do we address and grow beyond ourselves, in terms of the mission and the problems in the world, that we definitely want to attack.’ I tried to talk a little bit about it in the Think Bigger chapter. We’ve made progress on a lot of things but on others, we need to make more progress than we do now. Let’s take climate change for example. That would be something I would love to think and write more about. But I'm focusing on this start-up, Rise, now.
You mentioned Rise which I think it's good timing. Smart calendars are not entirely new and you know people like us who are in the corporate world, Microsoft Outlook is the go-to. What's the difference with Rise?
With Rise, basically what I'm seeing with the different kinds of solutions out there, is that having a good week starts with you being disciplined. With you being able to make good decisions about how to have a good day. And about how your colleagues like to work, right? This is something that we should talk about, but there is no calendar that takes this into account. And you know this as well as anyone, that the amount of energy you have on any given day, is crucial to doing good work. On the other hand, we’re just throwing appointments on parts of the day where for everyone, it’s clear that this is not the best part of the day to do that meeting, right? With Rise, we’re trying to do the opposite from Grip. Because Grip says that you have to do some work, in order to have a better week. With Rise, I’m really trying to explore how we could take some of those items that you think about, out of your hands, translate that into some kind of a rule-set that understands how the best teams function, and then re-order the meetings in a way to do that. That allows everyone to have more time to focus. And I guess that is the part that we try to do differently. We have an opinionated approach to what is a good week, and we try to help you schedule accordingly.
It sounds like you're trying to really optimise efficiency at the team level throughout a week or a month or whatever. It’s a bigger magnitude of efficiency compared to the individual.
Exactly, and like there's two big features that we have in the product. One is the idea of ‘focus guard’. You are probably familiar with the idea of time blocking, so you use it. But people find time blocking tedious because they block off time and then their colleagues are basically saying “Yeah you're never available because all the time is blocked off.” And then maybe you and I basically ignore those people and say, “Yeah but I need to do my work, so I’ll leave it in.” Most people actually find that so frustrating. They throw out all their focus blocks and revert to the way they were working before. Which is basically responding to emails, chats or incoming invites and then trying to fit their work in. Focus guard is basically saying how much time you have to focus and if that becomes problematic, we will block off the remaining time so you are more available to your team, until a certain point. This method offers the best of both worlds. Second is the idea of ‘flexible’ meetings. We have a bunch of meetings and we mark these as ‘flexible meetings’. We say, “Okay it's fine to move this around within the same day.” But then, at one point in time, we analyse the next day’s schedule for the whole team, and reorganise it in the most efficient way and make it theirs. So we set more flexible meetings and that takes the thinking out of your hands, basically saying to the computer, “Hey, decide for me what is good and help me do it,” and then we take all the individual perspectives into account and then optimise the best possible day.
I want to talk about AI because again, without naming names, a lot of calendars also do analysis and you know become more descriptive. It looks like your approach is to become maybe more predictive or even prescriptive, right?
I think with all of these kinds of technologies, the ground level is to make a meaningful guess, with just simple heuristics. For example, let’s take a team of 40 people. If I know each individual in the team, whether they like to do work in the mornings or afternoons, we can do a tonne of optimisations. And by batching, we’re making sure the travel times are covered and stuff like that. We’re not even on that level yet!
So that's one part and then the second part would be mind-blowing. But let’s say, we have some heuristics in place. Let's run this through a machine that can do all kinds of permutations and then discover like ‘Hey, what are their individual preferences and how effective would that be’. But you have to have a closed loop of feedback and that's the complicated part. Because how do you know if it’s a good schedule? So yeah, I think the next chapter for Rise, which will probably be somewhere this year or next, will be like how other platforms are. I know ClickUp is doing this. There’s some other products also working on what’s best for what moments you’re intertwining your meetings. I know Motion is also doing that. I think what we will see is if someone is able to create an effective learning loop that is a closed-loop. Then we can train and improve an engine or AI engine on that, and we could see huge improvements over worker productivity. We’re able to reorganise work in a way that people are not waiting on each other. Because I would love to know that the total time we spent just purely waiting on each other could be eliminated. Only a slice of that, that will be already very effective.
I hear you on that and I think it’s a good step. I think time wastage is probably a great area to tackle.
We're rolling out as we speak. We have early teams that are testing Rise. We have a calendar that's nearly feature-complete. If people are interested, they can just sign up at rise.com. So, we’ll just invite those people in a couple of weeks or months.
What's your thoughts on hybrid work? I'd love to know how you're approaching that personally and how do you see the trends around you?
I like hybrid work but it's too light on one really important point. I don't really care about location but about the fact whether work is synchronous or asynchronous. Because that can also be happening in an office. But I see that if we start to think about working away in a more asynchronous manner, that is transformative, whether remote or in the office. Which means that people think about their work before they sit together and talk. I often ask “Have you ever walked into a meeting where more than half are unprepared or did not read the stuff you're discussing?” I think almost three quarters of the hands would go up. People are not prepared. We're used to the idea of getting an invite, walking to the room, consuming the stuff that's actually on the table, thinking about it on the spot and giving a perspective. Well, there are actually a bunch of people that are not good at that. I'm one of them. I need a little bit of time to think and then write. The tooling that we have currently is not up to that, right? Slack is still too focused on reading everything in order to catch up, yeah? But I guess we will see a huge improvement over the tooling here. If you look at Whisper, for example, the new open AI thing. How about having the ability to have the transcription of any video summarising the highlights. Think about what could happen to meetings? I know it’s a privacy thing but think about what could happen if we are laying some ground rules.
So, it's not about the ‘why’, it's about the ‘how’, of hybrid work?
Exactly. 100%.
Okay, and there's so much out there that you talked about in terms of working asynchronously. What about collaboration? Will we see a little bit of that in Rise?
So as an early stage startup, you have to just make a lot of decisions really fast. One of the things that we know, from our previous companies, is that we have to focus even more than we think. So we are really committed to focus on reorganising meetings. Basically building this scheduling engine first. The actual early analysis that we did was that we can bring hundreds of minutes of focus time to teams every week. Well, let's first do that and build a really pretty calendar. And then we'll take it from there. I guess collaboration in software is really complicated. Maybe it's easier to integrate our calendar with something else like this. Yeah, that’s basically my take on it.