Growth & Graduation: Embracing Failure and Building Manageable Habits

Aydin Mirzaee (Fellow.app)  01:32

Dan, welcome to the show. 

Daniel Saks (AppDirect)  02:25

Hey, it’s great to be here. 

Aydin Mirzaee (Fellow.app)  02:26

There’s a lot that we’re gonna dive into today. You know, just to sort of kick things off, you started App Direct when you were 23, basically right out of school. And in 2015, you were Forbes 30 under 30. And today you advise Fortune 500 executives on software distribution. So usually we ask one of the questions we ask is, you know who’s been your favorite manager in your career, but I don’t know that you’ve had any coming straight out of school. So have you had a favorite manager before this,

Daniel Saks (AppDirect)  03:00

I was fortunate to do a ton of different summer internships and experiences when I was growing up. And one of the most memorable experiences is one summer I went with a friend to Australia and we worked on a ranch in Wagga, Wagga, Australia is to think of as the outback think of Crocodile Dundee. And my manager was Dean Hann, he was a rancher, we raised hundreds of cattle 1000s of sheep. And he had the responsibility to take care of the land and take care of the animals. And I had like zero experience in running on a ranch before that, you know, most of my focus was intellectual or, you know, working in retail. When we arrived, it was just so fascinating. Because here’s this guy that, you know, wakes with a son and lives for work. And the first minute we arrived, he said, there’s an easy way and a hard way to do everything here. And I’m going to teach you the easy way. But you’re probably going to do it the hard way and fail. And then you’ll come back, you know, after failing a few times. And you’ll say hey, what was the instructions in that easy way? And I never forgot that lesson. Because I find that when it comes to managing people, they can drive so much more ownership if they have the ability to learn not just what to do, but how and why. And so I think embracing risk and failure in experiences and in grooming talent is so important, because it gives them the context of knowing you know why there’s a better way and how to do that. So Dean was just a phenomenal leader. You think of like true grit and resilience and conviction and passion and respect for nature and respect for the animals. So learn so many things that summer. It was fantastic.

Aydin Mirzaee (Fellow.app)  04:48

That’s really interesting. Why is it that after, like you think you’ve been told the easy way that you might still want to do it the hard way?

Daniel Saks (AppDirect)  04:56

So it was funny every you know, there are examples with everything like you know, you had 1000s of sheep, and you have to inject a, like a pill in the sheep’s mouth, and it’s super dirty, and you have to tackle the sheep, and you have to use all these different strategies. And of course, as someone who’s doing this for the first time, I think, Oh, I could do this better, I could do this different or what if I try to, you know, bribe the sheep with food, and then maybe they’ll come up to me, or what if I tackle the one sheep and have my friend, you know, take the others. So we can, you know, do all put in the medicine. And I think that those experiences and learning why it doesn’t work gives you more respect for why there’s process and why things are the way they are. But I think having some freedom in space and ownership early on in your career, to make mistakes is supercritical. And what I’ve learned as a manager is you want to make sure that you give those opportunities to your team, but also in a way that’s safe for your business and your customers. And also for them, so they’re failing and learning but not in a way that’s catastrophic to your business outcomes. So we focus a lot on how we can enable our teams to have ownership on the ground, even at, you know, early levels in their career, but giving them safe ways in room to fail.

Aydin Mirzaee (Fellow.app)  06:08

Yeah, like everything is fully determined. And you might know the very, very specific course, to take by just saying it all upfront, maybe they won’t really understand why. And they’ll miss out on a bunch of lessons that are harder to learn if they were told exactly what to do.

Daniel Saks (AppDirect)  06:25

Yeah. And not only that, I find, you know, people who are going to take risks, we’re going to make meaningful change, we’re going to innovate, they’re likely not the people who are going to follow 100 rule instruction books and memorize it, line by line. So what I found in any endeavor that I do is that if I, you know, learn and fail and learn why I then have a deeper appreciation for the process or the steps that go into driving an outcome. And we can continuously refine and make it more efficient. But at the speed of change in which business takes place today, you know, particularly in our organization, we can’t expect that we’re going to write a rule book of 100 rules on how one rule does something and that robot is going to be relevant a year or two later. So instead, we try to drive guiding principles. We tried to get autonomy, we tried to get space, mentorship, to enable team members to quickly iterate in the face of you know, extremely fast-changing environments.

Aydin Mirzaee (Fellow.app)  07:23

Yeah, what drove you to actually just jump into starting a company straight out of school?

Daniel Saks (AppDirect)  07:29

It’s interesting, because from the, you know, from the youngest memories I have, I always brainstormed different business ideas and wanted to start a business. And as I went into school, you know, I kind of fell into that potential trap that people say is, oh, well, you need to get a 4.0. And then you need to go to an investment banker consulting firm, and then you need to go to MBA, and then private equity. And then based on that, maybe you can raise money to start your business and, you know, but it’s gonna be hard, and you’re going to be making a lot of money. So maybe you won’t want to take the risk. So I think that there’s this like, conventional path that many people take, and I realized life is often about risk. But what was interesting was at the time, I was graduating and just so passionate about entrepreneurship, I was interviewing, you know, many different investment banks and different firms on Wall Street. But at the same time, I was brainstorming ideas with my co-founder, we had spent, you know, years before, you know, starting the business, just brainstorming ideas, talking about founders we admired, talking about the types of values we’d want in an organization. And at that time, you know, we started having conviction, that cloud would be an amazing opportunity to democratize technology, and to enable people at work around the world to have access to the tools that they need in order to thrive and compete. And we started to have so much conviction in this vision that we really started to question like, does it make sense for me to spend three years of my life sitting, you know, in investment banking, or private equity or MBA, when I know, I can make a huge impact on the organization today, or on the world today? And we tested it by saying, Okay, if we put together a really good deck, do you think we can raise you know, Angel round? And then from there? Do you think we can raise a series? A, when you have that much conviction in an idea, it’s very hard, I think, to tell yourself that you shouldn’t do it. So we really drove out at heart and proved that we could, you know, raise the capital and sell a first customer. And ultimately we went, you know, went and took it from here.

Aydin Mirzaee (Fellow.app)  09:26

Yeah, just get a sense of scale for how big AppDirect is. How many people work there today?

Daniel Saks (AppDirect)  09:33

Yeah. So we started an apartment with two of us, and we’re now approaching 1000 people around the world. Oh, wow.

Aydin Mirzaee (Fellow.app)  09:39

That’s incredible. What a journey it’s been. So then I have to ask you, so you know, you started with two people in an apartment to 1000 people. You were leading teams very early on. I would imagine when you first started, that you’ve made some mistakes. I’m curious what were some of the early mistakes and the early learnings In building up the team,

Daniel Saks (AppDirect)  10:01

yeah. So I think that you learn a lot and make mistakes. So I think the one thing in anyone’s culture and ability in such fast-changing environments is to encourage failure and risk, and encourage people to talk about it and encourage a culture where people share their lessons learned. But one of the things that I’d say is always a challenge is assuming that someone who comes in is going to be in that role for life. So when we had our first team of 10, people, you know, there was someone who did sales, and somebody did biz dev and someone who did product. And because it was our first time at it, we kind of set this expectation that like, this company is going to be huge in 30 years, we’re all going to be running the company. And I think what I realized is that in a fast-paced environment, you need to really identify a mission for people. Reed Hoffman has a philosophy calling it the Alliance where you have an alliance with your team members where they come in for a mission for a defined period of time. And then they can find the next mission at the company. But it’s setting the expectation that, you know, you’re not doing the same thing in the same way forever. John Chambers, the CEO and chairman, for many years at Cisco, when I met him, his number one piece of advice to me was always looking at and set the expectation that you need to evolve your leadership team based on the size and scale and dynamic of the operations that you’re operating in. So I think that setting the expectation with team members that you’re going to be in one role for a long time and that those leaders need to manage in order to progress in their careers. I think that is unfair to those team members because it sets unrealistic expectations. And, you know, I think even today, what I try to encourage, you know, the organization is that there’s a lot of, you know, importance in people growing in their career other than having to manage people. And I think it becomes a really dangerous trap. When people evaluate their worth or success in an organization by how many people they manage or what their budget is. So I’d say like, the biggest takeaway that I have, is have a very defined period for a mission for everyone set very clear expectations and give very good feedback on how they’re executing on that mission, and reward, individual contribution and reward impact over just the number of resources or budget that the person has.

Aydin Mirzaee (Fellow.app)  12:24

Yeah, I mean, that’s so interesting. So what is a like, what, what would you say is an average, I guess, tour of duty length? You know, for people who come in at the leadership level? Like, is it a year? Is it six months, does it depend on the stage of the company,

Daniel Saks (AppDirect)  12:39

I think leadership and senior leadership tend to be longer, but when we were when we take the majority of people, I would say two is too short and four is, you know, approaching a long length. So what we’ve found is that, you know, people need to, it takes a long time to ramp people up in an organization or a culture. So we really set the expectation that, you know, we want people to be here for a four year commitment in terms of duration. But in that period, there’s the opportunity for them to have, you know, two to three opportunities to progress or to do something new. And I do think in order for you to gain competence and competence and experience in any role, you know, being in the place for six months isn’t worth it, or isn’t enough. So I do definitely encourage and set expectations that, you know, you want to spend the time in the role, you want to gain competence, you want to gain expertise. And then from there, there’s opportunities to progress.

Aydin Mirzaee (Fellow.app)  13:30

Yeah. Now, that’s super interesting. Certainly there are people that that do make it right, and are able to scale with the company. And, you know, there’s definitely like a lot of examples of that. So do you encourage those people through coaches or through mentors? Or like, how can people still expect to grow in that sort of role?

Daniel Saks (AppDirect)  13:53

Absolutely. So we have many people who have been in the organization for upwards of 10 years, and, you know, some more through acquisition, but I would say that you need to empower people to have control over their careers and have the autonomy to do what they want and to lead and to have different experiences. So I think that’s something that’s important that the organization can provide. But I think a lot of it is also about the individual managing their own career and expectations. And one thing that I didn’t recognize when we started is that burnout is real. Oftentimes, an organization can be predisposed toward creating burnout. But more often than not, it’s an individual that has a high expectation for themselves that can’t step out of their selves and kind of reflect on when they’re having challenges that can lead to burnout. So I would say that, we’ve seen many top performers that have gone through multiple tours of duty, and then face a challenge and hit a real burnout phase. And that’s real that can detract them. And in that case, it may be easier for them or for the organization for them to leave. But one of the things that we’ve done to really help minimize that is we’ve put in place what we call a peak performance philosophy at the organization, where we provide a lot of enablement, training and best practices around how team members can perform at their peak. And this includes trainings around mind body spirit, underlined, by habits, and we’ve really found in Nick and I, my co-founder, and I, you know, take ourselves as an example, is that the more ability we have to transform ourselves and to think critically about our own philosophies and management style, and values and approach, the more we can then be an effective leader to others. So we’ve really, really invested in World Class experiences, to enable our teams across the organization to be able to focus on their peak performance and define what success means to them define what risk means to them, to find what burnout could look like, and really be able to be much more attune of elements of their performance, even outside of work, things, including how are you sleeping? How’s your nutrition? Are you working out? What’s your heart rate variability? Like? Do you meditate when you’re faced with challenges you freak out and get an argument? Or do you stay calm and collected? So we really spend a lot of time and have a lot of capability to enable our team members to perform at their best?

Aydin Mirzaee (Fellow.app)  16:23

Yeah, I love that. And it’s so amazing that you just very openly speak about, you know, just some of the realities and, and what to watch out for and create self-awareness. I love that. That’s really cool. So I guess one of the one question that comes to mind that I think is related is that you must also have a tour like I would imagine, you would have this concept of a tour of duty almost for yourself because your role probably has also changed many times since like being two people in a bedroom to where you are today. What has been the most challenging, like in this whole phase? Like, was there a particular point where you felt that, Oh, God, I really need to uplevel or I really don’t know how to do this, or like, what has been the most challenging period?

Daniel Saks (AppDirect)  17:09

Yeah, so I definitely try to fire myself every year. And the more elegant word for that, that I use with my team is graduate. So you know, look at everything that you were doing last year, and try to automate or graduate from there. And I think the amazing thing about technology is you can get more efficient per capita, per person in your organization, versus needing to hire more people to replace yourself. So what I’m always looking at is, are there ways to automate the decisions that I’m making, are there ways to delegate the decisions I’m making, are there ways to automate the technology, so we can work in different ways. And I really encourage our team members to graduate from one tour of duty to another as soon as possible. But a lot of that is, you know, learning how to, you know, operate in the role of failing, learning from those lessons, documenting them, becoming really competent, and then figuring out how to automate that and graduate. So there is a lifecycle and every tour of duty that can apply to me just as much as anyone in the organization. And what I’ve done is become maniacal about planning, I’ve gotten much more sophisticated in my annual planning cycles. And just as you know, in leading organizations, you may have three to five-year plans, you may have, you know, leadership offsites, you might have objectives and key results, quarterly business reviews, I do the same thing for my personal life. So I spend a couple of days, you know, in the fall, normally, October of every year, I really tried to reflect on, you know, what my accomplishments were, where I struggled, where the team was strong, what I can, you know, graduate from, and really then break it down into, you know, objectives for myself that are measurable. And then I have a methodology to hold myself accountable on a quarterly basis, and bi-weekly basis, and even a daily basis in order to make sure that I’m trending and tracking and making progress. So that methodology and framework I think, has helped me tremendously. But again, I don’t think it’s something that could be applicable to everyone. I think people need to structure their own productivity framework that’s going to enable them to perform at their best. And that’s what this kind of peak performance philosophy is all about is how do you create a framework to identify how you can perform at your best underlined by great habits?

Aydin Mirzaee (Fellow.app)  19:29

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Daniel Saks (AppDirect)  20:40

Oh, for sure. And I do. I mean, there’s probably 100 private productivity hacks that I could share, but I’m mentioning it because it’s propping up my microphone right here on the desk, but I habit track. So every day, I have a list of things that I want to set an objective for to create a habit. So essentially, the way it works, and I do this on manual, it’s fine, I track a lot in automated data. But I also find the power of a journal is really valuable. I’ll, you know, go away in October, set the high level objectives kind of like you would with a company at a leadership off site, typically keep it to three core objectives with different key results. And based on that, I’ll recognize, hey, there’s certain things that I want to make sure that I’m able to do and reinforce. So on a monthly basis, I’m going to track to make sure that I’ve made progress on those objectives. And at the end of the night, oh, you know, read my journal, highlight, highlight, you know, gratitude for something and then I’ll have a track you examples of this could be everything from Hey, I realize that I’m not flossing and I want to floss. So I’m gonna have a track flossing. Or it could be something like outreach where I recognize that, you know, over the last couple months, I wasn’t reaching out to, you know, prospects or, or you know, new people as much. So I’m going to send an email every day, in order to get that check. That’s a cold email to double that outreach to learn from someone new.

Aydin Mirzaee (Fellow.app)  21:55

Yeah, that’s super cool. And so, I wonder how does this also translate, like to the cadence of the company? Do you guys also do your annual planning around the same time that you do your personal planning?

Daniel Saks (AppDirect)  22:10

Definitely. And, you know, I think we were on a calendar year cycle. So it’s similar, where in the fall, we’ll start our leadership off-site and budget planning and then flow through. But yeah, I’ve really borrowed similar methodologies from work in my personal life. And, you know, it’s interesting, because you could look at me and say, oh, wow, that’s so business or that. So, you know, structured, but I’d say it actually, it’s like a rhythm. And you just get used to this rhythm, and it becomes somewhat second nature. But it’s a great way for me to appreciate the accomplishments that I’ve had and the things I’m focused on. And a great way for me to prioritize things not only in work, but outside of work, that I want to be able to get better at or improve.

Aydin Mirzaee (Fellow.app)  22:56

Yeah, you’re right. Like it becomes second nature. And then it’s actually, I almost feel like it’s almost like a freeing thing, like, you don’t have to think about it. It’s just Oh, yeah, like, it’s that time. That’s what I do at that time. I don’t have to think and you don’t have to make decisions. Like every second of every day, what to do next. It’s you know, there’s a rhythm like you said,

Daniel Saks (AppDirect)  23:18

That’s exactly it. That’s a great resource on this. His name is James Clear, and wrote the book Atomic Habits. But it’s exactly that, you know, you can fall victim to decision fatigue. But if you can automate a lot of capabilities in your life, then it becomes second nature. And it’s really easy. So you could do a lot of things that you love really well without having to put too much cognitive capacity to it. And that allows you to spend time doing the things that you want to do great. An example of this is, a few years ago, my wife brought me to what was called a sound bath or sound meditation. So you’re in this room, there. In this case, it was a beautiful atrium at the Conservatory. And it had probably hundreds of people. And it’s fairly cold, like everyone’s lying on the ground with headphones, and, or eye masks, or whatever it is. And then people are there like meditation bowls, that really put your mind in a certain frequency. So you’re calm and having to meditate. This was my first experience with meditation. And after seven minutes of the 90-minute session, I’m like, freaking out in my head. I’m like, What is this? Why am I here? I have to leave. And I’ve just like, there’s talk in my head. It’s just constant, like, what’s going on how you know what’s going on with work, blah, blah, blah, blah. And then I realized, Oh, I have to pee. And then I think like, oh, but do I go up? Go up and interrupt the 100 people here, the hundreds of people here to go pee, and I’m like, should I go pee Should I not? And in the meantime, I’m thinking that this whole session is Going by but it was maybe going from like seven minutes to 10 minutes. I freaked out, went to pee and said like I’m done. And it was interesting because it showed how unable I was to be present and calm in my own head. But as I, you know, learned about the power of meditation and cognitive psychology and being able to calm the mind, I realized that that was a huge deficiency of mine. And I use this concept of habits to just get better at it. And, you know, the first year, my goal was to just try to potatoes to put on a comm app for 10 minutes every day, set the goal of 300 sessions, so it wasn’t literally every day. But that first year, I did it, and I struggled with it, you know, sometimes I wouldn’t even, you know, be multitasking and doing it. But just getting in a habit of 10 minutes of meditation enabled me to gain a stronger competency and cognitive ability, from a habit perspective to just kind of take that 10 minutes for myself. And then over the years, I’ve gotten way more sophisticated to where, you know, a couple years ago, I was in a theta state for like an hour. And I was in a similar sound bath, where I was just in a state of like a trance, and kind of like calm and I you know, it just like the time flashed by total flow. And now I’m able to replicate that, you know, to solve different problems. So I’ll go on productivity walks, or I’ll go in nature, and I’ll meditate and I’ll think about nothing, but then literally, there’ll be like a rush of ideas that I can capture. And it’s also enabled me to be a much more present husband and father. So it’s just an example of I think habits can take something that you’re so bad at and uncomfortable with. And over time, it becomes much easier, I always think going from zero to one is very difficult. But if you can break it down into tiny habits, that enable you to get closer to your goal that’s way more effective. The reason why I brought that whole example up is that I think with management, it’s the same thing, that if you take someone who’s never done something before, and your expectation is, hey, you’re gonna go from zero to one ratio from day one, it can be really challenging, and you can put someone out of their comfort zone where when they do you take a risk or stretch, they fail, and they don’t feel strong enough. So I do think as a manager, you have to break down success into little habits. And that’s why I always come back to Dean Han, the Australian rancher’s advice, because I think people need room to fail, they need room to learn. They don’t just want to follow the list of 100 things. But at the same time, you know, you want to give them the freedom to experiment in a safe way. So they’re not, you know, intimidated, and they don’t get discouraged or burnout,

Aydin Mirzaee (Fellow.app)  27:22

That is super valuable. And I guess it also relates to something that you had a quote in Forbes, where you said, If people had opportunities to hear from others, not only about successes, but specifically about challenges, it would be tremendously valuable. I’m curious after, like, how do you guys make it so that you’re not only talking about successes? Is there something like Do you ever celebrate failures? Or talk about them? Or how do you make sure that people know it’s okay to try crazy things,

Daniel Saks (AppDirect)  27:55

We really try to institutionalize lessons learned. So having a framework for the way people can describe their postmortem or what went wrong, or they’re learning. And we encourage people to do that in team meetings in quarterly reviews and town halls. But what I found particularly important is that you have to model it as a leader. And in the early days, or, you know, I’d say the better part of the decade, you know, I wasn’t the best at truly showcasing challenges and vulnerability. It’s not just about what. So it’s not just saying, here’s what I tried, here’s, you know what I failed, or what I failed at. And that’s it. It’s about taking them on the journey of your psychology on how it was hard on you, and how you didn’t feel comfortable and how it made you feel. I think the more you can, as a leader, tell a story that’s very vivid and personal and showcases the cognitive challenges and the emotional challenges beyond just the word challenges, I think that’s when you really start to create an organization and culture where people feel comfortable talking about failure. The other thing is that you can preach that we encourage people to take risks and fail. But the second you, you know, chastise or criticize someone for a failure, or shame, or whatever it might be, essentially, you lose all trust and ability to be able to encourage a culture of sharing the lessons learned. So I think training managers and having checks and balances that you know, that it is okay. And that that, you know, one statement from one manager in your organization that makes someone feel uncomfortable for a mistake they made essentially detracts from years of promoting an open culture of lessons learned. So I think really trying to train managers on that is really important. A good reference there is definitely Reed Hastings book from Netflix. No rules rules. I think it’s a great insight to transparency and how to learn how to really cultivate a culture through empowering managers to kind of be authentic.

Aydin Mirzaee (Fellow.app)  29:55

Yeah, I agree. That was a great, great book. We’re talking about people. I’m curious to hear your thoughts on, on hiring. You know, one of the interesting things is because you’ve hired so many people, you’ve also had a chance to figure out like, when you hired the right people, and maybe when you didn’t hire the right person, I’m curious, like, what advice do you have for people when they’re looking to hire? What are the major takeaways after hiring so many people?

Daniel Saks (AppDirect)  30:24

One thing is that there’s incredibly talented people out there. And just because they may not be successful within your organization, doesn’t mean that they’re not great talent. So we’ve had, you know, many directors who had maybe not performed at their best year, but performed phenomenally in other organizations, and vice versa. I think that good hiring is all about being transparent on your values, on your working norms on the culture, and really giving the candidate an opportunity to see what it truly is like to see if it’s an organization where they can thrive, what we really tried to do was figure out a way to see through the data, what would enable someone to be successful here over a longer period of time, we looked at data sets in people’s resumes, and then top performers at after act and others who maybe weren’t so successful. And we tried to look at algorithmic correlations on what makes someone thrive versus another person not, we put together what we call our Apogee aptitude assessment, which is a methodology to evaluate talent in the interview, you know, using a resume or LinkedIn, and this qualifies from them for the interview. So it doesn’t mean that you know, they can’t be hired or they can be hired. But we use this assessment criteria to say, you know, are you qualified for an interview here, and then we can assess other elements when we interview. And what I found is that it created a great alignment to train our team members on what we look for, and our philosophy of rewarding excellence and defining excellence. For us what we definitely found some of the strongest correlations, were, you know, in your past roles or career, did you have longevity, and were you promoted or recognized for, for success? So that typically, is the strongest correlation that we had, for someone being successful here a very long period of time. But there were other things that were, you know, super interesting, you know, things like, GPA in school, or, you know, were you an Olympic athlete? Or did you play professional sports, or were you professional, you know, gaming, you know, leader, anything, those types of things, what we recognize is, it’s less about the activity, but more if you were elite at what you did, and meant that you strive for excellence. So therefore, you could have a higher chance of reaching excellence in our organization. So I think that that has created a much more meritocratic format for us to encourage a diverse pool of team members, that really would have a higher chance of succeeding here at up direct.

Aydin Mirzaee (Fellow.app)  32:50

Yeah, that’s super interesting that that, yeah, you go through that level of rigor on hiring, you can tell that it’s a very important part. I mean, we talked about this a little bit earlier, which was just being, you know, very clear about, you know, values and, but also expectations. So, like, when you look to hire a leader say that, like, You’re, you’re looking to create a new part of the organization, or there’s a new project or something like that. And if it’s something that you’ve never hired before, for, how do you make sure that you’re, you’re going to be able to hire the right person, if you haven’t, if you’ve hired a role, you know, maybe, you know, a dozen times, you’ve seen good and great, and you’ve kind of figured that out, but what if it’s something new? How are you? How do you make sure you’re doing the right thing? Yeah, great question. So

Daniel Saks (AppDirect)  33:41

Definitely, the aptitude assessment that we have is about rewarding excellence and identifying great talent, regardless of role. So I think that’s the base to qualify you for an interview. One story that we have is that when Nicholas and I started the business, we didn’t have technology backgrounds. And we said, okay, in order to build a global subscription commerce platform, to enable businesses to access the cloud, we need to have a technical co-founder on the team that has competency in certain capabilities. And we researched, like, what would it take to build the tech platform for cloud, and we knew that commerce was important, and that multi-tenancy was important for SAS. And we knew that, you know, being able to deploy on industry, leading infrastructure, like AWS was important. And we knew that, you know, because we were younger, having someone with a, you know, more years of experience could be relevant. So we created a really long list of criteria that we thought would be relevant to discuss from our research, we then validated it with other leaders in the field. And you can also use interviews as a methodology to validate your, you know, role description. So if we were interviewing a CTO, we could say, you know, here are the things that we think are important for what we want to build. What do you think, and they can tweak it and you get smarter as you’re interviewing more people. But what was interesting is we created a list of probably 100 More people that fit the criteria. There weren’t many at the time. And at the top of the list was someone who had, you know, most of the capabilities, if not all, who is Andy Sen, who had built the Salesforce app exchange, which was the first app exchange of its time built in the cloud, and previously had worked, enabling a Walmart’s commerce platform in the 90s. So really, from creating that list, and refining it with other interviewees, it gave us confidence that, you know that this was the perfect person. And when we had the opportunity to work with Andy and bring him on the team that created an incredible outcome, and he’s our CTO today. So I still, I still think in terms of the role of a CEO, one of the most important things you can do is attract the right talent, and really be focused on talent. So, you know, when you don’t know what you don’t know, which is a lot, at least in my case, you can learn a lot from talking to others, and from creating a kind of rigorous criteria, and then getting validation of that as time goes on.

Aydin Mirzaee (Fellow.app)  36:00

Yeah, yeah. No, that’s, that’s super interesting. And that’s amazing that he’s still your CTO today. So definitely a good hire there. So Dan, I have to ask you about one more thing. So I mean, you know, I get the sense that you’re very, like, you’re very thoughtful about the way that you spend your time. It was really cool to hear some of the examples and productivity hacks and cadences you’ve implemented. But another thing I know about you is that you are generally a very positive person, and you take being positive very seriously as well. So I’d love to get your thoughts on that. And like, practically speaking, how does that impact, you know, what you do day to day?

Daniel Saks (AppDirect)  36:43

Yeah, when we started the company, we created five core values, one of them being a positive mental attitude, and ethics, a really important one. And then even my vows to my wife at our wedding, and our family values are positive, present, grateful. So really, you know, I tried to do everything I can to stay positive. And I think positivity is a hard thing, because everyone’s going to go through ups and downs. And the one thing I always share with my team is that values are not something you have or you don’t, you have to work toward them all the time. So I’ve had many moments where I might, you know, not be positive, or I might be negative, or maybe having challenges. And I think it’s important to be self-aware, to articulate to your team, you know, I value positivity, but look right now, and I’m struggling with this. And, you know, please empathize with me. But this is a hard one. So, you know, I think that it’s pretty easy and easy. For me, it’s a simple value, but it’s that, you know, you have only so many days, months, years to spend in your life. And it’s more fun to be positive, and why not spend time, you know, looking at things with a glass half full and learning from people and being curious, so I really try to bring positivity to everything I do. That being said, you know, there’s many moments where there are challenges and where, you know, it’s easy to revert to negativity. So I think valuing and keeping that value at the forefront is what enables me definitely to kind of realize, okay, stuff, check, you know, you’re not positive right now. Why? Like, you’re not having fun. Is there something wrong? Like how do we get there? How do we share with others the struggles, so they can help you along the journey as well.

Aydin Mirzaee (Fellow.app)  38:28

Positivity, and just like that, that energy around it is also a I mean, it’s contagious. Right? So would you ever cancel a meeting if  you weren’t, like in the right headspace?

Daniel Saks (AppDirect)  38:38

Good question. You know, what I probably do is, you know, it is very insightful. I’m self-reflecting now, and I would say that I probably should cancel more meetings, because I’m like, yesterday, for example, because I tracked my different biomarkers as well. I knew I had a really bad sleep, I knew I was, you know, struggling with my like mindset . In my meditation that day, it just didn’t go great. And there was a thought that crossed my mind saying, like, it was an internal meeting, you know, with a team member but or with a few team members. And I kind of turned the video off, I wasn’t present. I was kind of stretching or trying to relax. But it would have been way better in retrospect, to just cancel that meeting and say, like, hey, look, I want to be, I want to take this half-hour to really perform my best the next day. So maybe that’s a good, good lesson for me.

Aydin Mirzaee (Fellow.app)  39:28

Now, that’s awesome. Dan, this has been super insightful. I mean, there’s so many lessons all across the board. You know, I think one of the things that we kind of hinted at was this concept of because you have a podcast as well, which is called decoding digital. I would love for you to tell us about that. And like why you started that and what it’s all about.

Daniel Saks (AppDirect)  39:50

Yeah, I appreciate that. So what we saw over the, you know, the last decade of working with many enterprises and many small businesses and many technologies He’s around digital transformation is that transformation is actually not about the technology, it’s about the people, there’s a certain set of characteristics that lead our customers to be successful. And it included things like vision and foresight and ability to take risk and conviction. And all these characteristics, you know, we thought are so important to encourage the next generation of people who can digitally transform, what was interesting is the successful transformations at work always came down to these people who led a successful transformation of themselves through kind of sharing in these characteristics and being self-reflected. So what we wanted to do is be able to highlight these people. And at our conference for many years, we’ve given away digital heroes awards to reward those leaders, amongst our customers and community to recognize them for the efforts that they’ve made to digitally transform their organizations. We really thought like, wow, there’s so many amazing people out there and stories out there, what if we could capture it and share it? So last year, we introduced the Decoding Digital podcast, excited to have you as a guest as well. And we feature transformational leaders that are changing their respective industries, really speaking to the characteristics behind these transformations. And what’s interesting is that a digital hero can take place anywhere, they can come from any background, they can be at any level of an organization. But it’s really these shared characteristics that make them transformative. So we really dig into the insights of what drives these heroes to transform themselves and then ultimately, their organizations.

Aydin Mirzaee (Fellow.app)  41:38

Yeah, no, that’s, that’s super cool. And excited to be on the show. Dan, we’ve talked about a lot of things. And, and again, like very wide-ranging, and so many insights, but one of the questions that we ask each and every one of our guests, is for all the managers and leaders out there looking to get better at their craft of managing and leading people? Are there resources, tips or just words of wisdom that you would leave them with? 

Daniel Saks (AppDirect)  42:05

Definitely. So there’s a book that is not necessarily in white circulation that someone told me about, like almost like a folktale when I was at South by Southwest years ago. It’s called Leading at The Speed of Growth from the Kauffman Foundation, and essentially charts different phases of leadership, depending on the growth and scale of the organization and highlights pitfalls and lessons learned at each phase. And that was like an incredible textbook for me in order to navigate the differences in the evolution of how I need to lead. So I really would encourage that to any, any of the listeners here to check it out. You might have to buy it on eBay or, or something like that, but it’s called Leading Up to the Speed of Growth by the Kauffman Foundation.

Aydin Mirzaee (Fellow.app)  42:50

Oh, wow. Cool. Yeah, I hadn’t heard of that one. Definitely. Well, we’ll have to acquire it. And whatever means possible. Dan, thanks so much for doing this.

Daniel Saks (AppDirect)  43:00

Definitely will thank you for having me and really thrilled about what you’re doing. I think that part of being a super manager is definitely learning from others. So your podcast is just so phenomenal, inspirational, and really helping managers thrive. So thank you.

Aydin Mirzaee (Fellow.app)  43:14

And that’s it for today. Thank you so much for tuning into this episode of the Supermanagers podcast. You can find the show notes and transcripts at www dot Fellow dot app slash Supermanagers. If you like the content, be sure to rate review and subscribe so you can get notified when we post the next episode. And please tell your friends and fellow managers about it. It’d be awesome if you can help us spread the word about the show. See you next time.