🚀 Breathe.



“It’s very important to use the retrospective as a tool to develop psychological safety, where everybody feels that their team is a safe place to express opinions and that not only it’s a safe place but it’s everyone’s responsibility to contribute to that. Anything you can do to reduce groupthink in the retrospective and to encourage everybody to speak is very important.”

In this episode

In episode 40, Simon Stanlake highlights the importance of fulfillment and trust within a team.

Simon is the SVP of Engineering at Procurify – the leading spend management and procurement software platform. Prior to Procurify, he was the VP of Technology at Hootsuite and the CTO at TradeBytes Data Corp.

In today’s episode, we covered the difference between a charismatic leader and a great leader and which one Simon aspires to be.

Lastly, we also explored why he holds back on sharing what needs to be done in order to maximize his team’s learnings and why it’s okay to break things in order to ship features. 

Tune in to hear all about Simon Stanlake’s leadership journey and the lessons learned along the way!

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Pranking culture at Hootsuite


Becoming a leader


The important job of leadership


Learning leadership lessons from peers


Why feedback is crucial


The difference between a charismatic leader and a great leader


Not providing answers and building an environment of trust


The product is the team


Task Relevant Maturity


Introspection and adjustment


Feedback scoring system


The retrospective process


Should you plan more than three months ahead?


Raising the bar for new hires


Simons words of advice



Aydin Mirzaee (Fellow.app)  02:10  

Welcome to the show. 

Simon Stanlake (Procurify) 02:16

Thanks very much. Pleasure to be here.

Aydin Mirzaee  02:17

Yeah. So you are on the west coast of Canada today.

Simon Stanlake  02:23

That’s right. Yeah. recently moved to a small little town called Roberts Creek, which is a short ferry ride away from Vancouver.

Aydin Mirzaee  02:33

Very cool. Well, it’s good to have friends over on that corner. I don’t believe I’ve been there myself, but definitely sounds like it’s up on the bucket list.

Simon Stanlake  02:42

Yeah, this is awesome. We’re kind of on the side of the mountain, and also close to the water. So it’s got a little bit everything.

Aydin Mirzaee  02:49

Cool. That’s awesome. So assignment, there’s a lot that we’re gonna obviously dive into. But I thought it would be a fun way to start this conversation. You know, I was doing some research about you and your background and the things that you’ve done. And I went on YouTube and searched for your name. And lo and behold, the first video I found was this really funny video of you opening some curtains, I guess, in your office. So I’d love for you to tell this story and tell us like what that was?

Simon Stanlake  03:19

Yeah, okay, so. So that was from the early days at Hootsuite, that probably would have been about six months into my time of receipt. So 2010 we were about a dozen people at that time. And, you know, we were kind of a classic story of the startup fueled by Red Bull and pizza and like, our office was literally in a basement. And so as you can imagine, there was like a lot of pranking culture that came along with that. One of the things that we did was, like, this was a big thing when I you know, 10 years ago, I don’t know if it’s totally out of the pop culture now, but getting iced. So the trick was the hottest Smirnoff Ice somewhere. And if somebody stumbled into it, that they have to drink it. So it was my birthday that day. And the team have come into the office fairly and they’d rigged up this series of pulleys and leavers, so that when I opened the blinds and ice popped down out of the blinds, so that’s super clever. You know, yeah, they were all pretty proud of themselves.  Yeah, it was definitely an all time favorite when you look at the the ingenuity behind the the system of pulleys that they put together. They’re pretty impressive.

Aydin Mirzaee  04:32

Yeah, that’s awesome. And so by the way, part of the reason why I wanted to ask you about that is I feel like it’s not every boss that you can do that to you know, I feel like some people I mean, again, it I guess you probably made it seem like it would be okay if they did that to you. And so I just wanted to dig into that like the culture of pranking and, and that kind of relationship did that exist? Or do you think that you carried it with you there?

Simon Stanlake  04:57

Yeah. So it definitely existed, you know, I think that the team that we had at Procurify early on, just like such a special group of initial people. And, you know, I think I was, you know, I often say that the thing, the one thing I did best there was not screw up what was already happening. So they really weren’t great crew but, but that’s, that’s also a attribute of the way that I lead teams to is to is to definitely try to be, you know, to, to use an overused expression, you know, in the trenches with the team and, and building a lot of a lot of trust. So when you’re know, when people are making mistakes in the middle of a an outage firefighting situation they can, they can feel good, they can be open and transparent about that. And, yeah, you know, doing things like goofing around with them, and, and spending time with them is, is helpful in developing that trust. So that’s something that that’s something a team definitely had. But it’s also like something that I carry with me.

Aydin Mirzaee  06:02

Yeah, that makes a lot of sense. So, you know, just going through your background, obviously, today, your VP at Procurify. But you know, you’ve played a lot of roles. Even before that CTO at Hootsuite, you kind of refer to that story being from your Hootsuite times, but the team, I guess, you said was about a dozen. And I know that you grew it to about, you know, over 100, maybe like 120 or so people there. And you’ve also been at Tradebytes. So before we dive into a lot of what went on and some leadership lessons there, I just wanted to ask you, When was the first time that you actually led a team?

Simon Stanlake  06:40

So as a manager, the first time I led a team was at Tradebytes. We were pretty small niche company. And there was a team of about five developers that I was managing.

Aydin Mirzaee  06:54

Awesome. And so I have to ask you, so from those early days, and when you first started, were there any lessons that stood out or any mistakes that stood out that, you know, over the course of your career, you’ve just learned to correct and, and do differently?

Simon Stanlake  07:11

Yeah, I was, I was a terrible manager. When I started, I was just like, I totally did it wrong. Right off the bat, I really came from I’m not sure like, you know, I could do a lot of like introspection to figure out like, where all this came from, but I definitely came from the I developed a command and control sort of type of mentality with management, that it was about, you know, being the boss having the right answer all the time, and making sure that people were working. And yes, it was ineffective, and in not fulfilling for me either. And so yeah, like, I mean, when I first started, I was not not a great manager. As my career progressed. And particularly at Tradebyte, there’s part of me at Hootsuite, I was lucky enough to have some people on my team that taught me a lot about what the important job of leadership is. And, you know, I had a 111 individual in particular, Napoleon, who now works for a company called Commitment Viewer. You know, he was he, we hired him pretty early on, and he was clearly a better manager than I was, like, it’s doing a way better job. And I was just watching him and I was like, Okay, well I can do, I can do two things here, I can fall back on what I know, which is to be like, I need to assert myself as the boss. Or I can, you know, work to make as much space for this individual as I can, so that they can be as effective as possible. And to and to just do what I can to maybe make sure he’s got all the opportunity to implement his ideas, and that he has a good idea of where, in a more broad sense that the company is going. And, and so luckily, I chose the latter of those two. And that learning through working with knowledge and working with that early Hootsuite team, as has been the nut of how I do management today. So it’s a complete complete 180.

Aydin Mirzaee  09:20

Yeah, no, that’s really interesting. So no, actually then report it to you. Yeah. And so I guess, and then he had his own team underneath. Is that how it works? That’s really awesome. You know, it’s very interesting. Typically, when, when we have these sorts of conversations, it’s usually that I’ll say, well, who is a favorite boss or someone that you learned a lot from but this is this is completely novel in that, you know, you’re saying that actually someone that reported to you is who you learned a lot of leadership lessons from?

Simon Stanlake  09:51

Yeah, yeah. I never said I mean, honestly, there are a couple of individuals on on that early Hootsuite team that that just taught me a lot about you know, When you find yourself in the, with the huge responsibility of having these incredible, incredibly talented people, that you need to really pay attention to, like the things you do, and how that affects their ability to get their ideas rolling. And, you know, the idea of me making the decisions and me controlling quickly became obvious that that was not not a not a, an effective strategy, I use that, to unlock these people do everything I could to unlock is beautiful.

Aydin Mirzaee  10:32

So I have to ask you just a question on sort of self diagnosis, you know, for people listening to this and, and wondering if, you know, they are like operating in a command and control way, or if they are actually like, bringing out the best in people, you know, what are some signs or if there’s an example that you could tell of, you know, what’s something that you shouldn’t be doing? And like, What’s something that you should be leaning towards? Is there anything that can help people on that front?

Simon Stanlake  11:06

That’s, let me see. Well, I mean, I think that one of the one of the things that I’ve recognized, you know, kind of later in my career, I think, is that the feedback environment that you have on a team is, is crucially important, you need to you need to have people transparently talking about the experiences that they’re having, and sharing ideas and, and telling you whether you’re the boss or their peer or their report, how how your actions are, are impacting them and impacting the team and impacting productivity. So the question I would ask as a manager is to understand whether whether you’re operating in too much of a command or control one thing would be, what’s the feedback environment like? So is anybody coming to you and saying, Hey, you know, when you did this thing, it made you know that the impact was this and different from my expectations this way. And just I want to let you know, and dig into that. Because if nobody’s, like, guaranteed, you’re screwing up. So like, and nobody’s telling you that you’re screwing up, then that’s probably a sign that people don’t feel that they can trust you and talk to you about that. So probably probably means you’re operating in a little too heavy handed way. Yeah, that’s one thing that kind of pops to mind right away.

Aydin Mirzaee  12:29

Yes. That’s really interesting. So if you’re not hearing feedback about ways that you’re screwing up, it’s not that you’re really good. It could be that, you know, you haven’t created that culture where people can actually tell you where things could be better.

Simon Stanlake  12:42

Yeah, yeah. I mean, I think so. I don’t know. Maybe like, maybe I just screw up a ton. But like, that’s definitely my experience. Maybe there’s a perfect manager out there. So.

Aydin Mirzaee  12:53

Yeah, no, that’s awesome. Yeah, I think that that’s super, super valuable. And I think it’s kind of a really good segue into this quote that we have from you, which is, you know, you’ve said in the past that great leadership is making others feel like they can achieve the impossible. I think that sounds super inspiring. But I’d love for you to kind of like dig in and tell us more about what that means. And if you have an example of a time where you were able to do that for a team member or for a team, we’d love to hear that as well.

Simon Stanlake  13:31

Sure. Um, so this kind of idea is inspired by something I heard on The Knowledge Project Podcast. I’m not sure if you’re familiar with that.

Aydin Mirzaee  13:46

Yeah. I actually know Shane, he’s a great guy. Yeah. Yeah. Cool. Yeah.

Simon Stanlake  13:51

I mean, like I, yeah, majorly influential for me. But he interviewed a woman named Jennifer Garvey Berger, Cultivating Leadership. And one of the things she talks about was the difference between a charismatic leader and a great leader. And I’m paraphrasing, but the idea was a charismatic leader is somebody like when that person walks into a room, everybody in the room says, you know, we’re going to be fine, because that person is here, and that person is going to lead us through this. And then there’s the great leader, who is somebody that when they walk into the room, everybody else in the room goes, I can do this. I feel like I’m coming up with all these amazing ideas. I’m feeling so much more creative, I feel inspired, I’m gonna go charging out of the room. And, and so that’s, that’s the kind of leader that I aspire to be the one that makes others feel like they can achieve the impossible. I think that’s more I think that’s a more effective way to lead right? Because what happens when you’re not there for one thing, and you can’t possibly be there for all the many decisions that get made on a day to day basis for your team? And I think it’s just a more fulfilling way. I mean, like helping other people do what they feel is really important. It’s just a really fulfilling way to spend your time, I think.

Aydin Mirzaee  15:20

Yeah, no, that makes a lot of sense. Is there a story or an example of, of a time where, you know, there was a challenge or something really difficult and, and obviously, like, you’re the leader, you have the experience, but you really empowered someone on the team, or maybe a team to really take the challenge. And they rose to the occasion?

Simon Stanlake  15:43

Yeah, I think. So. When I started at Procurify, the engineering team was working, they were delivering software and like a bi weekly release train. So every two weeks, they do, you know, a bunch of manual testing and regression testing. And then they would pile up everything that everybody had written in the last two weeks, and they would ship that out the door. And inevitably get out where there’ll be a ton of bugs. And maybe there would even be an outage, and they end up rolling a pack. And so there was a big problem. I think actually, when I, on my first day, the team had not actually shipped any successfully ship for like six weeks or something. And they all wanted to get to continuous delivery, like the team knew that that was where they wanted to go. And it was the answer for the problem they had in the way they talked about it was we’re just getting ready. We need to do some things first before we can implement it. So I kind of watched this for a little while. And eventually, I was identified a couple of individuals on the team who were kind of clearly more excited about this idea. And basically just said, okay, like, You two are now the continuous delivery team. So go go kind of figure this out. And, but never, never told them what to do, like and speed the answer to do was just like start shipping, like and just wait for stuff that break. But that was what I wanted them to get to but, but I didn’t, I didn’t tell them that just give them a lot of resources connected them with people who had done this in the past, spent a lot of time with them. And I think over time, develop the confidence that if they were to try something that was kind of radical, like just pull out all the safety guards and just start shipping and see what breaking what breaks that the Dow would be okay, that like if if things blew up, that was kind of part of how we learn and get better. And I just actually remember a particular one day like one of the individuals on the team just literally, like kind of stood up flip the table. It’s just like, let’s let’s just deploy, like, what if we just deploy what’s what’s what’s gonna happen, you know, we’re already shipping bugs all the time anyways, let’s just do it. And it was like, yeah, let’s just do it. And, and literally, it just went from like, two weeks to every day, within the course of probably about two weeks. And we’re still working on it right now. But just to see that inflection point, when people kind of realize like, hey, like, we can, we can do this. And I mean, fantastic people on the team, I won’t take a lot of credit for it. But definitely one thing I did was try to not, not give the answers and just develop an environment of trust that it would be okay. We’ll get through whatever, whatever happened. So,

Aydin Mirzaee  18:41

yeah, that’s amazing. I mean, it’s very interesting, because I think like, there’s probably, you know, for a lot of people, there’s a Hey, there’s this problem, and I know exactly what needs to happen. But it’s interesting, you actually just held back like even though you knew, like, what the problem was, and potentially how to address it. You actually held back and didn’t tell them.

Simon Stanlake  19:05

Yeah, yeah. I mean, in this instance, and I think that’s like, in general, that’s what I try to do. It’s hard for me to be excuse me, especially in certain instances, like I’m thinking about right now. Like, for example, in an outage scenario, where like, the, the customers are, you know, their, their requests are piling up, and the team stressed out and like, I can look and see, like, I know exactly what’s wrong right now. Like, it’s really hard for me to stand back and just let things develop and let the team develop. But I always, whenever I’m able to do that, look back on that and realize it was the right thing to do. Because like, I mean, I don’t know, like all of this stuff. All of this stuff has like, happened before, and it’s gonna happen again. And we just like, we just get through it. Right. And so, you know, if it takes an hour, an hour and a half to resolve something, then like, as long as, as long as you’re maximizing your team’s learning through that process, like, it’s, that’s, that’s the most important thing.

Aydin Mirzaee  20:19

Yeah, it almost seems like obviously, even at Procurify, or anywhere else, you know, obviously, you are shipping this product, and that’s what customers want. And, but I get the sense that really for you, and you know, this is be putting words in your mouth, but it seems like really, for you, it’s your product that is actually the team. I don’t know if you would agree with that.

Simon Stanlake  20:47

So I actually had an exchange with somebody about this a little while ago, and I think I actually said, The product is the team. And, and then I went away and thought about it a little bit more. And, and I think more like, maybe the team is like, the customers, right? Sort of that is like, I treat my team as if they’re the customers and the product that I’m trying to deliver to them. It’s like their own kind of fulfillment, and in learning and development, right. So I really focus a lot on the idea of learning, and improvement. With my teams, they probably are all sick of hearing me talk about it, but like, that’s, that’s the number one thing I try to focus on. So I started trying to think about, like, my team is as a group of individuals who is really my responsibility to, to help them kind of extract maximum learning and, and feel fulfillment about what we’re doing.

Aydin Mirzaee  21:54

So I have to ask you, you know, a question about this. So, you know, I get the concept of trying to always make your team, you know, work better. And I think I can ask you this, because you’ve been at such fast growing companies. And it seems like you’ve had a very, like, you know, fast paced career trajectory, leading very large teams, you’ve obviously come across, you know, people who have reported to and I don’t know, if no, from earlier is an example of this, but could have been more senior than you maybe more experienced, maybe have like, an extra decade of experience? Do you behave? Or are there things that you do differently? When you feel that someone is more senior in that way? versus someone who is Junior? Or is it like the same sort of process of like, continuously trying to help them develop?

Simon Stanlake  22:49

I think it’s, I think it’s the same but on, like, you know, picture like a dial or a spectrum, right? Like, I think it’s like, Andy Grove has that task, relevant maturity, kind of concept, right. So the, the, the responsibility of the manager is to, like, assess, like, the, the, the maturity of the individual relative to the task that they’re assigned to do. And then you kind of like, apply yourself based on that. So if somebody is really, really, obviously, super senior, then are very, very effective, like naturally gifted, maybe not senior in terms of years, but just doing a great job, then that’s when you like, your responsibility shifts away from like, kind of directly, helping them like in a sort of first order way to creating space for them. And therefore kind of helping them in a secondary way, by making opportunities. And you make space for them by by, you know, challenging them, or, or giving them like, very, you know, a lot, a lot of scope to design, how they’re going to solve the problems they need to talk to somebody who’s, who’s less experienced or struggling for whatever reason, and that’s somebody that you kind of spend, you spend more time with that person and in your focus is less on creating the space around them to like, developing the comfort and the trust that that they can, that they can take the baby steps, baby steps and make mistakes and, and develop that way.

Aydin Mirzaee  24:29

Hey there before moving to the next part of the interview, quick interjection to tell you about one of the internet’s best kept secrets, the Manager TLDR newsletter. So every two weeks, we read the best content out there, the greatest articles, the advice, the case studies, whatever the latest and greatest is, we summarize it and we send it to your inbox. We know you don’t have the time to read everything. But because we’re doing the work. We’ll summarize it and send it to your inbox once every two weeks and the best news It’s completely free. So go on over to Fellow dot app slash newsletter and sign up today. And with that said, let’s go back to the interview. So I guess another kind of related question there is that, you know, so for a lot of the situations, for example, like on the continuous delivery example that you were just talking about, and trying to get people to, you know, ship the product every day versus say, once every two weeks. It sounds like in that case, you were there, and you kind of identified the problem like you, you saw a problem. And then you had the team solve it. Does it change when you have say, a more senior leader? Do you rely on them to find the problems? You know, is it the situation where like, hey, things are just great. And that’s not good? Like, you should be finding problems? Mister missus senior leader.

Simon Stanlake  25:53

Yeah, I mean, I would say so. Like, I mean, problems or opportunities, right? Like, which are sort of, maybe kind of the same thing. But yeah, like, I mean, we win, what do you have a more senior leader, I guess, like, the objectives become less, less clear and become more kind of, or maybe not clear, but tactical, right. So instead of like, shift this feature, you might say something like, you know, I want I need more, I need more visibility into what’s happening, the engineering team, or we, we need to figure out how to integrate with partners better, like, you know, something like something like that, which is a much broader scope thing. Or maybe just we need to figure out how to contribute an extra 30% of revenue this year. Right, go solve that problem?

Aydin Mirzaee 26:51

Yeah, so it seems like it’s much more directional broad. Yeah.

Simon Stanlake  26:56

Yeah, exactly. And then and then, and then, as you said, like that, that individuals tasks, then comes changes from like, you know, returning a set of requirements or, or whatever, to, to identifying what the obstacles are to achieving that kind of broader goal. They’re here, whether they’re, they’re problems you need to overcome or opportunities to leverage.

Aydin Mirzaee  27:20

Got it. So I guess, like, and you kind of referenced this as well. And you said that your team might be tired of hearing you saying this. And I think this relates to I know, again, like I, I’ve seen, you say many times constant introspection, and adjustments, that seems to be like a very core part of the way that you operate. And obviously, like, you know, you’re an engineering leader. But I think that I mean, would you say that those are important attributes for any team? Like, would you what are some things that, that you do often that, that you think that not only engineering teams, but other teams should also do in that respect, like any practices that you would recommend, with respect to with respect to

Simon Stanlake  28:06

introspection and adjustment, I think like on an engineering team, the most classic example of that would be like the retrospective, right? Which is like a ritual that’s part of like, pretty much all agile, agile teams. And that’s, that’s something that some, I mean, if I do anything different there, I would say that, that I really, you know, I hold the retrospective up on a pedestal of importance. In fact, we at Procurify, right now, it’s kind of developed this, this idea of like the the, the health dashboard, the health dashboard is about a bit of a digression, I hope that’s okay, if the health dashboard is is the idea is like, if you check in on these items, then you can and they’re all positive, or they’re all going in the right direction, then you can be sure that your team is an effective learning environment. And the learning environment is what we’re kind of striving for. And those pillars are experiments, feedback, the retrospective, and the input of new material in terms of learning to the team. So is the team performing experiments? Are there healthy feedback environments, the team going out and actually trying to learn and bring new information to the team? And are they setting aside quality time to just observe and reflect on what’s happened and and to to build learnings from that

Aydin Mirzaee  29:46

That’s really interesting for things like experiments and for feedback, is there some sort of like a scoring system or what does that actually look like?

Simon Stanlake  29:56

Yeah, I mean, we’re kind of working on that. A little bit. And the with, with, you know, retrospective experiment and learning, you can kind of develop a scoring system with that, right. Like, I mean, you sort of try to strive for, like a certain, you know, with retrospectives, you want to like, be pulling out insights with experiments, you want to just, you know, make sure that you’re actually performing them. And, and, and observing results learning, you want to make sure you’re reading books or taking courses. With feedback, it’s kind of a tricky one, you know, the, I think the ideal is something like in any in any sort of, like, period of time. So it says two weeks that you check in on this health dashboard, your feedback score could look something like, you know, the team delivered, or individuals on the team received, like x pieces of feedback, you know, at a constructive to, like, positive ratio of like five to one or something like that. Right? And you want to you want to make sure that that’s, that’s, I mean, I don’t know what the ideal number is, I think there’s a, there’s a positive to negative feedback, ideal number of five to one or something, but but you know, you want to make sure, basically, that is not zero, right. So that, like, I think it’s safe to assume that over the course of a week, there, every individual on the team should be receiving some kind of feedback for something. So salute should be not zero over the, over the course of a time period. But the difficult thing is that, you know, a couple pieces one is there’s obviously like kind of a privacy issue there. Like, though if you start recording feedback, people get concerned about that, and I think rightly so. And so you need to do it in a kind of non identifiable way. And then the other thing is that the feedback often happens, like really, you know, in an instance during a moment and conversation, and maybe doesn’t get a chance to get recorded. So, I don’t know. I mean, I think these are solvable things. It’s, I think it’s kind of the way to solve that is to just develop good habits about how you share feedback. And, and record feedback.

Aydin Mirzaee  32:14

Yeah. So it’s really interesting, it seems that at your level, again, it’s it’s health metrics for their team. So you’re kind of trying to identify what are the characteristics and things that would lead me to believe that this team is operating in the way that they should? And I think that’s, that’s very clever, like, just have health metrics for the teams that report into you. And, you know, one interesting thing is, you know, just because I know, this is something that you care a lot about this introspection, and you mentioned, like the retrospectives and you know, we had a previous guest, bow Bravo, who was a leader in the US Army, and obviously, in the army, they also have after action reviews, so it is a common thing. But I have to ask you, I feel like a lot of people, because they know that it’s something that they need to do. But I wonder that, you know, I feel like if you surveyed a lot of teams, they would say that actually, yeah, we do it. I don’t know how effective it is. We kind of do it. I’m wondering, in your experience, what are some pitfalls or common mistakes that people make? During the retrospective process?

Simon Stanlake  33:31

Well, so. So I mean, I think one for starters, you just need to do it, right? And you need to, you need to get into a mentality of no matter what is going on, like, literally no matter what is going on, if it’s retrospective time, it’s like pens down and you drag yourself into that room for an hour. Because it is like, the most important thing that that you’re going to do in the course of two weeks. And, and I think that by enforcing that habit, you are signaling that people better be thinking hard about how to extract maximum value out of it, right. So hopefully, hopefully, if you’re really reinforcing how important it is that people are, like, start thinking, Okay, well, I should really start paying attention. So that would be the thing I would start with, I think there’s a focus piece that people should be paying attention to and retrospectives. So, like, the objective is to identify, you know, the most important thing that is affecting the team either positively or negatively, and then to either try to address that or to you know, throw gas on the fire if it’s something good. And so, you need to find ways to get to that quickly without kind of polluting it with a ton of ideas. So like, you know, you see some retrospective boards, and there’s like, 45 stickies up on the wall and that like starts getting, you know you want to get, it can get a little bit difficult to kind of identify the most important thing. So, so really trying to get the team to find ways to get the team to focus on just just a handful of items. And it kind of related to that, I guess it is if you want to, you want it’s very important to to use it as a user retrospective as a tool to help develop that kind of psychological safety where everybody feels that their team is a safe place to express opinions. And not always a safe place. But it’s everybody’s responsibility to contribute to that. So anything you can do to you know, reduce groupthink in the retrospective and to encourage everybody to to speak is really important. So like, one of the ideas is that we’ve been doing is, instead of having my buddy go around and sort of talk about what they see said, spend 10 minutes at the beginning where everybody writes down at least one thing on a sticky note. So first of all, they first of all, they don’t get to bid on their ideas, they don’t get biased by what other people are saying before they get the note on paper. And secondly, it’s made clear that it’s everybody’s responsibility to contribute. Yeah, those are a couple things that I would say would be helpful. And in developing a good retro.

Aydin Mirzaee  36:27

Yeah, I think that’s super valuable, especially this last thing that you said to avoid groupthink, have people do homework ahead of time, or maybe during the beginning of the meeting without hearing what other people think. And in particular, obviously, like if people if you went for assignment, I feel like a lot of other people would have very similar ideas.

Simon Stanlake  36:49

Exactly. I mean, he totally likes I’ve seen that tons of times in retros, or any kind of meeting where all of a sudden you realize there’s only two people talking and there’s like 10 people here, what’s, what’s going on? So yeah, that’s something you want to try to avoid?

Aydin Mirzaee  37:02

Yeah, no, that’s awesome. Simon, there is something that I really wanted to dig in. Because I feel that this could be controversial in the sense that like, some people might think differently, and it just centers around planning. You know, I’ve worked at a lot of startups, and you’ve obviously most of your career has been at like very fast paced, high trajectory, growth kind of companies. And there’s this thing that you say that, you know, I have to say that I am partial towards that, but I feel like it might be controversial, and it’s basically that you can’t really plan out more than three months ahead. So I know this, this might be from something that you said a long time ago. So my first question is like, Do you still believe that to be true?

Simon Stanlake 37:48

Yeah. Yeah.

Aydin Mirzaee  37:51

Got it. So I’d love for you to go into more detail. And, and in particular, when I think about, you know, statement, like we can’t plan out more than three months ahead. Does that? Does that offer enough direction to the team? And does the team feel like they know what is going on? Or does it feel like does it feel ad hoc, and people don’t have direction?

Simon Stanlake  38:12

Yeah. So let’s see, let me back up and qualify a little bit like I live in a certain world, right, like so I often saw companies in SAS, which is like a, a, like, super quickly accelerating field and the dynamics are very different than a lot of other industries. So I’ve spent my entire career in a space where we’re three months a lot can change in three months. Right? So that’s like, I believe that people in that work for companies like I typically tend to work for cannot plan further ahead than three months. And I think that like when I say plan like I mean, I’m talking about really kind of specific roadmap items like what are the what are the epics and in what order what kind of are the stories etc. and but I still think that that planning process is really, really important. I was actually thinking about this recently. There Are two aspects to why I think that this kind of three months idea is a good heuristic to stick with. One is that one is just just you know, kind of like we were saying I get you just the landscape changes so quickly and so many things are gonna actually change when you put this plan into place. That spend a lot of time on stuff that happens three months out is probably not worth your while. But the other kind of like more subtle one, the more I thought about this is that it goes back to this this like I think it was like Eisenhower or idea like you know, plans are useless and planning is essential. So one of the things that that I think a team is doing when they are making a plan is they are Practicing decision making, right? So they are when they make a decision to put something into a plan, they have to evaluate that against what is important for them. Right? So they’re going through the steps of saying like, given this set of inputs, and this like a long term directional thing that we want to hit, what do we actually make this decision? Right? So you’re, you’re doing wraps on this kind of decision making muscle for your team. And I think that once you’ve done sort of three months worth of that decision making repetition, you’ve you’ve, you’ve exercised that muscle, right? So that you’ve got enough raw material for that team to go Okay, now, I now feel comfortable making decisions based on all of the information that we have available in our long term objectives. And so that, then, when you put this into play, and things inevitably changed, you have a well developed decision making muscle. And you just you just don’t need to, you don’t need to do it a year out to start to get enough reps of how to do that.

Aydin Mirzaee  41:14

Yeah, you know, I really liked that, because it sounds like even the muscle of like, deciding as a team and planning as a team is probably like an important thing. And on top of that, you know, when you do that, it just probably gets a lot more buy in from everybody who’s involved. And so once there is a plan, yet they’ve had a part in, in making that plan.

Simon Stanlake  41:37

Yeah, I mean, it’s, it’s the decision making, it’s also about, you know, building that trust environment with your team and, and working on like whether, you know, whether you’re whether everybody’s contributing, and all those all those team dynamics aspects, which are important.

Aydin Mirzaee  41:53

Yeah. So there’s something else that I did want to also ask you about, I know you’ve hired a lot of people in your career. So I do want to ask you about that. There’s this quote that I have from you from, I think, a relatively recent interview, where he said, something less obvious is that if your quality level isn’t consistently raised, you have this long, slow downward spiral. If you hire people that are not top caliber, then these people are obviously responsible for more hiring, and you end up with a mediocre team. So the thing that I found interesting about this quote, in particular, is, you know, you often hear people say things like hire a players, and so on and so forth. But I thought what was unique? And what you said was that if your quality level isn’t consistently raised, and so that’s an interesting thing. You know, when I, when I look at that, is this kind of like an impossible threshold to kind of reach like this ever increasing quality bar on hiring? How do you think about that?

Simon Stanlake  43:00

I think it’s, it’s more kind of, like, commonly known as like, No, do the bar raiser kind of concepts, right. So that every person they hire has to go through this evaluation as to whether they are better than 50% of the people at the company at the skill level they’re being hired for, right. And so like, to your question about whether it’s impossible, I mean, it’s, like, mathematically impossible, like, given a fixed population. But, you know, I think, like effectively, for, you know, the companies that people are going to typically work for, I don’t think it’s, I don’t think it’s an impossible goal to hit. So we at Procurify, we’ve implemented that as well, as well, we have a criteria around hiring and one of those criterias is that, you know, the individual can confer will perform at a level better than 50% of the people that currently have the company.

Aydin Mirzaee  44:06

Yeah, I love that always bringing the average up. So is this a gut feel thing that the people during the interview process? Is this a question that you ask everybody who’s like, part of the interview committee? Like, does this person bring up or bring down or average? 

Simon Stanlake  44:25

Yeah, it’s an explicit question on the criteria for an IRA. Very cool.

That’s actually a very good tactic.

Simon Stanlake  44:35

Sorry, I was just gonna say that, to your point about gut feel like yeah, it’s kind of a gut feel one.

Aydin Mirzaee  44:43

Yeah, I think it’s incredibly useful. And like, once you have that kind of a culture, I mean, again, like a great company is all about a great team. And that’s a pretty, pretty cool place. And very good tactical advice for people. Simon, I know we’re Running, you know, close to time here. I did want to ask you the final question. And we asked all of our guests. I know, there’s so many resources out there with so many tips but I just wanted to get your advice to all the managers and leaders who are constantly looking to get better at their craft? Is there any parting advice, resources, tips or any words of wisdom that you would leave them with?

Simon Stanlake  45:30

I mean, I think so. So, a word of advice is, is, I think, I guess I would say something like, you can never stop learning. You know, like, you’ve got, you know, your Warren Buffett and Charlie Munger out there who are still, you know, still devouring volumes of books every week. And, and really, that’s like, yeah, that that’s, that’s in when you, when you take that kind of mindset into into your work, I think that’s when you really start, you can really be effective at that leveraging your team and helping your team, but not only be like really effective, but just creating a really fulfilling environment for everybody. And everybody’s there, you know, for for this time, that you’re all together to try to, you know, achieve this business outcome. But really, you’re all meeting together on a on everybody’s kind of trajectory of their own learning. Right. Like, it’s just all about learning. So that would be the advice that you know, that you can see how that dovetails into things like the bar raiser idea, right. Like if you’re, if you’re constantly looking for people that are better than you are, like, you’re admitting to yourself that like you’ve got a lot of development to do. And then this is the way to learn. And that creates a great environment on our team. In terms of resources, like I can’t, I have to mention The Knowledge Project I know I already already did, and the Farnam Street website. For me, that was an order of magnitude increase in my understanding of how my own brain works, and how teams work and how to not just get better at what I do, but just find more, or enjoyment and fulfillment from my own life. So Shane and the crew, they’re doing a fantastic job. And if you’re not, if you’re not listening, then go do it.

Aydin Mirzaee  47:29

That’s awesome. Simon, thank you so much for all the resources. We’ll include them in the show notes. And thanks again for doing this.

Simon Stanlake 47:38

You bet. Thanks for having me. It’s been a lot of fun.

Aydin Mirzaee  47:41

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 transcript at www.Fellow.app/Supermanagers. If you liked the content, be sure to rate review and subscribe and 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 could help us spread the word about the show. See you next time.

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