[0:00] Do something different. A leadership podcast.

[0:05] We are taught that hard work and grit are the path to success. But what if actually doing less helped you accomplish more? Today, I am happy to have Guy Yalif with me. He is the chief evangelist at Webflow. He has joined Webflow after his company that he started and ran was acquired by Webflow. And that is one of four acquisitions that he has been a part of. And he has also worked at big tech companies with names such as Microsoft, Yahoo, and Twitter. I'm super happy to have Guy with us. He is a great guy, no pun intended, a great person, a great business person, and a great leader. So Guy, welcome.

[0:42] Rusty, thank you for having me. It is great to continue our conversation with a short-time friend of 20-plus years. I know. So Guy, you and I went to college together many years ago, studied engineering.

[0:56] But so let's rewind a little bit because i wanted to start with this idea that so many of us are programmed that the path to success is to put your nose down and just grind and work hard and crank it out i'm just curious where do you think that came from i humbly believe it came from school really you know that that it's the embodiment of uh jump through these hoops work harder and good things will happen. It's a little bit the American dream of, you know, you come and here you have the opportunity to do hard work and good things will happen out of that. And we would then celebrate things like going the extra mile. Oh, you pulled the all-nighter and got something done. In particular, when we were in school and early on in our careers. Yeah, for sure. It is definitely celebrated. It is. And I know actually one of the things you shared with me, which I kind of thought was funny, was that you tracked your hours. And not just like for a short period of time, but over years, you tracked your hours.

[1:59] Where did that idea come from? It's been well over a decade. And although I think most business books aren't that great, I read Peter Drucker's The Effective Executive, and it suggested doing this. And for me, over time, it landed more and more and more, because time's the

[2:17] one thing we will not get more off, right? Like startups fail because they run out of money. Time is the scarcer commodity. And so where time should go.

[2:27] That can shift in particular as a leader, right? I feel like the later we go in our careers, the more the needs get more and more diverse and heterogeneous week to week. I want to make sure I'm investing it in the right things. And so that time tracking, it sounds super duper onerous. It's not at all. The accuracy down to the minute, five minutes, even hour, it's just not important. You're looking for the broad trends. Did I devote my time and energy to the right thing last week? No. Okay, here's feedback loop. I thought I did. I didn't. Let me go adjust. So I think this is very interesting. It's one of the things I talk about with my clients, which is the way you used to allocate your time is not the way you should be allocating it in the future. If you want to keep growing in your career, because as you advance, as you explained, your time allocation should change. So I'm curious, do you have categories that you've tracked over time and how have they shifted and was that intentional or is it just something that you saw when you looked back?

[3:27] They have shifted over time and it has been, I think, like good goal setting relevant to the moment at hand. And so I, a few months ago, shifted to tracking 24-7, not just the work hours, because I wanted to know, am I moving my body enough? Am I, you know, doing the right balance of time to recharge versus time with family versus uh sleeping and other things like that and so it absolutely has changed in addition um.

[4:00] Co-founder, CEO, you know, you are one. Like, the job is, I think there are four things only the CEO can do. They are set culture, ensure you don't run out of money, set a talent bar for execs, and pick the next hill to take. Okay? In addition, it's whatever's needed. And so, oh, wait, you know, somebody's on vacation. Oh, we're looking for a new executive in this area. Oh, there's this thing that we, you know, is super strategic for the company. And you need to go deep and be supportive in the right way there. And if you're not, you are letting the company down. And so that this week, it's this morning, it's recruiting this afternoon, it's expense policy this evening, it's strategy. I happen to like that a lot, but tracking your time's helpful in that context. Yeah. So, I mean, the way you just laid it out, it certainly almost creates the case that says, well, if you're the CEO of a company, the incentive is to work more and longer and harder. Because there are certain things that only the CEO can do, but then you also have to step in in other particular critical areas. But I don't think that's unique to a CEO. I think many people in their role feel that way. It's like, hey, I'm doing something that no one else can do. And I'm curious for you.

[5:15] Like, where did this idea come from or where did the experiment happen that all of a sudden you worked a little bit less and you had this realization of, oh, I can actually be effective when I'm not just pedal to the metal the whole time? To your point, I do feel like this is, for most people, certainly for me, part of the journey of growing up professionally, where as you manage other people, realizing, yes, that particular thing, whatever it might be, the task at hand, you can do it better than the person on your team because you've done it for years and it's new to them. But that's not the right answer. And so part of letting go and maturing and mentoring other people and helping them grow in their careers is shrinking that list of things only you can do. It's intentional that...

[6:03] As founder ceo you who'd say i can do everything i can help on everything not that you're great at everything you hopefully you're hiring people that are much better than you at the given thing, but you can help anywhere and to realize no no there are only four things that only you can do everything else everybody else could do literally everything else there's nothing else only you can do and um in dot com one i was employee one at a startup had a ball i averaged 80 hours a week for two three years this is from tracking it peaked at 135 the week we launched v1 total self-actualization had a ball doing it i was not married i didn't have kids i was at a different stage in life i for sure got had more impact and moved the business forward more while being ceo of entelemise.

[6:54] Where the hours did not average 80 hours a week because i know my wife and two daughters and i wouldn't have been able to do that uh at those hours and so it was experimenting and um to your point it's the definition of like what got you here won't get you there felt working through frankly feeling guilty feeling like wait how how this isn't all right like how am i giving myself time to think through stuff but realizing uh experimenting with it a little bit getting coached on it some um that i actually moved the ball forward more when i did that yeah when i worked at Apple, I made a decision that I wanted to be home for dinner. And so I would leave at five o'clock in order to be home for dinner. And let me tell you, most of the time when I walked out, I walked out pretending I was going to a meeting because I felt so guilty about leaving at that hour because nobody left at five o'clock. I mean, five o'clock is like middle of the afternoon.

[7:51] And, you know, I did what I needed to do to be productive and so on. But I was able to be effective with many fewer hours than a lot of people were putting in and i felt guilty 100% and so i'm curious for you what did you do with that like what did you do with the fact that you felt guilty when you were ceo of a company and this kind of old voice in your head was saying you should be working more hours and you're realizing oh actually having time to think it's productive how do you handle the guilt associated with that um, Yeah, not easily, not well.

[8:27] I too, by the way, have the same story at Yahoo where my, at that point, wife, not yet mother of two children was like, I don't care if you work 14 hours a day. I care that when you say you're going to be home, you're home because I would perpetually say, oh, just five more minutes. Oh, just another half hour. And so I got into the habit for me, the excuse, the helper was the train. Excuse me, I was taking the train from Palo Alto to San Francisco. And I would literally in the middle of a meeting, dial on the Polycom in the room, my cell phone, continue on the meeting and walk out and tried to make that okay. And it was, I was able to continue.

[9:03] And then to your point, I felt guilty

[9:04] and we'd get back on later on in the evening, try to get stuff done. For me the turning point was with a coach a coach who said something that in retrospect for him was small and for me was literally life-changing it um uh he pushed me a lot on like you're committed to things being hard to your point like you have to you work hard in school you work hard you put all the hours in and you just like is it possible that some things might come more easily okay that was a part of it the big unlock for me was when he said playing to win so that you win versus playing to win because you like playing to win for me that that little concept changed everything it's it's it's not about you have the same passion the same energy the same desire to win it's not about slowing down in any way it's how you hold it are you are you attached you must win.

[10:01] Or do you have a preference for that outcome of course i have a preference to win i'd like way it feels really good to win but you hold it slightly differently and then you accept things like i don't actually control the outcome the only thing i control is how i show up uh and it's not that i as a founder ceo i had existential dread every single day no matter how much was in our bank account but this allowed me to go through the journey with the same energy and passion but holding the outcome differently and for me that those two concepts were really foundational to trying a little bit like oh wait i did give myself time to go take a walk around the block oh you know what i i had an hour free on my calendar which never ever ever happens and i used it to go think about something rather than like let me catch up on a hundred emails or slacks or whatever the small task at the moment.

[10:55] Small in terms of units of time task might be rather than taking the large task in terms of time and sitting and thinking and looking around the corner and trying to pick the right next hill or solve, The thing that having the privilege of taking that time would help you solve that was sorry, that feels meandering, but it's because it was a meandering journey. There was not a, oh, I don't feel guilty now. There wasn't that. Yeah, I heard a couple of things in there, which I want to tease out because I think there are important elements of this journey. That's that's it's not linear. It's not like do a and all of a sudden it's easier. It's not. It's it's a process and it does require learning. And one of the things you shared was kind of zooming out a little bit from the goal, right? Because so many of us get hyper-focused on the goal, and it's like, I must accomplish this goal. And if you can zoom out from that a little bit to say, well, okay, that goal's important to me, but it's not the end-all, be-all of me and my life and everything that I stand for. And if you can hold that perspective, you can still be very focused on the goal, but it's not in that same death grip kind of way.

[12:02] I am that seemed like an important element i think the other element that's important that i've seen and i heard this this come out in your explanation as well guy was this willingness to tolerate the discomfort like you know some of the things you're going to do are uncomfortable but that doesn't mean they're wrong or bad they're just different from what you've done in the past but it still requires tolerating that discomfort because that's the step forward that's the path forward great takeaways and uh on the first one not holding it with a death grip i remember sharing this because i thought it was such a big positive deal with my vp of sales at the time happened to be a guy he was like um you don't care about winning anymore and i was like no no no i want to win just as badly as i did yesterday i'm gonna work uh with just as much of energy as i did yesterday to your point it's the death grip it's the.

[12:56] In my little brain i would think it cannot be that we don't win like that universe cannot exist what do i do to help try to control that outcome because i want to win i want to win for all the everybody who's associated with this company um and holding that a bit differently uh and tolerating discomfort that resonates completely and it's guilty discomfort because you're like um i can't even talk about this to anybody like yeah to say i wasn't working like i have to keep this private well which is one of the values of having a coach or a thought partner or somebody, a mentor, whatever, someone you can talk about it with. So I want to go to this idea that you shared also as what you were explaining is when you have a block of time that for whatever reason is available on your calendar, do you spend it doing a bunch of little things or do you spend it doing a bigger thing? And I'm interested to hear a little bit, to hear your reflection on that and how much of that way you've allocated the time that's available to you has helped you to become more effective as a leader. I feel like I suck at this all the time because I will say, oh, hey, here's this bigger thing to think through that only over time did I realize having some unstructured time is important. I feel like this is why so often folks are like, oh, I was thinking about things as I got ready in the morning. You know, you hear the story like, oh, in the shower, I was thinking about blah, blah, blah, blah, blah. And this insight came to manufacture space to have that happen in the middle of the day is totally guilt ridden. And yet.

[14:23] So many of us as leaders, regardless of the position we're in, like, part of the job is to see around corners, is to use judgment, is to decide on the next hill to take. And that has an enormous multiplying effect on others because person years or decades or centuries will be spent activating the choices you make. And so, like, I'll have times where I will. I've tried blocking times. I recommend that to many other people. I utterly fail at it all the time, in particular because of externally facing meetings with partners or customers. And so what I'll more often practically do is say, oh, there is this hour there. I'm going to now that the calendar has slotted in with all these external things, I see that I'm going to block that. And then to your point, Rusty, I will do my best to not look at Slack or email. But once I touch it, it's like you get sucked in and you're like, wait, just another one, another one. Oh, wait, no, no, no. Or, oh, man, I didn't like feeling so guilty yesterday. I felt like I was letting my team down because I hadn't gone through all my slacks.

[15:26] And there's some truth to that. I am letting my team down by not having gone through all of those. And, boy, wouldn't it feel better to support my team than to think through this not urgent but important longer-term strategic thing. And that I wrestle with all the time. I don't know if you do. Yeah, I remember when I worked at Apple, walking from building to building, and it was always walking like fast, right? Because I'm always running a minute late. And so I'm just like chugging from building to building. I remember on multiple occasions, I would see Steve Jobs walking, just strolling around the facility, usually in a conversation with someone else. But he was not in a rush. You could tell it was this deep conversation. I just I could infer so much by watching them and of course, reading about him and so on. But it's doing exactly what you just described. And you think about someone like Steve Jobs and you're like, well, of course, Steve Jobs was doing that because that's what he was known for, seeing around corners and thinking deeply and all of that. And then you think, well, but isn't that what you want your leader to be doing? Isn't that exactly what you want your leader to be doing rather than sitting at their desk, pounding out emails and slacks?

[16:33] Absolutely. I had a board member who would beat me up from time to time in a very positive, constructive way. I don't mean that negatively on like, hey, you need to look around corners more. And I remember the first moment where we had a full executive team and everyone was great at what they were doing. It was the right moment for each person to do some of their life's best work. And I remember thinking, oh, this is what this feels like. I can do my job. I have the space. This job in particular, has a higher need for that time. I don't know Steve Jobs, that's a whole other level, but the need to go think more deeply.

[17:17] Um and i was like wow this is really helpful and roll the clock forward a little bit my leaders my team found it helpful they were like oh good you have thought through that oh this thing that's got lots of judgment or lots of shades of gray it's not black and white you've gone and given that some real thought and come back and shared that with us and that resonates or it doesn't but like you've moved the ball forward in a way that we're not going to find the time to do because we're doing these million other things and when i was pinch hitting for one of them because maybe that role was open i was terrible at finding the time for doing that and so it's definitely one of the learnings for me next time uh is to go ensure that that time does exist because it really, it really is helpful and it's a little bit the like there's an infinite supply of emails and slacks it doesn't mean you shouldn't get to them and so finding

[18:08] that balance of like are you answering them? Which ones do you answer versus finding that time is key. And I feel like I still suck at it. Well, I think part of what you're describing here reminds me of a phrase you said in a prior conversation that we had, which is this question, what are you optimizing for? And I love that question. And I'm curious, how often do you think about that question? How often do you ask yourself that? And so that you can recalibrate.

[18:37] It the life level like you know when i that question i i think about you know at a life level like typically you know on holiday or vacation when you have more time to think you know is it is it uh title is it money is it time with family is it happiness what does that happiness mean like that there's that level of question then there's for the business what are we optimizing for is it the next round is it customers being successful is it revenue is it culture. And I'll often find myself asking that question when I feel lost or when I'm thinking about longer term goals like quarterly or when everything seems to be going wrong or feels like we're making no progress. Those are times often when I'll be like, wait, what's the game we're playing? What are we optimizing for?

[19:28] Yeah, that's that's typically when it comes to mind for me. how about for you that's a great um i probably don't ask it often enough honestly uh and i think i think most of us don't we get on a path and we stay on that path and i think what you're pointing to is when all of a sudden the road gets really bumpy or you feel like you're lost you're like i'm not sure where i'm going anymore it's the logical time to pick your head up and say what am i what am i where am i going what what is the destination what am i optimizing for, And I would say I do that periodically, maybe quarterly, at least to, you know, maybe not in a very deep way, but at least in a superficial way to kind of stop and pause and think about, am I still going in the right direction? But I do think, you know, one of the things I've read and I believe is that one of the best ways to learn is through reflection. And I actually encourage people to do exactly what you described doing. Even if you aren't tracking your time in a detailed way, still to pause for five minutes at the end of the week and reflect on your week and just say, did I use my time effectively this week? And it can be a very subjective, qualitative kind of evaluation, but it's better than not doing it. And it gives you the opportunity to change course.

[20:39] Uh, and so I think whether it's on a weekly basis, a quarterly basis, but having some kind of reflection process practice, I think is really essential if you want to keep growing.

[20:48] Um, I have one last question for you, and then we're going to move to wrap up. But, um, if someone is feeling stuck, if they're kind of in that place of like turning the crank, they're on the path of just like charging down the path.

[21:00] If you had a step to recommend to them, one thing that you would suggest, try this or consider this, what would that be?

[21:11] Sleep. It's that simple. For me, I'm a six and a half year user of Aura. Pick your mechanism of choice for me. That feedback loop on sleep was very helpful. I went from three to five hours a night on weekdays to six to seven, sometimes seven to eight. And I kid you not, it was the same life, the same things. It felt like a Bambi movie. The clouds parted, the birds were chirping, the flowers bloom i was more i've always been a relatively positive even keel guy but the the emotional resilience when others would come with this stressful moment or that problem went up dramatically and i realized at least for me and i think for most it is a myth that when you're like.

[21:55] I need that extra hour. I'm going to sacrifice sleep for an evening. Sure, no problem. But to do that all the time, which I certainly was doing to our point of working harder, it's a myth. You actually get less done. I read some study that said if you're getting six hours of sleep a night by Friday, it's as if you'd pulled an all-nighter. And I don't know. I mean, that's what the study said. At least for me, I found when I went from three to five to six to seven, I felt miles of difference. How does that mean for you? Yeah. Yeah, I, I'm a big sleeper. I'm a big fan of sleep. And I've always slept more like eight hours.

[22:30] And I just I just don't operate very well when I don't sleep like that. I mean, a day or two, sure, not a problem. But you know, on a consistent basis, it's just I'm like, I'm a wreck.

[22:39] And if I do an all nighter, I like the next day, I'm done. I can't do anything. So I just don't do it. It just doesn't work for me. Guy, this is awesome. I always love talking to you. I think you've got such a practical and humble way of talking about some really important things about kind of how do you grow as a leader? Because what got you here will not get you there. Use that phrase earlier. I think that's right on. I know you do a few things here and there on social media or you're around. If someone wanted to connect with you is what would be a good way to do that? I'd love to engage on LinkedIn and welcome starting or continuing the conversation there. Yeah. Awesome. All right. I will put a link to your LinkedIn profile in the notes. And Guy, thank you so much. Rusty, thank you so much for having me. I appreciate being able to talk and compare notes with your humble, thoughtful, leadership advice. It's great to talk with you. Thanks, Guy.