🚀 Breathe.

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Guest

147

I learned from experience. So my advice would be seek guidance and inspiration and mentorship from other leaders, perhaps transformational leaders, both inside and outside of your company.

In this episode

Transformational leadership has a positive effect on mental health. 

Leaders who adopt a transformational approach inspire others by encouraging team members to engage in creative thinking and tailoring their approach to the individual needs of each employee.  

In episode #147, Nathan explains how to drive change within organizations by practicing transformational leadership. 

Nathan Trueblood has many years of experience including working at companies like Box, Yahoo, EMC, Hadoop, and OpenStack. He’s a technologist, product leader, founder and mentor. Today, he is the founder of Trueblood Advisory. 

Tune in to hear all about Nathan’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.


04:45

Distributed systems

11:25

Delegating a problem versus task

16:15

What is transformational leadership?

20:46

Transformational leadership and product teams

24:17

Leading through influence

32:11

Coalition of the willing

37:46

Design alliances

40:40

Doing a calendar audit

44:57

Parting words of advice


Resources


Transcript

Aydin Mirzaee (Fellow.app)  00:23

Nathan, welcome to the show. 

Nathan Trueblood 

Thanks, Aydin it’s great to see you.

Aydin Mirzaee (Fellow.app)  04:10

I know we met a few months ago recently in person, which is always nice to meet someone in person. So really glad to have you on the show. There’s a lot of stuff that we’re going to talk about. I mean, you’ve been in the world of product development, product development leadership for more than 30 years worked at companies like EMC, Yahoo, Western Digital, and most recently, you were a VP at box and watch it The stuff that we want to talk about. But one interesting fact about you and I’d love to start with this because to me this is very random, but also very interesting to me is that you are a beekeeper. So tell me about how you got into this.

Nathan Trueblood  04:45

Well, first of all, I’m a huge nerd. And so I’m just really curious about the world around us. And so I think it kind of starts there but honestly I worked on a project years ago for Western Digital. It was a storage project and it was a distributed system in our code names for this project, we know we had storage devices, which are disk drives, and we called them Hornets. And they lived in this big enclosure called the hive. And one day I’m like, you know, none of us know what we’re even talking about. And at the same time, I, my daughter, who was 12, was very concerned about the environment, as a lot of us are, and a lot of young kids are. And she was concerned about the bees because the bees were having a hard time. So we got into beekeeping. And what I realized was that bee hives are nature’s finest example of a distributed system. And I’m a person who [email protected] everything I was doing there was all about high scale infrastructure. It’s all a distributed system. And I just think these are fascinating that way. Because it’s a totally natural distributed system, instead of a network, you have pheromones. But it’s pretty amazing to see what they can do when they all work together. And there’s this amazing benefit, which is delicious, funny, which I can share with my neighbors and so forth. So yeah, so big time nerd. Oh, that’s

Aydin Mirzaee (Fellow.app)  06:00

super awesome that you say that. And it’s interesting. I’m recently one of the things I’m reading right now is this book called things called Thinking in systems. And so I’m like really thinking about systems and how companies or systems and teams or systems. And so tell me about this? You know, for those of us who want to learn more about distributed systems, why do you say that a beehive and everything surrounding it is a distributed system. Can you maybe explain that?

Nathan Trueblood  06:25

Sure. I mean, so everything that you know, so I work in the world of software as a service and cloud. And in order to achieve the kind of scale if you think of Google or Amazon, or you know, any of large scale apps that you use every day, those apps are powered by a distributed system, what does that mean? That means that you have a bunch of computers, each one of them an individual computer, or individual set of services, you know, little applications running on each of those computers. But they all work together to serve a single application. For example, in the case of box, everyone is there to do file sharing and collaboration, and so forth. But there’s this massive pile of computers sitting in a data center somewhere working together as a system. And that system has to respond to changes in demand as users come online or go offline. It has to respond to failure. What if something, you know, what if a datacenter power gets cut to a data center? What do you do about failure. So you have all these little individual components that all communicate with each other over a network and act together as a larger system. And so beehives are very similar, in that you have individual bees there, it all starts with the bee, it all starts with the computer, right? But then each of the bees and up differentiating to do different jobs, depending on the changing conditions. And so to me, the more I learned about bees, the more it makes me think about systems. I’m just like you were saying, that’s what I mean by distributed systems. It’s, you know, nature, in so many cases is already built, just vastly more elegant things. And we can even think of today. Yeah, I

Aydin Mirzaee (Fellow.app)  08:01

love the analogy. And now I’m super interested in probably going to spend some time on YouTube learning about beehives.

Nathan Trueblood  08:08

And if we’re not careful, this will turn into all of Nathan’s nerdy learnings about bees. But it all share one of the things like just like you might have a central system that regulates the kind of resources that are available to power, say the fellow app, the Queen regulates what the bees are doing with her pheromones. So she regulates just like an economy. So it’s all these different individual little parts, but they’re all being regulated by this one queen who’s sensing what’s going on and will say, oh, we need more workers right now. Oh, we need more nurses right now. Oh, we need more protection right now. That’s fascinating.

Aydin Mirzaee (Fellow.app)  08:41

super interesting. super interesting. So before we go into some of the more recent stuff that I know, you’re you’re super passionate about. One of the things we like to do on this show is start from the very beginning and ask you about some of the early mistakes like Do you remember, when you first started to manage or lead a team? What were some of those very first mistakes that you used to make?

Nathan Trueblood  09:04

In the early days, I guess, when I first became a manager, a couple of things. One was that I had a great opportunity to work for a startup that was really rapidly expanding. And for a lot of us who get those sorts of opportunities. I think we went from, you know, a handful of people, maybe 15 people to 150 people across five locations in about two years. And so I went from sort of clueless guy to managing a team that was also distributed very, very rapidly. So I made a lot of mistakes, because I’d never done it before and was kind of thrust into management. You know. So when I think about that thing, mistakes I made, I didn’t really know about things like one on ones thinking about career development for the people who work for me, I think that I viewed you know, I knew I had a job as a manager, but I didn’t know what it meant to be a good manager. Perhaps the first lesson I really learned the mistake I made was telling people what to do to get the work done because I thought that was what I was supposed to do as a manager and I think much later When I realized that what I needed to do was delegate problems, give people ownership, and then coach them on how to think about solving those problems. And that was how I really created leverage for myself. But it took a while, I’m, you know, I learned things the hard way, because I didn’t have much of a good manager at that time. And so I sort of desperately realized, I’m just going to emulate the good managers that I have around me. And that kind of led to a funny story. So around the same time, when I first got involved in management, I had a crazy boss when I worked at the University of California at Berkeley, where I was in school. And I worked in this funny job because I worked as a part time electrician, for the College of chemistry. And this wacky boss refused to tell me how to do anything, and I’m working with electricity, and I could potentially die, but he wouldn’t tell me how to do the job. He would every time, ask me questions and make me figure it out. Well, how would you approach this Nathan? He knew the answer. And I knew he knew the answer. But he would just stand there with his hands on his hips and insist that I get there on my own. It drove me crazy. Later, I looked back, and I realized he was possibly one of the weirdest and best managers I ever had. And to this day, I remember everything that he taught me, because he forced me to figure it out on my own terms, he coached me how to think, and he didn’t tell me what to do. So that was a huge learning mistake I was making, and a big learning from that I forgot from emulating someone else.

Aydin Mirzaee (Fellow.app)  11:25

That’s really interesting. So the idea is to try and to the best that you can delegate a problem versus a specific task. So what’s an example of a situation where you might take a problem, and then delegate that? You know,

Nathan Trueblood  11:41

just it’s maybe a bit generic, but we know in working with product managers in particular, which is my field, oftentimes product managers are looking for guidance on say, what should be the next feature? What should we prioritize next, so much of product management is about providing a guidance system to the business about what to do next to maximize value. And so oftentimes, you’ll have product managers that they’re not sure they’re learning things for the first time. So I asked you, what should we put next on the roadmap? What should be the next priority, and oftentimes, with my experience, I might have a very clear thinking on what we should put next. And I could tell them that, but now I’m robbing them of the growth opportunity to actually learn the craft of figuring out what to do next. So delegating the task would be like, Okay, well, here’s what you should put on the roadmap. Next, go make it happen. Delegating ownership is to say, well, you own this area. And I’m happy to coach you on how to think how you might want to think about prioritizing what’s next. But ultimately, the choice is yours. I think that I might coach and say, Well, if you make this choice, or that choice, here’s what I might see as the downsides, but making sure that the person owns the decision. And I think the reason why that’s so important is meaning, we all want to do things and do work for a purpose for meaning to create value. And if my purpose is to just do tasks for my boss, that’s not very fulfilling, if my purpose is to solve problems for the business, because I own those problems, that’s a lot more meaningful, and I’m probably going to step up and take more responsibility for the outcome. But I think as a manager, the other thing I would say about that is, it’s really hard. Because if you delegate the problem, rather than delegating the task, you’re giving responsibility of that problem to the person that you manage. And there’s a very high likelihood that they will fail. And what I’ve learned about that is if I sort of bubble wrap the whole situation, if I prevent them from having that struggle, or even potentially failing, I’m robbing them of the opportunity to grow as product managers and as managers in their own right. So delegating the problem sounds like you know, it’s catchy, it’s, you know, catch easy to say that, but it’s really about making sure that you’re giving the person the opportunity for meaning and reward and growth.

Aydin Mirzaee (Fellow.app)  13:59

I think the counterpoint or the objection that I’ve heard from different people, whatever, it’s Yeah, delegate the problem and go through all the steps is speed. I guess my question is, what do you say to that? If someone comes to you, you’ve been senior leader, you know, someone, another manager comes to you and says, Yeah, I mean, I get it, Nathan. But it’s so much faster. If I do this other thing, like, practically speaking, there are cases where you really should it’s an emergency and you just have to, but how do you answer that question about speed? How can a company continue to be fast if you’re gonna go about it this way?

Nathan Trueblood  14:36

That’s a great question Aiden, and I think it’s a reasonable question. It’s also a gigantic trap. So let me start with the trap, which is, especially any any business no one ever says we need to go more slow. And so speed is important because it’s really all about your speed, especially in product is all about how responsive are you to customers and changing business conditions. But the trick AP is as a manager, you’re like, Hey, we gotta go fast, this is super important, I’m just going to take this and do this and make this decision for you, you go do the task, I think there’s a trap there, which is you can easily say almost every problem where we, hey, we don’t have time for this, this isn’t a training exercise for you. And therefore, I’m going to just give you a task. So I think that’s the trap. In reality, I think it comes down to as a manager, you need to give people the right size problems. So in other words, if you give someone too much ownership over something too early, you have to really pay attention to their the skill of the person you’re delegating to, then if it’s a relatively small problem, you want them to struggle with the same time pressure that you do. You want them to make the problem smaller, but they still have to own the time pressure as well. And again, you know, I don’t really necessarily believe in absolutes anywhere. So like you said, if it’s an emergency, if it’s urgent, if there’s other things we have to pay attention to, then we might just say, okay, look, here’s what I would do. Here’s the approach, let’s talk that through. And you know, it becomes more of a delegating a task, because that’s what needs to happen. But I’m always bringing myself back to the importance of developing that employee by delegating ownership.

Aydin Mirzaee (Fellow.app)  16:17

I really liked that. So that’s the nuance there, which is you have to understand what problems can be delegated. And so maybe there’s a chunking activity that needs to be done. And, you know, I think that really clarifies it. So Nathan, I know that you care a lot about the idea of transformational leadership. And this is like very core to the way that you do things. So I thought maybe it’s a good place to start is to ask you, what is transformational leadership?

Nathan Trueblood  16:45

Great, Question eight. And so leadership and management is a big passion area of mine. And the term transformational leadership refers to a management style, where you really take into account the individual needs of each employee, and you tailor your approach to that employee. So to me, this is a came to me naturally by emulating the managers that I thought did the best job of managing me. So there’s transformational leadership. That’s one style. The other common ways to describe different leadership styles are sort of transactional leadership, which is less about taking the individual employees goals and unique strengths and weaknesses into account. And it’s more transactional, hey, you have this job, I have this job, here’s your task, you go do it. But it’s not terribly tailored to the employee. And then of course, you know, we all have experienced more sort of, you can pick your different terms are authoritative or more this sort of negative style of leadership, which is more like the desperate or the destruction, leadership style, where your boss is pretty aggressive and hostile. And it can have a really big impact on the employees mental health. So those are kind of transactional, transformational, and I would just say sort of authoritative, might be the different styles. And for me, I think I’ve become particularly passionate about transformational leadership in the last few years, because I think the impact of the pandemic, what it had on all of us revealed to me the importance of transformational leadership, most especially because of what kind of impact bosses have on people’s mental health, going through the pandemic put all of us through incredible strain. And being a boss or a manager during the pandemic revealed to me like, wow, I’m just your boss, but I have a huge impact on your mental health on the mental health of the team in the organization. And that became a lot more apparent when everyone was under a lot of strain. So this began to make me question or, you know, wonder about the relationship between managers, mental health and company results?

Aydin Mirzaee (Fellow.app)  18:57

One of the questions and I have is, why is transformational leadership better for mental health?

Nathan Trueblood  19:04

Well, a few things. The first thing I would say is, when I look at these things, and especially lately, there’s been a lot of really good research and articles and so forth. So I’ll give a quick shout out like one woman I came across. Her name is Daisy greenwall. She has been I actually came across her articles talking about the positive mental health benefits of different leadership styles. And she had a great article in Scientific American, which was evidence based, which is basically saying, you know, hey, when we looked at mental health impact, we found that, of course, not surprising, you know, aggressive bosses have a really negative impact on mental health. But what they also found was that the transformational leadership style had as much of a positive impact on mental health as aggressive bosses had on sort of negative outcomes. So there’s strong evidence to support something that I was already observing which is taking into account the individual by delegating ownership of the problem, and then coaching them on how to think all of these things actually lead to a lot more emotional resilience. And especially in product management, we deal with a lot of change, and a lot of uncertainty. And I think resilience is super important. And that’s a big part of, you know, to me of mental health. So that’s why I think it’s better. And there seems to be a lot of articles now coming out, we maybe you’ve come across it to aid and around sort of Compassionate Leadership is one way people describe it transformational leadership. And at first, it sounds like a lot of happy chat. But now we’re starting to see the scientific research coming out to say, actually, it produces better business results. So not only does it feel better, not only and better for mental health, but it gets better results.

Aydin Mirzaee (Fellow.app)  20:45

So thinking about product teams, what’s an example of being a transformational leader? Like, is there a story or an anecdote or something that we can talk about to really drive the point home of when leading product teams how you might practice transformational leadership?

Nathan Trueblood  21:02

Sure, I think maybe I’ll come at the question that a little bit differently, which is, a lot of crafts are learned through experience. And I think product is one of those areas, I would actually say management in general, is one of those things that comes from experience. There’s a lot of great books to read. There are many great frameworks. But the deeper wisdom comes from applying those frameworks in real life. And that’s possibly explains the popularity of your podcast here is people are looking for those real world stories and experience. So product management, to me is fundamentally entrepreneurial. And it’s learned from experience. So what does this mean? So I think we look at transformational leadership, what I found is product managers are looking for not only an opportunity to create something to create value for the customer, and to learn sort of the mechanics of the craft, they’re looking for the transformational leaders who will help them understand how to drive the best outcomes for the company. And you do that through influence. So to give an example, product management is very much a data driven field, we look at customer feedback, we look at activity, we look at all kinds of things. But also product management is a huge social game, so to speak. So product management is about creating alignment within the organization. So an example I would give this is at one point, I had a product manager fairly Junior one working for me. And oftentimes product managers will come at this saying, Well, if I present the best data, so I had a guy who’s like, Oh, if I present the best data, then naturally people will just come around to this decision, then we’ll all proceed with his recommendation is very logical. Yes, he’s very logical, and was an engineer who’d come into product. So this all made total sense to him, Hey, I have the formula. And here it is, I solved the equation now everyone will follow my lead. And my response was yes, except for the part where everyone says no, things like what do you mean? Like, it’s not just about presenting the best data, I wish it was that simple. Product Management is also about enrolling everyone in the mission and the vision of the company creating that sense of ownership. And so I think, in the case of this individual, I remember very clearly he he kind of had this epiphany, like, oh, so product management is a social game. So in his case, transformational leadership, where that came into play was understanding kind of where he was in his journey, recognizing that he was had sort of worked out the data driven side of product management and management in general. But we’re still early in figuring out how to connect with people and how to do the storytelling that illustrates the data, the decision we’re trying to make and so forth. I don’t know if that’s a specific enough example, Aidan. But I think when I think about any one of the product managers are people I have managed in the past, transformational leadership all starts with, what are your goals? What are you trying to accomplish in this job in your life, and beginning to learn sort of the strengths and weaknesses and then plotting with that employee a sort of a unique path that’s going to help them grow in the areas that they want to? This is very different from transactional approach.

Aydin Mirzaee (Fellow.app)  24:17

What’s interesting about product managers, when you don’t necessarily have direct reports, and of course, the more senior you become, you obviously get them but even at the beginnings of being a product manager, a lot of your leading is through influence, like you mentioned. And so the tricky thing is, and I’m sure you’ve had this happen, which is, maybe someone comes to you and says, you know, I’m trying to get this done, and it’s just not working. I know I have to lead through influence. I know I’ve got to do this coaching thing, but it would be so much easier if they maybe like the whole function reported to me, and I could just tell them what to do and then they would do it. It’s just so painfully slow, because I have to work through influence in this weigh, how do you respond to someone who comes to you and says that I mean, there is some, you know, if you just look at the facts, they might not be wrong, that it might be faster if they didn’t have to go about leading through influence. And yeah, just wondering what your thoughts are on that. Yeah,

Nathan Trueblood  25:16

I mean, on the one hand, you’re right, if everyone just reported to me, and if I was the king, then it would be a lot faster, except that if you understood what I was saying earlier about sort of authoritative leadership versus transformational leadership, I may not get the result, even if I’m the boss, and lo will make it so because I haven’t necessarily gone through the steps of enrolling everyone in the mission and the vision of what we’re trying to do. And why does that matter? It matters because I’m not the smartest guy in the room, I want other people caring about the problem as much as I do. If you take over that, sort of, I’m the king or queen over the whole thing, you may be taking away some of that ownership, that’s so essential. But you’re right, it can be faster, I will laugh about this, I had two product managers that worked for me a long time ago. And one had come from a very technical background had been an engineering manager and had led large teams, and she was brilliant. But she was new to product management. Um, then I had another product manager who was not super technical, didn’t have all that engineering management, or, you know, experience. And yet, when I asked the engineering teams, they preferred the less technical product manager versus the one who was a lot more knowledgeable as an engineer. And I remember asking them why, why do you prefer this amazing woman over this other amazing woman? And they said, Well, the one with less technical experience brings us insight. The other one brings us information. And I think in a funny way, the one who had been an engineering manager, she was used to saying, Okay, I got to this data team, you go figure it out. Whereas a product manager, they’re not going to do anything, if you just give them information, she would go through the data and pull out of the data, here’s what I think is the most essential things we should pay attention to. So she knew that they weren’t going to follow her just because she dumped a bunch of stuff on them, she had to bring value and had to bring insight. So I think in a funny way, not being the king or queen forced my other product manager to have to really think about what value she was bringing in order to lead people. People don’t follow product managers, because they’re in charge, they follow the one to bring the best ideas, and the best insight.

Aydin Mirzaee (Fellow.app)  27:30

Hey, there, just a quick pause on today’s episode to let you know that we’d really appreciate you helping us spread the word about the Supermanagers podcast, if you’re enjoying what you’re hearing so far, dial into your podcast app of choice, whether that’s on Apple, or Android or Spotify. And just leave us a quick review. Now back to the interview. One of the things that I’m a believer in is that even if you were in charge, and they did report to you, you still have to lead through influence, right? It really doesn’t change all that much. Not if you want really smart and awesome people on your team. Because those people like you said they want the autonomy, they want the growth they want. I mean, they’re working there because they want to solve the problems, right not to be told what to type in what to do. So I think that doesn’t really change. And I think it’s a super valuable lesson. And what an interesting story about how the non technical person was preferred for that reason?

Nathan Trueblood  28:27

Yeah, I was really surprised by that, frankly, because I fully I mean, these are very hardcore technical engineers, I was working on infrastructure products, and yet, they preferred the person who brought more value in terms of insight.

Aydin Mirzaee (Fellow.app)  28:40

One of the things that you’ve had a lot of exposure to is working with cross functional teams. So when you think about cross functional teams that you put together for large projects, what are some things that you’ve learned to get the most out of their collaborative nature?

Nathan Trueblood  28:58

You know, in a funny way, this makes me think about alignment. So product managers, you know, and alignment can be kind of a PTSD trigger word for product people, I argue for CEOs as well. Anyone who’s in a leadership position is keeping everyone focused on the most important problems that you face at the moment. So my job as a product leader is to create sort of maximum value for my customers and for the business. And so that often means I am leading large cross functional initiatives of one kind or another. So my job is to get everyone sort of enrolled in the vision and what we’re trying to accomplish with that particular cross functional thing. So the way I do this, and how I drive that influence is oftentimes it starts with identifying a coalition of the willing who are working on something and I will spend time as a product leader you know, my one on ones of course, I have one on ones with my team, but my one on ones extend way beyond my immediate team, to all the cross functional teams. Engineering, customer success, marketing, sales, sales, engineering and so forth. So as a leader in these situations, it seems like spending a lot of time I spend a lot of time in one on ones in these cross functional endeavors. You know, this is a huge part of what I do or was doing at box. So what I do, the tips I have is I make sure that I’m checking in on a regular basis with my cross functional stakeholders, that sort of coalition of people who are focused on the problem, it’s really important that I do that. So I understand the ground truth of what’s going on. And also, it allows me to understand where are the opportunities for my team to contribute back to that sort of, I understand where my employees are trying to grow, I can find opportunities for them. So in these cross functional efforts, I will adjust my one on ones to make sure that I am spending time with other people who are going to influence the outcome, so that I can understand where the problems are. And so I really think that that’s the key to driving outcomes. I remember even when I was interviewed at box, they asked sort of like, how do you how do you get things done in organization? I asked this question in interviews, how are you going to get something done? How are you going to drive change if you’re here? And oftentimes, you know, I got asked that question, it starts with identifying a coalition of the willing and then building those one on ones those relationships, then allows me to be influenced by them, and to influence the direction that we’re going in. I think the last thing I would say here is sort of, it really comes down to you want to boost innovative thinking, and encourage people who are subject matter experts to speak up. And for me, that means enrolling everyone in the mission, and then giving them the agency, when we talk in the one on ones people will share their fears, what they think is not going to go well give them that agency to overcome those fears and do what they know is right for the customer in the business in the team. This is the most essential alignment I worry about Aiden is not like, Oh, is it three weeks from now? Or is it four weeks from now? It’s like, are we aligned on what we’re really trying to do for the business and the customer. And then I’m trying to help people get the agency feel empowered to do what they already know how to do really well.

Aydin Mirzaee (Fellow.app)  32:11

So I have to dig in on this term that you use, which is identify the coalition of the willing, what does that mean? And how do you find this coalition? Oh,

Nathan Trueblood  32:22

I mean, I think it comes down to, and we all face this every day, oh, my gosh, and especially I guess I’m a startup guy, as a startup person, you never have enough people. I mean, even working at Box, even in a large enterprise, it turns out, you never have enough people to solve all the problems or sees all the opportunities you see. But sometimes you’ll see a problem that you think is really critical, or an opportunity that’s really, that can be really big. And you will find other people in the organization, it might be someone in another team, it might be someone in customer success, who sees that same thing. And you start talking to them, you know, I think we could do something about this. And then you find there’s another person who also shares that same passion about making something better. And so that’s what I mean is beginning to identify a cohort of other people in your organization that are passionate about solving that problem. That’s the beginnings of driving a cross functional initiative. Yes, you can have leadership that sort of makes requests, hey, here’s an objective, we want to drive something from top down. But even then you need to find that coalition of the willing, who’s with me on solving this problem, that then becomes that core set of people that you will spend time with in the coming weeks and months. And I will actually adjust where I’m spending my time with people to make sure that I’m staying connected with that coalition, and that we’re all communicating so that we can actually achieve the outcome.

Aydin Mirzaee (Fellow.app)  33:46

I think that definitely explains it. One of the things I was also going to ask about that you just mentioned in passing is, is all the series of one on ones that you do. So the sense that I’m trying to get is as a leader, part of your role is to make sure that people are largely aligned. Right, identify the changes that need to be made, it seems that these one on ones are a big part of it. And very specifically, I mean, we all know we should do one on ones with people on our team. I want to dig in on what kind of one on ones you do with people who are not directly reporting to you. And I wonder what the content of those one on ones look like? Are they more freeform? Or do you ask the same series of questions so that you can kind of compare and contrast between responses from different folks? What do those look like and what is your purpose in doing them? What do you get out of those sorts of conversations?

Nathan Trueblood  34:42

My approach is generally pretty freeform. It’s one on ones. I would say I’m a little bit more intentional with my employees because we’ve had a discussion about their career aspirations. We’ve we you know, I have a really much better sense of sort of what their strengths and weaknesses are Maybe, and so we can be a bit more intentional. And I will typically let the employee drive the agenda for the one on one, it’s not time for them to give me status, it’s time for me to be there for them. I take some of that into my cross functional one on ones, which is to want to make sure that it’s not just a status update that I’m actually checking in with the person that I’m hearing about what their concerns are. And it can change sometimes it may be the challenge of the day is just simply we’re both going through something. Other times, it might be much more sort of task focused. But what I realized Aiden, especially in the last couple of years was my approach to working with my direct reports sort of transformational style was to be pretty intentional about what are we trying to do here, my job is to set you up for success. And if I do that, well, you’ll do your job well, and our whole team will benefit, when I realized in my cross functional relationships was to actually ask the question to say like, what do you hope to get out of the relationship here? What do I hope to get out of the relationship, let’s have a little bit be a little bit intentional about what we’re doing in our one on ones. So even just establishing like, I like to ask the question, you know, okay, you’ve worked with other product managers in the past, what worked well, and what didn’t work? What do you find rewarding? And what do you not find rewarding? Again, it’s a little bit of being a bit more intentional in designing the partnership explicitly with each person. Now, not always that formal about it. But if we’re having on one on one, we’re going to work together, where can we have a partnership? So let’s talk about the partnership, what do we both want to get out of this? Oftentimes, his legs and so this is something I realized in the last few years, but the catchy term for this is designed alliances. I like that. And I could talk a lot about design alliances, it was actually something that I learned about, well, tomorrow, who’s on your show, she and I both have gone through level of EQ coaching. And it’s really about getting intentional about the relationship and what you and the other individual trying to get out of that. So it sounds like a lot of work. But what it really comes down to is every time I sit down with someone, I’m kind of religious about keeping my one on one notes. Maybe if we’ve had a discussion about design Alliance, maybe we capture that together at our shared one on one notes. And then throughout the week, I know I’m going to meet with you, Aiden, you know, in a couple of weeks, I might be jotting down into that journal. Oh, I should remember to talk to Aydin about this. And so the design Alliance kind of helps me wrap my head around what we’re both trying to accomplish together. And then I’ll use my one on one notes to make sure that we have topics to talk about. And if we don’t have topics to talk about, it may be Hey, no problem. Let’s skip for today. But I think I have naturally come round to the same, maybe not with the same rigor but the same approach, which is to be intentional about each one of those partnerships, so that I can make sure that I show up with the right mindset.

Aydin Mirzaee (Fellow.app)  37:46

I really like the term design alliances, because every now and then, you know, in business in work, there are these terms that are descriptive, and just the phrase itself conveys a lot. So in this case, like you said, these are partnerships, they’re alliances, and, you know, why not design them? very purposefully. So I really, really liked that term.

Nathan Trueblood  38:08

Let me call me one little bit further on design alliances. When I first heard about this, it sounds a little bit weird. Or it can feel a little bit weird, especially if you’re not an extrovert like I am. So like, Oh, my God, am I gonna talk to this other person about this? So I realized that it’s easier to talk about what are we trying to get out of the partnership than it is for me to say, you know, what are you doing? Or what am I doing? So if you if I need to give you feedback, and rather than saying eight, and I didn’t like it, when you did that, it’s like, Well, hey, we talked about, we’re both trying to get out of a partnership. And you know, what I find rewarding, or what I’m trying to get when you did that thing, you took that away from me, and that’s impacted our relationship, our partnership, it’s just a very different way of interacting with another person that I find to be a lot better. And that’s more productive. And they give you an example of this, somebody I worked really, really well with as she was my engineering manager, and I was her product manager. Our lines is pretty well defined. You can read books about product management, what you’re splitting how engineering managers and product managers are supposed to interact. Then she changed roles, and I changed roles. And I felt like we didn’t really have a roadmap for how we should interact. And we kind of struggled together for a while. And then I asked the question like, What do you actually find rewarding in your new role? And I realized that there were things I was doing in our partnership that was taking away her reward. And that was when I realized, Oh, by having this explicit conversation about how do we find meaning and work, what are we trying to accomplish in our careers, I realized that I was unknowingly stepping on that not and realizing that I was doing it. So that’s a good example of like, and this is somebody had a really high relationship with trust. We worked really well together, but we just never had the conversation. And I didn’t realize how clumsy I was.

Aydin Mirzaee (Fellow.app)  39:54

Yeah, I think that’s a great example and it goes to show just because you’ve been working with someone for a long time It doesn’t mean that there are not ways to make it better. And so yeah, those purposeful conversations can definitely go a long way. We’ve actually gone through a lot of material, a lot of really, really cool things. I did want to ask you very quickly about something very practical. There have been other guests on the show. We’ve talked about calendar audits. It’s a thing that I think all of our listeners know that one should do. I wanted to ask you specifically, because it sounds like you use your calendar audits in a very purposeful way. And it’s had a very material impact in your leadership. And so I’d love for you to just made me describe just tactically, what does a calendar audit allow you to do?

Nathan Trueblood  40:41

So fundamentally, what a calendar audit allows me to do today is, especially in a larger organization, but even in a small one is to think about where I’m spending is to be more intentional about where I’m spending my time, and where I’m trying to drive influence. So my story of calendar audit was kind of funny. At first, I did it as a survival tactic. You know, being a VP of product and a 2000, employee billion dollar company, you’re pretty busy, my calendar was terrifying. And so I like most people who do a calendar audit, I’m like, I don’t, I don’t seem to be able to get any hands on keyboard work done. So initially, the audit was just, hey, I’m trying to figure out how to get more done. Where am I spending my time? So I did the calendar audit. And I think I had like 125 rows or so in this spreadsheet of literally like every one on one every team meeting? And where am I spending my time? I was just trying to answer that question. So of course, the vast majority of my time was being spent in one on ones, you know, nothing particularly unique here. And so at first, it was just a way for me to be to sort of take an audit, take stock and make some changes, prune some things out of my calendar. But as I went on over the quarters with this approach, I began to realize that actually, my calendar audit, which I would typically do on a quarterly basis was becoming more like, where am I driving influence right now, because it would change from one quarter or maybe from one month to the next. So I kind of inverted the whole thing. And I’m like, wait a second, before I was just sort of organically spending my time here or there, depending on what was coming at me. Now. I’m like, wait a second, given what I know about, I want to adjust where I’m spending my time. So then I started to use the calendar audit is more like a prescription. Here’s where I’m going to spend my time and I’ll adjust the weights of where I’m placing my emphasis. What does that mean? It means, well, maybe I’m having weekly one on ones with one group of people for a quarter. But then the next quarter, maybe I’m not, hey, I’ll just let’s check in once a month or once a quarter. I think the other thing, so that allowed me then adjusting those weights in the calendar audit then allows me to be intentional about where I’m driving influence. The other thing I realized was that, especially if you’re in leadership, a lot of people want your time. So it was very important for me to be transparent about this, because I realized initially I was doing this sort of organically, I would adjust my time once a quarter, adjust those weights and re redo all of my one on ones. But it wasn’t necessarily telling people what I was doing. And so people would go from like, wow, we were weekly and now we’re once a quarter like, you know, like me anymore, like what happened. And so I’m was very transparent and said, Hey, this isn’t a reflection of the importance of our partnership. It’s just where I’m placing emphasis right now, my time I’m always available. So if you want to talk about something, let’s talk about it. And people had a really positive reaction to that, which they appreciate knowing what I was doing. And then they were more supportive and understanding sort of how I approach and using my time, time is that one resource, you know, we all say it’s like, it’s so precious. And so being really intentional about that, when I have no time allowed me to be really thoughtful about where I invest.

Aydin Mirzaee (Fellow.app)  43:50

Yeah, I really like that time is the ultimate equalizer. Right? The only thing that everybody has the same of

Nathan Trueblood  43:57

from a feature perspective, I hope you guys are working on some feature like this. Maybe you have it already. And I should know, but nobody has this, like if you do Google Calendar, it’ll kind of tell you where you’re spending your time. But I’m now sort of obsessed with this idea of being able to see the next week, month quarter. Where’s my emphasis?

Aydin Mirzaee (Fellow.app)  44:18

Yeah, it’s funny that you mentioned that as you’re talking, being able to do things like this is much more possible these days with all the latest AI tech. So you may see something like that from us for sure. This is super interesting. Nathan, this has been an awesome conversation. We’ve talked about a lot of things. We started with transformational leadership. We talked about identifying coalition of the willing, we’ve talked about designed alliances, calendar audits, so many great things and the question we always like to end on is for all the managers and leaders constantly looking to get better at their craft. Are there any final tips, tricks or words of wisdom that you would leave them with?

Nathan Trueblood  44:57

Sure, I would say from my own experience Most everything I’ve learned as a leader and as a manager has been by emulating others. Again, I read lots of books. But it’s then seeing others apply those principles. In practice, it’s been so important for me, I learned from experience. So my advice would be seek guidance and inspiration and mentorship from other leaders, perhaps transformational leaders, both inside and outside of your company. So find if you have people in your network, or listen to this podcast, but find people if you can, who will invest the time in you, I think, you know, leadership, especially in product management, but in any field, which is really experienced base, and that’s management, in general, it’s all rooted in experiential learning. So building relationships with managers past and present, that can serve as kind of a board of personal board of directors, that’s another catchy term people like to use. But like, maintain those relationships with your managers, because they’re already invested in you, and they are going to help you in your management journey. So hopefully, if you go from one company to the next, you might change jobs. But hopefully those managers, those leaders, that you really were inspired by, hopefully, you’re maintaining those relationships. And so for me today, as a leader, I feel whether it’s in reality, because I’m still friends with a lot of my former managers, or just in my head, I hear them, I hear the learnings. I have that personal board of directors there to help me grow as a manager, both from the past and in the present.

Aydin Mirzaee (Fellow.app)  46:31

That’s great advice, and a great place to end it. Nathan, thanks so much for doing this. Yeah. My

Nathan Trueblood  46:34

pleasure. And thanks so much for having me on the show. Let me know when you’ve got my calendar audit feature ready? All in early adopter. But yeah, really appreciate the conversation and great topic.

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